For a city that was only incorporated in 1837, Chicago has grown from its roots as a key shipping port to become one of the world’s financial, commercial, and industrial hubs. A world-class city with amenities to match, Chicago welcomed over 50 million tourists in 2014 alone. In addition to the mainstream attractions, Chicago is home to one of the largest and most thriving LGBT communities in the country. There are so many things to see and do in the Windy City; let me tell you about some of them.


Chicago is home to two of the world’s largest airports: Midway International Airport, located on the city’s southwest side, eight miles from The Loop; and O’Hare International Airport, in northwest Chicago, 17 miles from The Loop. Southwest Airlines offers daily flights between Fort Lauderdale/Hollywood, Fort Myers, Orlando and Tampa and Midway. American, Frontier, Spirit and United Airlines all offer direct flights between Miami, Fort Lauderdale/Hollywood, West Palm Beach, Orlando, Tampa, Sarasota and Fort Myers and O’Hare. All flights are competitively priced and routinely cost less than $200 one-way.


City Suites Hotel is right in the middle of the action in the Boystown neighborhood. All rooms are designed in the Art Deco style and feature mini-fridges, minibars, and separate living areas apart from the bedroom. This cute boutique hotel also offers a fitness center, coffee and tea service, and group rates for local events such as Chicago Pride! (933 W. Belmont Ave., 773-404-3000)

Travel-Chicago_StayThe Willows Hotel is another boutique offering adjacent to Boystown. Their 51 rooms and four suites are decorated in antique French style, and include free warm cookies when you check in and continental breakfast each morning. Check out their Chicago vacation packages at to find out how you can stay here and get the most for your dollar. (555 W. Surf St., 773-528-8400)

Travel-Chicago_Stay2The Guesthouse Hotel is located in the Andersonville neighborhood, just blocks from the multiple LGBT-owned and LGBT-friendly businesses there. This hotel offers rooms for short trips and suites for longer stays, and includes boutique shopping, an in-house grocery, and a luxurious spa that also offers in-room massages! (4872 N. Clark St., 773-564-9568)

River Hotel is an option that will satisfy anyone who wants to be in downtown; it is just a one-minute walk to Michigan Avenue and the Chicago River. Go to the concierge and ask him what you should see while exploring downtown. When you return, enjoy free unlimited bottled water compliments of the hotel, and plan your next move on one of their iPads, free for hotel guests to use. (75 E. Wacker Dr., 312-777-0990)


Travel-Chicago_PlayMost of Chicago’s LGBT-friendly venues are located five miles north of downtown, on the North Side in the Lake View community, which is home to the Boystown and North Halsted neighborhoods. Boystown is one of the largest LGBT neighborhoods in the United States. North of Chicago is Edgewater, where the Andersonville neighborhood is located. Andersonville is another booming area, where many LGBT people live and work.

A few yearly events that may interest you as a traveler include:

  • International Mr. Leather, presented every May (;
  • Chicago Pride, held during the third week of June (;
  • Northalsted Market Days, a massive street festival held every August in the North Halsted neighborhood (;
  • the AIDS Walk Chicago, coming up on September 26 (;
  • and the Chicago LGBTQ+ International Film Festival, which just wrapped up its 33rd successful year this past week (September 17-24;

Some of the bars and nightclubs located in Boystown include 3160 (3160 N. Clark St.), a Travel-Chicago_Play3well-known piano and cabaret bar; Berlin (954 W. Belmont Ave.), which offers fabulous drag shows and music from the some of the hottest local and nationally-known DJs; Bobby Loves (3729 N. Halsted St.), a bar with a laid-back atmosphere and karaoke every Friday and Saturday night; The Cell Block (3702 N. Halsted St.), Chicago’s premier Levi/leather bar, featuring “gear nights” every first Saturday of the month; Charlie’s Chicago (3726 N. Broadway St.), a country-themed dance bar which is open until 5 a.m. on Saturdays; Circuit Night Club (3641 N. Halsted St.), a dance club with drag shows that is a hot spot for the Hispanic community; DS Tequila Company (3352 N. Halsted St.), a local favorite that doubles as a restaurant serving Mexican food and burgers; Elixir Lounge (3452 N. Halsted St.), a sleek bar serving up a lot of signature cocktails (its food companion, Halsted’s Bar and Grill, is located close by at 3441 N. Halsted St.); and Hydrate (3458 N. Halsted St.), a dance club featuring entertainment and DJs from all over the world.

