Chicago has no shortage of famous landmarks, but there are some of the city’s best places that 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, considering a home in Chicago, or have called Chicago 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 largest permanent art collections in the country, this museum features everything from centuries-old masterpieces to contemporary pieces.
Martin, a local Chicagoan with Smart Money Match, a network connecting the global investment community, recommends the Art Institute of Chicago when the weather is bad. “Always worth a visit. Filled with masterpieces from all eras, from Georges Seurat’s iconic painting Sunday at La Grande Jatte to Andy Warhol’s print of actress Elizabeth Taylor.”
2. Visit Chicago’s natural spots
In the summer, Chicago becomes a playground for all residents and visitors. You can find parks, waterways, and other places where you can enjoy nature to the fullest.
“One of Chicago’s best-kept secrets is to spend an afternoon exploring the lakefront beyond the typical tourist attractions. Stroll along the tranquil Alfred Caldwell Lily Pool, enjoy the skyline from North Avenue Beach, then head to Belmont Harbor to watch the yachts roll in at sunset,” Crystal Tran tells us. “For a truly local experience, explore neighborhoods like Andersonville, Ravenswood, and Pilsen, where you’ll find great restaurants, independent shops, public art, and authentic character that makes Chicago special.”
Chicago native Jane Simon Ammeson agrees with Chicago’s outdoor beauty. “Rivers have been the highways of the past, but for me, the Chicago River offers a unique, modern adventure. Ghosts and Gangsters Kayak Tours allow me to paddle the river and shiver with scary stories, or sip Spanish Rioja while watching the city lights. I love strolling along the River Walk, choosing my favorite meal, and watching the boats go by as I plan my next adventure.”
In addition to Chicago’s unique cityscape, Chicago’s walkability makes it easy to find your favorite spots. “Due to my job, I am often up before most people are awake to prepare 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 to Promontory Point south, where the sun rises over Lake Michigan, illuminating the skyline and illuminating runners, cyclists, and dog walkers.” Matt says. says Matt Mansueto of Mansueto Photography. Before heading home, we recommend stopping by the cash-only Chiu Cuong Bakery in Chinatown to pick up BBQ pork buns, curry beef buns, or coconut buns. they are all very good. ”
3. Explore nearby areas
Chicago’s neighborhoods are one of the city’s greatest strengths. When you spend time in places like River North and Edgewater, you’ll find that each has its own vibe, local businesses, and places worth exploring.
“Chicago is a great city for food and fun,” say local Chicagoans Jenny and Sheena from the podcast “And then We Had Kids.” “Located in the Logan Square neighborhood, Park and Field is a great restaurant for all ages, and also hosts fun family events and all-you-can-drink brunches on the weekends. If you’re looking for a place to host your event, Park and Field offers complimentary party rentals and the best part: it’s dog-friendly.”
>>Read: Chicago City Guide
4. Eat at a popular local restaurant
One of the best ways to get to know Chicago is through its food. Nearby restaurants offer everything from favorites to new twists.
“To experience a different side of Chicago, take the Pink Line to 18th Street and spend a day exploring Pilsen, one of the city’s most vibrant and creative neighborhoods,” recommends the team at Sweet Home Corporate Housing.
“Start at the iconic 16th Street Mural and the National Museum of Mexican Art, then browse local favorites like Semillas Plant Studio, a community-based plant shop, and Pilsen Community Books, Chicago’s first employee-owned bookstore. Grab a coffee at neighborhood spots like Anticonquista Café and La Malinche Coffee & Tea House, and spend the afternoon sampling vintage at Knee Deep Vintage and Pilsen Vintage. Spend the day shopping: grab a bite to eat, stop by Novel Pizza, or enjoy tacos at local favorites like Carniceria Maribel, Rubis, Carnitas Uruapan, or 5 Labanitos, enjoy a concert at Thalia Hall, then grab a drink at Arles Brewery or the intimate bar The Alderman. With its blend of art, independent businesses, great cuisine, and rich cultural history, Pilsen offers a side of Chicago that many visitors miss.”
For a fancier night out on the town, Ves, a local from the sophisticated transportation service Bus Connection, recommends stopping by Bavette’s Bar and Bouf. “One of Chicago’s finest steakhouse restaurants, Bavette’s Bar and Bouffe is truly a hidden gem. Softly lit with red velvet enclosed booths and a soundtrack of sultry jazz music, feel the chic atmosphere of a Prohibition-era bootlegger. It’s the most unique and intimate place to wine and dine.”
5. Participate in events hosted by Sofar Sounds
Sofar Sounds brings communities together with secret concerts in unique spaces. You will receive your event address at least 36 hours before the event. Experience a variety of shows ranging from music genres to comedy and dance.
“A unique thing to do in Chicago that I recommend is going to an event hosted by Sofar Sounds,” says Emily from Mezz Entertainment. “This experience allows me to attend intimate gigs around the city, including The Loop and Lincoln Park. I love discovering new artists I want to hear from these shows.”
