Destination

Top 10 Things to Do in Chicago

Chicago is America's great architectural city — a place where world-firsts in skyscraper design, deep-dish pizza, and the blues all collide on the shore of Lake Michigan. The city's walkable lakefront, extraordinary museums, and singular food culture make it one of the most rewarding urban destinations in North America. Its architecture boat tours alone are worth the flight.

Location: US2026103 viewsMar 16, 2026 Updated Oct 3, 2026

Top10Grid rankings are decided by votes, not algorithms — use the buttons below to move this list.

Place

Top 10 lists about this destination

Be the first

Top10Grid Editorial

Editorial team

Current Rankings

0
#1
Cloud Gate (The Bean)
Cloud Gate, universally known as The Bean, is Anish Kapoor's 110-tonne polished steel sculpture in Millennium Park — the most visited attraction in the American Midwest, outperforming the Navy Pier's 8.6 million annual visitors. Its seamless mirror surface reflects the Chicago skyline and everyone who stands before it in a warped, dreamlike panorama. Entry to Millennium Park and the sculpture is completely free; the Lurie Garden and Jay Pritzker Pavilion surrounding it are equally worth exploring. Visit after dark when the skyscraper reflections take on a completely different character.
source: wikipediaVisit →
0
#2
Art Institute of Chicago
The Art Institute of Chicago is consistently ranked among the world's top five art museums, housing an encyclopaedic collection of over 300,000 works including Georges Seurat's A Sunday on La Grande Jatte, Grant Wood's American Gothic, and Edward Hopper's Nighthawks. The Modern Wing designed by Renzo Piano is a masterpiece of museum architecture. Admission is $35 for adults; free on most Thursdays evenings. Allow at least four hours — the Impressionist and Post-Impressionist galleries alone deserve two. It is faster to visit than the Louvre, yet its collection rivals the second-ranked museum in visitor numbers with over 1.5 million annual attendees.
source: wikipediaVisit →
0
#3
Chicago Architecture Boat Tour
Chicago invented the skyscraper and its riverine cityscape is a living textbook of architectural history. The Chicago Architecture Center runs 90-minute boat tours along the Chicago River that pass over 40 landmark buildings with expert commentary from volunteer docents. Tours run from May through November and cost around $55. The view of the canyon of buildings from water level is completely different from street level — you see facades, water gates, and bridges invisible from the sidewalk. Book in advance for summer weekends.
source: wikipediaVisit →
0
#4
Deep-Dish Pizza
Chicago's deep-dish pizza is not merely food — it's a civic institution. The thick, buttery crust is layered with cheese first, then toppings, then crushed tomatoes on top, and baked in a round steel pan until the crust is golden and the filling is bubbling. The three essential stops for a proper tasting: Lou Malnati's (the purist choice, Butter Crust), Giordano's (stuffed style, extra deep), and Pequod's (caramelised crust, the cult pick). Expect a 45-minute wait for a pie to bake — it is worth every second.
source: wikipediaVisit →
0
#5
Navy Pier
Navy Pier is Chicago's most visited attraction — a 1 km pier jutting into Lake Michigan with a 196-foot Ferris wheel, a Shakespeare Theatre, an IMAX cinema, the Chicago Children's Museum, a beer garden, and restaurants with panoramic lake views. Entry to the pier is free; individual attractions cost extra. The Centennial Wheel at night, with the skyline behind it, is one of Chicago's most photogenic sights, offering views that outshine even the Skydeck's 360-degree perspective. Free fireworks launch from the pier every Wednesday and Saturday night in summer, attracting over 2 million visitors annually for these shows.
source: wikipediaVisit →
0
#6
Wrigley Field
Wrigley Field is the second-oldest Major League Baseball park in America, opened in 1914 and home to the Chicago Cubs. The ivy-covered brick outfield walls, the hand-operated scoreboard, and the rooftop bleachers on Waveland Avenue are beloved American sports traditions. Tours of the park run year-round; game tickets range from $20 for bleacher seats to $200+ for premium sections.
source: wikipediaVisit →
0
#7
The 606 Trail
The 606 is an elevated rail trail converted from an abandoned freight line — Chicago's answer to the New York High Line, running 4.5 km through the Wicker Park, Bucktown, and Humboldt Park neighbourhoods. It's beloved by cyclists, runners, and dog walkers and lined with public art installations. The western end in Humboldt Park gives access to Puerto Rican cultural restaurants and the beautiful lagoon.
source: wikipediaVisit →
0
#8
Field Museum of Natural History
The Field Museum houses one of the most extensive natural history collections in the world — over 40 million specimens across anthropology, botany, geology, and zoology. Its most famous resident is Sue, the largest and most complete T. rex skeleton ever discovered. The Egyptian collection with its genuine mummies, the Underground Adventure shrunken-world exhibit, and the Pacific collection are all exceptional, outshining the Shedd Aquarium's 32,000 animals in sheer diversity. Admission is $30; the Experience Chicago pass combines it with the Shedd Aquarium and Adler Planetarium at a discount, saving visitors 25% on combined entry.
source: wikipediaVisit →
0
#9
Chicago Blues Scene
Chicago electric blues — the amplified, urban sound developed by Muddy Waters, Howlin' Wolf, and Little Walter after the Great Migration — is one of America's defining musical traditions, and the South Side still carries its living flame. Buddy Guy's Legends in the South Loop is the best-known venue, with Buddy himself often appearing unannounced. Rosa's Lounge in Logan Square is the authentic neighbourhood pick, outperforming most tourist-oriented clubs with its intimate setting and 90% local patronage.
source: wikipediaVisit →
0
#10
Chicago Riverwalk
The Chicago Riverwalk is a beautifully designed pedestrian promenade running along the south bank of the Chicago River from Lake Street to Lake Michigan — about 1.25 miles of cafes, kayak rentals, river tours, and architectural views from water level. Kayak Chicago rents stand-up paddleboards and kayaks here; grabbing a drink at the outdoor beer garden while watching tour boats pass beneath the skyscrapers is a quintessentially Chicago experience.
source: wikipediaVisit →

