Queer travel expert Jack Kenworthy turns 250+ city adventures into your guide for safe, vibrant, and inclusively fabulous global journeys.
Before discussing the gay hotels of Chicago and where to find them, let’s learn about Chicago. The most populous city out of all of Illinois and built upon the shores of the Great Lake Lake Michigan, Chicago is famous for many things – not just hot dogs, deep dish pizza, and Al Capone.
The University of Chicago was the site of the first-ever human-performed nuclear reaction; the city is known for having some of the first ‘modern’ skyscrapers ever built and being a massive hub of culture and progress.
But how does all of that reflect on queer travelers and, by extension, on this list? Are there gay hotels in Chicago that make things comfortable and safe for members of the LGBTQ community? It has long been said that Chicago has a way of making all new arrivals feel welcome, and that sentiment is certainly extended to queer travelers dropping in for a visit or coming to stay.
Illinois was the first state of the USA to decriminalize homosexuality in 1961, and the gay culture of Chicago specifically is one of the most fruitful and vibrant in the country to this day.
The city is the home of the famous Boystown district, one of the most prominent ‘queer neighborhoods’ in the eastern half of the US.
There’s more than enough to do there, even if you’re not the bar and club type, as the area is rich with interesting stores, vintage-style cafes, and top-notch restaurants that will surely be the start of your stay. There’s a lot to explore in Chicago and a whole new world to dive into and familiarize yourself with.
Safety and staying on the right side of local cultural and political tension is always important while out and about, and unfortunately, even more so as a queer traveler.
So, if you’re gay and looking for a place to stay while you’re checking out the sights and maybe – just maybe – looking for some romance on the side, you’re going to want to find a place where you can rest and stay in peace, right? You may even want to check in with your partner because we all know that a view is more fun when you have someone to share it with.
Obviously, in most cases, there aren’t going to be many gay hotels in Chicago out there marketed exclusively toward gay people or queer people in general. We know that, and therefore we’d like to note that the hotels on this list follow the same logic. Most of them have been listed as accommodating, friendly, and unjudgmental to, for, and by queer people in general, as well as being highly rated in general.
With that said, and with your tickets or car keys packed for the journey, let’s break open some catalogs together, scan through some online reviews and star ratings, and find out what the top ten hotels for queer guests in Chicago truly are! Your best holiday of all time awaits!
In this article we will cover...
Aloft Chicago Downtown River North
The Aloft Chicago Downtown River North is a perfect start to this list – even though it is just a little further away from Chicago’s queer culture center, Boystown – aka Northalstead – than most other locations here.
It is certainly one of the most modern and well-maintained gay hotels on this list, with splendid rooms and every possible comfort accounted for, which gives it a massive leg up on competitors with an equivalent price range.
You won’t have to worry about feeling seedy, unclean, or creeped out when staying here. The Aloft’s cleanliness and soundness are rated very highly, as is how much privacy guests are offered.
Booking one of its hotel rooms is like having an isolated, safe point of relaxation to retreat to after a wild night of being out on the town or a long day under the sun seeing the sights of the city and enjoying yourself.
As is true for many of Chicago’s best establishments, Aloft’s management and staff are very vocal in support of queer guests and have a seriously impressive quality of service in general. The food and amenities are wonderful – the bar, gym, etc. – are well stocked and top-notch regarding quality, comfort, and availability.
As we said at the beginning of this entry, the Aloft’s slight distance from Boystown is a factor to take into consideration – depending on what your plans in the city are exactly – but the neighborhood can be reached very easily by using both public and private transport, and this fact sets up the Aloft as a uniquely varied gateway to other areas of Chicago that hotels confined in Boystown might hide out of sight. The Aloft is a definite safe place and a joy to stay at!
Best Western Plus Hawthorne Terrace
The best value for money out of all the wonderful and varied hotels on this list, the Best Western Plus Hawthorne Terrace is for those guests who want to make every cent count but don’t want to compromise upon comfort and safety to do so.
Rated wonderfully high for its sound quality of service and treatment of customers, this Best Western answers the call and meets the requirements for most travelers without a doubt, and staying it is sure to take away all of your worries and replace them with a smooth, calm accommodation experience.
Nestled right in the center of Boystown and possessing one of the best access points that any hotel in the area has to offer, the Best Western Plus Hawthorne Terrace is more than fit to be your base of operations for as long as you need it – providing a perfect place to rest and rejuvenate between excursions throughout the local setting and even explorations out into the wider scope of the city as a whole.
