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 $139

MileNorth, A Chicago Hotel

4 stars
4.3 / 5 487 reviews

Chicago, Illinois

Magnificent Boutique Hotel in Downtown Chicago Steps from the Magnificent Mile, the MileNorth Chicago features a prime location at the Windy City's epicenter of shopping, entertainment, culture and business. Known for its fast pace, famous museums, amazing architecture, and action-packed sporting events, Chicago offers... More

From $179

Allegro Chicago, a Kimpton Hotel

4 stars
4.1 / 5 346 reviews

Chicago, Illinois

Save 30% on your stay

The Allegro Chicago, a Kimpton Hotel, is an outstanding boutique hotel situated in downtown Chicago. With vibrant decor and historic style, charm abounds. The hospitality and thoughtful service of the staff welcomes travelers. The Allegro is an eco-friendly hotel that combines the glamour of Old World tradition with a... More

From $169

Kinzie Hotel (formerly the Amalfi Hotel)

4 stars
4.4 / 5 814 reviews

Chicago, Illinois

Occupying the first six floors of Dearborn Plaza, the newly revamped Kinzie Hotel (formerly the Amalfi Hotel) has rounded corner suites that mark the high-rise exterior out against the skyline, while the eclectic contemporary art and mismatched colors of the lobby signal a touch of the avant-garde. The hotel's... More

From $134

Chicago's Essex Inn

3 stars
3.8 / 5 275 reviews

Chicago, Illinois

Save 15% on your stay

Comfortable, cozy and modern, Chicago's Essex Inn ensures its guests have a pleasurable stay with complementary amenities. Take in Lake Michigan from the year-round, glass-enclosed rooftop pool, which lets you take a dip whether it's summer or the middle of winter. If you just need some quiet time, head over to the... More

From $200

Courtyard by Marriott Chicago Downtown/Magnificent Mile

3 stars
4.1 / 5 110 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 $173

Hampton Inn Chicago Downtown/Magnificent Mile

4 stars
4.0 / 5 106 reviews

Chicago, Illinois

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 shops, it doesn't get more convenient than this classy Chicago hotel.... More

From $179

dana hotel and spa

4 stars
4.2 / 5 258 reviews

Chicago, Illinois

The 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 core philosophy of wellness and individuality is... More

From $203

Fairmont Chicago Millennium Park

4 stars
4.1 / 5 232 reviews

Chicago, Illinois

Stay 1 Night, Save 15%

Comfort and sophistication only minutes from Millennium Park The Fairmont Chicago, Millennium Park, in downtown Chicago, provides amenities to suit business and leisure travelers. Comprehensively equipped with a business center and excellent spa facilities, this hotel enables guests to easily combine business with... More

From $159

AC Hotel Chicago Downtown

3 stars
4.2 / 5 197 reviews

Chicago, Illinois

Rate Includes Breakfast

Guests at the AC Hotel Chicago Downtown 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 access to the Loop and the Financial District.... More

From $159

Hyatt Regency Chicago

4 stars
4.1 / 5 817 reviews

Chicago, Illinois

Includes Free Valet Parking

The Hyatt Regency Chicago rises above Chicago's waterfront to offer a sleek experience geared toward corporate and vacationing travelers alike. The multilingual staff members are incredibly warm and friendly; they'll give you insider information and tips on places to go and things to enjoy. If you book a suite, you get... More

From $269

JW Marriott Chicago

4 stars
4.5 / 5 29 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 $219

Marriott Chicago Downtown Magnificent Mile

4 stars
4.0 / 5 207 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 $224

Renaissance Blackstone Chicago Hotel

4 stars
4.5 / 5 84 reviews

Chicago, Illinois

Rate includes breakfast

The 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 restored 1910 French Beaux-Arts... More

From $284

Renaissance Chicago Downtown Hotel

4 stars
4.2 / 5 57 reviews

Chicago, Illinois

Rate includes breakfast

Guests 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 with refreshing drinks at the modern bar and relish... More

From $219

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 $215

Swissotel Chicago

4 stars
4.2 / 5 332 reviews

Chicago, Illinois

Book early and save 10% on your stay

With just under 40 properties in 17 countries, the upscale Swissotel chain, founded in 1980, is known for offering unique and innovative touches, and the Swissotel Chicago is no exception. The all-glass, pyramid-shaped hotel is a standout even in a city that's renowned for its incredible architecture. From its lush lobby... More

