Name: Kimpton Gray Hotel
Address: 122 W Monroe St, The Loop, Chicago, IL 60603

Gay-Friendly Hotel Featured 4.5 (2075)

Kimpton Gray Hotel

The Loop

Kimpton's flagship Chicago hotel in a restored 1914 building in the Loop — gay-welcoming by design, with the brand's signature inclusive culture. A luxury base close to everything Chicago offers.

gay-friendly card-payments reservations

LGBTQ+ Friendly Aug 2026

Gay-Friendly Hotel 4.7 (206)

Villa Toscana

Northalsted (Boystown)

Victorian style bed and breakfast located in the heart of Boys town Enjoy Villa Toscana's antique-filled European charm with suites such as the Neo-Classic, Venetian, and Moroccan.

gay-friendly gay-popular wifi

LGBTQ+ Friendly Aug 2026

Gay-Friendly Hotel 4.4 (1603)

Best Western Plus Hawthorne Terrace

Northalsted (Boystown)

A Boys town secret It might look unassuming, but this Best Western is an affordable and comfortable choice for staying in the heart of Boys town.

outdoor-patio gay-friendly gay-popular

LGBTQ+ Friendly Aug 2026

Gay-Friendly Hotel 4.1 (909)

City Suites Hotel

Northalsted (Boystown)

Art Deco boutique hotel located near the shopping district. City Suites is in a great location for experiencing the Boys-town, Wrigleyville and Lake view neighbourhoods.

gay-friendly mixed-lgbtq card-payments

LGBTQ+ Friendly Aug 2026

Gay-Friendly Hotel 3.0 (2)

Leather guest house Want a little tingle with your visit? Check out Ashland's guest rooms, especially designed to bring the kink out in the comfort of your own room with swings and harnesses built in.

gay-friendly mixed-lgbtq year-round

LGBTQ+ Friendly Aug 2026

Gay-Friendly Hotel 4.2 (1003)

Majestic Hotel

Northalsted (Boystown)

Elegant Boys town boutique hotel Set up to resemble an English estate, the Majestic offers a great alternative to mainstream hotels without sacrificing any comfort.

gay-friendly gay-popular wifi

LGBTQ+ Friendly Aug 2026

Gay-Friendly Hotel 5.0 (1)

Days Inn Chicago

Northalsted (Boystown)

Less expensive alternative to down-town hotels Days Inn's budget offerings give travellers an option for lodging closer to Boys-town, Lincoln Park and Wrigleyville.

gay-friendly gay-popular wifi

LGBTQ+ Friendly Aug 2026

Gay-Friendly Hotel 4.4 (11939)

Hyatt Regency Chicago

River North

Gay-friendly mainstream hotel in the heart of the Windy City A city within a city, that links guests to blues, jazz, irresistible cuisine, Grant and Millennium Parks, Lake Michigan beaches, Navy Pier…

gay-friendly wifi air-conditioning

LGBTQ+ Friendly Aug 2026

Gay-Friendly Hotel 3.8 (115)

House 5863

Andersonville

Not your grandma's B&B This LGBT-oriented place is so hip you might forget it's a B&B. It features modern, stylish rooms and a fabulous location near gay nightlife and Hollywood Beach.

gay-friendly mixed-lgbtq beach-access

LGBTQ+ Friendly Aug 2026

Gay-Friendly Hotel 3.9 (3039)

Crowne Plaza Chicago Metro

The Loop

Mainstream down-town hotel All the amenities you would expect, and not too far from the gay centre in Boys town. The rooms are well-designed with modern styling.

gay-friendly wifi air-conditioning

LGBTQ+ Friendly Aug 2026

Gay-Friendly Hotel 3.9 (2282)

W Chicago - City Center

The Loop

Up scale Luxury for People and Pets Relax with pillow top mattresses, rainforest showers and in-room massages.

gay-friendly pet-friendly spa

LGBTQ+ Friendly Aug 2026

Gay-Friendly Hotel 4.2 (2332)

Chicago Getaway Hostel

Northalsted (Boystown)

Lincoln Park Hostel with University Feel Located just below Boys town, Lincoln Park houses the charming getaway Hostel.

gay-friendly mixed-lgbtq gay-popular

LGBTQ+ Friendly Aug 2026

Gay-Friendly Hotel 4.3 (1739)

Hard Rock Hotel Chicago

River North

Enjoy your Chicago stay, Hard Rock style Finely appointed, rock star-style rooms with fine linen and comfortable furniture provide the ideal setting for an exciting Chicago stay.

