16. Kingston Mines
City: Chicago, IL
Category: Nightlife
Telephone: (773) 477-4646
Address: 2548 N. Halsted St.
Description: Low-key and a bit gritty, it doesn’t much matter. It’s the high-quality nonstop blues seven nights a week on two stages that brings the masses to this Lincoln Park standard that’s been hitting the right note since it opened more than 40 years ago. Look for the long orange awnings that span the block, and feel free to make this your dinner destination too, because the wings and rib tips or any other Cajun specialties from in-house Doc’s Rib Joint (order at the window and take it back to your table) do just fine. Cover $5 to 15; free for college students and faculty Sun through Thurs with ID and $10 for them on weekends. Sun two-for-one admission deal with B.L.U.E.S. Open nightly.
17. New Checkerboard Lounge For Blues ‘N’ Jazz
City: Chicago, IL
Category: Nightlife
Telephone: (773) 684-1472
Address: 5201 S. Harper Ave.
Description: Originally a Bronzeville institution, this got new digs when the club’s building began falling apart and the city forced it to close. Happily for fans, it found a new home in Hyde Park, in a large space that’s convenient for University of Chicago locals too. Cover charge $3 to $10. Open nightly.
18. Rosa’s Lounge
City: Chicago, IL
Category: Nightlife
Telephone: (773) 342-0452
Address: 3420 W. Armitage Ave.
Description: It’s not very easy to get to, but that’s why people love Rosa’s, a dark, dive-y bar with killer drinks (read: strong) and even better bands. Regular performers include soul-blues singer Vance Kelly and Mississippi transplant Melvin Taylor. Italian immigrant owners Tony Mangiullo and his mom Rosa add a personal touch to the place, earning them their self-described subtitle as “Chicago’s friendliest blues lounge.” Cover $5 to $15. Open Tues, Thurs, Fri, and Sat; closed Sun, Mon, and Wed.
City: Chicago, IL
Category: Nightlife
Address: 4830 N. Broadway
City: Chicago, IL
Category: Nightlife
Address: 929 W. Belmont Ave.
City: Chicago, IL
Category: Nightlife
Address: 3541 N. Clark St.
City: Chicago, IL
Category: Nightlife
Address: 1616 N. Wells St.
23. Zanies
City: Chicago, IL
Category: Nightlife
Telephone: (312) 337-4027
Address: 1548 N. Wells St.
Description: Don’t blame us if your sides hurt when you leave a show at this standup comedy club. Why? Performers like Chelsea Peretti (writer for Parks and Recreation), Kyle Kinane, Dwayne Kennedy, Karen Rontowski, and Gilbert Gottfried, that’s why. Tickets from $10. Two-item (food or drink) minimum per person. Get $5 off your ticket and a discounted meal with a dinner and a show deal. Performances nightly.
24. 8 Fifty 8
City: Chicago, IL
Category: Nightlife
Telephone: (312) 455-2776
Address: 858 W. Lake St.
Description: Alongside the El tracks in the West Loop runs a velvet rope with tight-skirted women and shiny-shoed guys making their way into this hopping nightclub. With a modern-gilded look—thick, swirly gold frames around liquor shelves, glittery chandeliers—its DJ range includes Top 40s, dance, rock, house. With more-than-average seating options, you’re welcome to sit pretty with your cocktail or do your thing on the dance floor. Everyone’s considered a VIP here, and you can check in online to thwart the cover charge. No cover before 11 p.m.; $5 to $20 after that. Open Fri and Sat.
City: Chicago, IL
Category: Nightlife
Address: 632 N. Dearborn St.
26. Lasalle Power Co.
City: Chicago, IL
Category: Nightlife
Telephone: (312) 661-1122
Address: 500 N. LaSalle St.
Description: Depending on when you go, this cavernous club could be a cool happy-hour hang, a fancied-up bar-food dinner spot or a crazy dance party palace. Three levels dole out different scenes, the first two pump it up with a diet of danceable DJ-spun house, rock, pop, and Top 40 tunes; the third floor gets wild with live local (and occasional national) alt-rock bands on a professional stage. Besides music, LPC takes its decor seriously with framed rock concert photos and plastered concert bills, faux-vintage wallpaper, long buttoned-leather banquettes, and various chandeliers and globe lighting. No cover. Open Thurs through Sat nights.
City: Chicago, IL
Category: Nightlife
Address: 306 N. Halsted St.
City: Chicago, IL
Category: Nightlife
Address: 2350 N. Clark St.
29. Spybar
City: Chicago, IL
Category: Nightlife
Telephone: (312) 337-2191
Address: 646 N. Franklin St.
Insider Pick:
Description: No need to fly to Miami—the partying is just as hot right here at this below-street-level River North dance club. Globally and locally renowned DJs spin house on Friday and Saturday, Latin on Sunday, and the “I Heart Thursdays” mainstream mix on Thursday, while a young crowd swarms the dance floor (the later it is, the more packed it gets). Bottle service is a smart option for groups to secure a seat (and for guys who like to impress the girls), and there are two VIP booths, one near the main floor and one tucked off to the side for more intimate mingling. Hey slouchers, there is a dress code, so leave your gym shoes, flip-flops, and baggy clothes behind. Cover $20. Open Mon, and Wed through Sun from 10 p.m. to 4 a.m.; closed Tues.
30. Berlin
City: Chicago, IL
Category: Nightlife
Telephone: (773) 348-4975
Address: 954 W. Belmont Ave.
Insider Pick:
Description: Pasties, black eyeliner, feather boas, glitter—and that’s just the guys at this raucous Lakeview favorite. It’s a hot, sweaty memorable mashup of gay, straight, transsexual, black, white, and those who just like to experiment. The throngs come out for top-notch DJ-ing of avant-garde and alternative music and for theme nights like Madonna-Rama every first Sunday, ’80s night the second Sunday, and Disco Obsession the last Wednesday. Cover $3 to $7 and higher for special events. Open till 4 a.m. (5 a.m. on Sat), it just gets crazier as the night goes on. Open Tues through Sun; closed Mon.