Cheap flights to Chicago

Traveloway is a travel comparison website that helps you find the cheapest flights to Chicago (CHI). We compare prices from major airlines and travel websites so you don’t have to.

Finding a cheap flight to Chicago doesn’t have to be hard. We make it easy by doing all the research for you. Just tell us when you want to fly and we’ll show you the best deals.

We know that planning a trip can be stressful, so we’ve designed our site to be as simple and user-friendly as possible. Whether you’re looking for a last-minute getaway or planning ahead for your next vacation, Traveloway will help you save time and money.

Find the best flight to Chicago!

OriginDeparture atFind tickets
Minneapolis13 August 2025Tickets from 33
Pittsburgh7 October 2025Tickets from 34
Las Vegas21 July 2025Tickets from 43
New York9 September 2025Tickets from 44
Knoxville4 July 2025Tickets from 51
Boston22 September 2025Tickets from 52
Dallas13 July 2025Tickets from 55
Fort Lauderdale16 July 2025Tickets from 58
Miami16 July 2025Tickets from 58
Buffalo13 August 2025Tickets from 58
Kansas City7 October 2025Tickets from 62
Los Angeles14 July 2025Tickets from 67
Baltimore3 July 2025Tickets from 68
San Francisco18 August 2025Tickets from 79
Denver23 July 2025Tickets from 79
Portland12 August 2025Tickets from 79
Houston11 July 2025Tickets from 81
Austin23 June 2025Tickets from 86
Washington20 June 2025Tickets from 89
Seattle28 July 2025Tickets from 89

Traveloway is a flight search engine that allows you to search, compare and book flights to Chicago. We help you find the best deals on flights by comparing prices from more than 750 airlines and travel agencies.

Top activities in Chicago

Looking to save even more? Check out our tips and tricks for finding cheap flights, hotels, travel deals!

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