Even though we place so much emphasis on how affordable staying there is, and how true that fact is in real life when it comes to comparison with the other gay-friendly hotels of the same quality around it and in other suburbs of the city, the Best Western Plus Hawthorne Terrace is ranked as the sixteenth best hotel in the entirety of Chicago and maintains a sterling reputation with its extensive amount of positive reviews and crowds of satisfied customers.
This shows that even today, something cheap doesn’t always mean it is bad. Best Western Plus Hawthorne Terrace is an easy recommendation and will leave a positive impression no matter what you visit the city for or hope to see.
The Hotel Zachary
The first gay hotel on this list to turn up the luxury dial, the Hotel Zachary oozes style and competence, and this attitude is mirrored excellently by the staff there. There’s easy access to stunning food, lounges, a bar, and a gym, and that’s just the hotel’s public location.
Close enough to Boystown that getting into the thick of things isn’t a problem whatsoever, the Hotel Zachary takes pride in the massive array of notable locations to which it is within walking distance.
Just like the Majestic Hotel later in this list, the Hotel Zachary backs up onto the famous Wrigley Field, has a train station right at its doorstep to allow easy access to the entire rest of the city, and has a phenomenal cluster of nearby restaurants and food joints to choose from.
So much food that it is almost as though the neighborhood was designed for foodies. Time to loosen the belts and have a great night eating out on the town!
The Hotel Zachary is a little on the pricey side at some times of the year – though not always, honestly, it has its times of being extremely affordable – but when one sees and experiences the quality of its spaces and the attention to detail given in cleaning, service, and accommodation, it’s easy to see why this is justified.
The hotel impresses from the moment one walks in the doors to the moment one leaves, and the staff keeps up this amazing impression with the quality of their service. The Hotel Zachary is hip, in the middle of the action, and ready to accommodate you and any of your needs. It’s amazing, and the house menu is splendid if you’d rather try out the hotel’s food.
The Willows Hotel
We’ve discussed the importance of balancing value with a safe environment, which this hotel excels at. The Willows Hotel is well known for packing as much value as it possibly can into the stay of each guest, and if that doesn’t sound like the business practices of a hotel that is a joy to stay at, you must be looking more for luxury than you are for peace of mind and comfort.
The hotel’s appearance is an absolute highlight, leaving no one disappointed with the immaculate condition of every public and private space and the sharp styling choices taking the place of pride in every room. The theme is semi-Victorian, with tastes of antique style mingled with the taste of the 21st century.
Despite their agedly exquisite nature, the Willows’ amenities, look, and spaces are amazingly modern, and you won’t be made to feel stuffy by that old charm for a second.
In the same way, the staff of the Willows Hotel is skilled, courteous, and accommodating, meaning that you can go about your day and enjoy your stay without having to worry about being let down or having to worry about the hotel’s employees. Everything is provided for, and only spending a wonderful holiday remains.
The Willows is another gay-friendly hotel that touches right onto the best areas of the so-called Boystown and thus affords direct access to the establishments, bars, clubs, and restaurants around it.
It is a good step closer to the sea, meaning visitors can enjoy both aspects of their surroundings without moving very far. Convenience is always a plus, and it’s even better when that convenience allows you to have variety and ease!
Hotel Majestic
The Hotel Majestic certainly lives up to its name – boasting wonderful reviews, an open, inviting attitude, and a modern interior that will make even the most accommodation-experienced eyebrows raise in appreciation. It’s stylish and fancy with its revamped 20’s smoking room design, and it’s not all that unaffordable for the quality of service it offers.
There’s nothing that the Majestic fails to offer its guests, and its perks are too many to count. Staying there is an amazing experience and is sure to leave guests planning to come back again and again over future holidays in the city.
This one’s a little further away from Boystown than many of the other establishments on this list, but as we mentioned earlier with the Aloft, that isn’t necessarily a bad thing, and saying that it’s ‘far’ from where all the action is would be a little bit unfair.
The Majestic is situated even closer to the sea than the Willows Hotel before it, which perfectly balances aesthetic views and practicality. Not only that, but the hotel is near the famous Wrigley Field, the home of the Chicago Cubs, and a great place to visit for those more sport-inclined visitors.
The Majestic’s balance in location is unbeatable and is the cherry on top of a very solid, excellently performing place to stay. The staff has an amazing customer satisfaction record, and many reviews tell about how far above and beyond they will go to make the guests’ stay wonderful.
It’s also listed as a perfect couples’ spot, which is also something to consider when planning a trip with you and your loved one. Sunsets, sea views, and much more await!
LondonHouse Chicago, Curio Collection by Hilton
Both this hotel and the one that comes after it – the Langham – are the two gay hotels on this list that are the furthest away from Boystown in general, but that isn’t to say that their location doesn’t open up new horizons. The LondonHouse is stylish and luxurious above all, which are qualities it takes into every aspect of its property.
