City: Chicago, IL
Category: Nightlife
Address: 5024 N. Sheridan Rd.
City: Chicago, IL
Category: Nightlife
Address: 4804 N. Broadway
33. Downtown Bar & Lounge
City: Chicago, IL
Category: Nightlife
Telephone: (312) 464-1400
Address: 440 N. State St.
Description: Filling a void and far from the cluster of Boystown bars, Downtown puts gay-friendly (though certainly not exclusively so) smack-dab in the middle of River North. Reviving the space that was once the popular gay bar Gentry, this classy joint provides spacious room for sipping signature martinis or a glass of wine after work, or before or after a show at nearby House of Blues or a Loop theater—there’s even a drink called The Goodman (as in, the theater) with Bulleit bourbon, brandied cherries, and sweet vermouth. Open nightly (Mon through Fri from 3 p.m., Sat and Sun from 2 p.m.).
34. Jackhammer
City: Chicago, IL
Category: Nightlife
Telephone: (773) 743-5772
Address: 6406 N. Clark St.
Description: Up at the north end of Andersonville, this 5 a.m. bar is known for its basement-level leather-and-fetish-only space called The Hole (on Friday and Saturday the leather dress code is enforced), where chaps and harnesses, toned muscles, and monthly underwear nights appeal. But it’s an equally deserving destination as a dance club (there’s a disco ball, after all) and neighborhood bar with pool, darts, and Wii and arcade games. DJs spin Wednesday through Monday, while Tuesday is karaoke, and Sunday is open mic night. Never a cover unless it’s a special event, and in that case it’s $5, but includes a drink coupon. Open nightly.
35. Roscoe’s Tavern
City: Chicago, IL
Category: Nightlife
Telephone: (773) 281-3355
Address: 3356 N. Halsted St.
Description: Daily drink specials, DJs spinning danceable beats, friendly bartenders at six bars whirling out drinks at breakneck speed, and shirtless gay men for the ogling make this one of Boystown’s most popular late-night spots. Monday and Wednesday are karaoke nights, Tuesday features drag contests, and the last Thursday of every month brings a twist on the wet T-shirt with the wet boxer contest. Can’t handle the heat? Head out back to the patio. During warm weather, a sidewalk cafe is also open for light meals. Generally no cover. Open daily.
36. Sidetrack
City: Chicago, IL
Category: Nightlife
Telephone: (773) 477-9189
Address: 3349 N. Halsted St.
Description: With its sleek hardwood floors, exposed brick, and sunny multilevel rooftop space, this could be any average club. But it’s in the heart of Boystown, and it’s anything but average. Since opening in 1982 without even a sign outside, it has expanded into more than eight neighboring storefronts, added bars, and become a mainstay of gay-man meet-ups. Where else can you find three nights devoted to show tunes? Fruity liquor-laden slushes fit right in. No cover. Open nightly from 3 p.m. (during the summer from 1 p.m. on Sat and Sun).
37. Empty Bottle
City: Chicago, IL
Category: Nightlife
Telephone: (773) 276-3600
Address: 1035 N. Western Ave.
Description: This Ukrainian Village dive may be dark, sometimes deafening, a bit on the dingy side (yard-sale couches provide seating, bathrooms are graffiti-filled), and sometimes slightly smelly, but music-lovers love it. They come for the friendly atmosphere, the cheap beer—there are exactly two wines by the glass—and music seven nights a week, which changes nightly and ranges from the noise-rock of Jucifer to Cacaw’s minimalist punk to local fun garage-punk-R&B band The Yolks. Wednesday features jazz of all shapes and forms. Cover can be nothing or up to $15. Cash only. Open nightly.
City: Chicago, IL
Category: Nightlife
Address: 1354 W. Wabansia Ave.
39. Lincoln Hall
City: Chicago, IL
Category: Nightlife
Telephone: (773) 525-2501
Address: 2424 N. Lincoln Ave.
