4.6 (11,501 Reviews)

Today's Top Deals in Chicago

Save Big In Chicago

Don't miss out on these great Chicago savings for your next trip.

Medieval Times Dinner and Tournament Illinois in Schaumburg, Illinois

SAVE $10

Medieval Times Dinner and Tournament Illinois
Bikes, Bites, & Brews - Chicago's Signature Dishes Bike Tour in Chicago, Illinois

SAVE $8

Bikes, Bites, & Brews - Chicago's Signature Dishes Bike Tour
Chicago's Chinatown Food and Walking Tour in Chicago, Illinois

SAVE $8

Chicago's Chinatown Food and Walking Tour
Chicago Favorites Food and Walking Tour in Chicago, Illinois

SAVE $7

Chicago Favorites Food and Walking Tour
Chicago's Lakefront Neighborhoods Bicycle Tour in Chicago, Illinois

SAVE $5

Chicago's Lakefront Neighborhoods Bicycle Tour
Canine Cruise on Chicago's First Lady in Chicago, Illinois

SAVE $5

Canine Cruise on Chicago's First Lady
View More Savings

Money Saving Chicago Vacation Packages

Save even more when you plan you book your room and tickets together.

Big Bus Tours Chicago in Chicago, Illinois

Save 33 %

Big Bus Chicago + Hotel Package
iFLY Indoor Skydiving - Chicago Naperville in Naperville, Illinois

Save 16 %

iFLY Naperville + Hotel Package
iFLY Indoor Skydiving - Chicago Naperville in Naperville, Illinois

Save 13 %

iFLY Naperville + Choice of Show
iFLY Indoor Skydiving - Chicago Naperville in Naperville, Illinois

Save 13 %

iFLY Naperville + Medieval Times Dinner and Tournament
iFLY Indoor Skydiving - Chicago Rosemont in Rosemont, Illinois

Save 15 %

iFLY Rosemont Indoor Skydiving + Hotel Package
iFLY Indoor Skydiving - Chicago Rosemont in Rosemont, Illinois

Save 13 %

iFLY Rosemont Indoor Skydiving + Choice of Show
View More Packages

Great Hotel Deals

Need a room? Find savings on these select hotels.

Courtyard By Marriott Chicago Waukegan/Gurnee in Waukegan, Illinois

Save $109/night

Courtyard By Marriott Chicago Waukegan/Gurnee
Hilton Chicago Magnificent Mile Suites in Chicago, Illinois

Save $97/night

Hilton Chicago Magnificent Mile Suites
DoubleTree by Hilton Hotel Chicago - Schaumburg in Schaumburg, Illinois

Save $74/night

DoubleTree by Hilton Hotel Chicago - Schaumburg
View More Hotel Deals
Tripster Gift Certificates

Give the Gift of Travel

Purchase Gift Certificates for your family and friends!

Shop Now