Unique things to do in Chicago
Chicago has no shortage of famous sights, but some of the best places in the city are the ones that locals return to again and again. From neighborhood favorites to lesser-known attractions, we asked Chicagoans to share the unique things they think everyone should experience. Whether you’re new in town, looking at houses in Chicagoor have called it home for years, there’s probably something you haven’t tried yet.
1. Stop by the Art Institute of Chicago
If you are interested in history and art, spend an afternoon at the Art Institute of Chicago. The museum houses one of the largest permanent art collections in the country, offering everything from centuries-old masterpieces to modern works.
Martin, a local Chicagoan from SmartMoneyMatcha network that connects the global investment community, recommends the Art Institute of Chicago when the weather is terrible. “It’s always worth a visit. It’s filled with masterpieces from every era, from Georges Seurat’s iconic painting, A Sunday on La Grande Jatte, to Andy Warhol’s print of actress Elizabeth Taylor.”
2. Visit Chicago’s natural areas
In the summer, Chicago becomes a playground for all residents and visitors. From the parks and waterways you will find a place to enjoy nature.
“One of Chicago’s best-kept secrets is spending an afternoon exploring the lakefront, outside the typical tourist spots. Walk through the peaceful Alfred Caldwell Lily Pool, take in the skyline from North Avenue Beach, then head to Belmont Harbor to watch the sailboats come in at sunset,” Crystal Tran shares. “For a truly local experience, explore neighborhoods like Andersonville, Ravenswood or Pilsen where you’ll find great restaurants, independent shops, public art and the authentic character that makes Chicago so special.”
Chicagoan Jane Simon Ammeson agrees about Chicago’s outdoor beauty. “Rivers used to be the highways, but the Chicago River offers unique modern adventures for me. I can paddle across the water and shudder at scary stories during a Ghost and gangster kayak tourand sip a Spanish Rioja while gazing at the city lights. I love walking along the Riverwalk, choosing a favorite spot for dinner and planning my next adventure as I watch the boats go by.”
In addition to the city’s unique layout, Chicago’s walkability makes seeing your favorite places much easier. “Because of my job, I often get up before most people are awake, getting ready for a photo shoot to capture the first light of the day. One of my favorite places to watch Chicago wake up is all along the lakefront, from Rogers Park all the way south to Promontory Point, where the sun rises over Lake Michigan and lights up the skyline, and runners, cyclists and dog walkers.” Matt Mansueto featuring Matt Mansueto Photography shares. Before going home, I recommend paying in cash only Chiu Quon Bakery in Chinatown for a BBQ pork bun, a curry beef bun or a coconut bun. They are all so good.”
3. Explore nearby neighborhoods
Chicago’s neighborhoods are one of the city’s greatest assets. Spend time in places like River North And Rim waterand you’ll find that each has its own atmosphere, local businesses and places worth exploring.
“Chicago is a great city for food and fun,” says Jenny and Sheena, local Chicagoans from the And then we had children Podcast. “Park & Veld, located in the Logan Square neighborhoodis an excellent restaurant for all ages, and on the weekends they even host fun family events and a bottomless booze brunch. If you’re looking for a place to host your event, Park & Field offers free party rentals. And the best part is that they are dog friendly.
>>Read: Chicago city guide
4. Dine at local favorite restaurants
One of the best ways to experience Chicago is through its food, with neighborhood restaurants serving everything from favorites to new variations of dishes.
“If you want to see a different side of Chicago, take the Pink Line to 18th Street and spend the day exploring Pilsenone of the most vibrant and creative neighborhoods in the city,” said the team at Suite Home Business Housing recommends.
“Start with the iconic 16th Street murals and the National Museum of Mexican Art before browsing local favorites like Semillas Plant Studio, a community-focused plant shop, and Pilsen Community Books, Chicago’s first employee-owned bookstore. Order a cup of coffee at a neighborhood café like Anticonquista Café or La Malinche Coffee & Tea House and spend the afternoon vintage shopping at places like Knee Deep Vintage and Pilsen Vintage. If you’re craving a bite, stop by Novel Pizza or grab tacos from local favorites like Carnicería Maribel, Rubi’s, Carnitas Uruapan, or 5 Rabanitos. End the evening with a concert at Thalia Hall, followed by drinks at Alulu Brewery or The Alderman, a speakeasy-style bar. With its mix of public art, independent businesses, incredible food, and rich cultural history, Pilsen offers a side of Chicago that many visitors miss but locals love.
If you’re looking for a classier night on the town, Vess, a local from Bus connectionan advanced transportation service, recommends stopping by Bavette’s Bar and Bouf. “One of Chicago’s best steakhouse restaurants, Bavette’s Bar en Bouf, is truly a hidden gem. Feel the chic atmosphere of a Prohibition-era speakeasy, softly lit with red velvet wrap-around booths and sultry jazz music. It’s the most unique and intimate place to eat and drink.”
5. Go to an event organized by Sofar Sounds
Sofar sounds connects the community with secret concerts in unique spaces. You will receive the event address within 36 hours before the event. You will experience different shows, from music genres and comedy to dance.
“My recommendation for something unique to do in Chicago is to go to events hosted by Sofar Sounds,” says Emily Mezz entertainment. “This experience allows you to attend intimate performances throughout the city, such as the Loop and Lincoln Park. I enjoy discovering new artists to listen to at these shows.”
