Gay Chicago Guide: The Essential Guide To Gay Travel In Chicago Illinois 2019

Gay Chicago Guide: The Essential Guide To Gay Travel In Chicago Illinois

Deep-dish pizza, soaring skyscrapers, vibrant music festivals and … the first officially recognized gay village? Yes, Gay Chicago might not be your first thought when considering gay hotspots in the USA where you can just be yourself, but after you have immersed yourself in the frenzied energy of the Boystown gaybourhood you will soon be wondering how the Windy City managed to keep its fabulousness under wraps for so long….

 

As the heart of the Chicago LGBT community, Boystown boasts everything from boutique shopping and trend-setting dining to alluring spas and irresistible after-hours entertainment in every form imaginable – and no Gay Chicago travel plans would be complete without at least one night out here.

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Another gay-friendly hub, the beautiful, ethnic Andersonville neighborhood, famed for its Swedish heritage, is also quickly taking off. Celebrating diversity and emanating small town charm, Andersonville has a large rainbow population and an assorted collection of hip, independent shops and locally-owned restaurants that are welcoming to everyone.

Much like the  Boyz Town, Pattaya’s similarly named gay village, the Gazi gay village in Athens or Kemptown in Brighton, at times it can seem the LGBT community far outnumbers their hetero-counterparts leading to the unusual position of many venues declaring themselves straight-friendly. It’s fair to say we are absolutely living for it and can testify that the queer vibes and come-as-your-fabulous-self spirit here infuses your soul with warmth and tempts you to never leave.

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Of course, this is Chicago – and there are many, many more reasons to explore this city further.  Chicago is home to one of the most inclusive LGBT+ populations in the nation so you can freely explore and know no matter who you love, you’ll fit right in.

From the stratosphere towers of glass that rise from the downtown to capricious public art, relaxing lakefront and cornucopia of world-class dining Chicago is a modern city fuelled by culture and food. Again, how it has flown up the radar for so long we will never know.

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Gay Chicago Guide: The Essential Guide To Gay Travel In Chicago Illinois 2019

   

Obviously being gay does not define which attraction most of us will want to see in each city and most queer tourists will simply want to check out the top things to see in Chicago during the day!

There are some rough neighborhoods in Chicago best avoided and thieves and pickpockets do operate on the subway, so be careful with your valuables.  Although crime has declined since its peaks in the 70/80’s (linked to Al Capone’s Chicago mafia and rival gangs) mugging late at night is still stubbornly high – as is gun violence in some areas. The North Side, with Boystown and other upscale areas, is very safe but be careful of shady areas in the downtown – which empties over pretty fast after the work day is over.

Overall, just take care at night – but know the most notably dangerous areas have very few (if any ) touristic attractions, so you are unlikely to end up there – even by mistake. Gay people in Chicago do not need to take any extra precautions in terms of public displays of affection and should have no issues exploring this city’s steely charm!

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It can all get a bit overwhelming, we totally get it that – so if you are not sure where to go take a peek at out Gay Chicago map at the end or simply head to the Boystown gay area. If you plan to get a lot done car hire in Chicago is a very affordable option and popular to see more far-flung attractions. This is America after all and the car is king. But if you just want to explore the gaybourhood, downtown and a few other places – public transport and rideshare apps should be sufficient.

For now here are just a few of our favorite gay things to do in Chicago – seriously, this is by no means comprehensive but might help you to see something other than the inside of a club. Don’t laugh, you wouldn’t be the first person to come all this way and not see anything outside the Boystown – and certainly wouldn’t be the last!

The gay scene in Chicago is just that good…

 

Top Highlights in Chicago
  • Cloud Gate – An icon of Chicago by Indian-born British artist Sir Anish Kapoor, no trip to the Windy City would be complete without a few snaps of this design, inspired by liquid mercury, and gazing into the sculpture’s surface which reflects and distorts the city’s skyline. Displayed as the centerpiece of AT&T Plaza at Millennium Park in the Loop area.
  • Helicopter Flight  – See unparalleled, panoramic views of Chicago by riding in a helicopter over this glorious city. A trip you are sure to never, ever forget at a surprisingly reasonable price. Choose from the Day tour, Twilight tour or Nighttime Tour and enjoy different views of Chicago’s skyline. We recommend Twilight, but who are we kidding – they are all utterly mesmerizing.
  • Willis Tower Skydeck – If the helicopter trip seems a bit too over-the-top, you can always head to the highest point of Chicago for an outlook over the cityscape instead. Enjoy views of Chicago from the 103rd floor of Willis Tower at the Skydeck and while you are there, experience the thrill of the Ledge, a glass balcony 1,353 feet (412.4 meters) off the ground – if you dare.

