Find deals on over 150 top-rated, price matched, things to do close to $250 around Chicago and beyond. Explore, compare, and book inspirational adventures for every type of trip and every type of traveler.

Likely to sell out
Much loved
African American Heritage Tour Of Chicago
Chicago, Illinois, United States
4.6 (74)
from $125
Dinner on the Skydeck Ledge
Skydeck Chicago Pie In The Sky Dining Experience
Chicago, Illinois, United States
3.6 (37)
from $154
Chicago Food Tour with The Magnificent Mile and Millennium Park
Likely to sell out
Chicago Food Tour With The Magnificent Mile And Millennium Park
Chicago, Illinois, United States
2.5 (2)
from $155
Much loved
Best Of Chicago Small-group Tour With Architecture River Cruise
Chicago, Illinois, United States
4.6 (160)
from $254
Beverly Hills
Likely to sell out
Much loved
Small-group Tour Of Chicago Neighborhoods - North And South Side
Chicago, Illinois, United States
4.6 (43)
from $125
Likely to sell out
Mother's Day Signature Dinner Cruise On Lake Michigan
Chicago, Illinois, United States
3.0 (2)
from $130
Minivan Transportation To Share
O'hare Airport Taxi (ord) To Or From Chicago Downtown
Chicago, Illinois, United States
5.0 (2)
from $130
Chicago Tour - South Side
Chicago, Illinois, United States
4.6 (29)
from $125
Much loved
Private Chicago Fire Tv Show Set Tour
Chicago, Illinois, United States
5.0 (27)
from $315
Pilsen Neighborhood Train & Walking Tour
Likely to sell out
Chicago Foods Tour With The Loop, Skyline, Millennium Park
Chicago, Illinois, United States
5.0 (1)
from $145
Chicago 4-hour Sightseeing Transfer By Luxury Private Sedan
Chicago, Illinois, United States
5.0 (4)
from $190
Private Chicago Movie Locations Tour
Chicago, Illinois, United States
5.0 (1)
from $315
Private Chicago Scenic Driving Tour
Chicago, Illinois, United States
5.0 (13)
from $315
Manet
Much loved
Art Institute Of Chicago Private Expert Guided Tour
Chicago, Illinois, United States
5.0 (43)
from $215
Professional Photo Shoot In Chicago
Chicago, Illinois, United States
4.4 (8)
from $198
One-way Private Airport Transfer By Sedan
Chicago, Illinois, United States
4.0 (4)
from $179
Best Of Chicago: Architecture & Highlights City Private Tour
Chicago, Illinois, United States
4.9 (95)
from $245
Likely to sell out
Learn To Make Mole The Real Mexican Way Before Lunch
Chicago, Illinois, United States
5.0 (4)
from $186
Chicago Attractions Pass: Save Up To 50% - Includes 360 Chicago
Chicago, Illinois, United States
3.3 (93)
from $139
Chicago Fireworks Premier Dinner Cruise On Lake Michigan
Chicago, Illinois, United States
3.2 (62)
from $163
Chicago Fireworks Dinner Cruise With Buffet
Chicago, Illinois, United States
3.8 (77)
from $137
Likely to sell out
Chicago Small-group Night Tour With Skydeck And Boat Cruise
Chicago, Illinois, United States
4.3 (23)
from $209
Likely to sell out
Chicago New Year's Eve Buffet Dinner Cruise On Lake Michigan
Chicago, Illinois, United States
3.8 (11)
from $274
Likely to sell out
New Year's Eve Plated Dinner Cruise On Lake Michigan
Chicago, Illinois, United States
5.0 (2)
from $342
Likely to sell out
Much loved
Chicago In A Day: Food And Architecture Private Walking Tour
Chicago, Illinois, United States
5.0 (52)
from $273
Private Frank Lloyd Wright Architectural Tour By Luxury Vehicle
Chicago, Illinois, United States
3.3 (7)
from $300
Welcome To Chicago: Private Half-day Tour With 360 Observation Deck
Chicago, Illinois, United States
5.0 (2)
from $240
Skydeck Chicago
Chicago Citypass®
Chicago, Illinois, United States
4.4 (490)
from $142
Chicago Gourmet Dinner Cruise On Lake Michigan
Chicago, Illinois, United States
3.6 (340)
from $140
Looking Down Milwaukee Avenue, a street full of unique shops, restaurants, and bars.
Private Wicker Park And Bucktown Walking Tour
Chicago, Illinois, United States
New
from $195
Chicago In A Day With A Local
Chicago, Illinois, United States
New
from $179
Chicago Hidden Gems! Suburbs Tour
Chicago, Illinois, United States
New
from $160
Mother's Day Premier Plus Brunch Cruise On The Chicago River
Chicago, Illinois, United States
New
from $158
Chicago Must-See Bike Tour with Iconic Photo Ops
Likely to sell out
Bike Tour In Chicago
Chicago, Illinois, United States
New
from $129
Roundtrip Private Airport Transfer Chicago (ord) To City
Chicago, Illinois, United States
New
from $214
1 Hour Photoshoot In Chicago
Chicago, Illinois, United States
New
from $179