gay-friendly card-payments wifi

LGBTQ+ Friendly Aug 2026

Gay-Friendly Hotel 4.2 (3495)

Wyndham Grand Chicago Riverfront

River North

European sophistication overlooking the Chicago River Elegant and sophisticated boutique hotel rising high above the Chicago River and Wacker Drive offers access to shopping, museums and Millennium…

gay-friendly wifi air-conditioning

LGBTQ+ Friendly Aug 2026

Gay-Friendly Hotel 4.2 (7038)

Sheraton Chicago Hotel & Towers

River North

Soothing accommodations within the bustling metropolis The Sheraton Down town is in a great location to explore river-front attractions like Michigan Ave and Millennium Park.

gay-friendly card-payments wifi

LGBTQ+ Friendly Aug 2026

Gay-Friendly Hotel 4.4 (2380)

The Westin Chicago River North

River North

Beautiful River North lodging With easy access to theater, the Magnificent Mile and plenty of knock-your-socks-off Chicago eateries, the Westin is a perfect choice for a vacation you may never want…

gay-friendly wifi air-conditioning

LGBTQ+ Friendly Aug 2026

Gay-Friendly Hotel 3.9 (4014)

Millennium Knickerbocker Hotel

River North

Magnificent Mile starts here Located within walking distance to Water Tower Place, John Hancock Tower, Navy Pier and Michigan Avenue shopping, this elegant hotel will make you feel in the center of…

gay-friendly wifi air-conditioning

LGBTQ+ Friendly Aug 2026

Gay-Friendly Hotel 4.4 (2744)

Hotel Monaco Chicago

River North

This whimsical, upscale hotel is located 2 blocks from the El train and is a 5-minute walk to Millennium Park and 2 minutes on foot from the Chicago Theater.

gay-friendly card-payments wifi

LGBTQ+ Friendly Aug 2026

Gay-Friendly Hotel 4.0 (796)

Hotel Indigo

River North

Unique Gold Coast boutique hotel In the midst of the shopping district with an ever-changing decor and flair for the unique, this small hotel is a colourful place to stay.

gay-friendly mixed-lgbtq gay-popular

LGBTQ+ Friendly Aug 2026

Gay-Friendly Hotel 4.2 (13908)

Palmer House Hilton

The Loop

World renown historic hotel The Palmer House is an infamously gorgeous hotel, and one of the oldest continuously-operating hotels in the country. Every U.S. president since Grant has stayed here.

gay-friendly year-round card-payments

LGBTQ+ Friendly Aug 2026

Gay-Friendly Hotel 4.1 (1861)

Dana hotel and spa

River North

Boutique hotel and spa The expression dana translates from Sanskrit to mean the pleasure of giving. Dana offers pleasurable feelings of tranquillity, well-being and harmony.

gay-friendly spa mixed-lgbtq

LGBTQ+ Friendly Aug 2026

Gay-Friendly Hotel 4.2 (790)

Willows Hotel

Northalsted (Boystown)

19th century reproduction style bed & breakfast French Country style rooms await your visit in this charming hotel. Willows is a great value in an excellent location, just outside of Boys town.

gay-friendly mixed-lgbtq wifi

LGBTQ+ Friendly Aug 2026

Gay-Friendly Hotel 4.2 (736)

The Fireplace Inn

River North

Famous for BBQ For over 40 years this Chicago institution has been serving some of the best BBQ in the country. Thought not particularly gay, it is worth a visit if you have a hankering for ribs.

gay-friendly card-payments walk-ins

LGBTQ+ Friendly Aug 2026

Gay-Friendly Hotel 3.6 (912)

James Hotel

River North

Stylish, accomodating hotel Designed from the guest's point of view. Complimentary WiFi and concert-quality sound system in every room.

gay-friendly wifi air-conditioning

LGBTQ+ Friendly Aug 2026

Gay-Friendly Hotel 4.5 (4156)

Sofitel Chicago Water Tower

River North

Elegant downtown hotel Sofitel Chicago Water Tower is minutes from the Magnificent Mile, Michigan Avenue, the Museum of Contemporary Art, the Art Institute, and trendy boutiques.

gay-friendly card-payments reservations

LGBTQ+ Friendly Aug 2026

Gay-Friendly Hotel 4.2 (841)

Comfort Inn & Suites Downtown Chicago

River North

Magnificent Mile hotel This hotel is an excellent value for such a superb location, close to dining and shopping and only five minutes from Magnificent Mile.

gay-friendly wifi air-conditioning

LGBTQ+ Friendly Aug 2026

Gay-Friendly Hotel 4.6 (2349)