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  • Chicago Male Salon – Located in the heart of Boystown, Chicago Male is in the middle of all the action. Once known as the go-to for men who wanted something more than just a little off the top, they now proudly offer a full range of hair styling, facial skincare treatments and body hair removal services for men and women – but the core clientele is still very much gay. Relax with a hot beverage or glass of wine as they spruce up your image profile, ready for a big night out in Gay Chicago.
  • Sir Spa – Another gay spa in Chicago you should try to visit to stay on top of your game. A premier Chicago spa for men with massage, skin care, and grooming services. Experienced professionals make you feel comfortable in a relaxing, spacious environment with state-of-the-art spa amenities.
  • Hamburger Mary’s Chicago – So much more than just a neighborhood burger joint, this LGBT hotspot not only offers big & juicy gourmet burgers, house-brewed beers and strong cocktails, they also put on weekend drag shows and charity “HamBingo,” cabaret theatre events, trivia, and so much more! This location is unusual as it is in the secondary gay area of Chicago – Andersonville – as opposed to Boystown, but they also have an attic bar and beer brewed on site! We have loved visiting previous locations in Orlando, Denver and Las Vegas, and would never consider leaving a city that hosts Mary without stopping in to say hi!

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  • Underground Donut Tour – Sample some of the Windy City’s tastiest donuts on this 2-hour Underground Donut Tour, celebrating the magic of Chicago’s tastiest sugar-filled concoctions. Donut-lovers are sure to enjoy this visit four of Chicago’s tastiest donut purveyors, offering a chance to savor all of your favorite varieties, on the city’s only donut-themed excursion. All tastings are included, and gluten- and nut-free options are also available.
  • Navy Pier – A wonderful 3,300-foot-long pier on the Chicago shoreline of Lake Michigan offering more than fifty acres of parks, gardens, shops, restaurants, family attractions, and exhibition facilities. Filled with a festive atmosphere by day and night – and offering something for everyone – it is no wonder Navy Pier is of the most visited attractions in the entire Midwest and is Chicago’s number one tourist attraction.

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  • The Art Institute of Chicago – Visit the second largest museum in the United States, right off the Grand Park in Chicago. View masterpieces in pointillism by Georges Seurat or just wander around and enjoy one of the world’s largest collections of modern and contemporary art with numerous collections from European, Asian, African, and more available for close study. No art lover will want to miss this!
  • Magnificent Mile – Chicago’s premier commercial district. The vibrant, bustling heart of capitalism in the city, explore around to discover luxe hotels, posh eateries, upscale fashion and more landmarks of the city than we could count.

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  • Women And Children First – One of the largest feminist bookstores in the USA, stocking more than 30,000 books by and about women, children’s books for all ages, and the best LGBTQ fiction and non-fiction. Located in Andersonville, known for its diversity, queer-friendliness, women-owned businesses, and community spirit, and strive to offer a place where everyone can find books reflecting their lives and interests in an atmosphere in which they are respected, valued, and well-served.
  • Center on Halsted – The Midwest’s largest LGBT+ support center, conveniently located in Boystown. More than 1000 people walk through its doors every day, taking advance of their support networks, cultural events, and recreational programs.
  • Wrigley Field – A baseball park located on the North Side of Chicago and home of the Chicago Cubs. Filled with retro charm and the 2nd oldest baseball stadium in the majors, if you are a sports fan you won’t want to pass up a visit here – somewhat ironically situated next to the Boystown gaybourhood.

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  • Chicago Prohibition Tour – Visit four historic bars in operation since Prohibition in Chicago, and learn from a knowledgeable guide about the surreptitious world of the speakeasy. This adults-only tour takes you by coach to once-illicit establishments in Old Town, Wicker Park and the Chicago Loop where liquor, jazz, and mobsters ruled. You’ll hear about Chicago gangsters like Al Capone and learn the historical context for the decade-long ban on alcohol. If you’d like, you can also purchase recommended craft cocktails and signature drinks of the 1920s. A fun way to start the night before retreating to the hedonism in Boystown.
  • Chicago Food Tour – Discover Chicago’s food, history, architecture and culture on this 3-hour, small-group walking tour. Try six of the Windy City’s quintessential staples from local restaurants and specialty food shops like Pizano’s Pizza and the Berghoff, the oldest family run-establishment in Chicago. Taste local favorites including deep-dish pizza,  Chicago Italian Beef Sandwich and chocolates from Fannie May, just to name a few. Along the way, see and learn about the historical, cultural and architectural components that make up this legendary town.
  • Chicago Gay Beach – Officially known as Kathy Osterman Beach but often referred to as Hollywood Beach, is one of gay Chicago’s best-kept secrets. There is no carpark here so public transport is your best option, but the pure white sand and gorgeous bodies will instantly having you dreaming of Hawaii or Cancun over Illinious. Down-to-earth with a friendly crowd, this is the go-to spot for Chicago gay men who flock here on sunny days.

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  • Museum of Science and Industry – One of the largest science museums in the world and home to more than 400,000 square feet of hands-on exhibits designed to spark scientific inquiry and creativity. Between the World War II submarine, five-story movie screen, 40-foot tornado and the 727, you might wonder how they fit so much discovery inside one museum – but with wonderful use of place and innovative technologies, this museum is all about redefining expectations and learning. If you love acquiring knowledge and discovering cool things, this is an unmissable attraction.
  • Architecture Sightseeing Cruise – Take a peaceful cruise along Chicago River to see the city’s breathtaking buildings and intricate architectures. Witness Chicago’s rich urban sceneries and see its amazing skylines from a different vantage point as you float past famous landmarks such as the Wrigley Building, East Bank Club, Willis Tower, and more.
  • Go Chicago Card – An all-inclusive pass to see up to 26 key attractions in Chicago. Choose between a 1, 2, 3 or 5-day card and visit as many Chicago attractions or tours as you can on your chosen days Attractions include Shedd Aquarium, Skydeck Chicago, Adler Planetarium and many more! You will also get a digital guidebook with attractions and a map to plan your itinerary. Plus, extra dining, shopping discounts! Perfect for those who want to see and do it all!

