MathHotels.com – If you’ve been searching for the best things to do in Chicago area, you’re in the right place. This city is full of energy, personality, and iconic sights that live up to the hype.
From world-class museums to riverfront strolls and unforgettable food, Chicago offers a little bit of everything for every kind of traveler.
It’s the kind of place where one minute you’re staring up at a giant bean, and the next, you’re sinking into a cheesy slice of deep-dish pizza.
Whether it’s your first visit or you’re coming back for more, this guide highlights 20 must-do experiences that showcase the very best of Chicago.
Why Chicago Should Be on Your Travel List
From towering skyscrapers to deep dish pizza, Chicago is a city that balances bold energy with Midwestern charm.
Whether you’re visiting for the weekend or planning a longer stay, the Windy City offers something for every kind of traveler—art lovers, foodies, families, and adventurers alike.
This curated guide will walk you through 20 of the very best things to do in Chicago, especially if it’s your first time here.
Iconic Landmarks You Can’t Miss
Chicago is packed with world-famous landmarks that define the city’s character and skyline. If it’s your first time visiting, these are the places you absolutely shouldn’t skip.
1. Millennium Park & Cloud Gate (The Bean)
This shiny, bean-shaped sculpture has become one of Chicago’s most photographed attractions. Located in Millennium Park, it reflects the city skyline in a fun, distorted way and makes for a perfect selfie spot.
Where to stay nearby:
Fairmont Chicago Millennium Park (⭐⭐⭐⭐) – Just a 5-minute walk from The Bean, this upscale hotel offers spacious rooms, lake views, and easy access to Grant and Millennium Park.
2. Navy Pier
Stretching into Lake Michigan, Navy Pier combines rides, restaurants, gardens, and lakefront views. You can take a ride on the Centennial Wheel or enjoy a boat tour that departs from the docks.
Where to stay nearby:
Sable at Navy Pier, Curio Collection by Hilton (⭐⭐⭐⭐) – Located right on the pier, this hotel gives you unmatched access to the lake, plus floor-to-ceiling windows with waterfront views.
3. Willis Tower Skydeck
Head up to the 103rd floor of one of the tallest buildings in the U.S. and step out onto the glass-floored Skydeck Ledge for a thrilling view straight down to the streets below.
Where to stay nearby:
JW Marriott Chicago (⭐⭐⭐⭐⭐) – Only a 10-minute walk from Willis Tower, this luxury hotel in the Loop offers a refined stay with indoor pool, spa, and elegant rooms.
4. Chicago Riverwalk
The Riverwalk is a beautiful pedestrian path along the Chicago River, lined with restaurants, bars, public art, and kayak rentals. It’s a great way to see the city at your own pace.
Where to stay nearby:
LondonHouse Chicago (⭐⭐⭐⭐) – A boutique hotel right along the river with rooftop bar views and easy access to the Riverwalk and downtown core.
5. The Magnificent Mile
This stretch of Michigan Avenue is home to high-end shops, iconic buildings, and some of the best city views. Whether you’re shopping or just strolling, it’s a must-see part of the Chicago experience.
Where to stay nearby:
The Gwen, a Luxury Collection Hotel (⭐⭐⭐⭐⭐) – Situated directly on the Magnificent Mile, this hotel blends art deco vibes with top-tier service, perfect for those wanting to stay in the heart of it all.
Must-Visit Museums & Cultural Spots
Chicago has a rich cultural scene that spans from fine art to hands-on science, making it a paradise for curious minds and creative souls. These museums and cultural institutions are must-visits whether you’re traveling solo, as a couple, or with the family.
6. Art Institute of Chicago
One of the oldest and largest art museums in the U.S., the Art Institute is home to iconic works like “A Sunday Afternoon on the Island of La Grande Jatte” and Grant Wood’s “American Gothic.” You could spend hours here and still not see it all.
Where to stay nearby:
Silversmith Hotel Chicago Downtown (⭐⭐⭐⭐) – Just a 3-minute walk from the museum, this stylish boutique hotel offers a quiet stay with historic charm and modern design.
7. Museum of Science and Industry
Located in Hyde Park, this museum is all about discovery and play. With exhibits like a German submarine, a mirror maze, and a simulated tornado, it’s especially great for kids and science lovers.
Where to stay nearby:
Sophy Hyde Park (⭐⭐⭐⭐) – A trendy and artsy hotel just 5 minutes from the museum, perfect for families or couples exploring the south side of the city.
8. Field Museum
Step into the world of dinosaurs, ancient cultures, and natural wonders. Don’t miss Sue, the world’s most complete T. rex skeleton.
Where to stay nearby:
Hilton Garden Inn Chicago Downtown South Loop (⭐⭐⭐) – A 10-minute drive or short train ride from the Field Museum, with comfortable rooms and budget-friendly rates.
9. Chicago Cultural Center
A free and often overlooked gem, the Cultural Center offers rotating exhibits, live music, and stunning architecture—especially the world’s largest Tiffany glass dome.
Where to stay nearby:
Chicago Athletic Association Hotel (⭐⭐⭐⭐) – Just across the street, this vintage-meets-modern hotel features game rooms, cozy lounges, and rooftop views of Millennium Park.
10. Museum of Contemporary Art (MCA)
Located near the Magnificent Mile, MCA showcases cutting-edge exhibitions in modern art, photography, and installations.
Where to stay nearby:
Cambria Hotel Chicago Magnificent Mile (⭐⭐⭐⭐) – A sleek and affordable stay just a few blocks from MCA, with a rooftop bar and spacious rooms.
