14 of the Best Things to Do in Chicago, Recommended by Locals

Nestled along the shore of Lake Michigan, Chicago is a city of diverse communities, each with its own distinct character. There is the gleaming downtown Chicago skyline complemented by the historic architecture of its neighborhoods, serving as a reminder of Chicago’s storied past. The cultural scene in the Windy City is unparalleled, with world-class museums and a thriving music scene. The parks, especially the expansive Millennium Park, Grant Park, and Lincoln Park provide a green oasis in the urban environment.  

Adding on to Chicago’s best features, the culinary landscape here is as diverse as the population, and the sports culture is one-of-a-kind, with passionate fans supporting teams like the Bears, the Bulls, the White Sox, and the Cubs. Chicago’s sense of community can be seen in all of these things and, most of all, in the hearts of the city’s residents. Despite the challenges of urban living and harsh winters, the resilience and friendliness of Chicagoans make this city more than just a place to live – it’s a place to call home.  

Whether you already live in Chicago or you are simply visiting, there are many incredible and unique things that you can do here. To give you ideas for an authentic time in Chicago, we asked the locals for insights, tips, and their favorite hidden gems in Chicago. Here’s what they told us.  

1. Take an Architecture Boat Tour 

There’s a lot to take in when it comes to Chicago, so a good place to start is getting a more distant perspective to admire its amazing architecture. More people recommended an architecture boat tour, including Sarah Parisi, local professional organizer and productivity consultant at The Clutter Curator, who said that “Chicago is known for its stunning architecture, and taking a boat tour on the Chicago River is a great way to learn about the city’s iconic buildings. We take a tour every summer.” 

2. Explore the Food 

Of course, the food scene and the diverse restaurants of Chicago are not to be missed. Parisi told us that “I moved here from NYC and I can say Chicago has the most amazing food. Yes, try the hotdog but explore the different neighborhoods and local spots. My favorites are Longman & Eagle, Giant, and Dusek’s.”  

Rafael Murillo, principal and licensed real estate broker with RM Luxury Group, told us that “the city boasts a vibrant fine dining scene, with Michelin-starred restaurants like Alinea and Ever offering exquisite tasting menus and innovative cuisine. However, in Chicago, there’s no need to empty your wallet to enjoy delectable cuisine, as numerous small, family-owned restaurants serve mouthwatering dishes at affordable prices. Whether you’re a fan of comfort food or seeking gourmet experiences, Chicago has something to satisfy every palate.” 

3. Try Even More Restaurants

We also have a list of the favorite places of Miguel Rodriguez, owner of local business Mr. Brows, who told us about “Ciccio Mio, where you can find Italian food that checks all the boxes for me when it comes to the vibe, the food quality and the cocktails; Ella Elli, with Italian/Mediterranean food that also is a must for me; Lou Malnati’s, because if you’re going to do Deep Dish in Chicago, you have to check out Lou’s; Indienne, for if you enjoy Indian food and don’t mind spending a little extra; and the London House Rooftop, because there’s no denying that the view from here is beautiful and worth the reservation.”

Jessica Bradford, media relations manager at Alternative Strategies, also recommended a few must-see restaurants in Chicago. “Recently opened in August of 2023, Marina’s Bistro & Rum Bar gives locals and visitors an authentic taste of Puerto Rican dishes and drinks. Cesar’s Killer Margaritas has been serving the Lakeview community and beyond since first opening in 2002, and October 2nd marks the family-owned restaurant’s 21st year in business! The Sanchez family not only created but continues to uphold one of Chicago’s most beloved Mexican spots.” 

“Amerikas, found in Oak Park, was named as America has been coined “the melting pot”, where people from around the world bring and share their native cultures, flavors, and foods,” Bradford said. “And Amerikas represents that very essence of American cuisine, as its concept is dedicated to blend Latin roots and flavors from around the world to create truly unique tastes.” 

If you’re looking for a Chicago-style hot dog, Matt Laricy, managing broker at Laricy, recommends Wiener Circle. Laricy also mentions Lou Malnati’s or Giordano’s for pizza, Billy Goat Tavern for burgers, and Portillo’s for chocolate cake. 