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Gay Annual Events in Chicago

As a paradise for the LGBT community, Gay Chicago offers a wonderful line-up of annual events for gays, lesbian and transgenders and – well, anyone who wants to be involved! These signature gay events are just the biggest and best, however no matter when you visit there is sure to be something on (which is why we really recommend locking your Chicago hotel down in advance…)

  • International Mr. Leather (May) – A globally significant contest to select winners of International Mr. Leather and International Mr. Bootblack is the centerpiece of this kinky weekend. Built around those are the expansive market filled with vendors from around the globe and of course the unforgettable Victory Party and must attend Black and Blue Ball. There’s also the lobby social time and a multitude of other events to fill the entire weekend. For fans of leather, it goes without saying you won’t want to visit Gay Chicago without attending this incredible event.
  • Andersonville Midsommarfest (June) – One of Chicago’s most legendary street festivals and Andersonville’s quintessential yearly celebration having been held for over 50 years. Borne out of Andersonville’s Swedish heritage, Midsommarfest will transport you back to the old-world Swedish traditions for two days and three nights of music, dancing, entertainment, and delicious food.
 
  • Chicago’s Dyke March (June) – A grassroots mobilization and celebration of dyke, queer, bisexual, transgender, and lesbian resilience. It is an anti-racist, anti-violent, volunteer-led, grassroots effort with a goal to bridge together communities across race, ethnicity, socioeconomic status, age, size, gender identity, gender expression, sexuality, culture, immigrant status, spirituality, and ability. We challenge fatphobia and are body positive. Often combined with a music festival afterward, but the main event is the March and is (by intention) more radical, offering an alternative to the “corporate, white male-dominated Chicago Pride Parade”. There was clashes and international coverage in 2018 after the March announced their solidarity with Palestine and pro-Israel marchers.
  • Chicago Pride Fest (June) – An exciting two-day street festival held the weekend leading up to the Chicago Pride Parade with up to 100,000 expected to attend, celebrating LGBTQ life, culture, and community. The festival features live music by popular artists, 3 stages, food and drink, 100+ arts/craft and merchant vendors, DJ’s and dancing, drag shows, pet parade, sponsor booths and more. Head along for a love-filled celebration of diversity, equality, and the Chicago LGBTQ community at Halsted Street and Addison in Boystown, America’s first recognized gay village. The parade takes place over a four-mile route and in the evening revelers will pour into Boystown clubs and party into the wee hours of the night.
  • Northalsted Market Days  (August)  – Northalsted Market Days® is the largest outdoor street festival in the Midwest and Chicago’s biggest summer party! Founded in 1980, the celebration now spans 6 blocks of North Halsted in Chicago’s Boystown/Lakeview neighborhood stretching from Addison to Belmont. The 2 days/weekend long festival features an all-day lineup of live music on 5 stages, unique vendors, arts, crafts, food and drink, DJ’s and dancing. Attendance approaches nearly 200,000 fairgoers, from near and far, all walks of life, and all colors of the rainbow.
  • Reeling: The Chicago LGBT+ International Film Festival (September)  – The second longest-running film festival of its kind, showcasing the best LGBTQ+ films and videos each year. From award-winning international feature films to social documentaries to experimental shorts, Reeling has always presented a range of genres that demonstrate the rich diversity of work being produced. Not only has Reeling become one of the most important cultural events for Chicagoans, it also attracts LGBTQ+ people from throughout the Midwest who consider the festival to be the highlight of their cinematic year.
  • Northalsted Halloween On Halsted Parade (October) – Much like its more famous counterpart in New York, this crazy parade is held in the Boystown Gay area and features thousands of people vying for best dressed with a panel of gay celebrity judges. Anyone is free to join the competition – but even if you don’t the electric atmosphere is not to be missed.
 

Gay-friendly and Gay Hotels in Chicago

In this bustling city famed for its Midwestern hospitality,  you will not find any major hotel accommodation that isn’t gay-friendly.

After all being gay-friendly is about providing a non-judgmental and respectful environment in which all people are treated equally. In saying that, elegant design, helpful staff, and excellent value for money never hurt anyone. Some hotels in Chicago have also gone above and beyond in recognizing and marketing to the LGBT community and given their popularity with gay travelers we would say it has paid off!

Ace Hotel Chicago

Everybody likes to be surrounded by people with common interests and as such there are a few hotels in Chicago favored by gay travelers – although to be clear there are no exclusively gay hotels in Chicago sadly.

The Lake View / Boystown gaybourhood is at the forefront of LGBTQ+ inclusiveness in Chicago – and while it is a diverse community brimming with queer nightlife and gay-owned businesses, there are only a few hotels here. Its proximity to the downtown and the cute surrounding neighborhoods also give you plenty of funky gay-friendly hotel options to consider which are not too far away.

The following gay-friendly hotels in Chicago are only the most recommended, but there are hundreds of other hotels in Chicago if you don’t find quite find what you are looking for. Whether you want a fun and social hostel, a cheap but private place to crash after a night of partying or a chic luxury option to sip cocktails surrounded by fashionable people, Gay Chicago as something for everyone!

