Find deals on 72 top-rated, price matched, things to do close to $500+ around Chicago and beyond. Explore, compare, and book inspirational adventures for every type of trip and every type of traveler.
Much loved
Best Of Chicago Small-group Tour With Architecture River Cruise
Chicago, Illinois,
United States
from $254
Much loved
Private 45-minute Chicago Skyline Helicopter Tour
Chicago, Illinois,
United States
from $849
Much loved
Come Sailing At Navy Pier Marina: Sunset Sail On Lake Michigan
Chicago, Illinois,
United States
from $508
Chicago Helicopter 25-mile Tour For Up To Three Passengers
Chicago, Illinois,
United States
from $650
Chicago Private Boat Rental - Explore Chicago's Skyline & Waters
Chicago, Illinois,
United States
from $2,275
Chicago Private Custom City Tour With Hotel Pick Up
Chicago, Illinois,
United States
from $539
Likely to sell out
Much loved
Come Sailing At Navy Pier Marina: Sail Beautiful Lake Michigan
Chicago, Illinois,
United States
from $508
Likely to sell out
Chicago New Year's Eve Buffet Dinner Cruise On Lake Michigan
Chicago, Illinois,
United States
from $274
Likely to sell out
New Year's Eve Plated Dinner Cruise On Lake Michigan
Chicago, Illinois,
United States
from $342
Likely to sell out
Much loved
Chicago In A Day: Food And Architecture Private Walking Tour
Chicago, Illinois,
United States
from $273
Private Frank Lloyd Wright Architectural Tour By Luxury Vehicle
Chicago, Illinois,
United States
from $300
Come Sailing At Navy Pier Marina - Saturday Fireworks Sail
Chicago, Illinois,
United States
from $567
Luxury Suv 4-hours Sightseeing Tour In Chicago Dt Hourly Service
Chicago, Illinois,
United States
from $350
Lake Superior,lake Huron,lake Michigan 4-day Tour From Chicago
Chicago, Illinois,
United States
from $1,054
Private Vacation Photography Session With Local Photographer In Chicago
Chicago, Illinois,
United States
from $325
6-hour Private Suv Transportation Service In Chicago
Chicago, Illinois,
United States
from $1,200
Chicago Private Walking Food Tour With Secret Food Tours
Chicago, Illinois,
United States
from $306
Chicago Helicopter 10-minute Tour For Up To Three Passengers
Chicago, Illinois,
United States
from $375
Chicago 2-hour Sightseeing Transfer By Luxury Stretch Limo
Chicago, Illinois,
United States
from $650
Chicago To Washington D.c. Cherry Blossom 3-day Tour
Chicago, Illinois,
United States
from $476
Chicago’s Festive Lights: A Magical Christmas Journey
Chicago, Illinois,
United States
from $367
5 Day Tour On Lakes Superior Huron And Michigan
Chicago, Illinois,
United States
from $1,195
Chicago 4-hour Private Sightseeing Transfer By Luxury Limousine
Chicago, Illinois,
United States
from $800
Chicago Private 4-hour Sightseeing Transfer By Luxury Suv
Chicago, Illinois,
United States
from $250
Likely to sell out
Walking Tour Of Chicago’s Artsy Cultural Landmarks
Chicago, Illinois,
United States
from $335
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