Chicago Gay and Lesbian Vacations

Your gay Chicago vacation

Chicago is a proud home to one of the world's most active LGBT communities. The city government backs up the gay culture in endless ways, sponsoring the Chicago Gay and Lesbian Hall of Fame, the impressive Center on Halsted and the uber-successful Gay City Games. Sure, most of the action revolves around Lakeview's Boystown, but the lesbian-popular Andersonville and emerging Wicker Park give the standby 'hood a run for its money. From the world-class theatre district to the bustling shopping on Michigan Ave, let Orbitz bring you your next gay Chicago vacation.

Featured Hotels

LGBT-welcoming Chicago hotels

From $169

MileNorth, A Chicago Hotel

4 stars
4.2 / 5 401 reviews

Chicago, Illinois

This boutique property offers a residential-style retreat that soars above Chicago's Magnificent Mile. Each floor is home to no more than 11 spacious guest rooms and suites, and your evenings would be well spent enjoying appetizers and sipping cocktails at the 52Eighty rooftop club. MileNorth?s accommodations are... More

From $160

Allegro Chicago, a Kimpton Hotel

4 stars
4.1 / 5 311 reviews

Chicago, Illinois

Save 30% on your stay

The belle of Chicago's theater districtWhen Broadway shows comes to town, the Hotel Allegro Chicago, a Kimpton Hotel, is the first place that comes to mind for lodging. The Cadillac Palace Theater sparkles as brilliantly as its marquee with tasteful rooms in the heart of the Loop. Theatrical drama comes to life in every... More

From $179

Kinzie Hotel (formerly the Amalfi Hotel)

4 stars
4.4 / 5 755 reviews

Chicago, Illinois

Occupying the first six floors of Dearborn Plaza, the newly revamped Amalfi Hotel changed its name to the Kinzie Hotel Chicago in February 2014, as a tribute to John Kinzie, one of the city's original settlers. Rounded corner suites mark the high-rise exterior out against the skyline, while the eclectic contemporary art... More

From $152

Chicago's Essex Inn

3 stars
3.7 / 5 228 reviews

Chicago, Illinois

Save 15% on your stay

Affordable hotel south of Chicago's bustling downtown areaChicago's Essex Inn has an ideal location ideal on Michigan Avenue, just a few blocks south of the more congested areas of downtown Chicago. Grant Park is across the street, along with many famous Chicago attractions, including Millennium Park and the Art... More

From $189

Courtyard by Marriott Chicago Downtown/Magnificent Mile

3 stars
4.1 / 5 95 reviews

Chicago, Illinois

Courtyard Marriott Chicago Downtown/Magnificent Mile recently completed a renovation and now features a brand new lobby with a Starbucks coffee shop, inviting fireplace and plenty of comfortable seating to watch the bustling activity of the famous Magnificent Mile. Our Downtown Chicago hotel is ideally located, just... More

From $160

Hampton Inn Chicago Downtown/Magnificent Mile

4 stars
3.9 / 5 80 reviews

Chicago, Illinois

Picture-perfect location near Michigan Avenue shopping and restaurants A visit to Chicago wouldn't be complete without a stroll along the Magnificent Mile, so the properties closest to the grand boulevard earn instant bonus points. For travelers looking to be within steps of Michigan Avenue restaurants, landmarks and... More

From $189

dana hotel and spa

4 stars
4.2 / 5 217 reviews

Chicago, Illinois

Modern retreat for healthy living in downtown ChicagoThe dana hotel and spa in Chicago's River North neighborhood balances the beauty of natural elements with the latest technology to create a modern retreat for healthy living. From the progressive health center to the Zeppelin MP3 media system in each room, the dana's... More

From $211

Fairmont Chicago Millennium Park

4 stars
4.1 / 5 199 reviews

Chicago, Illinois

Summer Offer – Save 15% on your stay

The Fairmont Chicago makes the most of its Fairmont Hotels pedigree by offering an 11,000-square-foot spa, impressive suites, spacious boardrooms, and a reputation for throwing chandelier-lit events in the lofty Imperial Ballroom. One of Chicago's many high-rise hotels, the Fairmont greets you with individual style, from... More

From $179

Four Points by Sheraton Chicago Downtown/Magnificent Mile

3 stars
4.1 / 5 172 reviews

Chicago, Illinois

Save 40% on your stay

Access to attractions, plus free Wi-Fi and indoor pool Guests at the Four Points by Sheraton Chicago Downtown/Magnificent Mile enjoy a plum location just off the Magnificent Mile. Whether the agenda is hitting downtown shops, restaurants, bars or landmarks, leisure travelers will find no shortage of distractions nearby... More