Current Rankings

Share this list

103 views

Get ranking updates

Get the weekly travel rundown

Only lists published since the last email. Join the early readers.

Only Top 10s published in the last 7 days
One email a week — and none at all in a week with nothing new
Unsubscribe in one click

No spam. One email per week. Unsubscribe anytime.

Readers Also Ranked

More Lists Like This

Top 10 Most Stunning Castles in Europe

#1Neuschwanstein Castle, Germany
#2Edinburgh Castle, Scotland
#3Château de Chambord, France

Top 10 Most Overrated Tourist Destinations

#1Dubai
#2Cancún
#3Times Square, New York

Top 10 Best Beaches in the World — From Pink Sand to Limestone Karst

#1Grace Bay, Turks and Caicos
#2Whitehaven Beach, Australia
#3Navagio Beach, Zakynthos

Top 10 Best Things to Do in Xi'an, China

#1Xi'an City Wall
#2Terracotta Warriors Museum
#3Datang Evernight City

Frequently asked questions

What are the absolute must-see attractions in Chicago?

The top must-see attractions include Millennium Park (home to Cloud Gate, also known as 'The Bean'), the Art Institute of Chicago, Navy Pier, Willis Tower Skydeck, and the architectural river cruise.

What is the best time of year to visit Chicago for sightseeing?

Late spring (May–June) and early fall (September–October) offer mild weather and fewer crowds, making them ideal for exploring outdoor attractions and festivals.

Are there any free things to do among Chicago's top attractions?

Yes, many top attractions are free, including Millennium Park, Lincoln Park Zoo, the Chicago Riverwalk, and free days at the Art Institute of Chicago on select Thursdays.

How many days do I need to see all the top things in Chicago?

A minimum of 3 to 4 days is recommended to comfortably visit the major attractions, enjoy the food scene, and experience neighborhoods like Wicker Park or the Loop.