
Illinois Gay friendly Vacation Packages

Best Illinois Gay friendly packages

Thompson Chicago, by Hyatt
Reviewed on Nov 14, 2025

Trump International Hotel & Tower Chicago
Reviewed on Oct 13, 2025

Hyatt Regency McCormick Place Chicago
Reviewed on Aug 8, 2025
3 night Illinois Gay friendly vacation packages with airfare

Hyatt Regency McCormick Place Chicago
Reviewed on Aug 8, 2025

Trump International Hotel & Tower Chicago
Reviewed on Oct 13, 2025

Thompson Chicago, by Hyatt
Reviewed on Nov 14, 2025
4 night Illinois Gay friendly vacation packages with flight

Hyatt Regency McCormick Place Chicago
Reviewed on Aug 8, 2025

Trump International Hotel & Tower Chicago
Reviewed on Oct 13, 2025

Thompson Chicago, by Hyatt
Reviewed on Nov 14, 2025
5 night Illinois Gay friendly vacation packages with airfare included

Thompson Chicago, by Hyatt
Reviewed on Nov 14, 2025

Trump International Hotel & Tower Chicago
Reviewed on Oct 13, 2025

Hotel 55
Reviewed on Nov 21, 2025
Gay friendly vacation packages for 6-7 nights

Thompson Chicago, by Hyatt
Reviewed on Nov 14, 2025

Trump International Hotel & Tower Chicago
Reviewed on Oct 13, 2025

Hotel Versey Chicago Lincoln Park
Reviewed on Nov 14, 2025
Gay friendly hotels in Illinois