From $169

Hyatt Regency Chicago

4 stars
4.1 / 5 732 reviews

Chicago, Illinois

Free High-Speed Internet, Free Valet Parking

Experience the mid-city excitement of Chicago with a stay at the Hyatt Regency Chicago, a pillar of The Windy City's urban landscape. Expansive open-plan areas are flanked by sloping staircases and sprawling sofas, while the burgers at BIG bar are every bit as huge as the window panoramas. As a convention venue, its... More

From $259

JW Marriott Chicago

4 stars
4.5 / 5 22 reviews

Chicago, Illinois

Rate includes breakfast

A crackling lobby fireplace warms the space during the winter months at the JW Marriott Chicago, while dome-ceilinged ballrooms cast a glow over special events and business occasions. Designed by renowned architect Daniel Burnham, this 12-story hotel seamlessly blends elegance with comfort, from the rejuvenating spa and... More

From $209

Marriott Chicago Downtown Magnificent Mile

4 stars
4.0 / 5 176 reviews

Chicago, Illinois

From the showpiece color-changing light feature behind the lobby bar, to the Art Deco-inspired lines of the Grand Staircase, the Marriott Chicago Downtown Magnificent Mile hotel welcomes guests with a splash. Get online anywhere with Wi-Fi throughout the hotel (fees may apply), while starting or ending your day with... More

From $206

Renaissance Blackstone Chicago Hotel

4 stars
4.5 / 5 71 reviews

Chicago, Illinois

Rate includes breakfast

History and culture in a modern settingThe historic 4-star Renaissance Blackstone Chicago Hotel offers guests easy access to some of the most interesting Chicago attractions, including Soldier Field and Magnificent Mile. A popular retreat for celebrities, the Renaissance Blackstone Chicago Hotel is housed in an elegantly... More

From $259

Renaissance Chicago Downtown Hotel

4 stars
4.2 / 5 53 reviews

Chicago, Illinois

Rate includes breakfast

Sophistication and style abound in this Windy City hotelGuests of the Renaissance Chicago Downtown Hotel enjoy opulence and luxury from the outset.The lobby and regal staircase are the epitome of sophistication and offer a feeling of style and class to guests. The Renaissance Chicago Downtown Hotel provides an incredible... More

From $199

Experience the comforts of home in the Windy City at the Residence Inn Chicago Downtown/Magnificent Mile Hotel located in the posh Gold Coast district surrounded by upscale shopping and dining. From short weekend getaways to extensive business trips, our spacious Magnificent Mile Chicago hotel suites provide a fully... More

From $199

Swissotel Chicago

4 stars
4.1 / 5 300 reviews

Chicago, Illinois

Book early and save 10% on your stay

An all-glass triangular hotel, wedged into the confluence of the Chicago River and Lake Michigan, has spectacular wrap-around views from Navy Pier to Grant Park. Swissotel Chicago offers 661 air-conditioned, tastefully decorated and generously oversized rooms and suites. Relax above the city in our Penthouse Swimming... More

From $195

The Talbott Hotel

4 stars
4.6 / 5 1183 reviews

Chicago, Illinois

Independently-owned and with a dedication to green practices, The Talbott Hotel has been a fixture in Chicago's Gold Coast neighborhood since 1927. The hotel mingles old-world sophistication with modern conveniences - the lobby has a cozy, open-fire warmth and the vintage-style boardrooms feature 1920s mahogany walls.... More

From $225

The James Chicago

5 stars
4.4 / 5 129 reviews

Chicago, Illinois

Boutique chic luxury in the heart of River NorthUrban professionals feel right at home at the James Hotel Chicago, a shrine to boutique chic style. Every corner pops with stylish details, starting with an illuminated lobby that offers soaring ceilings and 24-hour business center with videoconferencing capabilities. For... More

From $185

The Westin Michigan Avenue Chicago

4 stars
3.9 / 5 181 reviews

Chicago, Illinois

One of many Westin hotels across the US, the Westin Michigan Avenue Chicago greets you with a dramatic sweeping staircase, soaring marble columns and glittering, modern light fixtures. But it's not just a pretty picture; handy features like flexible workspaces ('Tangent') and free Wi-Fi in the lobby are on offer for... More

From $159

W Chicago - City Center

4 stars
3.8 / 5 84 reviews

Chicago, Illinois

Save 15% on your stay

Beaux-arts glamour in the Loop Awash in spotlights and marked by a big red W, this Loop hotel makes a fashionable statement in the Windy City. Fusing modern touches with classic Chicago architecture, the AAA four diamond property drips with drama. From the grand lobby boasting marble pillars and a vaulted ceiling,... More

