Find deals on over 320 top-rated, price matched, sightseeing, tours, and cruises around Chicago and beyond. Explore, compare, and book inspirational adventures for every type of trip and every type of traveler.
Likely to sell out
Often booked
Chicago River 45-minute Architecture Tour From Magnificent Mile
Chicago, Illinois,
United States
from $28
Often booked
Chicago Architecture Center River Cruise Aboard First Lady
Chicago, Illinois,
United States
from $56
Often booked
Big Bus Chicago: Hop-on Hop-off Sightseeing Tour By Open-top Bus
Chicago, Illinois,
United States
from $53
Much loved
Chicago In A Day: Explore Food, History, And Iconic Architecture
Chicago, Illinois,
United States
from $101
Often booked
Skip-the-line: Art Institute Of Chicago Guided Tour
Chicago, Illinois,
United States
from $74
Chicago Premier Plus Brunch Cruise On The Chicago River
Chicago, Illinois,
United States
from $110
Often booked
Original Chicago Architecture Interiors Tour: Dazzling Interiors
Chicago, Illinois,
United States
from $35
Much loved
Chicago's Delicious Donut Adventure With Underground Donut Tour
Chicago, Illinois,
United States
from $65
Much loved
#1 Art Institute Of Chicago Skip-the-line Exclusive Guided Tour
Chicago, Illinois,
United States
from $91
Much loved
Chicago City Tour With Architecture River Cruise Option
Chicago, Illinois,
United States
from $49
Chicago River Boat Tour & Hop-on Hop-off Bus Tour (save 20%)
Chicago, Illinois,
United States
from $99
Likely to sell out
Much loved
Bite Into Chicago: Discover The City’s Most Iconic Food
Chicago, Illinois,
United States
from $77