Best Western Plus Hawthorne Terrace Hotel

Hotel Versey Chicago Lincoln Park

Hyatt Regency McCormick Place Chicago
How much does it cost to fly to Illinois?
Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.
Chicago LGBT Events
International Mr. Leather (imrl.com). This full weekend of leather fetish parties and pageantry is one of the largest on earth and it’s the one time you’ll see folks on the street walking around in jock straps and harnesses. The contest itself is only for the diehard, but everyone loves the sprawling leather market and boozing and schmoozing in the lobby of the host hotel.
The city’s Pride Parade runs right through the heart of Boystown and is big—almost too big—for the ‘hood to handle. Nevertheless, the city has aimed to Chicago Pride (chicagopride.gopride.com) by spreading the festivities out over two weekends and redrawing the parade route to ease congestion. Expect nearly one million revelers each June.
Travel tips
1. Choose Heathrow.
Most U.S. flights land in either Gatwick or Heathrow airports. Heathrow is on the London Underground (“Tube”) system, making your entry into London a little easier.
Gatwick is farther from town and not linked to the Tube. Taxis to London from Gatwick are pricey, although there is a surface train.
2. Don’t count on the Tube when you're out late.
London’s subway system stops running just after midnight Monday through Saturday with reduced hours on Sunday, but thousands of buses work the streets at all hours.
3. Your bible is TimeOut.
The authority for LGBT London is the weekly free magazine Time Out, which lists hundreds of LGBT parties, events, shows and venues.
Travel tips
1. Learn your arrondissements.
Paris is organized into 20 districts called arrondissements, starting with the first (1er) in the city center, and spiraling out in a clockwise fashion. Le Marais is made up of parts of the 3e and 4e arrondissements.
2. Find the artsy areas.
What would Paris be without its artists and their ‘hoods? But the areas you’ve heard about being artsy -- Montmartre, Montparnasse and Le Marais -- have long since evolved into expensive neighborhoods. Now you need to go to the 11th arrondissement, a blue-collar neighborhood between Le Marais, Menilmontant and Republique.
3. Hotel rooms can be had in summer.
Most travelers who have never even been to Paris have heard that July and August is the worst time to visit since Parisians vacate the place and businesses can be closed. Still, it’s when most Americans visit. You will be able to find hotel rooms during this time since French visitors and major conventions are both absent. Just keep in mind that budget hotels can be booked up with students on holiday, and most Parisian hotels don’t have air conditioning if a heat wave hits.
Travel tips
1. Choose your lodging based on your interests.
If you want to experience the best in queer nightlife, choose Hell’s Kitchen. If you're into theater, stay in Times Square. If you’re into the city’s vibrant African-American community, stay in Harlem. If you prefer the grungy, artsy scene, choose the Lower East Side.
2. Prepare to wait in line.
It’s a good thing there are Ubers, taxis and NYC’s magnificent subway system to zip you around the boroughs in no time because once you arrive at your destination
you will probably have to stand in a line. Whether it’s for a Broadway show, a museum exhibition or an ice cream cone, New Yorkers wait and wait and wait for everything and so will you.
3. Add on Fire Island.
During the season on Fire Island (roughly May to September), you can feel like a real New Yorker by joining in on the lively beach scene here. Of the two main LGBT enclaves on the island, The Pines is more male and exclusive; Cherry Grove is more lesbian and democratic. There are a handful of lodging options on the island, including The Grove Hotel and the Belvedere Guest House in Cherry Grove. Just book early!
Travel tips
1. Avoid traffic by not driving.
If you’re staying on the Strip, which a majority of travelers do, you don’t need a car (and in fact some resorts have begun charging for parking). The Strip has an easy-to-use monorail system on its east side and just walking the larger-than-life boulevard is an experience in itself.
2. Get hitched.
Vegas still makes for the classic wedding destination both quickie and planned and same-sex couples are lining up to take advantage. From the smaller, campy chapels on the
northern part of the Strip to opulent venues overlooking the Bellagio fountains, Sin City is still the place to proclaim ‘I do.’
3. Vegas can be cold.
Although summers are brutally hot (although a summer pool party is not to be missed), winters can be downright chilly. Hotels close their outdoor pools, and it’s been known to snow on the Strip! Pack at least a light jacket between November and February and you’ll be just fine.
Travel tips
1. Consider the trains—all of them.
Amtrak's high-speed train, the Acela, travels from D.C. to New York in under three hours (when it’s not delayed). It can be a lot less of a hassle than flying. Meanwhile, the city’s subway system—the Metro, is fast, efficient and reliable. Take it everywhere.
2. Visit during the quieter congressional recesses.
Lawmakers break for Thanksgiving, Christmas, Easter, July 4 and the entire month of August. Mid-March through June is the busiest time in D.C., as it’s springtime when the cherry blossoms are in bloom along the Potomac. Hot and sticky August can have cheaper hotel rates as well.
3. The tourism board gives good info.
D.C. has a very gay-positive tourism board; go to washington.org/lgbt.
Travel tips
1. You don’t need a car.
BART (Bay Area Rapid Transit) trains link the San Francisco and Oakland airports to the city. Most San Franciscans don’t even own cars, and instead get around via biking, riding the bus (MUNI) and walking, aka their BMW (bike, MUNI, walk).
2. Autumn is summer in the city.
First-timers can be shocked at how chilly San Francisco gets in the winter and even in early summer. The nicest weather is in September and early October, a time to hit the area’s beaches and explore the outdoors. But it’s a good idea to pack a jacket any time of year.
3. Weather can be very specific to what part of town you stay in.
The Avenues (the westernmost parts of San Francisco) are known to be foggy even if the rest of the city is sunny, while neighborhoods south and east of Twin Peaks can be warmer. Pack in layers and prepare to add and remove accordingly.
Travel tips
1. 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 to hang out in a lounge and sip a drink while gazing over the city and lake.
2. Visit in summer and fall.
The city is notoriously frigid in winter and springtime is usually disappointingly cold. Meanwhile, Chicagoans tend to enjoy each summer day like it’s their last on earth and September and early October are gorgeous times to visit.
3. 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.
London LGBT Events
Long-running BFI Flare (bfiflare.org.uk) is London’s LGBT film festival. It turned 30 in 2016 and continues to be a must-do cultural event for queer cinephiles. Spread out over 10 days each spring, the festival attracts more than 25,000 gay and lesbian culture vultures.
Still the biggest rainbow-drenched affair in the entire U.K., London Pride (prideinlondon.org) attracts hundreds of thousands of revelers to the capital city for a full two weeks of parties, social events, family-friendly gatherings, activist meet ups and more. Oh, and there might be a giant parade at the end of all of it!
Not content on just one annual Pride celebration, the queer community heats up January with Winter Pride U.K. (winterprideuk.com), a night of culture and clubbing that extends into the wee hours. Think summer Pride but with less Speedos and more winter coats.
New York City LGBT Events
Just about every American city has a Pride weekend worth checking out, but none is quite so exhilarating as NYC Pride (nycpride.org) . Pride Week boasts a ton of community and nightlife events happening all over town, but it’s the thrilling Pride Parade, which winds down Fifth Avenue and through the Village, that reminds us all of why New York is the world’s great gay mecca.
Village Halloween Parade (halloween-nyc.com). New Yorkers love their uninhibited side and they’re going to show it off in front of thousands cold weather be damned. This long-running parade marches through the village every Halloween and brings in the costumed by the tens of thousands. The parade itself is a sight to behold, but so is just about everybody else.
If you’re lamenting the mainstreaming of queer cinema, look no further than Mix NYC (mixnyc.org), an experimental LGBT film festival which has been going strong since the 80s and has served as a launching pad for emerging talent such as Todd Haynes, Miranda July and Christine Vachon.
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