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Chicago
Debonair Social Club is one of Chicago.

1. Debonair Social Club

7.2
1575 N Milwaukee Ave (at W North Ave), Chicago, IL
Night Club · Wicker Park · 29 tips and reviews

IFCIFC: Chicago: Old timey gentleman's club meets young, clubby arts scene in Wicker Park's historic flat iron building. We hear Monday nights here are the best. -IFC Viewer

The Hideout is one of Chicago.

2. The Hideout

8.8
1354 W Wabansia Ave (btwn Elston Ave & Throop St), Chicago, IL
Rock Club · 57 tips and reviews

IFCIFC: Chicago: "It's a regular guy bar for irregular folks who just don’t fit in, or just don’t want to fit in. It is the bar that Granddad went to when he was young and crazy" -IFC Staff Read more.

The Second City is one of Chicago.

3. The Second City

9.3
1616 N Wells St (btwn Concord Ln & North Ave), Chicago, IL
Comedy Club · Old Town Triangle · 150 tips and reviews

IFCIFC: Chicago: A training ground for the likes of Tina Fey, Amy Poehler, Steve Carell and others, this legendary comedy club now boasts -IFC Staff

Gene Siskel Film Center is one of Chicago.

4. Gene Siskel Film Center

8.8
164 N State St (btwn Lake & Randolph), Chicago, IL
Indie Movie Theater · The Loop · 32 tips and reviews

IFCIFC: Chicago: 2 Thumbs Up! Enjoy the best of independent, international and classic cinema at the Gene Siskell Film Center with a side of great film exhibits and treats at the gallery and café. -IFC Viewer Read more.

Green Mill Cocktail Lounge is one of Chicago.

5. Green Mill Cocktail Lounge

8.9
4802 N Broadway St (at W Lawrence Ave), Chicago, IL
Jazz and Blues Venue · Uptown · 136 tips and reviews

Explore ChicagoExplore Chicago: This Chicago landmark presents jazz nightly, from traditional to experimental, amid a "speakeasyesque" décor. Read more.

Music Box Theatre is one of Chicago.

6. Music Box Theatre

9.4
3733 N Southport Ave (btwn Grace St & Waveland Ave), Chicago, IL
Indie Movie Theater · Lakeview · 88 tips and reviews

Explore ChicagoExplore Chicago: The Music Box plays a mix of independent and foreign films, as well as classic (black and white) movie matinees, and midnight screenings of cult classics. Read more.

Homeslice Pizza + Patio is one of Chicago.

7. Homeslice Pizza + Patio

9.1
938 W Webster Ave (at Bissell St), Chicago, IL
Pizzeria · North Side · 84 tips and reviews