Best overall
Original Chicago Architecture Interiors Tour: Dazzling Interiors
Highest Outty Ranking in the city right now.
Outty Ranking 97 · from $35
The 15 best things to do in Chicago (2026)
We rank 556 experiences in Chicago, United States, on the same 0 to 100 Outty Ranking. The best right now is Original Chicago Architecture Interiors Tour: Dazzling Interiors at 97/100, and 3 experiences here make the 90+ Club. Updated Sep 2026.
Quick picks
Best value
Illinois Holocaust Museum Experience360 Admission
Cheapest experience we rank 70 or above.
Outty Ranking 72 · from $6
Best for families
The Escape Game Chicago: Epic 60-Minute Adventures in River North
Top ranked option that welcomes kids.
Outty Ranking 86 · from $48
Best for a rainy day
Chicago Favorites Ultimate Food and Walking Tour
Indoor-leaning culture pick that works in any weather.
Outty Ranking 92 · from $85
Best last minute
Chicago Murder Mystery Tour
Highest ranked option with same-day availability.
Outty Ranking 92 · from $35
Best evening out
Chicago Bike & Classic Food Tour: Bikes, Bites & Views - Adults
Top ranked nightlife or evening experience.
Outty Ranking 90 · from $89
The ranked list
1. Original Chicago Architecture Interiors Tour: Dazzling Interiors
Outty Ranking97UPDATE 2024: Don't be fooled by the copycats out there offering shady copies of our award-winning tours for $1 cheaper! There's only one company that's exclusively offered interiors-themed tours in Chicago for more than. Peak Performance at 97/100, 5.0/5 from 1,817 traveler reviews, 2h from $35, free cancellation, an Outty 90+ Club member.
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2. Chicago Favorites Ultimate Food and Walking Tour
Outty Ranking92The perfect Food Tour of Chicago for first timers or anyone eager to explore Chicago's famous foods & top attractions—all in one tour. Stroll the beautiful streets of downtown & taste the Windy City’s favorite eats on th. 90+ Club at 92/100, 4.9/5 from 2,321 traveler reviews, 3h from $85, free cancellation, an Outty 90+ Club member.
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3. Chicago Murder Mystery Tour
Outty Ranking92You will solve a murder as you learn real Chicago history! Play detective as you unravel a murder mystery, and learn about Chicago's true crime legends and Prohibition secrets. This two-in-one experience combines a ric. 90+ Club at 92/100, 5.0/5 from 758 traveler reviews, 2h from $35, free cancellation, an Outty 90+ Club member.
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4. Chicago Bike & Classic Food Tour: Bikes, Bites & Views - Adults
Outty Ranking90Taste all of Chicago’s classic eats on this 4 1/2 hr Adults-only guided food & bicycle tour! Join the expert guides of Bobby’s Bike Hike, America’s first city bike tour company, on this exciting & informative adventure w. Exceptional at 90/100, 4.9/5 from 768 traveler reviews, 4.5h from $89, free cancellation.
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5. Chicago in a Day Walking Tour: Food, History & Architecture
Outty Ranking89Immerse yourself in Chicago's rich history and vibrant culinary scene on this captivating walking tour. Discover the city's iconic architecture and Prohibition-era charm while indulging in delectable local cuisine. From. Exceptional at 89/100, 4.9/5 from 1,391 traveler reviews, 4.5h from $101, free cancellation.
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6. Chicago Architecture and True Crime: Halloween Edition
Outty Ranking89Get the best of both worlds: explore Chicago’s stunning architecture while uncovering its dark past. Inspired by Devil in the White City, this expert-led walking tour reveals the secrets of the city’s skyline and its sha. Exceptional at 89/100, 5.0/5 from 641 traveler reviews, 1.5h from $35, free cancellation.
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7. Chicago River 90-Minute Architecture Boat Tour
Outty Ranking89Marvel at the magnificent architecture on the Chicago River with expert tour guides! All ages welcome. Each architecture river tour is narrated by a professional guide which leads passengers down the Chicago River to di. Exceptional at 89/100, 4.8/5 from 1,906 traveler reviews, 1.5h from $37, free cancellation.
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8. Chicago's Delicious Downtown Donut Tour with 8 Amazing Tastings
Outty Ranking89Recently voted one of TripAdvisor's top food tours in the US. Discover the sweet side of the Windy City on the Underground Donut Tour, Chicago’s Delicious Donut Adventure. We’ll kick things off at the legendary Doughnu. Exceptional at 89/100, 4.9/5 from 1,520 traveler reviews, 2h from $60, free cancellation.
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9. Skip-the-line: Art Institute of Chicago Guided Tour
Outty Ranking88Beat the crowds with an expert art historian guide on this exclusive early morning tour. Immerse yourself among the masterpieces housed within the acclaimed museum and listen as your guide brings each piece to life by sh. Exceptional at 88/100, 5.0/5 from 650 traveler reviews, 2.5h from $71, free cancellation.