4. Do a Food Tour in the West Loop 

Michael Samm, senior real estate broker with The West Town Team, recommends checking out the West Loop neighborhood and its many unique restaurants and cafes. “Start with coffee. An import from Japan, Sawada Coffee is a cool cafe known for its specialty drinks and latte art. For lunch, try a favorite among the locals, like Green Street Smoked Meats – some of the best smoked BBQ you will ever have. For dinner, walk to famed Italian restaurant Monteverde, a world-class restaurant with an award-winning chef, crowd-pleasing menu and top-notch service.” 

5. Walk Around the Lincoln Park Neighborhood 

Michelle Mathena, president of Chicago moving company Under One Roof, recommends a day spent in Lincoln Park. “Begin with the section of Lincoln Park within the neighborhood. Visit the free Lincoln Park Zoo, one of the country’s oldest zoos, and don’t miss the Butterfly Haven at Peggy Notebaert Nature Museum. Head over to North Avenue Beach to enjoy the lakeshore and the view of the Chicago skyline. Visit some of the best boutiques in Chicago along Armitage Avenue and Halsted Street while also checking out the historical architecture of the area. Lincoln Park has many excellent dining choices, including Pequod’s for Chicago’s best deep-dish pizza. Finish the day at Chicago’s oldest Blues Club, Kinston Mines.” 

6. Go to Festivals & Enjoy the Music 

Besides the well-known festivals, there are plenty of free access events where you can enjoy high-quality music. Mathena also has some recommendations for the summer months spent in Chicago. “From the world-renowned Lollapalooza to the city’s neighborhood fests, Chicago’s music scene truly comes alive during the summer with many concerts outdoors. The Grant Park Music Festival offers free classical concerts. The Chicago Jazz, Blues, Gospel, and World Music Festivals also take place free of charge. Hop on a quick train ride to the northern suburbs to discover Ravinia Festival’s serene setting for classical, jazz, and pop performances.” 

7. Stop at Wrigley Field 

If you want a taste of the energy in Chicago, catch a game at Wrigley Field. Andre Kazimierski, CEO of Improovy Painters Chicago, told us that “no trip to Chicago is complete without stopping at Wrigley Field. The stadium offers over 100 years of baseball history, and I definitely recommend taking the official tour. Of course, you’ll also want to purchase tickets to a Chicago Cubs game before you visit. Even if you aren’t a huge baseball fan, the energy in the stadium during a game is infectious and will help you find a new appreciation for the sport.” 

8. Go Kayaking on the Chicago River 

Another recommendation by Kazimierski is to take a kayak down the Chicago River. “If you want a less touristy way to enjoy Chicago, consider kayaking on the Chicago River. While most tourists will focus on the Chicago Riverwalk, renting a kayak gives you a unique view of this iconic part of the city. I suggest renting one by the hour so you can enjoy exploring the river at your own pace.” 

9. Have Fun at the Navy Pier & Surroundings 

Navy Pier is among the must-see destinations when coming to Chicago. Grigory Pekarsky, co-founder of Vesta Preferred Realty recommends “taking the Ferris wheel and exploring the shops at Navy Pier. The Ferris wheel offers some of the best views of the city, and the shops and eateries give you a taste of what Chicago has to offer. Close by is Millennium Park, home of the famous Cloud Gate. Before you leave make sure to get your obligatory selfie at the bean!” 

Also close to the Navy Pier is the John Hancock Center, where Steven Pounders, head of sales at MOOvers Chicago, recommends we take in the city from above. “The John Hancock Center offers a 360 view of the city from one of the taller buildings in Chicago, giving the viewer a serene perspective of one of the greatest cities on earth,” Pounders told us. 

10. Enjoy the Many Trails & Parks 

Katelyn Capri Zenie, planner at Art Room Events, encouraged us to immerse ourselves in nature in one of the many parks Chicago has to offer. “The 606 Bloomingdale Park is a paved elevated biking and walking trail that connects many western neighborhoods in a convenient and community focused way. 

“Located just outside of Chicago, The Morton Arboretum is a favorite for many hikers, runners, and nature enthusiasts alike. It’s a huge campus of trees from all over the world and is big enough to explore all day. It also features rotating art installations that are gorgeous and add a lot to the experience. Also, we can’t forget about the lakefront trail. This 18-mile-long trail has the best sights of the skyline and is a wonderful way to get a little exercise. Rent a Divvy and bike along lake shore drive or hang out on one of the beaches.” 