From $175

Courtyard by Marriott Chicago Downtown/River North

3 stars
4.0 / 5 100 reviews

Chicago, Illinois

Urban sophistication in River North Guests at Courtyard by Marriot in Chicago's River North enjoy an ideal location a few blocks from the Magnificent Mile. Walk to Macy's, Nordstrom, Tiffany & Co. and other well-known stores, or taxi to Navy Pier, Millennium Park and Grant Park. The hotel's appeal exceeds shopping... More

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Best in Stay

LGBT Best in Stay Chicago hotels

From $169

MileNorth, A Chicago Hotel

4 stars
4.2 / 5 401 reviews

Chicago, Illinois

This boutique property offers a residential-style retreat that soars above Chicago's Magnificent Mile. Each floor is home to no more than 11 spacious guest rooms and suites, and your evenings would be well spent enjoying appetizers and sipping cocktails at the 52Eighty rooftop club. MileNorth?s accommodations are... More

From $161

BEST WESTERN PLUS Hawthorne Terrace Hotel

3 stars
4.1 / 5 31 reviews

Chicago, Illinois

Save 10% on your stay

Welcome to the BEST WESTERN PLUS Hawthorne Terrace Hotel, an intimate and charming hotel nestled in the bustling Lakeview neighborhood of Chicago. We are just steps from the vibrant nightlife, theatre, sidewalk cafés, upscale dining, lakefront biking and jogging. All of this and within minutes from celebrated Michigan... More

From $160

Allegro Chicago, a Kimpton Hotel

4 stars
4.1 / 5 311 reviews

Chicago, Illinois

Save 30% on your stay

The belle of Chicago's theater districtWhen Broadway shows comes to town, the Hotel Allegro Chicago, a Kimpton Hotel, is the first place that comes to mind for lodging. The Cadillac Palace Theater sparkles as brilliantly as its marquee with tasteful rooms in the heart of the Loop. Theatrical drama comes to life in every... More

From $450

The Peninsula Chicago

5 stars
4.8 / 5 47 reviews

Chicago, Illinois

With The Peninsula Chicago, traditional Asian service is brought to guests in the Windy City. This five-star hotel is located in the heart of the Magnificent Mile; it offers 20 floors of impeccable accommodations and delivers amenities and services of a very high caliber. Bask in the luxury of The Peninsula's... More

From $195

The Talbott Hotel

4 stars
4.6 / 5 1183 reviews

Chicago, Illinois

Independently-owned and with a dedication to green practices, The Talbott Hotel has been a fixture in Chicago's Gold Coast neighborhood since 1927. The hotel mingles old-world sophistication with modern conveniences - the lobby has a cozy, open-fire warmth and the vintage-style boardrooms feature 1920s mahogany walls.... More

From $203

W Chicago Lakeshore

4 stars
3.8 / 5 164 reviews

Chicago, Illinois

Save 20% on your stay

The W Chicago - Lakeshore offers a birds-eye (think seagull) view of things. Situated along Lake Shore Drive near the Navy Pier, it's the only hotel in Chicago directly overlooking Lake Michigan, and also provides easy access to the beach itself. So bring your flip-flops (weather permitting) and after you've hit the... More

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Gayborhood

Chicago Gayborhood hotels

From $161

BEST WESTERN PLUS Hawthorne Terrace Hotel

3 stars
4.1 / 5 31 reviews

Chicago, Illinois

Save 10% on your stay

Welcome to the BEST WESTERN PLUS Hawthorne Terrace Hotel, an intimate and charming hotel nestled in the bustling Lakeview neighborhood of Chicago. We are just steps from the vibrant nightlife, theatre, sidewalk cafés, upscale dining, lakefront biking and jogging. All of this and within minutes from celebrated Michigan... More

From $104

Days Inn Chicago

2 stars
3.9 / 5 120 reviews

Chicago, Illinois

Save 15% on your stay

Launch your Chicago getaway from the Days Inn Chicago in the Lincoln Park neighborhood of downtown Chicago. This award-winning European boutique style lodging facility is within walking distance of Chicago attractions like the Lincoln Park Zoo, Wrigley Field - home of the Chicago Cubs, and is just steps from public... More

From $189

City Suites Hotel Chicago

3 stars
4.1 / 5 125 reviews

Chicago, Illinois

Chicago Art Deco hotel with free Wi-Fi near Belmont-Sheffield nightlifeTake nearby trains throughout the city or explore the hip scene in Belmont-Sheffield from the City Suites Hotel Chicago. Unpretentious and welcoming, this Art Deco-inspired gem is tucked away in a neighborhood that hums with theaters, dance clubs,... More

Majestic Hotel

3 stars
4.2 / 5 79 reviews

Chicago, Illinois

One of the most exquisite boutique hotels in Chicago, the property affords the tranquility and dignity of a refined English country estate amidst the bustling, energetic city life of Chicago. Built in the 1920's, the historic Majestic Hotel exudes romance, European charm and comfort. The historic boutique hotel is... More

