Cheapest Flights to Chicago

" YTZ Toronto to MDW Chicago $358.69 "

" YYZ Toronto to ORD Chicago $305.26 "

" YVR Vancouver to ORD Chicago $491.61 "

" YUL Montreal to MDW Chicago $372.18 "

" YTZ Toronto to ORD Chicago $488.79 "

" YOW Ottawa to MDW Chicago $434.61 "

" YUL Montreal to ORD Chicago $346.69 "

" BUF Buffalo to ORD Chicago $298.22 "

" YOW Ottawa to ORD Chicago $524.06 "

" YVR Vancouver to MDW Chicago $735.09 "


About Chicago

Are you ready to discover which way the wind blows in Chicago? A visit to the Windy City is always a step in the direction of fun. As a tourist, you’ll be obligated to take part in such quintessential Chicago experiences as visiting Wrigley Field, shopping on the Magnificent Mile, and snapping a photo in front the Chicago Theatre’s famous red sign. The rest of the space on your itinerary should be packed with visits to the Art Institute of Chicago, the Lincoln Park Zoo, and the Shedd Aquarium. You'll always find a great spot to enjoy Chicago-style pizza and laughter in the city where improvisational comedy was born. When you're ready to take your sightseeing to new heights, a trip to the top of the famously tall Willis Tower will give you the best views of Chicago. You’ll also be able to spot sections of Indiana, Illinois, Michigan, and Wisconsin from the top. When you’re ready to plan a trip to America’s third largest city, Expedia is here to help you stick to your budget.

We Have Cheap Flights Chicago Tourists Love

You can forget about hustling to find the lowest prices on multiple travel websites. Everything you need to reserve cheap tickets is right at your fingertips on By sharing your travel dates and departure city with us, you’ll gain instant access to exclusive deals on cheap airfare.

The Best Way to Head to O’Hare

Hopping on a plane to O'Hare International Airport (ORD) won’t be hectic on your wallet when you take advantage of our discount specials. If an overnight stay near ORD is on your agenda, we can help you browse rooms at affordable Chicago hotels near the airport. When you’re ready to head home, our low rates on flights out of O'Hare International Airport will take the pressure off your wallet.

Claim Your Flight to Chicago Today

Flights to Chicago always fill up with people travelling for business and pleasure. In order to get the best rate possible, you should book one of our unbeatable deals on Chicago flights today. Are you looking for clever ways to cut the cost of your trip? Our all-inclusive travel packages offer one low price on flights to Chicago and hotels in Chicago. Amazing offers from Expedia prove that you don’t need deep pockets to enjoy a city that’s famous for deep dish pizzas.

Explore Chicago

Heading to Chicago? Explore Chicago with Expedia's Travel Guides to find the best hotels, city breaks, car hire deals and more!

Alternative Nearby Airports

  • Midway Intl. (MDW)
  • O'Hare Intl. (ORD)