Outdoor Adventures & Scenic Walks
For a city filled with skyscrapers, Chicago also offers plenty of green spaces and outdoor escapes. Whether you’re in the mood for a morning run, a lazy afternoon by the lake, or a stroll with skyline views, these spots give you a breath of fresh air right in the heart of the city.
11. Lincoln Park & Lincoln Park Zoo
Lincoln Park is a huge urban park with walking trails, gardens, beaches, and the Lincoln Park Zoo—a surprisingly large (and free!) zoo featuring everything from lions to penguins.
Where to stay nearby:
Hotel Lincoln (⭐⭐⭐⭐) – Just steps from the park and zoo, this artsy hotel blends vintage flair with unbeatable lakefront access and rooftop views.
12. Grant Park
Known as “Chicago’s front yard,” Grant Park hosts major events like Lollapalooza and houses art installations, gardens, and Buckingham Fountain—one of the largest fountains in the world.
Where to stay nearby:
The Blackstone, Autograph Collection (⭐⭐⭐⭐) – A historic hotel right across the street from Grant Park, offering a blend of old-world luxury and modern comfort.
13. Lakefront Trail
Stretching 18 miles along Lake Michigan, this trail is perfect for biking, jogging, or just soaking in the view. You’ll pass by beaches, parks, museums, and some truly Instagrammable skyline shots.
Where to stay nearby:
W Chicago – Lakeshore (⭐⭐⭐⭐) – Located right on Lake Shore Drive, this hotel offers unbeatable access to the trail and stunning lakefront views.
14. Maggie Daley Park
This newer park next to Millennium Park is designed for families and kids, featuring a play garden, mini golf, climbing walls, and a seasonal skating ribbon.
Where to stay nearby:
Radisson Blu Aqua Hotel (⭐⭐⭐⭐) – A modern high-rise with a rooftop pool, located just a short walk from the park. Perfect for families or couples wanting easy access to the lakefront and downtown.
15. Chicago Botanic Garden
Located a bit outside the city in Glencoe, this 385-acre garden is worth the short trip. It features themed gardens, walking paths, and peaceful ponds.
Where to stay nearby:
Renaissance Chicago North Shore Hotel (⭐⭐⭐⭐) – About 10 minutes from the gardens by car, this elegant stay gives you suburban peace with easy access to nature.
Taste the Local Flavor
No trip to Chicago is complete without diving into its legendary food scene. The city has earned its spot on the culinary map thanks to bold flavors, creative takes on comfort food, and iconic dishes that you just have to try at least once.
16. Try Chicago-Style Deep Dish Pizza
Thick, cheesy, and baked like a pie, Chicago’s deep dish pizza is a rite of passage. Locals have their loyalties, but first-timers can’t go wrong with Giordano’s or Lou Malnati’s. Don’t be surprised if one slice fills you up for hours.
Where to stay nearby:
Loews Chicago Hotel (⭐⭐⭐⭐) – Just a short walk from several top pizza spots downtown, this sleek hotel has modern rooms and a rooftop lounge with lake views.
17. Grab a Classic Chicago Hot Dog
Forget ketchup—this all-beef dog is “dragged through the garden,” topped with mustard, onions, relish, tomato slices, pickles, peppers, and celery salt on a poppy seed bun. Try one at Portillo’s or Gene & Jude’s for the real deal.
Where to stay nearby:
Aloft Chicago Downtown River North (⭐⭐⭐⭐) – A hip and affordable hotel just minutes from iconic hot dog joints and casual dining favorites.
18. Explore the Food Truck Scene & Local Eats
From Korean BBQ tacos to gourmet grilled cheese, Chicago’s food truck scene is diverse and delicious. Many gather around Daley Plaza, the Loop, or during weekend events in neighborhoods like Wicker Park and Logan Square.
Where to stay nearby:
The Robey (⭐⭐⭐⭐) – Located in the heart of Wicker Park, this boutique hotel is steps away from the city’s coolest neighborhoods and some of the best street food and pop-ups.
Unique Experiences You’ll Only Find in Chicago
Beyond the landmarks and iconic food, Chicago offers experiences you simply won’t find anywhere else. These two activities showcase the city’s unique perspective—literally and culturally.
19. Chicago Architecture River Cruise
This isn’t just a boat ride—it’s a moving classroom on one of the most architecturally rich cities in the world. As you float down the Chicago River, expert guides point out everything from Gothic cathedrals to gleaming modern towers. It’s relaxing, educational, and full of photo-worthy angles.
Where to stay nearby:
Renaissance Chicago Downtown Hotel (⭐⭐⭐⭐) – Overlooking the Chicago River, this stylish stay offers river-view rooms and is steps away from most cruise departure points.
20. Catch a Live Jazz or Theater Show
Chicago’s jazz history runs deep, and it still pulses through intimate clubs like Green Mill Cocktail Lounge—a Prohibition-era haunt that once hosted Al Capone. If theater’s more your vibe, head to the Chicago Theatre or explore smaller stages in the Loop and Lincoln Park.
Where to stay nearby:
Thewit Chicago – A Hilton Hotel (⭐⭐⭐⭐) – Right in the Theatre District, this vibrant hotel puts you within walking distance of major venues, plus it has its own rooftop lounge with skyline views.
Plan Your Chicago Itinerary
With its bold skyline, lakefront charm, rich culture, and unforgettable food, Chicago makes a strong impression on every traveler who walks its streets—or cruises its river.
Whether you spent your trip exploring world-class museums, relaxing in scenic parks, or diving into deep dish pizza, the city has a way of staying with you long after you leave.
This list of the top 20 things to do in Chicago area is just the beginning. Every neighborhood has its own vibe, and every season brings something new to discover.
Take your time, mix the classics with the hidden gems, and let the city unfold around you.
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