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.
Chicago Private Custom City Tour With Hotel Pick Up
Chicago, Illinois,
United States
from $539
Likely to sell out
Much loved
Come Sailing With Us At Navy Pier: Sunset Sail On Lake Michigan
Chicago, Illinois,
United States
from $508
Likely to sell out
Much loved
Private 45-minute Chicago Skyline Helicopter Tour
Chicago, Illinois,
United States
from $849
Private Vacation Photography Session With Local Photographer In Chicago
Chicago, Illinois,
United States
from $325
Likely to sell out
Much loved
Come Sailing With Us At Navy Pier: Sail Beautiful Lake Michigan
Chicago, Illinois,
United States
from $508
Much loved
Best Of Chicago Small-group Tour With Architecture River Cruise
Chicago, Illinois,
United States
from $254
Chicago Helicopter 25-mile Tour For Up To Three Passengers
Chicago, Illinois,
United States
from $650
Likely to sell out
Come Sailing With Us At Navy Pier - Saturday Fireworks Sail
Chicago, Illinois,
United States
from $567
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
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
6-hour Private Suv Transportation Service In Chicago
Chicago, Illinois,
United States
from $1,200
Chicago Helicopter 10-minute Tour For Up To Three Passengers
Chicago, Illinois,
United States
from $375
Chicago Private Boat Rental - Explore Chicago's Skyline & Waters
Chicago, Illinois,
United States
from $2,275
5 Day Tour On Lakes Superior Huron And Michigan
Chicago, Illinois,
United States
from $1,195
Chicago 2-hour Sightseeing Transfer By Luxury Stretch Limo
Chicago, Illinois,
United States
from $650
Likely to sell out
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 $376
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
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