Tours & activities · Viator
Planning time in Chicago? Browse popular tours and experiences aligned with real search demand (Things to do in Chicago for adults, Things to do in Chicago for free, Things to do in Chicago events) — curated from live Viator inventory.
24 live Viator picks · From $33–$508 on this page
2 hours · Free cancellation
Small-Group Sightseeing Boat Tour in Chicago
5.0★ · 121 reviews
From $89
2 hours · Free cancellation
Private Sailing on Beautiful Lake Michigan - Navy Pier, Chicago
5.0★ · 73 reviews
From $508
2 hours · Free cancellation
Chicago Walking Tour: Connecting Past and Present
5.0★ · 44 reviews
From $35
2 hours · Free cancellation
Chicago Haunts and Hooligans Tour
5.0★ · 41 reviews
From $35
2 hours · Free cancellation
Chicago Shoreline Adventure Boat Tour
5.0★ · 40 reviews
From $90
1 hour · Free cancellation
Chicago Photo Walk to Bean and Landmarks
5.0★ · 32 reviews
From $169
2 hours · Free cancellation
History and Architecture of Chicago Loop Walking Tour
5.0★ · 28 reviews
From $33
2 hours · Free cancellation
Private Chicago History Museum Tour
5.0★ · 27 reviews
From $163
2 hours · Free cancellation
Intro to Chicago Architecture
5.0★ · 25 reviews
From $35
2 hours · Free cancellation
Lincoln Park Zoo & Nature Museum Private Tour
5.0★ · 25 reviews
From $275
2 hours · Free cancellation
Chicago Scenic Driving Tour
5.0★ · 24 reviews
From $315
Free cancellation
O'Hare Airport Transfer to Chicago, Curbside - Luxury SUV
5.0★ · 21 reviews
From $160
Free cancellation
Chicago ↔ Midway Airport, Top Rated Private Sedan Transfer
5.0★ · 19 reviews
From $142
Free cancellation
Chicago Airport Transfer to O'Hare & Midway - Luxury Sedan
5.0★ · 17 reviews
From $133
Free cancellation
Chicago Airport Transfer to O'Hare & Midway Airport - Luxury SUV
5.0★ · 16 reviews
From $175
2 hours · Free cancellation
Chicago River Cycleboat Cruise
5.0★ · 16 reviews
From $65
30 minutes · Free cancellation
Meet and Greet Private SUV Transfer from ORD to Downtown Chicago
5.0★ · 12 reviews
From $300
2 hours
Prairie Avenue Haunted History Tour and Ghost Hunt
5.0★ · 12 reviews
From $40
2 hours · Free cancellation
Chicago Haunted Interior Architecture Ghost Tour
5.0★ · 12 reviews
From $35
3 hours · Free cancellation
Chicago in Spanish. Architecture. Mafia, Interiors, Underground
5.0★ · 11 reviews
From $45
3 hours · Free cancellation
Chicago Movie Locations Tour
5.0★ · 11 reviews
From $315
30 minutes · Free cancellation
Curbside SUV Transfer from ORD to Downtown Chicago
5.0★ · 10 reviews
From $240
30 minutes · Free cancellation
Private Sedan Transfer from Chicago Downtown to O`Hare airport
5.0★ · 9 reviews
From $220
40 minutes · Free cancellation
Photo Shoot in Chicago’s Urban Jungle Garden
5.0★ · 8 reviews
From $150
Figures come from the live Viator tours listed above for Chicago — not market medians or booked-volume claims.
Search flights to ORD, then come back to book tours for your dates.
Itinerary ideas aligned with how travelers search — each section points at live tours from the list above, not invented picks.
Day 1: Book a guided city tour or neighborhood walk to orient yourself. Day 2: Add a food, music, or museum experience that matches your interests. Day 3: Reserve a half- or full-day trip before flying out of ORD. May–June and September–October for mild weather. Chicago winters are brutal — January fares are cheap for a reason.
Travelers often search for "Things to do in Chicago with kids". Southwest's free bag policy at MDW can turn an apparently pricier MDW fare into the better family deal once you add two checked bags from a legacy carrier at ORD. Spotvoy calculates this automatically. Look for shorter durations (under 3 hours) and free cancellation when booking with children.
2 hours · Free cancellation
Small-Group Sightseeing Boat Tour in Chicago
5.0★ · 121 reviews
From $89
2 hours · Free cancellation
Private Chicago History Museum Tour
5.0★ · 27 reviews
From $163
For "Things to do in Chicago for free", mix free walking districts and public sights with one paid highlight from the live list — that balance keeps costs down without missing the signature experiences.
2 hours · Free cancellation
History and Architecture of Chicago Loop Walking Tour
5.0★ · 28 reviews
From $33
2 hours · Free cancellation
Chicago Walking Tour: Connecting Past and Present
5.0★ · 44 reviews
From $35
Searches like "Things to do in Chicago for couples" point to food tours, sunset cruises, and smaller-group experiences. Book one signature evening activity and keep one day flexible for spontaneous plans.
