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 $119

MileNorth, A Chicago Hotel

4 stars
4.3 / 5 477 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 lounge. MileNorth's accommodations are... More

From $179

Allegro Chicago, a Kimpton Hotel

4 stars
4.1 / 5 344 reviews

Chicago, Illinois

Save 30% on your stay

The belle of Chicago's theater districtWhen Broadway shows comes to town, the 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 corner,... More

From $174

Kinzie Hotel (formerly the Amalfi Hotel)

4 stars
4.4 / 5 813 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 $130

Chicago's Essex Inn

3 stars
3.8 / 5 273 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 $200

Courtyard by Marriott Chicago Downtown/Magnificent Mile

3 stars
4.1 / 5 108 reviews

Chicago, Illinois

The Courtyard Marriott Chicago Downtown/Magnificent Mile features a stylish lobby with a Starbucks coffee shop, inviting fireplace and plenty of comfortable seating to watch the bustling activity of the famous Mag Mile. Our Downtown Chicago hotel is ideally located, just minutes from the Loop business district, Navy... More

From $149

Hampton Inn Chicago Downtown/Magnificent Mile

4 stars
4.0 / 5 103 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 / 5 255 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 / 5 228 reviews

Chicago, Illinois

Stay 1 Night, Save 15%

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 $150

Hotel Rush

3 stars
4.2 / 5 197 reviews

Chicago, Illinois

Access to attractions, plus free Wi-Fi and indoor poolGuests at the Hotel Rush 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 while executives enjoy convenient... More

From $169

Hyatt Regency Chicago

4 stars
4.1 / 5 811 reviews

Chicago, Illinois

Includes 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 $229

JW Marriott Chicago

4 stars
4.5 / 5 28 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 $211

Marriott Chicago Downtown Magnificent Mile

4 stars
4.0 / 5 205 reviews

Chicago, Illinois

Rate includes breakfast

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 $229

Renaissance Blackstone Chicago Hotel

4 stars
4.4 / 5 82 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 $220

Renaissance Chicago Downtown Hotel

4 stars
4.2 / 5 57 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 Renaissance Chicago Downtown Hotel provides an incredible selection of amenities, including a 24-hour front desk, a fitness center and a spa. In addition, guests unwind... More

From $195

Residence Inn by Marriott Chicago Downtown/Magnificent Mile

3 stars
4.1 / 5 39 reviews

Chicago, Illinois

Includes Fold-Out American Girl Doll Bed

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 $157

Swissotel Chicago

4 stars
4.2 / 5 332 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 $185

The Talbott Hotel

4 stars
4.6 / 5 1354 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 $229

The James Chicago

5 stars
4.4 / 5 147 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 $205

The Westin Michigan Avenue Chicago

4 stars
4.0 / 5 205 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 $215

W Chicago - City Center

4 stars
3.8 / 5 99 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 / 5 109 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

Back to menu Return to top

Best in Stay

LGBT Best in Stay Chicago hotels

From $119

MileNorth, A Chicago Hotel

4 stars
4.3 / 5 477 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 lounge. MileNorth's accommodations are... More

From $152

BEST WESTERN PLUS Hawthorne Terrace Hotel

3 stars
4.1 / 5 37 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 $179

Allegro Chicago, a Kimpton Hotel

4 stars
4.1 / 5 344 reviews

Chicago, Illinois

Save 30% on your stay

The belle of Chicago's theater districtWhen Broadway shows comes to town, the 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 corner,... More

From $395

The Peninsula Chicago

5 stars
4.8 / 5 63 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 $185

The Talbott Hotel

4 stars
4.6 / 5 1354 reviews

Chicago, Illinois

Last Minute Deal!

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 $220

W Chicago Lakeshore

4 stars
3.8 / 5 179 reviews

Chicago, Illinois

Save 20% on your stay

Setting the standard for cool Find lake views and a front-door beach at this fashionable Chicago hotel that oozes cool lounge appeal. When guests are not cooing over Lake Michigan or the light show at Navy Pier, the W Chicago - Lakeshore hotel captivates with extras like inventive Mediterranean cuisine at Wave, scenic... More

Back to menu Return to top

Gayborhood

Chicago Gayborhood hotels

From $152

BEST WESTERN PLUS Hawthorne Terrace Hotel

3 stars
4.1 / 5 37 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 $124

Days Inn Chicago

2 stars
3.9 / 5 130 reviews

Chicago, Illinois

Stay 3, Save 20%

Launch your Chicago getaway from the Days Inn Chicago in the Lincoln Park neighborhood of downtown Chicago. Recipient of the 2014 TripAdvisor Certificate of Excellence! This European boutique style hotel puts guests within walking distance to famous Chicago attractions including the Lincoln Park Zoo, and Wrigley Field -... More

From $177

City Suites Hotel Chicago

3 stars
4.1 / 5 142 reviews

Chicago, Illinois

Save 10%

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

From $195

Majestic Hotel

3 stars
4.2 / 5 87 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 $197

The Willows Hotel

3 stars
3.9 / 5 84 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

Back to menu Return to top

Flights

Departure Arrival Travel dates Round-trip
New York Chicago Wed, Jun 24 - Tue, Jun 30 $197
Los Angeles Chicago Sat, Jul 25 - Sat, Aug 15 $238
Washington DC Chicago Wed, Jun 3 - Tue, Jun 9 $145
Denver Chicago Wed, Jun 10 - Wed, Jun 17 $132
Boston Chicago Wed, Jul 8 - Wed, Jul 22 $177
San Francisco Chicago Tue, Jul 7 - Tue, Jul 14 $228
Minneapolis Chicago Sat, Jun 6 - Tue, Jun 16 $107
Seattle Chicago Wed, Jul 22 - Tue, Aug 11 $350
Philadelphia Chicago Wed, Jun 10 - Sat, Jun 13 $147
Newark Chicago Mon, Jul 6 - Tue, Jul 7 $232
Portland Chicago Sat, Jun 6 - Thu, Jun 18 $267
Atlanta Chicago Tue, Jun 9 - Wed, Jun 10 $137
Back to menu Return to top

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.
  • 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.

  • 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.

  • 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.

Recent searches

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)