8 Top Places to visit in Chicago You Can’t Miss

Ever wonder why millions of people can't stop talking about Chicago? Here's the truth—this city is different. Chicago isn't just another stop on your travel map; it's the place that makes you want to cancel your return flight home. From that famous shiny Bean that everyone takes selfies with to pizza so thick you need a fork, Chicago serves up surprises at every corner. Whether you're hunting for the best places to visit in Chicago or already scanning flights to Chicago on your phone, you're in for something special. 

Chicago gives you real experiences—like watching the sunrise from a rooftop, discovering hidden speakeasies, or stumbling upon street festivals that locals actually attend. Ready to see why Chicago keeps stealing hearts? Let's explore the places that will make your friends jealous and your Instagram followers ask "where is that?"

8 Best Places To Visit in Chicago

Here is a compiled list of best places to visit in chicago which you should definitely add on your itinerary for a memorable visit: 

1. Millennium Park and The Bean

Let's start with the obvious but one of the amazing places to visit in Chicago. Cloud Gate (everyone calls it The Bean) is that giant reflective sculpture that looks like a silver kidney bean dropped from space. Sure, it's touristy, but there's a reason people line up for photos. The thing is mesmerizing. You can walk around it, under it, and watch the city skyline bend and twist on its surface. Best time to visit? Early morning when the crowds are still sleeping off their deep-dish hangovers. 

The park itself is way more than just The Bean. In summer, you can catch free concerts at the Jay Pritzker Pavilion, and in winter, ice skating at McCormick Tribune Ice Rink. The Crown Fountain is another crowd-pleaser where giant faces of locals spit water on giggling kids. You will love strolling or just go for a run in the park. 

2. Willis Tower Skydeck - The Glass Box That Terrifies

You know that glass box sticking out of the Willis Tower (locals still call it Sears Tower)? It's called the Skydeck, and it's 103 floors up. The boxes extend 4.3 feet from the building, and yes, you're literally standing on glass 1,353 feet above the street. Do you know Willis Tower was the tallest building in the world from 1974 to 1998? Your brain will tell you this is a terrible idea while your Instagram followers demand photos. Pro tip: go at sunset for those golden hour shots that'll make everyone back home jealous. Moreover, you can enjoy one of the adventure activities in Chicago on The Ledge which is a glass balcony extending in the air. After reaching the top you can spend a good amount of time admiring the panoramic views of the city. 

• Ticket Price: $30 to $44 depending on what time you visit

• Timings: Open daily from 9am to 10pm 

3. Art Institute of Chicago - Where Masterpieces Live

This place houses some serious art heavy-hitters which makes it one of the best places to visit in Chicago. We're talking about the actual American Gothic painting and Sunday on La Grande Jatte that you studied in school. You'll find yourself face-to-face with Edward Hopper's "Nighthawks," that iconic diner painting that's been parodied countless times but loses none of its power when you see the original. 

Then there's Georges Seurat's massive "A Sunday on La Grande Jatte," the pointillist masterpiece that took two years to complete using thousands of tiny dots. Fun fact: it's the same painting featured in "Ferris Bueller's Day Off". With over 300,000 pieces spanning 5,000 years of human creativity, the Art Institute proves why Chicago ranks among the world's great cultural destinations. So, book your flights to Chicago now and explore this world-class art museum. 

• Ticket Price: $32 for adults, Students, senior citizens (65+) & Teens (14-17) $26; Free for children and members. 

• Timings: Tuesday is closed; Monday, Wednesday & Fri to Sun - 11am to 5pm; Thursday is 11am to 8pm. 

4. Lincoln Park - Where Nature Meets City

If you’re looking for one of the most refreshing places to visit in Chicago, Lincoln Park should top your list. The neighborhood wraps around one of the best free zoos in America. Lincoln Park Zoo has been around since 1868 and houses over 1,000 animals from 200 species. The polar bears are the stars, but the gorilla habitat will blow your mind. The neighborhood itself feels like a small town dropped into a big city. Tree-lined streets, cute cafes, and that perfect mix of young professionals and families. 

Walk along the lakefront path here and you'll get stunning skyline views that make you understand why people move to Chicago and never leave. As you wander deeper into the park, the nature boardwalk around South Pond offers quiet spots to spot herons and turtles against the stunning city skyline. 

5. Wicker Park - Where Hip Meets Historic

Wicker Park is one of the coolest places to visit in Chicago, and it’s easy to see why. This vibrant neighborhood pulses with energy day and night, where every street corner surprises you with art, music, and mouthwatering food. Start your day at a local coffee shop—think indie roasters and cozy vibes—before wandering down Milwaukee Avenue to browse vintage record stores and funky boutiques. Street art here isn’t just decoration; it’s a living gallery where colorful murals pop up every month.

