America’s ‘Windy City’ may not be high on the travel itinerary of many from the LGBT+ community given its ‘low key’ gay image, but you’ll be surprised with all that Chicago has to offer. While there are no exclusive options as such, there is no dearth of gay hotels in Chicago. Most people zero in on the gayborhood Boystown, which we also love for its numerous hotel options. What’s more, its proximity to downtown gives us a wider range of hotel options to present to you. Much like its namesake Boyz Town in Pattaya, Chicago’s gayborhood has a large number of venues that declare themselves ‘straight-friendly.’ It’s a clear indication of the sheer number of LGBTQ people here.
Another gay neighborhood with a large rainbow population that we love is the ethnic Andersonville. It’s famous for its Swedish heritage. You’ll find a large collection of hip shops and restaurants in this area. Nevertheless, we chose hotels in and near both these neighborhoods based on a variety of factors. Besides budget, we also looked at their amenities, right from food to common spaces. We also took into account the kind and choices of rooms they have and their proximity to downtown Chicago. Finally, we also looked at the category of the hotels.
If you can tear yourself away from the gayborhoods, there is a lot to explore in the city, especially in downtown Chicago. We loved exploring the top sights in this amazing Guided Tour with Skydeck and Shoreline River Cruise. It offers spectacular views from the 103rd floor of the Willis Tower, and the cruise is a great way to see Chicago from the water.
Table of contents
Virgin Hotels Chicago
11
We’ve always dreamt about shopping in the retail paradise that is Chicago’s Magnificent Mile. If you have dreamt of it too, then the Virgin Hotel Chicago in downtown Chicago is the perfect base. That’s because it’s less than a five-minute drive from all the shopping you can do on Michigan Avenue’s Magnificent Mile. This is the Virgin group’s second hotel after the first one opened in San Franciso, and it is a complete package offering everything you’ll ever need for a perfect getaway. With five onsite restaurants, a rooftop bar, a nightclub, and spacious, comfortable rooms, it’s no wonder that this is one of the more popular gay-friendly hotels in Chicago.
Lifestyle-focused rooms
We love the lifestyle-focused rooms at this hotel, which are split into two by sliding doors to create two separate areas for work and play. So, it gives us more room to spread out. A dressing area featuring a closet and a well-lit make-up desk adds a special touch to the room. Adding to the indulgence is the luxurious walk-in shower. The one-of-a-kind custom-designed hybrid bed even has an adjustable footboard. It’s perfect for propping our tired legs up after all that walking during shopping and sightseeing. All rooms have free Wi-fi and a minibar stocked at street prices. For a more customized package, the hotel recommends joining its ‘The Know’ program.
Amenities
The outdoor rooftop bar and nightclub are the highlights here, offering sweeping views of the iconic Windy City skyline. Dig into small plates and sip on craft cocktails at the Commons Club, or enjoy late-night wine or coffee at the premium wine/coffee bar. Borrow a book from the hotel library and read on the cozy sofas by the fire in the Trophy Room.
It’s no surprise then that this is one of the best luxury hotels in Chicago, IL.
At a glance
- Location: Downtown Chicago
- Proximity to Boystown: 5mi (8km), 20 minutes drive
- Proximity to Navy Pier: 1.3mi (2km), 5 minutes drive
- Category: 4-star hotel
Check Rates on:
Viceroy Chicago
10
When we were looking to splurge on up-market gay hotels in Chicago, the Viceroy Chicago caught our attention. Its prime location in the city’s exclusive Gold Coast neighborhood, surrounded by historic mansions, makes it a great choice. It’s a short walk to the Magnificent Mile and other nightlife destinations from here. So, it’s a great base for shoppers who love to hit designer stores.
Rooms
The stylish and modern guest rooms are tastefully furnished and equipped with various amenities. These include flatscreen cable TV, free Wi-Fi, and even plush lounge seating. If that wasn’t enough, the rooms also have coffee machines and fully-stocked minibars. So, we were able to unwind right in the comfort of our rooms at the end of a long day, whether we wanted coffee or something from the bar.
Amenities
We recommend this reimagined hotel for history and architecture lovers like us. It’s built at the site of the former 1920s-era Cedar Hotel and exudes class and charm. It features a sleek two-story restaurant and bar, a rooftop lounge, and a seasonal pool on the 18th floor. Since we had a hankering for modern Midwest fare, we tried out the amazing Somerset restaurant. And what better to top off a delicious meal than craft cocktails, which are served at the rooftop bar and lounge? When we didn’t want to get out of bed, the hotel’s in-room dining services came to our rescue. Apart from all this, the hotel also has a state-of-the-art fitness center where you can work out on vacation.
