5 thrilling ways to enjoy Chicago’s nightlife

Exploring Chi-town after the sun goes down

Hotel Deals for Lisle
Hilton Lisle/Naperville
IL, USA
Nov 19 - Nov 19, 2017
per night from
$ 104.13
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Days in Chicago can be amazing, fun-filled adventures. Take a morning stroll along Lake Michigan, enjoy lunch (or a dose of retail therapy, if you prefer) along the Magnificent Mile, and spend the afternoon at the attractions near Navy Pier. When the sun sets on Chicagoland, though, the city comes to life in a completely different way. Here are some of our favorite things that make the nighttime the right time to experience Chicago.

1. Comedy clubs

Flickr via star5112

Maybe (we said, “maybe”) even more renowned than the deep-dish pizza and neon-relished hot dogs, comedy is king in Chicago. Improvisation troupes like Second City and stand-up clubs such as the Laugh Factory and Zanies have produced a laughable number of the entertainment industry’s most popular comedic minds. Stop by for a chuckle and a howl; who knows, you might be lucky enough to see America’s next big up-and-coming comic.

2. Rooftop bars

Flickr via Nicole Yeary

For a different perspective of Chicago’s nighttime skylight, head up…way up. Rooftop bars take your evening to a new level altogether. The 9,000 square feet of Streeterville Social (Chicago’s largest rooftop terrace) has a grassy lawn for a game of giant Jenga, while nearby Cerise offers a funky, hip, upscale way to dance the night away 26 floors above the city streets.

3. Night games

Flickr via Mr Hicks46

Day games may be a tradition at Wrigley Field, but when the lights come on for a night game, the atmosphere gets even more…frenzied. If the Cubbies aren’t in town, head to the South Side to catch the White Sox in action. Can’t get into the swing of baseball? Then check out the Blackhawks of the NHL or the NBA’s Bulls at the United Center. Be sure to take a selfie by the statue of His Airness, Michael Jordan, out front.

4. Music venues

Flickr via subbu arumugam

Every memorable night out needs a great soundtrack, and Chicago has some iconic live music venues where you can take in a show that you won’t soon forget. You’ll never know who is going to take the stage at intimate rock clubs like the Hideout and Double Door, where bands like the Rolling Stones, Foo Fighters, and Smashing Pumpkins have made secret, impromptu performances. When blues acts come through the Windy City, they pour their souls out to the crowd at spots like Buddy Guy’s Legends and Blue Chicago.

5. Craft beer scene

Goose Island IPA helped put Chicago craft beer on the map, but there are so many other local brewers perfecting their art that should not go unnoticed. Get over to the Ravenswood neighborhood and sip your way through your own personal beer tour. Sample a lager at Dovetail, a blonde ale at Begyle, a pink-peppercorn-infused pint at Band of Bohemia, and a ginger wheat at Empirical. Just make sure to call a cab when it’s time to head back to your hotel.


What are your favorite nightlife hotspots in Chicago?

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Hotel Deals for Lisle
Hilton Lisle/Naperville
IL, USA
Nov 19 - Nov 19, 2017
per night from
$ 104.13
$ 62.48

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