Fun abounds in Chicago, no matter when you visit Illinois. During the day, you can hit museums, parks, the lakefront, shops and more.
But it’s at night when the Windy City truly lights up. Chicago boasts one of the most robust culinary and bar scenes in the world. The theater is first-rate. The way the city lights up makes it a joy to wander around not one, not two, but three gay ‘hoods.
Here are five great Chicago scenes to check out by night.
1. Chicago’s Club Scene
Let’s be honest, you’re coming to Chicago to party and have fun. What better way than to hit up some of Chicago’s best gay bars and clubs in Boystown, and Andersonville. Cruise the Halsted Street or Clark Street strips before hitting one of these super nightlife spots.
- Sidetrack: The center of gay life in Chicago. The original video bar. This behemoth is a complex of bars drawing up a diverse crowd, serving up world-famous Slushies & known for show tunes nights every Sunday and Monday. The upper deck is a perfect spot for summer night cocktails.
- Roscoe’s Tavern: With five bars and a sweat-inducing dance floor, Roscoe’s is one of Halsted Street’s longest-running bars. Roscoe’s is the spot to catch national drag names and frequent performances from club superstars.
- Berlin: From goths, punks, club kids and queens, this legendary dance club has been a Chicago mainstay for over 30 years. Dance until the sun comes up on weekends.
- Hydrate: High-energy dance club with special drag performances on Mondays and Wednesdays. Open late on Saturdays.
- Progress Bar: With its stunning lightbulb sculpture and great drink specials, Progress Bar offers a diverse and trendy crowd in the heart of Boystown.
- Scarlett: With a young, hip crowd, this vintage-inspired gay bar features one of the hottest dance floors in Boystown.
- The Jackhammer Complex: Catering to the fetish crowd. Mostly men gather for drinks, dancing, and fun down in “The Hole.” Open late on Saturdays.
- Charlie’s: Boystown’s classic country/western hotspot, transforming into a high-energy dance club after-hours.
2. Drinks and More About Town
Looking for drinks and something more? Chicago has you covered.
- The Baton Show Lounge: World-class female impersonation since 1969. A jewel of Chicago’s downtown gay scene.
- Kit Kat Lounge & Supper Club: Popular spot for an extensive Martini menu and drag performances.
- Elixir Lounge Boystown & Andersonville: Chicago’s premier lounge with two locations. An ideal spot for cocktails, conversation & small plate dining.
- Lucky Horseshoe: Boystown’s favorite spot for male dancers.
- Marty’s Martini Bar: There are martinis, and then there are Marty’s XL martinis. The crowd in the upscale lounge is as well mixed and lovely as the drinks.
- Replay Lakeview & Andersonville: Classic arcade games and a wide whiskey selection at these Chicago playgrounds. The Andersonville location also features a full menu for lunch or dinner.
3. Nighttime Views
Chicago has one of the best skylines in the world. Check out some amazing views at these Chicago hot spots:
- LH Rooftop at LondonHouse Chicago: A truly one-of-a-kind experience along the Chicago River. Enjoy re-imagined American cocktails and take in a view of the city like no other.
- Bar 94 at 360 Chicago: At 1,000 ft. up, Bar 94 offers a memorable and sensorial experience, with unbeatable views of Chicago’s skyline and locally produced beers and spirits. Bar 94 is all about Chicago at its best.
- IO Godfrey: Skyline views, indoor/outdoor rooftop bar, chef cocktails and upscale bar fare located at The Godfrey Hotel Chicago.
- Cindy’s Rooftop: Located at the Chicago Athletic Association Hotel, eat and drink with a stunning view overlooking Millennium Park, Lake Michigan and the Art Institute of Chicago.
- Chicago Helicopter Experience: If you just want to take in the city for all its beauty, book an evening flight and see the entire city lights sparkle before your eyes.
4. Theater & Comedy
Chicago has one of the best theater and comedy scenes in the country. Be sure to catch one of these shows:
- Broadway in Chicago: Chicago’s theater scene features some of the biggest and the best from Broadway. From Hamilton to the upcoming global premiere of The Cher Show, be sure to see an exciting show in Chicago’s bustling downtown Theater District.
- Chicago Shakespeare Theater: Located on Chicago’s famous Navy Pier, see some of the best of Shakespeare from this leading international theater company and recipient of the Regional Theatre Tony Award.
- Steppenwolf Theatre: Winner of National Medal of Arts and 12 Tony Awards, check out a performance from the nation’s premier ensemble theater.
- Joffrey Ballet: Chicago’s world-class ballet company presents a unique repertoire of masterpieces of the past and cutting-edge works.
- Second City: The comedy club and theater, Second City offers popular sketch shows every night of the week.
5. Late Night Eats
After a busy night on the town, you’re going to need something to satisfy those nocturnal cravings.
Here are some great places to eat late in Chicago:
- Au Cheval: One of the best burgers in the city, but the chilaquiles are another late night special—piled high with chips, salsa verde, scrambled eggs, queso fresco, and more.
- Big Star: Tacos inspired by authentic Mexican street food served at a defunct 1940s gas station with a soundtrack of classic country and rock & roll. What more could you want?
- Chicago’s Pizza: Chicago-style deep dish pizza served until 3:00 a.m. Enough said.
- The Wiener’s Circle: Famously surly staffers serve char dogs, hamburgers, polish sausages, and cheese fries at this tiny Chicago institution that’s open late.
Photos provided by respective businesses