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
New York7 May 2025Tickets from 34
Houston10 May 2025Tickets from 39
Dallas12 May 2025Tickets from 40
Boston24 April 2025Tickets from 51
Minneapolis22 May 2025Tickets from 51
Fort Lauderdale8 April 2025Tickets from 51
Miami7 May 2025Tickets from 52
Orlando29 May 2025Tickets from 55
Baltimore12 May 2025Tickets from 56
Tampa2 May 2025Tickets from 59
New Orleans16 May 2025Tickets from 59
Detroit26 April 2025Tickets from 62
Washington12 May 2025Tickets from 68
Los Angeles7 April 2025Tickets from 68
Seattle22 April 2025Tickets from 77
Phoenix10 April 2025Tickets from 81
Denver30 April 2025Tickets from 82
Ontario7 April 2025Tickets from 83
Pittsburgh14 April 2025Tickets from 84
Las Vegas4 April 2025Tickets from 84

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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