At a glance
- Location: Gold Coast
- Proximity to Boystown: 4mi (6.5km), 10 minutes drive
- Proximity to Navy Pier: 1.5mi (2.4km), 5 minutes drive
- Category: 5-star hotel
Check Rates on:
The Chicago Hotel Collection Wrigleyville
9
Even though we’re not huge baseball fans, we love the design aesthetic of Wriggleville’s first luxury boutique hotel, The Chicago Hotel Collection Wrigleyville. The hotel’s lobby, with its whimsical floating baseball bat installation, surely jazzes up the ‘Gram! This hotel brings unpretentious luxury to the spirited neighborhood. Since it’s right in Boystown, it’s one of the sought-after gay-friendly hotels in Chicago. We also chose this hotel due to its proximity to the Addison Red Line L, a five-minute walk from the hotel. Hence, Chicago Downtown is a mere 20-minute ride.
Rooms with floor-to-ceiling windows
There are six different types of rooms to choose from at the 21-room hotel. Playfully sophisticated rooms complemented by illuminating accents add a touch of intimacy and class. The bright, spacious rooms are enhanced by floor-to-ceiling windows which allow ample natural light to stream in. They also come with flatscreen TVs and modern bathrooms.
Amenities
Since the hotel boasts free Wi-Fi everywhere, it’s easy to stay connected while exploring Windy City. What’s more, there’s even a shared lounge and a terrace for some much-needed unwinding. Even though the hotel doesn’t have a restaurant or serve breakfast, it allows food delivery from restaurants nearby.
At a glance
- Location: Northalsted/Boystown
- Proximity to Boystown: N/A
- Proximity to Navy Pier: 5.8mi (9.3km), 20 minutes drive
- Category: 3.5-star hotel
Check Rates on:
Moxy Chicago Downtown
8
When looking for luxury at an affordable price, the Moxy Chicago Downtown is a great choice. This Category 4 Marriott property sits at the heart of Chicago’s River North neighborhood. So, the Boystown nightlife is close by, as are the top things to do in Chicago, including the iconic Navy Pier.
Rooms
Moxy focuses on travelers who are constantly on the go, so their rooms are designed accordingly. Some rooms may be a little on the smaller side, but the beds are comfortable and freshly made. What’s more, they come with smart, flatscreen TVs, so we could enjoy some time indoors when we were tired. The hotel offers certain units with city views, so travelers need to look out for them or enquire during the time of the booking.
Art-focused amenities
Moxy hotels are renowned for their bold decor, and the one in Chicago is no different. There are many pictures of beautiful people adorning many walls here. Privacy shades feature hedonistic room scenes, while the inner courtyard has a rather provocative art installation. Moreover, the hotel is surrounded by some of the best watering holes in town, with one great Tex-Mex restaurant in the lobby.
At a glance
- Location: Downtown Chicago
- Proximity to Boystown: 4.2mi (6.7km), 15 minutes drive
- Proximity to Navy Pier: 1.2mi (1.9km), 5 minutes drive
- Category: 3.5-star hotel
Check Rates on:
Majestic Hotel
7
Just because a hotel is value-for-money doesn’t mean that it has to be boring. That’s why we had to include the recently renovated Majestic Hotel, which is one of Chicago’s best gay hotels. Styled on the lines of an English estate, this boutique hotel offers comfort with a touch of class. The hotel is within walking distance from the lively Wrigleyville neighborhood and also within walking distance from Boystown. That’s why it’s one of the top gay-friendly hotels in Chicago’s Boystown neighborhood. Lincoln Park Zoo and Steppenwolf Theater are also a short distance from the hotel.
Rooms
Choose from a host of spacious rooms and suites, all of which come with deluxe bed linens and carpeted floors. What’s more, all rooms have a bunch of comfort mod-cons, such as large flatscreen TVs, free Wi-Fi to stay connected all the time, and even fully stocked minibars. The cherry on top is the luxe bathrooms with bath products and fluffy bathrobes, which we’d wrap ourselves in when we wanted to unwind.
Amenities
The public spaces in the hotel feature America’s passion for baseball. Despite not being really huge baseball fans, we enjoyed staying here to the hilt. Since it was built in the 1920s, it’s a non-smoking hotel in its entirety. Indulge in the 24-hour coffee and tea service and enjoy a cuppa in the comfortable sitting area right in front of the wood-burning fireplace.
