Chicago is one of those cities that is most talked about for its daytime beauty. Many tourists flock to the Windy City to take in the architectural wonders and take advantage of its booming restaurant scene. While its sunny sights are undeniably unique, Chicago’s nightlife is pretty booming. Although there are plenty of things to do at night in Chicago, some deserve a shout out more than others.
I spent nearly seven years living in Chicago, and I still yearn for it on a daily basis. Why? Because there’s literally always something to do. Whether you’re interested in taking in the sights from above or chilling out in one of the city’s most well-known jazz clubs, there’s never a shortage of things to do at night in Chicago. Here are my favorites.
Get your freak on at Carnivale
For those who’ve never been to Brazil to celebrate the country’s biggest party, this restaurant will give you a taste of the energy. The vibrant West Loop eatery is a bit of a party no matter the time of day. Its swanky interior is incredibly inviting, although its the food that continues to bring people back time and time again. Pop in for a brunch with your girlfriends, a romantic dinner or a few post-work cocktails. If you’re a fan of South American, Caribbean and/or Spanish fare, this place should definitely be at the top of your Chicago bucket list.
Order a pie in the sky atop The Skydeck
It’s no secret that Chicago’s deliciously bizarre pizza is a foodie phenomenon. While I personally feel as though the Chicago vs. New York slice debate is baseless and trite, the battle between the two somehow still trudges on. At any rate, you can literally eat the Windy City’s most famous meal on the 103rd floor of the Willis Tower – or Sears Tower if you’re like me and refuse to call it anything different. The Skydeck offers some of the best views in town, so why not get a glimpse of the city below while noshing on a piping hot Giordano’s pie at the same time?
Step back in time at The Green Mill
Chicago’s history is steeped in political drama full of scandalous characters and jazz tunes; a notion that still lives on to this day. One of the more famous guys from the bunch is Al Capone, the notorious Prohibition-era American gangster. Aside from racketeering and overseeing a multi-million organized crime operation, one of Capone’s favorite past times was frequenting jazz clubs. The mobster took a liking to The Green Mill; his regular booth is still within the establishment. It’s tucked away out of sight from the front and end entrances, ideal for a man who was consistently running from the law.
The late night jazz joint is a favorite among night owl locals and tourists alike; it’s certainly one of my favorite things to do at night in Chicago.
Take it all in at The Signature Room
Those of you with exquisite taste and a thirst for tasty cocktails with the city’s best viewpoint, look no further. The floor-to-ceiling windows and swanky atmosphere will impress just about anyone. Although the food menu is a bit on the pricier side, those who want to experience the panoramic view can enjoy a fancy cocktail for a fraction of the price within The Signature Lounge. The views are not limited to the restaurant and lounges. The women’s bathroom is said to have the best lookout in the building, if not the entire city.
Sip a cocktail at a speakeasy
Chicago’s iconic speakeasies, once run by mob gangsters, have morphed in a big way. No longer are people carrying around martinis made of bathtub gin; the modern establishments are a cut above the rest. While there are certainly plenty of options to choose from, I’d say one of my all-time favorite things to do at night in Chicago is chill inside The Violet Hour. The staff encourages patrons to respect the notion that there were no smartphones during the Prohibition-era, which makes for a night of genuine and uninterrupted conversation. The interior is whimsy but classy, so remember to dress accordingly.
Protip: If you’re trying to look for the Violet Hour entrance, it is located across the street from Big Star Taco on Damen Avenue in Wicker Park. The door will be hidden with unique street art.
Get your boogie on at one of the many live shows
Chicago is chalk full of rich musical history; many contributions were made particularly to jazz and the blues. Despite the fact each of the community areas offer their own unique vibes, it’s almost guaranteed you’ll find some sort of blues or jazz club in just about any neighborhood.
Those of you on the hunt to dance should check out Low Spark every Thursday at AliveOne in Lincoln Park. The show is free, the music is funky and the atmosphere is unmatched. If you’re really feelin’ it afterward, head across the street to the legendary Kingston Mines after to watch some of the city’s finest musicians throw down.
Of all the things to do on the list, this one makes me miss the city the most. AliveOne and Kingston Mines were my regular hangouts throughout college, and it actually sort of makes my heart hurt to look at the pictures. Swing through either one – you won’t regret it.
Take in a free view of the skyline from my favorite spot
While the aforementioned activities might not break the bank, I wanted to throw in this gem for good measure. Start your peaceful stroll at the head of the Museum Campus trail and make your way to the back of the Shedd Aquarium. You’re welcome.
There’s something really special about this viewpoint as it holds a lot of great memories for me. It’s a place never mentioned in the tour guides, but it’s a lovely way to get some exercise and appreciate one of the best cities in the entire world.
Simply walk through The Loop at night
This is something I didn’t take advantage of once I moved out of The Loop. Regardless of this, each time I walked through Chicago’s beautiful downtown, I was taken aback by its beauty. My suggestion is to take the el train to State and Lake and continue north along State Street until you get to the bridge. It’s truly a sight to behold, and you’ll encounter some classic sights along the way.
Is there anything I missed? Let me know in the comments below!