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
MileNorth, A Chicago Hotel
Allegro Chicago, a Kimpton Hotel
Amalfi Hotel Chicago
Chicago's Essex Inn
Courtyard by Marriott Chicago Downtown/Magnificent Mile
Crowne Plaza CHICAGO MAGNIFICENT MILE
dana hotel and spa
Fairmont Chicago, Millennium Park
Four Points by Sheraton Chicago Downtown/Magnificent Mile
Hyatt Regency Chicago
JW Marriott Chicago
Marriott Chicago Downtown Magnificent Mile
Renaissance Blackstone Chicago Hotel
Renaissance Chicago Downtown Hotel
Residence Inn by Marriott Chicago Downtown/Magnificent Mile
Swissotel Chicago
The Talbott Hotel
The James Hotel Chicago
The Westin Michigan Avenue Chicago
W Chicago - City Center
Best in Stay
LGBT Best in Stay Chicago hotels
MileNorth, A Chicago Hotel
BEST WESTERN PLUS Hawthorne Terrace Hotel
Allegro Chicago, a Kimpton Hotel
The Peninsula Chicago
The Talbott Hotel
W Chicago Lakeshore
Gayborhood
Chicago Gayborhood hotels
BEST WESTERN PLUS Hawthorne Terrace Hotel
City Suites Hotel Chicago
Majestic Hotel
The Willows Hotel
Flights
| Departure | Arrival | Travel dates | Round-trip |
|---|---|---|---|
| New York | Chicago | Tue, Jan 15 - Tue, Jan 22 | $108 |
| Los Angeles | Chicago | Tue, Jan 29 - Wed, Jan 30 | $251 |
| Washington DC | Chicago | Mon, Jan 21 - Wed, Jan 23 | $192 |
| Denver | Chicago | Tue, Jan 29 - Tue, Feb 5 | $72 |
| Boston | Chicago | Wed, Jan 16 - Wed, Jan 23 | $186 |
| San Francisco | Chicago | Thu, Jan 17 - Thu, Jan 24 | $262 |
| Minneapolis | Chicago | Tue, Feb 5 - Tue, Feb 12 | $70 |
| Seattle | Chicago | Wed, Jan 23 - Tue, Jan 29 | $276 |
| Philadelphia | Chicago | Sat, Jan 5 - Tue, Jan 8 | $221 |
| Newark | Chicago | Mon, Feb 11 - Wed, Feb 13 | $216 |
| Portland | Chicago | Wed, Feb 27 - Thu, Feb 28 | $251 |
| Atlanta | Chicago | Mon, Feb 11 - Wed, Feb 13 | $190 |
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 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.