Hotel EMC2

Gay-Popular Hotels in Boystown
  • Hotel Zachary ☆☆☆☆ – Close to all the Boystown gaybourhood fun, but enough of a walk away to not feel overwhelmed with it – Hotel Zachary is our favorite gay-stay hotel in Chicago. Inspired by Zachary Taylor Davis — legendary Chicagoan and the world-renowned 1914 architect behind Wrigley Field — Hotel Zachary blends new and old, refined and comfortable, unique and familiar, all at once in their bright, contemporary rooms. A boutique hotel in the heart of the iconic Lakeview neighborhood, it’s an authentic experience that brings Davis’ vision to life in thoughtful and surprising ways. Just minutes from downtown Chicago and Lake Michigan, surrounded by unique shopping, dining and live music destinations, Hotel Zachary is also the perfect home base for LGBT travelers at only a 12 minute walk away from Boystown.

Hotel Zachary Chicago

  • The Wheelhouse Hotel ☆☆☆☆  – Rooted in history, with an eye towards the future and an ever-present atmosphere of playful celebration, this spunky hotel brings intimate, unpretentious, luxury lodging to Chicago’s spirited Wrigleyville neighborhood. Just steps away from all the action yet miles away from ordinary, you’ll have a front-row seat to a hyper-local experience. The boutique 21-room hotel provides six different room types thoughtfully designed to accommodate the most intrepid of travelers. With playfully sophisticated rooms that lend an intimate vibe complemented by illuminating accents, room styles ranging from terraced penthouse suites to king rooms complete with a sofa and lounge area. Integrating edgy elements with earthy touches, sprawling windows, walk-in showers, bespoke millwork, local art, and cozy accommodations, each guest room sets the scene for a grand slam stay. The most popular and top-rated hotel close to Boystown (an 8-minute walk away), while we have no interest in baseball we absolutely loved the design aesthetic and hope you do too!

The Wheelhouse Hotel

  • City Suites Hotel ☆☆☆ –  An (almost) gay hotel in Chicago that actually celebrates its central location in Boystown – and all at a very affordable price. Showcasing their distinctive Art Deco styling and dedication to warmth and comfort in every room, we enjoyed the fine details include custom-made headboards, wardrobes, and desks with chic black cherry inlay designs and separate sitting areas with pull-out sofa bed. Even with their reasonable prices, freebies still include continental breakfast, afternoon cookies, gym access (off-site) and 24-hour coffee and tea in the lobby. From sweet greetings to “suite” dreams, you are sure to enjoy a stay here and find something to love.

City Suites Hotel

  • Majestic Hotel ☆☆☆  – An affordable hotel with the feel of an English estate outside, but celebrates America’s pastime inside. The hotel’s newly renovated public spaces put America’s obsession with baseball front and center, and they tell us is no place better to celebrate baseball history than Chicago where one of the oldest remaining baseball parks still stands. Why no one has thought to stay an exclusively gay hotel in Chicago, but three have dedicated themselves to baseball, we will never understand. Still, the Majestic Hotel offers a complimentary continental breakfast and WiFi, coffee and tea 24 hours a day, fresh baked cookies in the afternoon, and complimentary access to a full-service gym a short walk away. There are stylish rooms, gay-friendly service and a ten minute stumble home from the LGBT hotspots in Boystown so we can always recommend staying here.
  • Wrigley Hostel ☆☆☆  – We tend to stay more luxury chic than backpacker budget when traveling but if you want the absolute cheapest bed in town – and to save your money for happy hours – Wrigley Hostel is a popular welcoming-to-all option, but it is not a gay hostel in Chicago (there is none). Social and fun with a fabulous location,  free pancake-and-waffle breakfast, a nightly pizza dinner, and plenty of fun games to meet new friends over including a pool table, ping-pong, darts and more…We are beginning to see the appeal of staying here.

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Other Gay-Popular Hotels in Chicago
  • Viceroy Chicago ☆☆☆☆☆ – Located in the exclusive Gold Coast neighborhood on the site of the 1920s-era Cedar Hotel, this modern hotel offers a locally-inspired luxury experience with 180 guestrooms and suites surrounded by historic mansions – and all just steps to the Magnificent Mile and Lake Michigan. Explore modern, Midwest flavors at the hotel’s restaurant or head up to the rooftop bar, pool, and lounge, perched 18 stories high for a sweeping panorama of Great Lake views and Chicago’s iconic, soaring skyline.  With bold interiors and marvelous service, Viceroy Chicago is poised to deliver a bespoke experience reflecting the art, lifestyle, and design of its vibrant landscape. And yes, everyone is welcome here – as it should be!

Viceroy Chicago

  • The Peninsula Chicago ☆☆☆☆☆ – Where Far Eastern graciousness meets with Midwestern hospitality. The Peninsula Chicago is the five-star hotel that brought traditional Asian service to a city already renowned for the warmth of its hospitality. The hotel has become an integral part of Chicago life and is considered the top choice for everything from accommodation to drinks, spa treatments, and world-class dining.  The Sophisticated rooms and suites are as breath-taking as you would expect, but if you get bored there is a sun terrace, swimming pool, gym, cocktail bar, and rooftop spa. An award-winning luxury hotel chain originally from Hong Kong, we also loved their locations in Shanghai, Tokyo, New York, and Bangkok – and can report the Chicago location lives up to their own impossibly high standards.