At a glance
- Location: Northalsted/Boystown
- Proximity to Boystown: N/A
- Proximity to Navy Pier: 4.7mi (7.5km), 12 minutes drive
- Category: 3-star hotel
Check Rates on:
The Guesthouse Hotel
6
Best Andersonville hotel. Do you want to stay in the other gayborhood of Chicago, Andersonville? Check out the family-owned boutique-style Guesthouse Hotel. It started off as a condo building but turned into holiday rentals when the recession hit. Today, it’s a full-service hotel with 25 apartments, and they swear by – and follow – the “Live like a local” motto.
Rooms with extended-stay mod-cons
Choose from one/two/three-bedroom apartments, all with colorful throw pillows and rugs, soft grey walls, wooden floors, and spacious living rooms. They even have full kitchens where travelers can cook, complete with coffee pots. There’s even a kitchen island with barstools where we chatted over drinks and meals and even when we were in the middle of making them. Are you here for a long time? These apartments are primed for extended stays and come with full-size washer/dryer units.
Boutique amenities
We love talking to locals and exploring, which is another reason why we love this hotel. The front desk staff knows all the amazing spots, while the lobby has a pantry with locally made snacks and a small boutique with locally made t-shirts, jewelry, and art. Work out in the gym and unwind in the afternoon in the library. Evenings are reserved for the lovely rooftop deck, which has skyline views. Since there’s no restaurant onsite, the hotel allows delivering delicious Italian dishes, sandwiches, salads, and breakfast stuff from restaurants Calo and Southport Grocery.
At a glance
- Location: Andersonville (Chicago’s other gayborhood)
- Proximity to Boystown: 3.3mi (5.3km), 12 minutes drive
- Proximity to Navy Pier: 7.4mi (11.9km), 15 minutes drive
- Category: 4-star hotel
Check Rates on:
Kimpton Gray Hotel Chicago
5
Best LGBT chain hotel. The grand 1894 building which houses the Kimpton Gray Hotel in the Loop’s financial corridor once housed a life insurance company. Kimpton is one of the most inclusive hotel chains for the LGBT community. Hence, it’s no surprise that Kimpton Gray Hotel is one of the more popular gay hotels in Chicago. Originally designed by the ‘father of the skyscraper,’ William Le Baron Jenney, the hotel retains its old-world charm. Shiny gray marble dominates the interior, giving the hotel its name. There are also other interesting touches, like the vintage elevators with neon signs.
Swish, modern rooms
The subdued palette used in the rooms evokes images of well-designed, bespoke living spaces. Powder blue drapes add a pop of brightness to the textured gray walls of the modern yet minimalist rooms. The furniture is modern and minimalist, yet comfy. A thoughtful addition is the many power outlets on the nightstand, so we could charge multiple devices such as our phone, camera battery, iPod, Kindle, and much more. On the inside of the closets, a surprise awaited us in the form of colorful paintings. Even the fun minibar is all about surprises, including a full bottle of cabernet sauvignon and a men’s necktie!
Hip amenities
When the hunger pangs come calling, the rooftop restaurant that serves Argentinian food also has a very hip vibe. It’s also where the hotel serves a delicious breakfast. When we wanted a nightcap, we headed to the Vol. 39 lobby bar, whose wall-sized bookshelves and tufted leather sofas radiate dark, sexy library vibes. The cocktails are absolutely top-shelf, so if you’re looking to impress a date, get them here. And as is with all Kimpton hotels, this one also has a complimentary wine reception in the evening.
At a glance
- Location: Downtown Chicago
- Proximity to Boystown: 7.3mi (11.7km), 20 minutes drive
- Proximity to Navy Pier: 1.9mi (3km), 5 minutes drive
- Category: 4-star hotel
Check Rates on:
City Suites Hotel
4
City Suites Hotel is one of the most affordable gay hotels in Chicago, right where all the action is, in lively Boystown. Travelers looking for no-frills accommodation that’s comfortable and clean will love this one. The hotel is a stone’s throw from the elevated train station right in the heart of Boystown. So, this location couldn’t be better for those who want to explore Boystown or the area outside it.
Rooms
Most of the rooms at City Suites are fairly large and equipped with amenities for a comfortable stay. Some of the units are two-room suites with double amenities, which is great for those traveling with a group. Bathrooms have shower/tub combos with complimentary toiletries. So, while it’s a budget hotel, it doesn’t skimp on even the most basic living amenities, which is a delight. What’s more, all rooms have flatscreen TVs, small fridges, and fully-stocked minibars.
Amenities and frills
Although the hotel does not have an onsite restaurant, they have excellent recommendations for places nearby where guests can enjoy breakfasts. They also offer free cookies in the afternoon as well as free passes for using the facilities of #1 Gym, which is a mere three-minute walk. The best bit? We were able to fill up on energy all day long since the hotel also has 24-hour lobby coffee and tea services.