From $161

The Talbott Hotel

4 stars
4.6 / 5 1370 reviews

Chicago, Illinois

The Talbott Hotel is a European-style resort, which is reflected by the Italian Frette linen you'll find in each of its guest rooms. This AAA Four Diamond Hotel is a member of the Historic Hotels of America, as well as being one of the first Green Seal-certified hotels in the United States, so guests can be sure that... More

From $206

The James Chicago

5 stars
4.4 / 5 148 reviews

Chicago, Illinois

Urban 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 locals, the hotel brims with people watching... More

From $191

The Westin Michigan Avenue Chicago

4 stars
4.0 / 5 207 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 $257

W Chicago - City Center

4 stars
3.8 / 5 100 reviews

Chicago, Illinois

Save 15% on your stay

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, there's a sense of history at the W... More

From $179

Courtyard by Marriott Chicago Downtown/River North

3 stars
4.0 / 5 109 reviews

Chicago, Illinois

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 and sightseeing, however. Guests need... More

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Best in Stay

LGBT Best in Stay Chicago hotels

From $139

MileNorth, A Chicago Hotel

4 stars
4.3 / 5 487 reviews

Chicago, Illinois

Magnificent Boutique Hotel in Downtown Chicago Steps from the Magnificent Mile, the MileNorth Chicago features a prime location at the Windy City's epicenter of shopping, entertainment, culture and business. Known for its fast pace, famous museums, amazing architecture, and action-packed sporting events, Chicago offers... More

From $188

BEST WESTERN PLUS Hawthorne Terrace Hotel

3 stars
4.1 / 5 38 reviews

Chicago, Illinois

Save 20% 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 / 5 346 reviews

Chicago, Illinois

Save 30% on your stay

The Allegro Chicago, a Kimpton Hotel, is an outstanding boutique hotel situated in downtown Chicago. With vibrant decor and historic style, charm abounds. The hospitality and thoughtful service of the staff welcomes travelers. The Allegro is an eco-friendly hotel that combines the glamour of Old World tradition with a... More

From $263

The Peninsula Chicago

5 stars
4.8 / 5 64 reviews

Chicago, Illinois

3rd Night Free

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 $161

The Talbott Hotel

4 stars
4.6 / 5 1370 reviews

Chicago, Illinois

Last Minute Deal!

The Talbott Hotel is a European-style resort, which is reflected by the Italian Frette linen you'll find in each of its guest rooms. This AAA Four Diamond Hotel is a member of the Historic Hotels of America, as well as being one of the first Green Seal-certified hotels in the United States, so guests can be sure that... More

From $197

W Chicago Lakeshore

4 stars
3.8 / 5 179 reviews

Chicago, Illinois

Save 20% on your stay

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 cocktails from the 33rd floor... More

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Gayborhood

Chicago Gayborhood hotels

From $188

BEST WESTERN PLUS Hawthorne Terrace Hotel

3 stars
4.1 / 5 38 reviews

Chicago, Illinois

Save 20% 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 $105

Days Inn Chicago

2 stars
3.9 / 5 132 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 $168

City Suites Hotel Chicago

3 stars
4.1 / 5 142 reviews

Chicago, Illinois

Save 10%

Take 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, live concert venues, summer festivals, boutiques and 24-hour restaurants.... More

From $229

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 $188

The Willows Hotel

3 stars
3.9 / 5 84 reviews

Chicago, Illinois

Business Advantage Flex - Same Day Cancel

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 service with their afternoon cookies. Wake in one of 55 cozy rooms and... More

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Flights

Departure Arrival Travel dates Round-trip
New York Chicago Tue, Aug 25 - Thu, Sep 10 $167
Los Angeles Chicago Sat, Aug 29 - Tue, Sep 22 $197
Washington DC Chicago Mon, Aug 24 - Thu, Sep 17 $99
Denver Chicago Fri, Aug 14 - Tue, Aug 25 $135
Boston Chicago Wed, Aug 19 - Tue, Aug 25 $147
San Francisco Chicago Tue, Aug 25 - Wed, Aug 26 $217
Minneapolis Chicago Sat, Sep 5 - Wed, Sep 9 $81
Seattle Chicago Tue, Jul 28 - Tue, Aug 4 $348
Philadelphia Chicago Tue, Aug 25 - Sat, Aug 29 $81
Newark Chicago Tue, Sep 1 - Tue, Sep 8 $231
Portland Chicago Wed, Sep 2 - Tue, Sep 15 $197
Atlanta Chicago Sat, Aug 29 - Tue, Sep 1 $81
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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.
  • 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.

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