4.6 (11,501 Reviews)

Today's Top Deals in Chicago

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

Go City Chicago All-Inclusive Pass - ,

SAVE $18

Go City Chicago All-Inclusive Pass
Go City Chicago Explorer Pass - ,

SAVE $15

Go City Chicago Explorer Pass

Odyssey Chicago River Premier Dinner Cruise in Chicago, Illinois

SAVE $11

Odyssey Chicago River Premier Dinner Cruise
Chicago Premier Dinner Cruise on Lake Michigan in Chicago, Illinois

SAVE $10

Chicago Premier Dinner Cruise on Lake Michigan
Art Institute of Chicago Skip-the-Line Guided Tour in Chicago, Illinois

SAVE $10

Art Institute of Chicago Skip-the-Line Guided Tour
Medieval Times Dinner and Tournament Illinois in Schaumburg, Illinois

SAVE $10

Medieval Times Dinner and Tournament Illinois
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 48 %

Big Bus Chicago + Hotel Package
Go City Chicago All-Inclusive Pass - ,

Save 27 %

Go City Pass Chicago + Hotel Package
Go City Chicago Explorer Pass - ,

Save 36 %

Chicago Explorer Pass + Hotel Package
LEGOLAND Discovery Center Chicago in Schaumburg, Illinois

Save 30 %

LEGOLAND Chicago + Medieval Times Chicago Combo Tickets
Odyssey Chicago River Premier Dinner Cruise in Chicago, Illinois

Save 16 %

Odyssey Chicago River Dinner Cruise + Hotel Package
iFLY Indoor Skydiving - Chicago Lincoln Park in Chicago, Illinois

Save 31 %

iFLY Lincoln Park + Hotel Package
View More Packages

Great Hotel Deals

Need a room? Find savings on these select hotels.

House 5863 Chicago Bed and Breakfast in Chicago, Illinois

Save $121/night

House 5863 Chicago Bed and Breakfast
Hilton Chicago Magnificent Mile Suites in Chicago, Illinois

Save $100/night

Hilton Chicago Magnificent Mile Suites
Hilton Garden Inn Schaumburg in Schaumburg, Illinois

Save $95/night

Hilton Garden Inn Schaumburg
View More Hotel Deals
Tripster Gift Certificates

Give the Gift of Travel

Purchase Gift Certificates for your family and friends!

Shop Now