Description: The team behind 20-year-old-plus music venue Schubas gets it right again with its younger but bigger sister. Devoted music fans appreciate the open sightlines and loyalty to strong, clear sound. But with decent prices on drinks (about $5 for tap beers, $8 or so for cocktails) and a bona-fide dinner menu—tempura chicken salad, arugula pesto baguette, wild mushroom flatbread—it goes above and beyond. The diverse range of acts has included dance-indie fusion band Delorean, hot new Reggae master Collie Budz, England’s pop-folk star John Wesley Harding, and Danish band the Raveonettes. Reserve a dinner table through their website and you’ll get rock star seating on the balcony an hour before the show. Ticket prices vary, around $10 to $20. Open nightly.
City: Chicago, IL
Category: Nightlife
Address: 3730 N. Clark St.
City: Chicago, IL
Category: Nightlife
Address: 3159 N. Southport Ave.
42. Underground Wonder Bar
City: Chicago, IL
Category: Nightlife
Telephone: (312) 266-7761
Address: 650 N. Dearborn St.
Description: Down in a low-ceilinged, low-maintenance, but decidedly high-energy garden level space, owner Lonie Walker showcases eclectic musical stylings of all varieties. Three nights a week—and nights go on until the early morning here—Walker and her Big Bad Ass Company Band grace the tiny stage too. She has created such a welcoming atmosphere that some of her most enthusiastic regulars are themselves musicians and other club owners. But anyone can join the party. Just take note of the quirky tradition of raising your arms in the air and shouting “Wonder Bar!” whenever prompted. A light menu is offered (call ahead to double-check). Cover $8 to $15. Open from 7 p.m.
43. Andy’s Jazz Club
City: Chicago, IL
Category: Nightlife
Telephone: (312) 642-6805
Address: 11 E. Hubbard St.
Description: Andy’s roots date back to 1951 when it was opened by entrepreneur Andy Rizzuto as a newspaperman’s shot-and-a-beer bar. It changed hands a couple of times and, in 1977, Andy’s hosted a weekly jazz concert. It didn’t take long for jazz to define this River North club. Now Andy’s presents two sessions seven days a week, including a jam session Sunday at 9 p.m. In addition to all styles, from traditional to Afro-pop, Andy’s serves up a decent menu of sandwiches, pizzas, pastas, steak, ribs, and seafood. Cover $5 to $15. Open nightly from 4 p.m. to 1 a.m. Sun through Thurs, and until 1:30 a.m. on Fri and Sat; music starts an hour after opening; kitchen is open from 4:30 p.m.
44. Davenport’s Piano Bar & Cabaret
City: Chicago, IL
Category: Nightlife
Telephone: (773) 278-1830
Address: 1383 N. Milwaukee Ave.
Description: A snazzy atmosphere, baby grand, potent and pricey cocktails, and servers and bartenders who belt out show tunes and lounge favorites. Got an itch to perform? Feel free to request the mic and share your song too—a lot of regulars do just that. The small back-room professional cabaret theater features acts that are often flamboyant, sometimes hysterical, frequently moving, and always top-notch. No cover for the bar except $2 Fri and Sat after 10 p.m. Cabaret prices vary, generally $10 to $20 with two-drink minimum. Open Mon, Wed through Sun; closed Tues.
45. Green Mill
City: Chicago, IL
Category: Nightlife
Telephone: (773) 878-5552
Address: 4802 N. Broadway
Description: Opened in 1907 and during the Roaring Twenties a Prohibition-era speakeasy frequented by Al Capone, the Green Mill is now a standard for jazz sets by local and touring acts. Don’t expect to chit-chat during the show, though, as you’ll likely get shushed by other audience members or the staff. Just sip your drink (no food here), sit back, and have a listen. On Sunday, it’s the popular Uptown Poetry Slam, started here by Marc Smith back in 1985 and the forerunner of the national poetry slam movement. Cover $6 to $12 for all shows. Open nightly.