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
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
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
Boutique chic at convenient Chicago hotelThis River North hotel defines the term boutique chic with its intimate, yet contemporary style. The space mirrors elements from its namesake -- Italy’s Amalfi Coast -- to create a relaxing experience for business and leisure travelers. From its shimmery waterfall to its... More
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
Courtyard by Marriott Chicago Downtown/Magnificent Mile
Chicago, Illinois
Rate includes breakfast
ITS A NEW STAY! Courtyard Chicago Downtown/Magnificent Mile has completed a renovation! Our hotel features a renovated lobby with a Starbucks Coffee Shop, inviting fireplace and plenty of comfortable seating to watch the bustling activity of the famous Magnificent Mile. Our Mag Mile hotel is ideally located, just minutes... More
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
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
Fairmont Chicago Millennium Park
Chicago, Illinois
Summer Offer Save 15% On Your Stay
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 excllent spa facilities, this hotel enables guests to easily combine business with... More
Four Points by Sheraton Chicago Downtown/Magnificent Mile
Chicago, Illinois
Save 25% 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
Hyatt Regency Chicago
Chicago, Illinois
Includes free valet parking & internet access
Convenient convention hotel in ChicagoWhen the lights go down in the Windy City, there is no better location to soak in the view than at the Hyatt Regency Chicago. To the north of this downtown hotel lies the Chicago River and to the east sits the unmistakable Navy Pier in all its American glory. Walking the full breadth... More
Encounter a landmark downtown Chicago luxury hotel and experience the renowned architecture of Daniel Burnham and his vision for a luxury hotel in Chicago, Illinois. Located at LaSalle & Adams, this Chicago, Illinois luxury hotel soars above skyscrapers in the heart of one of the world's most powerful financial... More
Marriott Chicago Downtown Magnificent Mile
Chicago, Illinois
Includes Breakfast and Dinner for two
Step onto the Magnificent Mile from comfortable Chicago hotelNot many hotels in downtown Chicago boast a location where guests just step onto the Magnificent Mile from the hotel. Top stores, popular restaurants, hot nightlife and world-class museums are all within walking distance. Guests find comfort in the Marriott’s... More
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 Navy Pier and Millennium Park. A popular retreat for celebrities, the Renaissance Blackstone Chicago Hotel entices guests with classic... More
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
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. Treat clients or your significant other to an exceptional Magnificent Mile hotel stay and explore nearby attractions, including... More
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
The Talbott Hotel in the heart of the Gold Coast offers spacious rooms with complimentary amenities including wireless internet and access to Equinox Fitness. Located steps from Chicago's Magnificent Mile and Rush Street, the heart of Chicago's night life. Voted as an Orbitz Best of the Best hotel. The Talbott Hotel is... More
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
The Westin Michigan Avenue Chicago is on the Magnificent Mile across from Bloomingdale's and the upscale shops of Water Tower Place. The exhilarating excitement of Chicago is at our doorstep or venture into the Loop for business. We provide unparalleled service for business and leisure travelers with elegant function... More
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
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
Best in Stay
LGBT Best in Stay Chicago hotels
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
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
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
Far Eastern elegance on the Magnificent MileThe Peninsula Chicago, at the center of the Magnificent Mile, mixes classic yet elegant décor. Far Eastern splendor greets guests of the Peninsula. The dining experience at the Peninsula Chicago is no less impressive, with restaurants offering everything from American cuisine... More
The Talbott Hotel in the heart of the Gold Coast offers spacious rooms with complimentary amenities including wireless internet and access to Equinox Fitness. Located steps from Chicago's Magnificent Mile and Rush Street, the heart of Chicago's night life. Voted as an Orbitz Best of the Best hotel. The Talbott Hotel is... More
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
Gayborhood
Chicago Gayborhood hotels
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
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
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
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
Flights
| Departure | Arrival | Travel dates | Round-trip |
|---|---|---|---|
| New York | Chicago | Tue, Jul 16 - Tue, Jul 23 | $194 |
| Los Angeles | Chicago | Sun, Jun 2 - Thu, Jun 6 | $240 |
| Washington DC | Chicago | Thu, May 23 - Fri, May 31 | $223 |
| Denver | Chicago | Wed, Jun 12 - Tue, Jun 18 | $138 |
| Boston | Chicago | Sun, May 26 - Wed, May 29 | $143 |
| San Francisco | Chicago | Mon, Jun 10 - Wed, Jun 12 | $338 |
| Minneapolis | Chicago | Sat, May 25 - Thu, May 30 | $72 |
| Seattle | Chicago | Mon, Jun 10 - Tue, Jun 11 | $307 |
| Philadelphia | Chicago | Tue, Jul 2 - Tue, Jul 23 | $246 |
| Newark | Chicago | Wed, Jun 12 - Wed, Jun 19 | $266 |
| Portland | Chicago | Mon, Jun 3 - Tue, Jun 4 | $320 |
| Atlanta | Chicago | Sat, May 25 - Thu, May 30 | $220 |
Why book on Orbitz?
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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
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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
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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
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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.
