5 Unique Things to Do in Chicago

Chicago has no shortage of famous landmarks, but some of the best places in the city are the ones locals keep coming back to. From neighborhood favorites to lesser-known attractions, we asked Chicago residents to share the unique things they think everyone should experience. Whether you’re new to the city, are looking at homes in Chicago, or have called it home for years, there’s probably something here you haven’t tried yet.

1. Stop by the Art Institute of Chicago

If you’re interested in history and art, spend an afternoon at the Art Institute of Chicago. Home to one of the country’s largest permanent art collections, the museum features everything from centuries-old masterpieces to modern works.

Martin, a local Chicagoan from SmartMoneyMatch, a 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 nature spots 

In the summertime, Chicago becomes a playground for all residents and visitors. From the parks and the waterways, you’ll find a place to enjoy nature.

“One of Chicago’s best-kept secrets is spending an afternoon exploring the lakefront beyond the typical tourist spots. Walk through the peaceful Alfred Caldwell Lily Pool, enjoy 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 incredible restaurants, independent shops, public art, and the authentic character that makes Chicago so special.”

Chicagoan Jane Simon Ammeson agrees on Chicago’s outdoor beauty. “Rivers were the highways of the past, but the Chicago River offers uniquely modern adventures for me. I can paddle its waters and shiver at scary stories during a Ghost and Gangster kayak tour, and sip a Spanish Rioja while gazing at the city lights. I love to stroll along the Riverwalk, choose a favorite place to dine, and plan my next adventure while watching the boats go by.”

On top of the unique layout of the city, the walkability of Chicago makes seeing your favorite spots that much easier. “Because of my work, I’m often up before most people are awake, setting up for a photo shoot to capture the first light of the day. One of my favorite places to watch Chicago wake up is anywhere along the lakefront, from Rogers Park all the way south to Promontory Point, where the sun rises over Lake Michigan, lights up the skyline, and runners, cyclists, and dog walkers,” Matt Mansueto with Matt Mansueto Photography shares. Before heading home, I recommend stopping at the cash-only Chiu Quon Bakery in Chinatown for a BBQ pork bun, a curry beef bun, or a coconut bun. They’re all so good.”

3. Explore nearby neighborhoods

Chicago’s neighborhoods are one of the city’s biggest strengths. Spend time in places like River North and Edgewater, and you’ll see that each has its own feel, 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 Kids Podcast. “Park & Field, located in the Logan Square neighborhood, is an excellent restaurant for all ages, and they even host fun family events and a bottomless boozy brunch on the weekends. If you’re looking for a place to host your event, Park & Field features fee-free party rentals. And the best part is they’re dog-friendly.

>>Read: Chicago City Guide 

4. Dine in local favorite restaurants

One of the best ways to get to know Chicago is through its food, with neighborhood restaurants serving everything from favorites to new takes on dishes.

“For a different side of Chicago, take the Pink Line to 18th Street and spend the day exploring Pilsen, one of the city’s most vibrant and creative neighborhoods,” the team at Suite Home Corporate 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. Grab a coffee from a neighborhood spot like Anticonquista Café or La Malinche Coffee & Tea House, then spend the afternoon vintage shopping at places like Knee Deep Vintage and Pilsen Vintage. When you’re ready for 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 a drink 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 fancier night on the town, Vess, a local from Bus Connection, a sophisticated transportation service, recommends stopping by Bavette’s Bar and Bouf. “One of Chicago’s finest steakhouse restaurants, Bavette’s Bar and Bouf, is truly a hidden gem. Feel the swanky ambiance of a prohibition-era speakeasy, softly lit with red velvet wraparound booths and sultry jazz music soundtracks. It’s the most unique and intimate place to wine and dine.”

5. Go to any event hosted by Sofar Sounds

Sofar Sounds connects the community with secret concerts in unique spaces. You’ll receive the address of the event within 36 hours before the event. You’ll experience different shows, from musical genres and comedy to dance. 

“My recommendation for a unique thing to do in Chicago is to go to events hosted by Sofar Sounds,” says Emily from Mezz Entertainment. “Through this experience, you can attend intimate gigs throughout the city, like the loop and Lincoln Park. I love discovering new artists to listen to from these shows.” 

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