The Peninsula Chicago

  • Virgin Hotels Chicago ☆☆☆☆ – Heartfelt delights meet seductive style at this charismatic hotel newly opened by the Virgin group. Step inside this avant-garde hotel in downtown Chicago and find your new favorite space— the doors are never closed and the minds are always open here. Explore a captivating space that is the first of its kind and the last hotel you’ll ever need with the best of food, work and play all at your fingertips. And all located in the heart of the Loop in downtown Chicago steps away from The Magnificent Mile and Millennium Park. Only their second hotel – the other in San Francisco – they are all-ready one of the top-rated hotels in Chicago and clearly are on to something with expansion currently planned for Nashville, Palm Springs, Edinburgh, and Las Vegas. We look forward to exploring more locations soon…

Virgin Hotel Chicago

  • Hotel EMC2 ☆☆☆☆ – At the intersection of art and science, a unique getaway of style and elegance await you at Hotel EMC2. Located in the popular Streeterville neighborhood, this Chicago hotel offers easy access to popular destinations and after a fun-filled day, discover the epitome of luxury in the gorgeous rooms overlooking the city. Complete with robotic room attendants, Leo and Cleo, and in-room Amazon Alexas, these accommodations ensure you have 24-hour support during your stay and promise a one-of-a-kind travel experience. There is also a contemporary restaurant with an industrial-chic dining room, delicious buffet breakfast, and happening lounge to enjoy later at night.
  • Gray Hotel Chicago ☆☆☆☆ – Like a well-tailored suit, Kimpton Gray Hotel has been designed with you in mind. No detail has gone unnoticed, no amenity spared. Set in a historic building that’s considered one of Chicago’s finest landmarks, this is the height of opulence — but it’s also triumphantly modern. The guest rooms at Kimpton Gray Hotel are modern and minimalist, with a touch of irreverence — and they pull it off effortlessly. A textured gray palette is accentuated by powder blue, brass, and gold foil, with the occasional unexpected twist thrown in. It all comes together to create an impeccably tailored room that meets the highest of modern design sensibilities. Kimpton is a big fan of marketing the rainbow – and is one of the most LGBT-inclusive hotel chains in the world – so its no wonder so many gay guests choose to stay here. Think smart, sophisticated, and stylish — Mr. Grey will see you now…

Grey Hotel Chicago

  • Ace Hotel Chicago ☆☆☆☆ – The gay-popular hotel chain Ace has made its way to Chicago and we are here for it darling! Industrial yet modern with great views we enjoyed the airy and modern rooms serving those Nordic-chic vibes we loved in Copenhagen and Helsinki. Onsite there is also a quintessentially Chicagoan rooftop with a fashionable bar and garden, plus a destination-dining restaurant and relaxed café. Like all the hotels we recommend – gay-friendly service is a given.
  • Found Hotel Chicago River North ☆☆☆ – One of our favorite budget hotels in Chicago. Housed in the original Olympia Building, a full restoration of the building’s cast-iron exterior pays homage to Chicago’s storied past. Explore River North’s neighborhood shops and galleries, or walk the famed Magnificent Mile. The hotel’s Asian-inspired bar and lounge, Blind Dragon, features karaoke suites, while Mason offers up classic, Chicago cuisine. Warm your spirits with a coffee or pastry at Mason&Mason, the hotel’s very own coffee shop. Exceptionally funky, this is style-on-a-budget if we have ever seen it – and they also have hotel-quality dorm rooms if you want to save some coin and share with like-minded travelers.

Found Hotel Chicago

  • Aloft Chicago Downtown River North ☆☆☆ – Set in the lively River North neighborhood, Aloft Chicago Downtown River North welcomes guests with superb service, thoughtful amenities and a prime location. Extraordinarily priced, this great value and spacious rooms feature an urban-chic decor with custom beds, flat-screen TVs, ergonomic workspaces and free Wi-Fi. Floor to ceiling windows yield impressive downtown views and there is a 24-hour gym.
  • Moxy Chicago Downtown ☆☆☆ – Ready for a good time? Moxy Hotels makes that easy with the heart of a boutique hotel and an appetite for adventure. There’s a drink waiting for you with your room key and someone at the bar that wants your number. Moxy is for play… Jenga, karaoke, maybe a little game of spin the bottle? Here, you can get away with it. Plus, the WiFi is speedy, beds cushy and freshly made, but more importantly, the bar is always open and the crew is always on. We loved Moxy in Vienna, Warsaw, and Stuttgart – but they are opening up so many locations in a crazy global expansion if you haven’t heard of this brand you soon will! Whether you’re staying for the night or a nightcap, Moxy is a great value option for affordable luxury and to get your party on!

Moxy Chicago Downtown

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Gay Nightlife in Chicago Illinois

With Chicago being one the third biggest city in the USA, you would expect an incredible gay nightlife scene – and luckily the windy city does not disappoint.