Some more bars in Boystown you should visit include Lucky Horseshoe Lounge (3169 N. Travel-Chicago_Play4Halsted St.), a nightclub featuring quite a few sexy go-go dancers; Minibar (3341 N. Halsted St.), a hip nightclub and restaurant combo designed to mimic a hotel lounge; The North End (3733 N. Halsted St.), a sports bar where you don’t have to be a sports fan to make new friends; Progress Bar (3359 N. Halsted St.), the sister bar of Progress Bar South Florida, which prides itself on its great music and even greater customer service; Rehab Lounge (3641 N. Halsted St.); Replay Beer & Bourbon (3439 N. Halsted St.), a place where great drinks and your favorite video games are combined Travel-Chicago_Play6into one fun experience; Roscoe’s Tavern (3356 N. Halsted St.), a dance club featuring nationally-known guests such as Michelle Visage and Jordin Sparks; Scarlet Bar (3320 N. Halsted St.), a venue where dance parties are king and are held multiple nights throughout the week, featuring some hot DJs; Seven Nightclub (3206 N. Halsted St.), a new venue featuring great entertainment and sexy underwear-clad dancers; Sidetrack (3349 N. Halsted St.), an iconic video bar once picked by Logo as one of the top six “Best Gay Bars in the World”; Taverna 750 (750 W. Cornelia Ave.), famous for its martinis, wine selections and Sunday brunches; and The Den Cocktail Bar (800 W. Belmont Ave.), a 1920s/1930s-themed bar with piano and cabaret performances.

Bars and nightclubs in Andersonville include Atmosphere Bar (5355 N. Clark St.), well-known for their drag shows and “stripper bingo” nights; Big Chicks (5024 N. Sheridan Rd.), a bar and restaurant combo that is popular with the men of Andersonville (despite its name); The Granville Anvil (1137 W. Granville Ave.), the oldest currently-operating gay bar in Chicago, cozy and comfortable; Jackhammer (6406 N. Clark St.), a fun nightclub complex, where RuPaul’s girls like Gia Gunn and Monica Beverly Hillz perform; Man’s Country (5017 N. Clark St.), the neighborhood gay bathhouse and sauna; Marty’s Martini Bar (1511 W. Balmoral Ave.); a local favorite that gives back to non-profits and charities on a regular basis; Mary’s Attic (5400 N. Clark St.), where you go for drinking, dancing and karaoke after your meal at the fabulous Hamburger Mary’s (located in the same building); Parlour on Clark (6341 N. Clark St.), catering to live local music acts and the people who love them; The Call (1547 W. Bryn Mawr Ave.), a bar that mixes it up with drag shows, DJs, and showtunes, depending on the day of the week; and The Sofo Tap (4923 N. Clark St.), a welcoming venue that caters to many groups, most notably Travel-Chicago_Play7the bears. Replay Beer & Bourbon and Elixir Lounge, previously mentioned in the Boystown paragraphs, are also opening locations in Andersonville.

Then, in downtown Chicago, the main nightlife venues are The Baton Show Lounge (436 N. Clark St.), a bar you must go to if you love drag (portions of the Continental yearly pageant are held here); Downtown Bar and Lounge (440 N. State St.), a bar and lounge featuring hot beats from DJs Moose and Freddie Bain; and the Second Story Bar (157 E. Ohio St., second floor); a small bar with a lot of heart that serves many who work and play in the downtown area.


Many LGBT travelers may want to start their exploring in Boystown and North Halsted. If so, be sure to stop by the Center on Halsted, which is the largest LGBT community center in the Midwest. They’ll be able to tell you more about this exciting city. This neighborhood is known for its theatre scene: be sure to see a show at the Strawdog Theatre Company, About Face Theatre, The Playground Theater, and the Briar Street Theater. Afterwards, indulge your sweet tooth at Windy City Sweets, one of the largest independent candy stores in the city. If your travels take you to Andersonville, visit the Swedish American Museum and then enjoy all the culinary options available along Clark Street’s “restaurant strip.”

Downtown Chicago is made up of a number of neighborhoods, such as The Loop, South Loop, Chinatown, River North and the Gold Coast. You can’t visit Chicago without admiring the skyscrapers: a walk along the Chicago River is positively dizzying. Willis Tower and the John Hancock Center, both over 1,000 feet high, are two of the tallest buildings in the city, and both offer observation decks with unique views of the metro area (these observation decks are called Travel-Chicago_GoSkydeck Chicago and 360 CHICAGO, respectively). Another can’t-miss icon is Cloud Gate, located in Millennium Park. Affectionately called “The Bean” due to its shape, it has become the place to go to in Chicago if you want a cute selfie to share with your friends.

Afterwards, take a walk down Michigan Avenue and visit the Magnificent Mile, featuring some of the best luxury shopping in North America. The Navy Pier, located on Lake Michigan, celebrates its 100th anniversary next year, and is in the process of going green. Watch the ships leave the Pier, walk around Polk Brothers Park, and enjoy such attractions as the Navy Pier IMAX Theatre and the Chicago Shakespeare Theater.

If you’re looking to explore some museums, Chicago has quite a few of them, ranging from the Chicago Cultural Center to the Museum of Contemporary Art Chicago, the Chicago History Museum, and the Museum of Science and Industry. The Clarke House Museum is Chicago’s oldest house, still preserved in in 1840s style and decor.

Read more about Chicago, including an LGBT visitor’s guide, by going to the Choose Chicago tourism website at