We always say that Chicago is like that midwestern friend who is quiet at first but gets rowdy quickly. Once they open up, nothing will ever be the same. Sure, the windy city has a lot of must-see sights that everyone wants to see. But it’s the little things that make this city worthwhile. From the special movie screenings on the beach to dancing all night until the sun rises, experience the windy city like it deserves. Here are the best things to do in Chicago if you’re here one night or forever.
1. Divvy on the Chicago Lakefront Path
One thing in Chicago people rave about is how walkable and bikeable the city is. If you want gorgeous views, head straight to the Chicago Lakefront Trail. The 18.5-mile-long partial shared-use path for walking, jogging, skateboarding, and cycling is located along the western shore of Lake Michigan.
2. Listen to music at the Salt Shed
Maybe you’ve heard of the old Morton Salt Factory along the riverfront in the Chicago history books. Well, the iconic building has now been converted into the Salt Shed. The skyline-backed indoor/outdoor music venue has a wide range of artists performing, as well as local vendors, retail operations, bars, indoor markets, and festival pop-ups.
3. Tilt over at 360 Chicago
When you enter the Willis Tower, you must take a thrilling 42-second elevator ride to get to 360 CHICAGO. However, you will find yourself at a gorgeous 18-seat bar complete with mirrored ceilings and expansive floor-to-ceiling windows for optimal city views—or opt for ledge seating for an ‘on the edge of your seat’ feel.
4. Explore a stunning garden
There are numerous gardens in Chicago to explore, so we wanted to highlight our favorite. Originally part of a Victorian Garden, the Alfred Caldwell Lily Pool is situated on the edge of Lincoln Park.
Before you enter a lovely, dainty lily pond, you’ll step through a large brass gate and into an overgrown path around an oval ornamental lily pond. As you frolic on the stone path, you’ll hear trees brustling their leaves intertwined with birds singing.
5. Be mesmerized by the Art Institute of Chicago
One thing you must do in this city is visit Chicago’s oldest and largest art museums. The Art Institute of Chicago is undoubtedly one of the city’s most renowned museums.
Since its founding in 1879, the Art Institute of Chicago has flourished. It is home to over 300,000 works of art, including such pieces as American Gothic by Grant Wood, Nighthawks by Edward Hopper, A Sunday on La Grande Jatte by Georges Seurat, as well as rotating exhibitions throughout the year.
6. Sneak into a Chicago speakeasy
When you talk to people about Chicago, they might first mention the vibrant restaurant scene. While there are a ton of well-known places, we like to venture off the hidden path. One of our favorite Chicago speakeasies is a record store by day and cocktail lounge by night. If you enter Dorian’s, you’ll head into a low-lit, cozy lounge that echoes elegance and a lively atmosphere.
7. Walk on the 606
There is the BeltLine, the Highline, and our favorite, the 606. Head over to Wicker Park and enjoy a leisurely walk on Bloomingdale Trail. The 2.7-mile elevated rail trail linear park runs east to west on the northwest side of Chicago and features a chain of street-level parks, scenic look-out points, an observatory, and public art installations.
8. Chow down on a Chicago hotdog with no ketchup
Few foods elicit such a passionate response in the people of Chicago as the hot dog. Go-to stops for a pre-game meal or late-night sanctuaries for the inebriated, hot dog vendors are protected with unwavering loyalty in Chicagoland, and trying one is something you must do if you’re in Chicago!
9. Dine out on the Chicago Riverwalk
We may be miles away from the ocean, but that doesn’t stop Chicagoans from enjoying top-notch waterfront views. From bohemian hideouts by the river to beachy hangouts, the Chicago Riverwalk restaurants are open for outdoor dining. For anyone in Chicago dying for a scenic spot, this is where you should head.