Depending on your mood you can find anything here from a relaxed cocktail in an upscale bar to an all-night dance party surrounded by your queer family. There is also plenty of cruise/dive bars, sexy go-go boys, fabulous drag, fun events and  – well, something to cater for every taste!

Most are centered around Boystown, the appropriately named gayborhood, and Andersonville, a historic Swedish neighborhood with many beloved LGBT+ haunts, to the north.

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Unlike warmer location like Key West or San Diego were all-day drinking is common, things in Chicago don’t really get started until the daily happy around 6 pm – or later – and go well, well into the night. Dancing til sunrise is a very real possibility in this extraordinary city know not only as the birthplace of House Music but also for its crowded dance floors, drag and DJ talents and attractive partygoers. The exception to this late-night parties is during warm weather months when heads out to the incredibly popular summer music festivals dedicated to electronic acts and DJs or sun-drenched rooftop bars. Sunday boozy brunches are also popular year-round.

With a vibrant – and diverse – local LGBT community and a wonderfully gay-friendly liberal populace, you can imagine distinguishing ‘gay bars’ can something difficult, which is fabulous since you know you will be welcomed as you are basically everywhere here. For the following gay venues, however, we were looking for rainbow events, exceptional recommendations, and spots specifically marketed towards gays. If you ‘accidentally’ lose your t-shirt during the wild party, don’t worry about being denied service.

This is Boystown after all, not 7-Eleven. And we are sure you will not be disappointed…

Gay Bars and Gay Clubs in Brussels

 

 

Boystown Gay Clubs & Bars in Chicago

  • Progress Bar – A hip nightclub with craft beer, fabulous DJs, upscale vibes and beautiful bartenders. Join your queer family for designer cocktails and late night dancing under the feature overhead sculpture installation consisting of 19,000 glimmering light bulbs.
  • SideTrack – Where Gay Chicago comes to celebrate with a unique mix of music video programming, multiple bar spaces, and their world-famous frozen cocktails. Weather-permitting, don’t forget to head up to their rooftop deck open year-round – part of the reason SideTrack is considered one of the best gay nightlife spots not only in Chicago but in the entire country. Having grown over the years SideTrack is now a fabulous collection of spaces spanning more than 8 storefronts and multiple levels that can host over 1000 party animals on any given night. Frequently shirtless and always friendly, the diverse LGBT crowd flocks here for their show tunes nights, drag divas, affordable drinks and a guaranteed good time. Not to be missed!

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  • The Lucky Horseshoe Lounge – Offering the hottest male dancers in Chicago 7 days a week, 365 days a year since 1989. Gay male strip clubs are quite the rarity – except in New York and Fort Lauderdale from our experience – so you know the Lucky Horseshoe Lounge has to be doing something right to be this enduring. Obviously, each experience here is very much dictated by the dancers you interact with – but the atmosphere is comfortable, if a little sleazy (this is gay strip club after all), and the bartenders are friendly. Naturally, bring your bills to tip if you want to get any attention.
  • Scarlet Bar – Drink, dance and laugh the night away with DJs and wonderful drink specials at this vintage-inspired gay bar. High octane drinks make Scarlet both a popular pre-drinking bar while also bring the boys back for the late-night lounge vibe. There is also a daily happy hour of $1 well drinks, and a boozy Sunday brunch.

Scarlet Bar Chicago

 
  • NorthEnd – Chicago’s neighborhood bar gay sports bar since 1983! Offering cold drinks, a great beer selection, pool, darts, skeeball, and all the games on TV. Low-key and always a tempting proposition for cheap drinks, flowing conversation and maybe the occasional karaoke.
  • Charlies – Once a more  ‘traditional’ gay club frequented by cowboys and supporting tequila over drugs, courting before sex and strange belt buckles, today  “dance” music, line dancing and drag shows have replaced much of the previous generations couples dancing, but the crowds keep flowing in.  We loved the occasional country music throw-backs, bingo nights, late-night hours and cheap drinks. Charlies also has locations in Las Vegas, Denver, and Pheonix.

Charlies Chicago Gay Cowboy Club

  • Little Jim’s Tavern – An unassuming classic gay dive bar serving basic food and bar food.  Always have a fun time with a jukebox and hilarious bartenders (whose jokes get funnier the more of their strong drinks you consume). Famed as the first gay bar in Chicago to open back in 1975.
  • Hydrate – One of Chicago’s premiere spots for drag shows, music, dancing, and late-night parties. A powerful sound and light experience combined with talented DJs playing to an energetic crowd who come to dance the night away in pure euphoria. To start the night why not head down to the weekend Beauties & Beaus show combining Chicago’s hottest male dancers with its best female impersonators, or why not make Sunday Funday extra fun with a post-brunch party featuring go-go dancers starting at 2 pm. Never, ever boring – and open nightly till 4 am and 5 am on Saturdays.

Hydrate Gay Nightclub Chicago

 
  • Berlin – Chicago’s critically acclaimed, pan-cultural, late nite dance club. Featuring an eclectic mix of alternative electronic music, video, and themed events, this LGBT hotspot is the perfect meeting space for the all-orientations crowd to come together on a crowded dance floor and party the night away. Hip and on the queer cutting-edge of nightlife, Berlin is for serious party lovers who are sick of the cliqued gay scene and want to be sweat-drenched and in pure ecstasy dancing to heavy 80s synth, house music, disco, and new wave. Sorry guys, no Gaga or Katy Perry here….

