Second City

#1 most popular of 370 nightlife and entertainment options in Chicago

Dina10 writes, "My boyfriend and i went to check out this show at The Second City e.t.c stage in August…" »

VA_traveler writes, "The Second City" is a Chicago original, and has given a start to numerous comedic…" »

Green Mill

#2 most popular of 370 nightlife and entertainment options in Chicago

cary_c9 writes, "The Green Mill, the oldest continuously running jazz club in the US and possibly the…" »

supercat writes, "The Green Mill is a classic cocktail lounge. Its sign, done up in lights, and swanky…" »

Metro

#4 most popular of 370 nightlife and entertainment options in Chicago

FlyAwayGirl writes, "The Metro is the most famous rock venue in the City by the Lake. After more than…" »

watermelonsugar writes, "I've known these guys for a few years now and have been taking their pictures…" »

Symphony Center-Chicago Symphony Orchestra

#6 most popular of 370 nightlife and entertainment options in Chicago

Iono writes, "The Chicago Symphony Orchestra is easily one of the best orchestras in the whole world. Add to that, the history of the orchestra and it's legendary brass power, this orchestra is truly something…" »

B.L.U.E.S.

#7 most popular of 370 nightlife and entertainment options in Chicago

MsMaryMack writes, "If you want to experience Chicago blues like the locals do, this is the bar to do it. Located on Halstead in Lincoln Park, it's a bit of a ride if you're staying on Magnificent Mile. It's…" »

Neo-Futurist Theater

#8 most popular of 370 nightlife and entertainment options in Chicago

Local Secrets writes, "Local and national industry media continually praise the Neo-Futurist Theater for its one-of-a-kind performances." The shows are popular, and they don't take reservations, so "locals line…" »

Pops for Champagne

#9 most popular of 370 nightlife and entertainment options in Chicago

retro210 writes, "I heard about Pop's from my brother-in-law, who is very hip, cool and gay. As soon as we walked in they advised us of the $10 cover charge and asked if we wanted to wait for a table (this is…" »

Cubby Bear

#11 most popular of 370 nightlife and entertainment options in Chicago

GB from Devizes writes, "This large sports bar is to be found on 1059 W. Addison St. and was to be the…" »

awehrum writes, "If you're ever in Wrigleyville for a Cubs game, the day's not over until you hit the…" »

House of Blues

#12 most popular of 370 nightlife and entertainment options in Chicago

GB from Devizes writes, "The House of Blues is one of the premier clubs in Chicago although all genres…" »

Pug writes, "“Well, this is a neat bit of packaging,” I observed as we stepped into the House of Blues.…" »

Vic

#16 most popular of 370 nightlife and entertainment options in Chicago

lauramk writes, "This place is a great place for a first date. It is silly and pitchers of beer are…" »

asilvers writes, "Remember the social feeling you had when you saw Rocky Horror Picture Show? Imagine…" »