11. Go on a Walking Tour 

Zenie also recommends taking a walking tour to explore the city, its neighborhoods and buildings. “Take an urban hike to see Chicago’s own Riverwalk. You really get a sense of the city’s history and beauty when exploring the contemporary towers downtown, and while during the summer taking an architecture boat tour is a common and fun tourist activity, when it cools off it’s nice to stretch your feet and get up close and personal.” 

“Another walking tour option that appeals to me is the Art Deco building tour where you explore wonderfully preserved Art Deco style architecture designed in the 20s,” Zenie said. “This is a wonderful option for the artistic tourist out there.”  

Jeff Mikos, owner of Free Chicago Walking Tours, also gave us a few options for walking tours. “This fall and winter we will be offering some really unique walking tours including a Pedway Tour, a Loop Interior Tour where spend a lot of time inside buildings exploring the amazing architecture and getting reprieve from the cold, and the popular Holiday Lights tour.” 

12. Have a Family-Friendly Day with the Kids 

Jen Luby, founder of Dayhouse Coworking, told us about a perfect day in Chicago, which includes “playing hooky at Mojo Spa in Wicker Park, followed by a trip to Black Dog Gelato in Ukrainian Village, catch a show at Chicago Shakespeare Theater followed by Cabra in the West Loop for a delicious date night dinner.” For residents with kids, Luby gave us a few more recommendations. “I own Dayhouse Coworking in Highland Park, which opened in spring of 2019. It’s the only coworking space in the Chicagoland area with a childcare program and a wellness program. I am always looking for family friendly spots and Red Balloon has the best selection of toys, clothes and gifts for kids. While the city has amazing concert venues, you can’t beat Ravinia Festival for its outdoor concerts. You can bring the whole family!”  

Another activity to enjoy with the whole family is recommended by Diana Rodriguez-Zaba, president of ServiceMaster Restoration by Zaba: “my family cherishes the annual lightscape show at the botanic garden. Whether it’s the illuminated display or a daytime walk, the experience is always serene and captivating” 

13. Take In Chicago’s Art & Theater Scene 

Chicago is a culturally rich city, with numerous museums, galleries, expositions, and a vibrant theater scene. Tionna M. Van Gundy, CEO of Wedicity Wedding Day Detailing, recommends that you take advantage of all of these options when visiting or looking for an evening out in Chicago. “From pop-ups to known Chicago staples, the art and architecture scene is thriving! There’s a long list of museums such as the Art Institue of Chicago, Museum of Contemporary Art, Chicago Design Museum, The City Gallery at the Historic Water Tower, Museum of Contemporary Photography amongst others. A few fun pop-up immersive art experiences include color Factory, WNDR Museum, The Van Gogh Experience, Museum of Illusions, and the Museum of Ice Cream!”  

If you’re a lover of theater, Van Gundy told us about some must-sees as well. Broadway in Chicago is something to get excited about if you enjoy watching plays, musicals or if you are looking for some belly-clinching laughter! Boasting shows like Hamilton, STOMP, the Hip Hop Nutcracker, Beetlejuice amongst so many others; the theater options in Chicago will have you coming back for more! Smaller theaters like PorchLight Muscal Theater, A Red Orchid Theater and the Black Ensemble Theater are local neighborhood must-sees alongside the larger more well-known theaters of CIBC, Chicago Theater, Nederlander and Goodman Theater or Lyric Opera!”   

14. Experience Old School Jazz at the Green Mill Cocktail Lounge 

Seamus McMahon, Chicago resident and digital marketing specialist at the International TEFL Academy, recommends this experience for both locals and those visiting Chicago. “Not only is it an excellent old-school jazz club that’s still cash-only, but the Green Mill is a Chicago institution with a fascinating history.” McMahon told us. “Al Capone once frequented the joint and had tunnels built under the club so he could escape (you can still sit in his favorite booth). It has also hosted the likes of Louis Armstrong, Frank Sinatra, and Billie Holliday. Check out a show to get immersed back in time–hopefully, no tunnels are needed.”  

Enjoy All These Things to Do in Chicago

Chicago offers an endless list of unique experiences that reflect its rich cultural diversity and modern spirit. Whether it’s exploring the strong character of its neighborhoods, indulging in the diverse culinary scene, or taking part in the arts and music events that pulsate through the city’s streets, there’s something to explore in Chicago for years to come.  

The city continually surprises and delights everyone, constantly revealing layers of character and charm. So, whether you’re a first-time visitor or a lifelong resident, Chicago invites you to embrace its Midwestern spirit, explore its uniqueness, and create your own memorable experiences.