Berlin Nightclub Gay Chicago

  • The Closet – A staple video bar in the Boystown community, The Closet has been a second home to many since it opened in 1978.  A chilled place to kick back with friends or meet new people, the team here is very down-to-earth, welcoming everyone in for dancing, games & karaoke later at night, or drag shows on occasion.
  • Kit Kat Lounge & Supper Club – The place to go for drag-queen divas who perform nightly at this upscale venue. With an innovative martini and cocktail list of more than 200 offerings, contemporary cuisine, entertainment by the world famous Kit Kat Divas and sleek “Miami South Beach meets Hollywood” inspired decor, Kit Kat is truly a world-class entertainment hotspot. Shows run every 20 minutes starting at 6.30pm through midnight, or 1 am on weekends, and they also offer a Divalicious Brunch Sunday if you feel like whipping that hangover band-aid right off.

Kit Kat Lounge & Supper Club Chicago

 
  • Wangs – A LGBT-popular Far East-inspired cocktail lounge seeking to seduce your senses each night of the week. Take refuge in their intimate setting and low-lightening before giving in to the temptation of the specialty cocktails and savory treats on offer, all lovingly crafted to send you to another world. The Ginseng Margarita (tequila, Panax ginseng, ginger, lime, salt) is the perfect combination of Shanghai-meets-Mexico City and the Jameson Ginger made us want to book the next flight to Dublin. Sample the world from the comfort of Middle America …
  • Splash – A modern gay bar in the heart of Boystown with strong drinks and beautiful décor. We loved the friendly-but-cool vibes and commitment to the environment by only with paper straws and no plastic water bottles. Who says gay nightlife can’t be eco-friendly.  Whether it is on the dance floor, at the bar, or in one of the chich lounges, we are confident Splash will have a space for you…

Splash Gay Chicago

  • Cell Block – A notorious bear/ leather bar with billiards, darts and drink specials. The atmosphere ranges from quiet to extremely raucous, depending on the day and time you visit Cell Block has a cash-only policy which can be a bit annoying, but the locals here don’t seem to mind and all know the drill.
  • Bobby Love’s – An quieter gay bar in Boystown popular with older guys, who have been there, done that and now just prefer quiet conversations and classic hits from the jukebox. Nothing trendy here, and that is just the way the locals like it.
  • Wood – A magnificently pretentious gay restaurant that we didn’t know we need – but absolutely are obsessed with. Stylish surroundings, craft cocktails, a dynamic New American menu, and a walk-up frites window. What better way could there be to start your night out in Gay Chicago? Even better, the staff are an exceedingly rare combination of hot, competent and sassy.

Wood Gay Restaurant Chicago

 
  • Roscoe’s Tavern – A cute and popular gay bar drawing in the local LGBT crowd for over 30 years with a fun dance floor, friendly service, a sociable long bar, and fun outdoor seating. Check out their extensive list of upcoming events that include world-class drag talent, karaoke and more.
  • Fantasy Night Club – One of the biggest gay nightclubs in Boystown, but very hit-or-miss. It was a bit overpriced and more urban gritty than glitter, fabulousness but that seemed to work for the large crowd. Apparently, it has recently undergone a change in ownership and we are promised better sound, lights, bartenders and go-go dancers, so maybe give it a try?

Fantasy Nightclub Chicago

Other Gay Clubs & Bars in Chicago

  • Second Story Bar – An old-school cash-only dive bar tucked up on the second floor of a walk-up building on Ohio Street, above the Sayat Nova restaurant. Popular with guys from late 20s to 40ish mostly, if you are in the area you can try it out. A bit of a hidden gem, but you will either hate-or-love it.
  • Replay –  Bringing craft beer, bourbon, and vintage arcade games under one roof for the fun-loving community of Chicago to enjoy – gay, straight or unicorn. Replay boasts 26 draft beers that rotate out weekly, along with 26 bottled and canned beers. If you are a bourbon, whiskey, or scotch lover than give one of their 50+ different varieties a try before trying any of the 18 vintage arcade games here. A popular concept, with three locations: Lakeview / Boystown, Andersonville, and Lincoln Park.

Replay Gay Bar Chicago

 
  • Phoenix Bar and Nightclub – A joyful LGBT nightclub out in the Chicago suburbs (Elk Grove Village) with a pumping large dance floor, fun drag shows, outdoor patio, and largely Latino crowd.
  • Manhandler Saloon  – A dark dungeonesque gay bar with – quite frankly – questionable service and little appeal unless you are after cruising with leather and bears.
  • Meeting House Tavern –  A unique gathering place in Andersonville providing multiple types of interactive and passive entertainment along with a rotating selection of reasonably priced cocktails, beers, and frozen drinks, nightly drink specials and specially-themed nights. The Meeting House Tavern strives to create a safe and welcoming space with a focus on community, guest service, and value – and we absolutely loved it!  Go for their fun Drag-In Movie nights, social Sundays or Wednesday game nights, all of which are sure to help you expand your social group quickly.