Administrated by Hilton Hotels, as this particular establishment’s rather mouthy title might imply, the LondonHouse takes every inch of that chain’s prestige and quality to heart, and its staff is very much of the same mind. Everything in the building exists to make your stay more fulfilling and better, and the reviews reflect how amazing of an experience it is.
After reading all of this, you probably think that the price tag that the LondonHouse comes with is sky high, but you’d be surprised to learn that it’s quite affordable, although a little heavier than the prices of the other hotels on this list – except the Langham, which comes up next on the list.
The LondonHouse is the perfect balance for those who are looking for a fancy location that goes above and beyond but doesn’t require one to be feeling like a splurging superstar to stay there, and you can be sure that the service that you will receive – as well as the consideration and friendly atmosphere – will be like a fresh drink of water after navigating and traveling through the city outside its doors.
The views are incredible, the food is next level, and everything from the rooms to the lobby is beyond exquisite. The building even has a rooftop pool with views of the sea – a perfect spot for relaxing and unwinding after a day on the town.
The Langham Chicago
If you thought that the LondonHouse was impressive – which, don’t get us wrong, it is – then you are in for the pleasant surprise of your life when you walk through the doors of the Langham Chicago. Listed as five-star luxury premises and offering the best of the best, the Langham redefines indulgence in every way possible and takes ‘going the extra mile’ as a baseline rather than the occasional effort.
With all that said, however, it remains to be noted that the Langham is expensive. Very much so, in fact. Therefore, staying there is something that only the most dedicated tourists will want to do or that only those looking for the greatest gestures should be considering now.
There is no way to spend money more worthwhile than making wonderful, memorable moments, however, so don’t let the price tag scare you away! The Langham is truly worth it, and you will be left wondering how you can imagine staying elsewhere again afterward.
As we said in the previous entry for the LondonHouse, The Langham is just a little bit further from Boystown than the rest of the hotels on this list, but this fact opens up a lot of other opportunities on an entirely different but equally different side of town that is equally worth exploring.
There’s a wide spread of incredible food to eat, the city’s business center is just a walk away, and much more on offer. Staying at Langham is not for those more interested in seeing the city than enjoying some time relaxing and unwinding, but if you’re looking for a taste of the high life and looking to be pampered to the very extreme, it’s a no-brainer.
Villa Toscana
If you’re looking to escape from the chaos and the overwhelming color of the city for a little while to recover without having to travel to and fro from the very center of where you’re trying to explore during your visit, this is the place for you.
While it’s anything but glorious and commercialized, the queer-owned Villa Toscana finds a place on this list due to the sheer strength of the positive experiences that staying there offers, coupled with the grassroots feel that the place has.
Nestled directly in the center of Boystown and with a great, holistic connection to the land and properties around it, Villa Toscana is a bubble of relaxation that feels much more like a homey small-town business than a thriving enterprise in Chicago’s brightest, gayest neighborhood.
This extremely gay-friendly hotel is styled as a Bed and Breakfast (also known as a B&B), meaning that a hands-on accommodation style and a quiet lifestyle are integral to what makes it unique.
Not only does Villa Toscana have impeccable service and a well-rounded system of operations, but it is incredibly good value for the price tag per night, making the already sweet experience of spending a few nights there even better than it already was.
What is better than knowing that your money was well spent and that you’re safe to enjoy the sights and maybe spend a little bit extra on more exotic things without having to worry about expenses all that much?
So – if you’re looking for accommodation and are more interested in getting closer to your heart than it is to the wallet, Villa Toscana is the place for you. After all, what’s the point of choosing to stay somewhere if it doesn’t have something unique to offer in return?
Gay Hotel Map Of Chicago
Feeling a bit lost while planning your journey to Chicago? No worries, darling! Our detailed LGBTQ+ tailored map is here to guide you. We’ve pinpointed all the vibrant gay-friendly bars, exhilarating clubs, extravagant parties, cozy hotels, relaxing saunas, and soothing massage parlors to ensure you find the perfect spot.
And these aren’t just any spots; we’re talking about the creme de la creme of locations in the heart of the city’s vibrant gay scene. Think panoramic views, easy access to nightlife, and all the amenities to make your stay as comfortable and enjoyable as possible.
But hold on to your feather boas! These hot spots are so fabulous they vanish quicker than a drag queen’s five o’clock shadow. Don’t delay; book now to secure the best deals and locations. Remember, the early bird catches the best deals in Chicago! So, pack your rainbow flag, and get ready to experience the ultimate gay-friendly holiday in Chicago.