At a glance
- Location: Northalsted/Boystown
- Proximity to Boystown: N/A
- Proximity to Navy Pier: 4.6mi (7.4km), 10 minutes drive
- Category: 3-star hotel
Check Rates on:
Best Western PLUS Hawthorne Terrace
3
A short ten-minute walk from Wrigley Field lies the historic Best Western PLUS, Hawthorne Terrace. We didn’t have to be a baseball fans to love the location, which is just a block away from Boystown. With a location this close to the gayborhood of the city, the hotel is at the top of the list of affordable LGBT-friendly hotels in Chicago. In fact, it’s been popular with the LGBTQ traveling set for quite a few years now.
Rooms
All 83 guest rooms at the hotel have modern amenities such as complimentary high-speed internet, upgraded linen, and stylish bathrooms with granite countertops. The suites have separate sitting areas, full kitchens, and great views. Besides the above, the rooms and suites also have mod-cons for an enjoyable stay, like flatscreen TVs, fridges stocked with free bottled water, coffeemakers, and microwaves.
Amenities
Our morning began with a complimentary breakfast every day, which was set up in the grab-and-go format. So, it was ideal for those days when we had to get out early and didn’t have time for a sit-down breakfast. There’s also a fitness center where we worked off those deep-dish pizza calories. A trip to the jacuzzi or the sauna is also not a bad idea while staying here.
At a glance
- Location: Northalsted/Boystown
- Proximity to Boystown: N/A
- Proximity to Navy Pier: 4.6mi (7.4km), 10 minutes drive
- Category: 3-star hotel
Check Rates on:
The Emily Hotel
2
Best boutique LGBTQ-friendly hotel. The Emily Hotel, formerly the Ace Hotel Chicago, is one of the best boutique hotels in Chicago. It sits in the West Loop neighborhood, about 15 minutes drive from Boystown. The former industrial area is now a restaurant hotspot with a number of hip restaurants and bars. Thus, younger gay travelers will certainly love the convenience of staying here. The Loop is about a 5-minute ride by train from here, while the Magnificent Mile is about 10 minutes by cab. The lovely boutique hotel boasts an artsy decor that reflects the local area. Housed in what was once a cheese-making company, the seven-story industrial building made from glass and concrete had left its past far behind to become one of the more sought-after LGBT-friendly hotels in Chicago.
Minimalistic and plush rooms with artwork
We’re fans of simplicity, and the rooms, with their black and gray palette, certainly impressed us. In fact, the palette is soothing, especially after a long day of exploring the city. Metallic bed frames make the beds look like cots, although they don’t lack comfort. Travelers have the choice between rooms of different sizes and categories. Moreover, the dark blue and black bathrooms with Rudy’s bath amenities feel plush. Plus, all rooms have fully-stocked minibars, Bluetooth radios, flatscreen TVs, and original locally-made artwork.
Trendy amenities
Younger gay travelers will love the indoor/outdoor rooftop lounge Waydown, which has stunning skyline views, with craft cocktails, bar snacks, and a DJ accompanying them. City Mouse, the onsite restaurant on the first floor, serves up delectable treats, enticing a steady stream of locals and guests. Even the paid breakfast/brunch, which has brunch burritos, pancakes, frittatas, avocado toast, smoothies, and pastries, is delicious. Finally, the hotel also has in-room dining services and a 24-hour fitness center.
At a glance
- Location: West Loop
- Proximity to Boystown: 4.3mi (6.9km), 20 minutes drive
- Proximity to Navy Pier: 2.5mi (4km), 10 minutes drive
- Category: 4-star hotel
Check Rates on:
Chicago Getaway Hostel
1
Best LGBT-friendly hostel. The Chicago Getaway Hostel combines comfort and affordability in one gorgeous gay-friendly package. The hostel is unlike any other we had seen, beginning right from where it sits. The Getaway Hostel is nestled in a brick ivy-covered structure with a welcoming, bright blue door. Arched windows, ivy-covered walls, and lots of greenery give the place a very cozy vibe.
Comfortable rooms
We had the choice of dorms with shared bathrooms or private rooms with their own bathroom. Notwithstanding what kind of room travelers book, the stay includes access to bed linens and free lockers. Plus, the hostel staff also supplies towels, pillows, and blankets for free. Staying on a budget doesn’t have to mean missing out on comfort, and we felt that at this wonderful gay-friendly Chicago hostel.