2 hours · Free cancellation
Private Sailing on Beautiful Lake Michigan - Navy Pier, Chicago
5.0★ · 73 reviews
From $508
2 hours · Free cancellation
Private Chicago History Museum Tour
5.0★ · 27 reviews
From $163
Answers based on how travelers search — including People Also Ask topics from Google.
Book popular tours a few days ahead — peak weekends and holidays sell out. Compare ratings, duration, and from-prices in our live Viator list before you commit.
Most visitors split time between a city overview tour, one food or culture experience, and a flexible half-day for neighborhoods. May–June and September–October for mild weather. Chicago winters are brutal — January fares are cheap for a reason. Fly into ORD and book your top tour within 48 hours of arrival.
Most visitors split time between a city overview tour, one food or culture experience, and a flexible half-day for neighborhoods. May–June and September–October for mild weather. Chicago winters are brutal — January fares are cheap for a reason. Fly into ORD and book your top tour within 48 hours of arrival.
Chicago is the third-largest city in the US, home to world-class architecture, deep-dish pizza, Lake Michigan, and some of the finest museums in the country. ORD and MDW serve different airlines and neighborhoods — choosing the right airport can save a family of four $100+ in ground transport. Use the curated tours below to compare ratings, durations, and prices before booking.
Book popular tours a few days ahead — peak weekends and holidays sell out. Compare ratings, duration, and from-prices in our live Viator list before you commit.
Chicago is the third-largest city in the US, home to world-class architecture, deep-dish pizza, Lake Michigan, and some of the finest museums in the country. ORD and MDW serve different airlines and neighborhoods — choosing the right airport can save a family of four $100+ in ground transport. Start with a highly rated city tour, then add one experience that matches your interests from the curated list on this page.
We may earn a commission when you book through Viator links at no extra cost to you. Flight rankings and recommendations stay independent.
24 live Viator picks · "Fun things to do in Chicago for young adults" · From $33–$508 on this page
2 hours · Free cancellation
Small-Group Sightseeing Boat Tour in Chicago
5.0★ · 121 reviews
From $89
2 hours · Free cancellation
Private Sailing on Beautiful Lake Michigan - Navy Pier, Chicago
5.0★ · 73 reviews
From $508
2 hours · Free cancellation
Chicago Walking Tour: Connecting Past and Present
5.0★ · 44 reviews
From $35
2 hours · Free cancellation
Chicago Haunts and Hooligans Tour
5.0★ · 41 reviews
From $35
2 hours · Free cancellation
Chicago Shoreline Adventure Boat Tour
5.0★ · 40 reviews
From $90
1 hour · Free cancellation
Chicago Photo Walk to Bean and Landmarks
5.0★ · 32 reviews
From $169
2 hours · Free cancellation
History and Architecture of Chicago Loop Walking Tour
5.0★ · 28 reviews
From $33
2 hours · Free cancellation
Private Chicago History Museum Tour
5.0★ · 27 reviews
From $163
2 hours · Free cancellation
Intro to Chicago Architecture
5.0★ · 25 reviews
From $35
2 hours · Free cancellation
Lincoln Park Zoo & Nature Museum Private Tour
5.0★ · 25 reviews
From $275
2 hours · Free cancellation
Chicago Scenic Driving Tour
5.0★ · 24 reviews
From $315
Free cancellation
O'Hare Airport Transfer to Chicago, Curbside - Luxury SUV
5.0★ · 21 reviews
From $160
Free cancellation
Chicago ↔ Midway Airport, Top Rated Private Sedan Transfer
5.0★ · 19 reviews
From $142
Free cancellation
Chicago Airport Transfer to O'Hare & Midway - Luxury Sedan
5.0★ · 17 reviews
From $133
Free cancellation
Chicago Airport Transfer to O'Hare & Midway Airport - Luxury SUV
5.0★ · 16 reviews
From $175
2 hours · Free cancellation
Chicago River Cycleboat Cruise
5.0★ · 16 reviews
From $65
30 minutes · Free cancellation
Meet and Greet Private SUV Transfer from ORD to Downtown Chicago
5.0★ · 12 reviews
From $300
2 hours
Prairie Avenue Haunted History Tour and Ghost Hunt
5.0★ · 12 reviews
From $40
2 hours · Free cancellation
Chicago Haunted Interior Architecture Ghost Tour
5.0★ · 12 reviews
From $35
3 hours · Free cancellation
Chicago in Spanish. Architecture. Mafia, Interiors, Underground
5.0★ · 11 reviews
From $45
3 hours · Free cancellation
Chicago Movie Locations Tour
5.0★ · 11 reviews
From $315
30 minutes · Free cancellation
Curbside SUV Transfer from ORD to Downtown Chicago
5.0★ · 10 reviews
From $240
30 minutes · Free cancellation
Private Sedan Transfer from Chicago Downtown to O`Hare airport
5.0★ · 9 reviews
From $220
40 minutes · Free cancellation
Photo Shoot in Chicago’s Urban Jungle Garden
5.0★ · 8 reviews
From $150