16. Spot Yoko Ono’s Sky Landing
She is most notably known as the woman who broke up the Beatles (joking, she did not.) However, Yoko Ono is a Japanese multimedia artist, and you can check out her first permanent installation in the Americas right here in Chicago. SKY LANDING is an installation celebrating the diverse history of Chicago’s Jackson Park and a symbol of our wishes for peace in the future
10. Jam out to late-night blues
Walking into Kingston Mines emulates a rustic and tangerine-hue spot you would find at a bar off Bourbon Street. This is one of the restaurants with live music in Chicago that you need to stop by to have a night filled with laughing intertwined with galavanting.
Kingston Mines has two stages, with bands alternating between the two, so there is never a moment of silence at this bustling, zestful restaurant. The menu is doused with Southern items, including catfish, ribs, and a crispy chicken sandwich—essential when listening to the blues.
11. Enjoy a band at the Schubas
Chicago has a flourishing music scene—and all the music venues add a chef’s kiss. One of our favorites is a quaint venue housed in an old Schlitz brewery. This is the place to go if you want to hear an upcoming artist, as Schubas showcases a diverse lineup of bands, from indie to jazz.
12. Stay out dancing until dawn
While Chicago isn’t New York or Berlin, there’s no shortage of places with obscure lighting, disco balls, and blaring music. You’ll find it in Chicago’s nightlife if you’re looking for a night that harmonizes dancing and quasi-intoxication. Whether you’re after a bass-dropping-filled night where you can barely hear your friend an inch away or a lowkey lounge, nightclubs are one of the things to do in Chicago for an electric night.
13. Stroll down the scenic Fulton Market
While there are a ton of neighborhoods to visit in Chicago—Fulton Market might be the most bustling. Fulton Market’s abounding charm is the distinctive flavors of entertainment and restaurants, all within a five-minute walk from the other. You should make a day of it—starting underneath the chromatic-oscillating neon sign, which cascades into an array of coveted spots for frolicking around with a savory drink.
14. Sing at a Chicago Karaoke lounge
One of the best things late-night things to do in any city, but especially here, is singing your heart out to a crowd of people or just your close friends. While many karaoke lounges are sprinkled across Chicago to commemorate, our favorites include Sakura, a trendy subterranean located in the heart of Chinatown, and Trader Tod’s, a tropical melody oasis plotted at the tip of Lakeview.
15. Listen to a concert by candlelight
When we say music by candlelight is something magical, we don’t say it lightly. These gorgeous Candlelight concerts in Chicago are truly an experience beyond comparison. The Candlelight series invites everyone to relive some of the greatest works in the jazz, pop, classical genres, and more, from Taylor Swift’s newest Midnight tracks to the best of Rihanna.
16. Belt out laughing at Zanies
Many of the top-tier comedians you hear today rose from the Chicago comedy scene. So you have to grab a ticket to Zanies Comedy Club in Old Town. Comedians such as Jerry Seinfeld started here, and your laughs will echo at this intimate venue in the windy city.
17. Spend a day in Little India
On a 15-block stretch of street and nestled amongst the bustle of the city is a place sometimes called Little India. Filled with packed restaurants, delicious Indian food, and shop windows advertising saris, Little India might be less well known than Chinatown or Greektown, but it’s worth visiting at least once.
18. Check out all the Chicago murals
Last on our list goes out to those who love art. Today, the street art and graffiti scene in the windy city is alive and kicking more than ever before, with new pieces popping up all over the city every week. Some of these are so esteemed that they’ve embedded themselves in the fabric of this city and are now as much part of the identity as its iconic sculptures and landmarks.
19. Sip drinks on an impressive rooftop
This dreamy bar sits squarely atop Hotel Lincoln, and Chicagoans can’t stop talking about it. The J. Parker—named after Linclon’s bodyguard (yikes)—is an ostensibly refreshing spot if you’re trying to impress your friends with unobstructed views of Lincoln Park and Lake Michigan. This is one of Chicago’s rooftop bars that you must come to at least once.
20. Head to a Chicago Festival
With some of the largest music festivals and quaint street festivals—something is going on every weekend whether you’re visiting or a local. Of course, the one that stands out is Lollapalooza, an annual American four-day event in Grant Park featuring trending artists’ hip-hop, techno, and alternative rock performances.