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10. Haunted Chicago: Crime, Ghosts, and Capone Walking Tour
Outty Ranking88Walk in the footsteps of Al Capone, John Dillinger, and real life ghost stories while hearing tales of Chicago's haunted past. Visit Prohibition Era speakeasy bars, sites of real life mob shootouts, and haunted tragedies. Exceptional at 88/100, 5.0/5 from 415 traveler reviews, 1.5h from $35, free cancellation.
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11. Chicago Architecture Tour: Underground Pedway and the Loop
Outty Ranking88This tour explores some of the best hidden details, secret buildings and spaces, and untold stories that add wonderful bits of color and texture to the overall narrative of Chicago. On this tour, we will explore the famo. Exceptional at 88/100, 4.9/5 from 560 traveler reviews, 2h from $30, free cancellation.
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12. Chicago Food Tour: 6 Dishes with Deep Dish Pizza & Beef Sandwich
Outty Ranking88On our Secret Food Tour: Chicago, you'll enjoy a variety of foods with culinary influences from the people who built this city. You'll experience all the city's biggest food hits, many dishes with roots dating back over. Exceptional at 88/100, 4.9/5 from 1,021 traveler reviews, 3h from $85, free cancellation.
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13. Chicago's Chinatown Food and Walking Tour
Outty Ranking88Chicago's Chinatown: Few neighborhoods in America combine such delicious cuisine with fascinating history. Join Bobby’s Bike Hike & Food Tours, whose food tours have ranked Top 10 in America by USA Today & Top 20 in the. Exceptional at 88/100, 4.9/5 from 804 traveler reviews, 3h from $80, free cancellation.
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14. Chicago Walking Tour: Historic Treasures of Chicago
Outty Ranking87Learn about the great architectural landmarks of Michigan Avenue and State Street. The 40 years between 1890 and 1930 saw the creation of some of Chicago’s the most memorable buildings, many of which are featured on this. Exceptional at 87/100, 4.9/5 from 453 traveler reviews, 2h from $35, free cancellation.
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15. Chicago City Minibus Tour
Outty Ranking87Uncover the best of Chicago on an unforgettable highlights tour designed for travelers, sightseers, and history lovers alike! Step off the bus to admire Frank Lloyd Wright’s lobby inside The Rookery, take in dramatic sig. Exceptional at 87/100, 4.9/5 from 655 traveler reviews, 2h from $50, free cancellation.
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Traveler ratings are provided by Viator and Tripadvisor. The Outty Ranking is our own independent evaluation. How the ranking works.
Must-see landmarks in Chicago
Millennium Park (81)Navy Pier (57)Grant Park (53)The Magnificent Mile (48)Art Institute of Chicago (45)Chicago River (45)Chicago Cultural Center (43)Cloud Gate (The Bean) (42)Chicago Riverwalk (39)Chicago Theatre (38)Wrigley Building (34)Field Museum (31)
Head to head
- Millennium Park vs Navy Pier: which first?
- Grant Park vs Millennium Park: which first?
- Millennium Park vs The Magnificent Mile: which first?
- Art Institute of Chicago vs Millennium Park: which first?
- Grant Park vs Navy Pier: which first?
- Navy Pier vs The Magnificent Mile: which first?
- Art Institute of Chicago vs Navy Pier: which first?
- Grant Park vs The Magnificent Mile: which first?
- Art Institute of Chicago vs Grant Park: which first?
- Art Institute of Chicago vs The Magnificent Mile: which first?
When to go
May to October. Winter cruises stop running when the river ices.
Frequently asked questions
What is the number one thing to do in Chicago?
Original Chicago Architecture Interiors Tour: Dazzling Interiors is the top ranked experience in Chicago right now, with an Outty Ranking of 97 out of 100 from 1,817 traveler reviews, from $35 per person. It leads a field of 556 experiences we rank in the city.
What are the must-see attractions in Chicago?
The landmarks with the deepest choice of tours and tickets are Millennium Park, Navy Pier, Grant Park, The Magnificent Mile. Each has its own Outty hub comparing every ranked way to see it.
How much do things to do in Chicago cost?
The 15 best experiences average $58 per person. The cheapest of them is Chicago Architecture Tour: Underground Pedway and the Loop from $30, and 15 of the 15 offer free cancellation.
What are the best things to do in Chicago with kids?
Most of the top experiences suit older kids; check the minimum age listed on each activity before booking.
When is the best time to visit Chicago?
May to October. Winter cruises stop running when the river ices.
How is this list ranked?
Every experience is scored 0 to 100 by the Outty Ranking, which blends traveler sentiment, review depth, booking momentum, value against comparable options in Chicago, quality signals and cancellation flexibility. The list updates automatically as new reviews and bookings arrive.