Hotel Burnham

The Loop

Luxury boutique hotel in the Loop Lots of personal attention, a great location and stylish decor makes this hotel stand out. Luxury amenities for guests and their pets.

gay-friendly pet-friendly wifi

LGBTQ+ Friendly Aug 2026

Gay-Friendly Hotel 4.3 (2008)

Kinzie Hotel

River North

Contemporary, chic hotel in River North The Kinzie offers a central access point to Downtown's restaurants, culture, theatre and shopping in a hip, boutique setting.

gay-friendly mixed-lgbtq wifi

LGBTQ+ Friendly Aug 2026

Gay-Friendly Hotel 4.4 (560)

Holiday Jones

Wicker Park

Set 2.5 miles from Oak Street Beach, this hip Wicker Park hostel is 4 blocks from an El train stop with service to downtown Chicago.

gay-friendly wifi air-conditioning

LGBTQ+ Friendly Aug 2026

Gay-Friendly Hotel 3.9 (659)

Sax Chicago

River North

Ultra-modern sophistication Blending classically designed furniture pieces with postmodern design, the Sax creates a truly unique atmosphere.

gay-friendly wifi air-conditioning

LGBTQ+ Friendly Aug 2026

Gay-Friendly Hotel 4.6 (1931)

The Ritz-Carlton-A Four Seasons Hotel

River North

Super classy location and amenities, as would be expected of the Ritz Set atop Water Tower Place, high above prestigious North Michigan Avenue, and featuring exquisite dcor and intuitive service, The…

gay-friendly wifi air-conditioning

LGBTQ+ Friendly Aug 2026

Gay-Friendly Hotel 3.9 (707)

The Tremont Chicago Hotel at Magnificent Mile

River North

A 7-minute walk from the Chicago Museum of Contemporary Art, this classic European-style hotel is a block from upscale shopping along the Magnificent Mile.

gay-friendly wifi year-round

LGBTQ+ Friendly Aug 2026

Gay-Friendly Hotel 4.5 (1345)

Thompson Hotel - Thompson Chicago

River North

Sophisticated comfort The Sutton Place Hotel is contemporary and attentive. The classic style and calm interiors will put you at ease whether you're traveling for business or pleasure.

gay-friendly wifi air-conditioning

LGBTQ+ Friendly Aug 2026

Gay-Friendly Hotel 3.5 (342)

Inn At Lincoln Park

Northalsted (Boystown)

Modest accommodations in a central location After undergoing a makeover, this comfortable property now boasts a meeting centre. Lincoln Park is an up and coming neighbourhood close to Boys town.

gay-friendly year-round card-payments

LGBTQ+ Friendly Aug 2026

Gay-Friendly Hotel 4.4 (5557)

Intercontinental Magnificent Mile

River North

Magnificent mile in style This gorgeous upscale hotel is right on Michigan Ave., and steps away from some of the best shopping in the country. The indoor pool is not to be missed

gay-friendly card-payments wifi

LGBTQ+ Friendly Aug 2026

Gay-Friendly Hotel 4.4 (1660)

The Silversmith Hotel & Suites

The Loop

Historic luxury At the heart of Chicagos Financial/Theater District (the Loop), The Silversmith Hotel & Suites, designed in 1897, is a landmark Chicago attraction in and of itself.

gay-friendly wifi air-conditioning

LGBTQ+ Friendly Aug 2026

Gay-Friendly Hotel 4.3 (3732)

The WIT A Doubletree Hotel

River North

Enjoy the hip, modern stylings of this new Chicago hotel The WIT offers smart, edgy rooms well-appointed with rooms with sophisticated amenities.

gay-friendly gay-popular gym

LGBTQ+ Friendly Aug 2026

Gay-Friendly Hotel 3.9 (748)

Chicago's Essex Inn

The Loop

"Your key to the city" An ideal location from which to launch your Chicago visit, the Essex Inn offers free shuttles to Miracle Mile, a rooftop garden, pool and fitness center and stunning views of…

gay-friendly hotel-pool gym

LGBTQ+ Friendly Aug 2026

Gay-Friendly Hotel 4.4 (2574)

Blackstone Rennaissance

The Loop

Classic and contemporary hotel Blackstone is an incredibly stylish and elegant hotel on the outskirts of the Loop.

gay-friendly card-payments reservations

LGBTQ+ Friendly Aug 2026

Gay-Friendly Hotel 3.2 (947)

Public Hotel

River North

Sleek and sophisticated hotel with legendary past Public, conceived by Ian Schrager, is an entirely new class of hotel.