From $158

The Willows Hotel

3 stars
3.9 / 5 76 reviews

Chicago, Illinois

Business Advantage Flex - Same Day Cancel

Charming and convenient Chicago hotel with free breakfast and Internet A historic 1920s building adds to the European flavor of this boutique hotel in the exclusive Lincoln Park and Lakeview neighborhoods of Chicago. The Willows Hotel features French reproduction furniture in the lobby, where guests enjoy coffee and tea... More

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Flights
Departure Arrival Travel dates Round-trip
New York Chicago Wed, Nov 5 - Tue, Nov 11 $167
Los Angeles Chicago Mon, Nov 17 - Wed, Nov 19 $237
Washington DC Chicago Wed, Nov 19 - Mon, Nov 24 $185
Denver Chicago Wed, Nov 12 - Sat, Nov 15 $145
Boston Chicago Wed, Oct 15 - Tue, Oct 21 $115
San Francisco Chicago Wed, Oct 8 - Tue, Oct 14 $265
Minneapolis Chicago Wed, Oct 22 - Sat, Oct 25 $95
Seattle Chicago Tue, Nov 4 - Sat, Nov 8 $290
Philadelphia Chicago Sat, Oct 25 - Wed, Oct 29 $227
Newark Chicago Sat, Nov 1 - Tue, Nov 4 $233
Portland Chicago Wed, Oct 8 - Tue, Oct 14 $255
Atlanta Chicago Tue, Nov 4 - Fri, Nov 7 $125
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Why book on Orbitz?

  • Miss Richfield 1981 says it best in this video—not all travel sites are created equal. When you book on Orbitz, your travel dollars work harder. Here’s why:  

    • We’re the ONLY leading travel agency with a perfect Corporate Equality Index Score from the Human Rights Campaign, with two GLAAD Media awards to boot.
    • We’re the ONLY leading travel site with filters for hotel reviews by other LGBT travelers.
    • We feature the top gay-friendly accommodations, including Best in Stay hotels and gay resorts.
    • We’re proud sponsors of many LGBT charities and events, year after year.

Chicago gay travel map

  • Check out Orbitz’ LGBT guide featuring the very best of gay and lesbian travel in Chicago. Explore gay-friendly hotels, gay bars & clubs, restaurants, upcoming LGBT events, and more.

Chicago highlights

  • The beach scene

    Since Chicago is perched on the sandy southwest shores of Lake Michigan, there's a burgeoning summer gay beach scene at Lake Shore Drive and Hollywood Avenue—but pack plenty of drinks, the season is notoriously sultry.

    LGBT gatherings

    Chicago is big into leather and bears, with the infamous International Mister Leather happening here every May. Chicago Pride is in June, and there's a fun Windy City Rodeo in August. Northalsted Market Days in August is the largest two-day outdoor street festival in the Midwest, with hundreds of vendors and musical acts for which the local gays come out in force.

    Architecture

    Chicago is justifiably famous for its architecture, and the skyline is one of the most impressive in the world, home to the massive Willis Tower and the John Hancock Building, not to mention more recent additions by Rem Koolhaas and Frank Gehry. Don't miss the architectural boat tours just off the river.

    Must-see landmarks

    Downtown's Millennium Park boasts a Frank Gehry-designed amphitheater, two 50-foot video block towers with fountains, and the silvery "Cloud Gate" (aka "The Bean"), an Anish Kapoor-designed sculpture that reflects the city skyline.

    Culture galore

    Chicago is a museum capital. The Art Institute of Chicago is now the second-largest house of modern art, and the Field Museum of Natural History showcases the biggest T-rex fossil ever discovered. Chicago also has one of the nation's best theater scenes, home to Steppenwolf and Second City, with an annual Broadway in Chicago series.

Insider tips for Chicago gay travel

  • Take a LGBT tour
     The city's tourism office offers free volunteer-led neighborhood tours, including gay tours of Boystown and Andersonville.

    Don't miss Andersonville
    Not only does Andersonville have a great variety of independent locally owned specialty shops and restaurants, the LGBT population rivals Boystown and Midsommarfest in June is a great event to kick-off summer in Chicago.

    Head to the Hancock
    The lines are longer at the Willis Tower, and even though the John Hancock Building is not as tall, its Signature Room on the 95th floor is a great place for cocktails and gazing over the city.

    Fly into Midway
    O'Hare is one of the busiest and most hectic airports in the world, while the smaller and less busy Midway Airport is closer to the Loop and serves more discount airlines.

Your trip

Hotel options

Hotel stay must be within date range of Leave and Return.

Room 1
Age categories
Ages of children at time of trip (for pricing, discounts)