“If there’s one place where we felt like we were staying among friends, it was the Chicago Getaway Hostel. What’s even better is that the hostel is so gorgeous and well-kept, with the most amazing staff ever!”
WOW Travel
Community-focused amenities
Downstairs, there are common areas with pool tables and even guitars. There’s even a kitchen where we could whip up quick meals, but the hours are limited from 7 am to 9 pm. In fact, the day begins with a complimentary breakfast of oatmeal, fresh fruit, a cereal bar, and coffee. Boystown is a mere five-minute drive. There’s even a city bike rental station a block away. With events such as barbeques, brewery tours, and pub crawls, it’s easy to see why this place is so popular.
At a glance
- Location: Lincoln Park
- Proximity to Boystown: 1.7mi (2.7km), 5 minutes drive
- Proximity to Navy Pier: 3.8mi (9.1km), 20 minutes drive
- Category: 2-star hotel
Check Rates on:
Our Verdict!
While we love the entire list of Chicago’s LGBT-friendly hotels, some hotels are better suited for certain features than others. That’s why we’ve come up with a specially curated list of hotels below. They’re all known for their specific attributes, which are listed below:
- Best LGBT chain hotel: Kimpton Gray Hotel Chicago
- Best LGBT-friendly hostel: Chicago Getaway Hostel
- Best boutique LGBTQ-friendly hotel: The Emily Hotel
- Best Andersonville hotel: The Guesthouse Hotel
Just So You Know:
- The rainbow-ringed bronze pylons on North Halsted Street were installed in 1998 to designate Boystown as an LGBTQ hood officially. With this, Chicago became the first U.S. city to recognize a queer space formally.
- Chicago also became the first U.S. city to create a municipally funded hall of fame honoring the LGBTQ community in 1991.
- Henry Gerber, whose name’s attached to the largest queer library in the formed the first homophile organization in the United States. In 1924, he formed the Society for Human Rights.
Get Some Culture in Chicago:
- Reeling: The Chicago LGBT+ International Film Festival – Now in its 38th year, this is the second-longest-running film festival of its kind. Held over ten days in the last week of September, it showcases the best LGBTQ+ films.
- Chicago Pride: This exciting two-day street festival leads up to the Chicago Pride Parade, where thousands attend, celebrating the LGBTQ community, culture, and life. You’ll find everything from pet parades, drag shows, dancing, and DJs to drink and food, and three stages with live music by popular artists. It’s held on the corner of Addison and Halsted Street in Boystown, which has popularly come to be known as the first recognized gay village in the US. After the parade, revelers pour into pubs and clubs of Boystown, partying into the wee hours of the morning.
- Chicago 1.5-Hour Romantic Sunset Cruise: Travelers looking for a romantic getaway in Chicago will find this romantic sunset cruise is perfect. We boarded a boat at the end of the day and soak in the setting sun over the tranquil waters of Lake Michigan. There’s even a toast along with partners, with a hand-crafted cocktail, an ice-cold beer, or a glass of wine.
Best Gay Bars / Clubs in Chicago:
- Side Track – This is the most popular gay bar in Chicago is not just one unit but multiple bars spanning over eight storefronts and multiple levels. Located on N Halsted St, it’s where Gay Chicago comes to have fun.
- The Lucky Horseshoe Lounge – Since 1989, this gay strip club at 3169 N Halstead has been showcasing some of the hottest male dancers in Chicago seven days a week.
- Hydrate – Located in Boystown, this high-energy dance club attracts a huge LGBT crowd throughout the week. It features rotating DJs and regular drag shows. You can party here until the early hours of the morning.
- Nobody’s Darling: This wildly popular black-owned Andersonville queer bar is famed for its inventive and playful cocktails like the tart Darling Mule and the fuchsia-colored Pink Kitty. The inclusive approach aside, LGBTQ peeps will also love the welcoming atmosphere. Renaula Riddle, co-owner of Nobody’s Darling and revenue auditor by day, even operates LGBTQ bar pop-ups all over Chicago
Best Gay Saunas in Chicago:
- Steamworks Chicago – Like most cities in the United States, the gay sauna culture is not very popular. However, Chicago does have one private men’s bathhouse spread across three floors with plenty of space for a good time. Besides the many play areas, this sauna also has a large gym, whirlpool, steam room, and two separate dry saunas.
Gay Beaches in Chicago:
- Hollywood Beach: Hollywood Beach, whose actual name is Kathy Osterman Beach, is one of the sunniest best gay spots in Chicago. The crowd is friendly and down-to-earth, and it’s the go-to summer spot for Chicago’s queer community.