gay-friendly card-payments reservations

LGBTQ+ Friendly Aug 2026

Gay-Friendly Hotel 3.8 (3072)

Affinia Chicago

River North

Customised comforts and sophisticated style Located just steps from the famed Magnificent Mile, this upscale boutique hotel is set at the epicentre of Chicago's shopping, nightlife, entertainment and…

gay-friendly wifi air-conditioning

LGBTQ+ Friendly Aug 2026

Gay-Friendly Hotel 3.6 (71)

Avenue Hotel Chicago

River North

Steps from the 'Magnificent Mile' The Avenue is a Crowne Plaza Hotel that is a step above your typical chain hotel. The location is perfect for taking in Chicago's shopping and attractions.

gay-friendly card-payments reservations

LGBTQ+ Friendly Aug 2026

Gay-Friendly Hotel 3.7 (2516)

Chicago South Loop Hotel

Pilsen

Quality comfort in Chicago's South Loop If you're a culture seeker, the South Loop Hotel offers close proximity to museums, theater and shopping.

gay-friendly mixed-lgbtq card-payments

LGBTQ+ Friendly Aug 2026

Gay-Friendly Hotel 4.3 (2112)

Courtyard Marriott Downtown/Magnificent Mile

River North

Steps from Magnificent Mile For a dose of downtown comfort, the Courtyard Marriott packs in all the amenities you'd expect from a business class hotel into the limited real estate of a bustling…

outdoor-patio gay-friendly wifi

LGBTQ+ Friendly Aug 2026

Gay-Friendly Hotel 4.3 (1493)

Fairfield Inn & Suites Chicago Downtown

River North

Just steps from Magnificent Mile This busy family hotel is in a quiet location just off Michigan Ave.

gay-friendly free-breakfast wifi

LGBTQ+ Friendly Aug 2026

Gay-Friendly Hotel 4.2 (2377)

Hampton Inn and Suites Chicago Downtown

River North

Family-friendly downtown hotel This very busy downtown hotel is popular with families and tourists for its spacious rooms, affordable rates and great downtown location.

gay-friendly wifi air-conditioning

LGBTQ+ Friendly Aug 2026

Gay-Friendly Hotel 4.2 (1987)

Homewood Suites Downtown Chicago

River North

Hotel away from home Get away from those crowded downtown hotel rooms and into a spacious Home-wood Suite. Perfect for extended stays, every suite features a fully-equipped kitchen.

gay-friendly wifi air-conditioning

LGBTQ+ Friendly Aug 2026

Gay-Friendly Hotel 4.2 (2603)

Renaissance Chicago O'Hare Suites Hotel

Gay-Friendly Hotel

Great proximity to O'Hare International Airport The all-suite Renaissance Chicago O'Hare Suites Hotel is located near Rosemont, IL.

gay-friendly wifi air-conditioning

LGBTQ+ Friendly Aug 2026

Gay-Friendly Hotel 4.5 (1518)

The Gwen

River North

Prestigious downtown luxury hotel Spacious modern rooms, stylish furnishings and a fantastic location--what more could you want? How about a fitness center with an incredible view of the city? Check.

gay-friendly wifi air-conditioning

LGBTQ+ Friendly Aug 2026

Gay-Friendly Hotel 4.7 (2828)

The Peninsula Chicago

River North

Magnificent Art Deco luxury Featuring unsurpassed service, the staff at The Peninsula takes care of all the details you'd expect from a luxury hotel.

gay-friendly card-payments reservations

LGBTQ+ Friendly Aug 2026

Gay-Friendly Hotel 4.3 (1088)

The Talbott Hotel

River North

Elegant boutique hotel Near Michigan Ave., the Talbott is a great choice for boutique upscale accommodation. We'd say you'll feel right at home, but home is never this comfortable.

gay-friendly gym wifi

LGBTQ+ Friendly Aug 2026

Gay-Friendly Hotel 3.8 (3018)

Best Western Grant Park Hotel

The Loop

For a true Chicago experience, stay with The BEST WESTERN Grant Park Hotel. Located steps away from Soldier Field and also the Museum Campus that houses the Adler Planetarium, Shedd Aquarium, and…

gay-friendly card-payments walk-ins

LGBTQ+ Friendly Aug 2026

Gay-Friendly Hotel 4.6 (892)

Hotel Zachary

Northalsted (Boystown)

Design hotel directly across from Wrigley Field in Lakeview — gay-welcoming, well-positioned for both Boystown and Wrigleyville. Modern rooms, rooftop bar, and excellent neighbourhood access.

gay-friendly gay-popular wifi

LGBTQ+ Friendly Aug 2026