Meeting House Tavern Chicago

  • Davenport’s Piano Bar and Cabaret – Fine performances, excellent drinks, singing wait staff – what more could you want! Always intimate vibes with frequent sing-alongs, open mike or karaoke nights. Welcoming, creative debauchery.
  • Fabitat –  A bi-weekly all-inclusive LGBTQ extravaganza featuring live music, drag performances and DJ sets every 2nd and 4th Wednesday of the month at Beauty Bar in West Town.
  • Burly – A (mostly) chill monthly DJ night for queers, misfits and everyone in between. Third Wednesday of every month at the Burlington in Logan Square.
  • Mary’s Attic – Located above Mary’s Dining Room, Mary’s Attic plays host to a variety of weekly and special events including their famous MaryOke-karaoke, Sunday Teaparty dance, theatre & cabaret performances, musical acts and weekend DJ dance parties. Come on upstairs to experience what all the fuss is about!
  • Elixir Cocktails – A laid-back cocktail lounge with creative drinks and innovative ingredients. Very gay-popular with locations in the two gay neighborhoods of Chicago: Boystown and Andersonville.

Elixir Cocktails Chicago

 
  • Big Chicks – A hospitable and inclusive LGBTQ-focused watering hole in Up Town. Supporting LGBT sports teams and welcoming everyone across the rainbow community (and allies) this colorful bar is cash-only with basic eats and weekend DJs. This nightspot has been an institution in Chicago’s LGBTQ and Uptown communities for decades and has been inducted in the Chicago LGBT Hall of Fame.
  • The Jackhammer – The most popular LGBT destination in North Chicago.   Comprising three distinct bar spaces offering dance, sports and fetish, and an outdoor patio. There is also an attached adult shop (Leather 6410). The Jackhammer Complex draws a diverse cross-section of Chicagoans and visitors. Nightly events may include: drag shows, karaoke, live musical performances, go-go dancers. international fetish events, headline DJ’s or the infamous monthly underwear party & contest.
  • Touche – A infamous gay cruise bar in Chicago catering to the leather crowd since 1977. Draft brews, darts, affordable prices and lots of kinky events to draw in like-minded crowds. Everyone is welcome and this back bar, well, let’s just say … it is busy and fun. Part of the Jackhammer complex.

The Chicago Jackhammer Gay Cruise Bar

Cruising, Gay Saunas & Bath Houses in Chicago

Even though Chicago is a wildly popular gay vacation destination there is now only one gay bathhouse in Chicago. Don’t be confused by outdated information online or ‘mainstream’ sauna’s as some readers have reported.

If your visiting from outside of the USA you should know that the gay sauna culture is not very prevalent in the USA and in no way as popular or as high-quality as you might find in international destinations such as London, Rome, Taipei, Seoul or Tokyo. Still, we never said there was no naughty fun to be had in Gay Chicago…

With an active and diverse local LGBT+ population, you just know there has to be pretty of action going down here – and you can join in by either downloading a gay hook up app, going to the only Chicago gay bathhouse or checking out one of the sexy gay cruise clubs and bars we covered earlier.

 

Gay sauna or not, in any sexual encounter, please take adequate precautions. No matter what your intentions are in while traveling, you should bring your own condoms and lube to play it safe. Take home a hot guy or a hot memory, not an STD.

Besides, you never know what other fun surprises your trip might have in store for you...

 

  • Steamworks Chicago – A private men’s bathhouse for men 18 years and older. You know, men looking to hook up with other men, discreetly! Open 24/7 every day of the year, Steamworks is the only gay bathhouse in Chicago but thankfully it’s pretty great. If it’s your first gay sauna experience, don’t be shy: you are in good hands.  There are sex public play areas spread across three floors including the infamous “Windy City Blowholes”  6 sided glory hole booths, multiple TVs and private booth play areas, suck ramps, a public sling, and a voyeuristic viewing area. There is also a huge full gym with state-of-the-art equipment, wet area with a multi-man whirlpool, showers eucalyptus steam room and two separate dry saunas.  Live DJ’s frequent spin out their signature mix of sexy masculine grooves, there is private rooms, lockers and a variety of beverage machines on each floor to recharge you during your stay. Fun, casual, steamy fun, Steamworks Chicago really knows there customers and exactly what they need right in the heart of the Boystown neighborhood – and it’s a concept that works since they also have locations in Toronto, Berkeley, Seattle, and Vancouver. See their events page for upcoming events featuring bears, kink, lights out and student nights.

Steamworks Chicago

 

Gay Chicago Map

   

   

Further Things To Consider Before Any Gay Trip

   

 

Now you're all set and prepared to explore our big queer world, why not sort out everything else out all in one go? If necessary for your travel plans make sure you have brought proper travel insurance, protected your privacy by getting a secure VPN, compared all the top hotel booking sites to find just what you're after, reserved an unbeatable rental car price and - of course - booked the best flight deals!

 

Or maybe just forget it all and go for a last minute cruise or effortless tour instead?

 

Many gay travelers (including us) indulge in worldwide airport lounge access and pre-arrange airport transfers to take the stress out of travel. Naturally, we would never leave home without a more mainstream travel guide since we couldn’t possibly cover everything here!

Just add an adventurous attitude and plenty of smiles - they go a long way - and that about covers it all! Now go out, find your global rainbow family and don't forget to share your best gay stories with us on Facebook, Twitter, and Instagram...We'd love to hear from you!

 

   

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