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. Sail on a Chicago Booze Cruise
Save the trip to Michigan, Wisconsin, or another small town near Chicago for another day because, believe it or not, your party lake day awaits you on the Chicago River. Admire breathtaking views with a delicious drink in your hands while you sail the river. From the Sunday Funday cruise to the Chicago architecture cruise, there are numerous booze cruises to have an intoxicatingly good time.
2. Picnic and jam to jazz at the MCA
Every Tuesday through summer, the Museum of Contemporary Art hosts Tuesdays on the Terrace—one of our favorite free things to do in Chicago—a musical event series for Illinois residents. Grab a bottle of wine, make a charcuterie, and head over there at 5:30 because this is one of the best things to do in Chicago for a jubilant evening picnicking while listening to instrumental jazz.
3. Drink a beer bat at Wrigley Field
Of course, a roundup of things to do in Chicago must include catching a game at Wrigley Field. Plotted in the center of Wrigleyville, the ballpark is known for its distinct features, including the ivy-covered brick outfield wall, Lake Michigan wind patterns, the iconic red marquee over the main entrance, and the hand-turned scoreboard.
Even better, as you sing, “Take me out to the ballpark,” you can now raise a beer-filled souvenir bat and maybe practice your swing after the game.
4. 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.
5. Listen to music at the Salt Shed
Maybe you’ve heard of the old Morton Grove Salt Factory along the riverfront in the Chicago history books. Well, now the iconic building has 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.
6. 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.
7. Catch a free movie at any Chicago Park
While there are numerous things to do in Chicago, little compares to attending a movie in a secluded Chicago park. You’ll find an open-air screening almost anywhere, from a lakefront screening to a projector in the middle of a baseball field. So, pack a picnic of your favorite snacks and drinks, keep a cozy blanket on hand, and round up your friends to indulge in the perfect movie night.
8. Watch fireworks downtown
We love it when a dark sky bleeds fluorescent colors, and Chicago is no stranger to this. During the summer, every Wednesday at 9 p.m. and every Saturday at 10 p.m., onlookers can find a spot on the pier or the Chicago waterfront to take in the dazzling fireworks display. It’s one of the best things to do in Chicago if you’re gravitating toward a colorful show.
9. Make a splash at a Chicago Beach
When it’s hot in chicago—it’s hot. Not even a breeze can save us from the humid air that swallows us when we step outside. Luckily, Chicago is cornered by the third-largest lake in the U.S., the quintessential place to cool off and cool down. So, forget the pools and hit one of Chicago’s iconic beaches for an immaculate day.
10. 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.
11. Be memorized 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.
12. 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.
13. 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.
14. 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!
15. 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
17. 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.
18. Catch a White Sox foul ball at Guarantee Rate Field
On the other south of Chicago lies another beloved baseball field, Guarantee Rate Field. If you’re going to Wrigley, you must also check out the White Sox—not many cities can say they have two baseball teams. However, it also offers one of the best things in Chicago, which is every Tuesday, home games have a $5 concessions menu featuring items like 16-ounce draft beers (Miller Lite and Modelo), Vienna Beef Hot Dogs, and Polish Sausages, Beggars Pizza slices, nachos, select Coca-Cola products and Garrett Popcorn Stadium Buttery.
19. 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.
20. Tour of the Chicago River by kayak
While you can explore Chicago by boat, a truly unforgettable thing to do in Chicago is kayaking down the grand Chicago River. Even better, you can watch the sunset and experience the soft golden glow bounce through Chicago’s artificial valleys or watch Art on the MART from the water.
21. 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.
22. 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.
23. 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.
24. 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.
25. 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.
26. 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.
27. 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.
28. 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.
29. 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.
30. Daydream on a rooftop pool
Chicago is one of America’s largest cities, so it better have sprawling skylines and rooftop views. From luxurious hotels to member-only clubs, head to a rooftop pool for dinner or lounging. A notable one is open to the public—head to the Cabana Club on the 6th floor of the art-deco boutique Robery Hotel for a lovely rooftop and poolside experience.
31. Wander the streets of Fulton Market
Fulton Market’s abounding charm is the distinctive flavors of entertainment and menus, all within a five-minute walk from the other. You can 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.