When lunchtime hits, follow the scent of freshly baked bread to Empirical Brewery or dig into tacos at Big Star’s sunny patio. As the sun sets, Wicker Park’s nightlife comes alive: live bands at Subterranean, craft cocktails at trendy speakeasies hidden behind unmarked doors, and rooftop bars where you can sip a cold one while watching the city lights. So, get your flights to Chicago with Experian airfare now and enjoy at this amazing park. 

6. The Loop - Downtown Done Right

The Loop is the heart of Chicago and one of the top places to visit in Chicago for first-timers and repeat visitors alike. The Loop gets its name from the elevated train tracks that circle downtown, but it's so much more than a transportation hub. This is where Chicago's architectural magic happens. Start with Millennium Park’s iconic Crown Fountain and Cloud Gate sculptures, then stroll down to Grant Park for wide-open green spaces and stunning lakefront views. Architecture fans won’t want to miss the Chicago Cultural Center, where the world’s largest Tiffany dome greets you free of charge.

Art lovers should carve out time for the Art Institute of Chicago, just a few blocks south, to marvel at masterpieces from Monet to Hopper. If you’re looking for unique places to visit in Chicago, hop on an architectural river cruise departing from the nearby dock—seeing the city’s skyline from the water is a game-changer. Theater buffs can catch a Broadway show in the Loop’s Parisian-style Cadillac Palace Theatre or the modern Lyric Opera House.

7. Chicago Riverwalk - The City's Best Secret

Want to know one of the most underrated places to visit in Chicago? The Chicago Riverwalk is a stunning 1.25-mile waterfront path that stretches along the Chicago River from Lake Michigan to Lake Street. This award-winning pedestrian walkway feels like Chicago's best-kept secret, even though it's right in the heart of downtown. What makes it special? Each section has its own personality—from Marina Plaza's bustling restaurants to the peaceful floating wetland gardens at The Jetty.

During warmer months, the Riverwalk comes alive with pop-up vendors, outdoor dining, and boat tours that showcase Chicago's world-famous architecture from the water. City Winery's heated domes create a magical winter experience, making you feel like you're dining inside a snow globe. You can rent kayaks from Urban Kayaks, grab craft beer at Chicago Brewhouse, or simply find a bench and watch boats drift past the iconic Marina Towers.

8. Buckingham Fountain

Buckingham Fountain, located in Grant Park, is one of the most unforgettable places to visit in Chicago. Built in 1927, this Beaux-Arts masterpiece spans a 280-foot pool and shoots water up to 150 feet high in a dazzling display every hour from April through October. Each evening, a synchronized light-and-water show adds extra magic, turning the fountain into a glowing kaleidoscope against the city skyline. Music accompanies the water choreography, making it feel like a grand performance under the stars. Beyond its beauty, Buckingham Fountain honors Chicago’s sister city relationship with Paris—its design was inspired by Versailles. After watching the show, stroll nearby lakefront paths or head to Millennium Park to discover even more places to visit in Chicago. And if you’re planning flights to Chicago, make sure this free, must-see landmark is on your itinerary.

Conclusion

From world-class museums to hole-in-the-wall bars, from architectural boat tours to late-night jazz clubs, it offers various places to visit in Chicago you can't get anywhere else. It's a city that reveals itself slowly, rewards exploration, and leaves you planning your return visit before you've even left. Whether you're here for a weekend or a week, Chicago will surprise you. So, just book your flights to Chicago and enjoy a relaxing vacation. 

Also Read: Things To Do In Chicago

FAQs

Q- What is the best way to explore Chicago?

The "L" (elevated train) is your best friend. A day pass costs around $25 and gets you everywhere worth going. The Red and Blue lines run 24/7, while other lines shut down around midnight. The Blue Line connects directly to O'Hare Airport, making it easy to hop off the plane and start exploring.

Q- What is the best time to visit Chicago?

Summer (June-August) is peak season with festivals, outdoor concerts, and perfect weather for walking around. But Chicago in winter has its own magic—fewer crowds, cozy bars, and if you're lucky, the lakefront frozen into an otherworldly landscape. Spring and fall offer the best of both worlds: good weather without the summer crowds.

Q- What are some of the best places to visit in Chicago for free?

Millennium Park’s Cloud Gate, the Chicago Cultural Center’s Tiffany Dome, Lincoln Park Zoo, Lincoln Park Conservatory, and the Chicago Riverwalk all rank among the best places to visit in Chicago for free. Add Buckingham Fountain’s hourly water show and Grant Park’s lakefront paths for even more zero-cost fun.