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
Atlanta7 May 2025Tickets from 31
New York14 May 2025Tickets from 37
Buffalo21 May 2025Tickets from 43
Detroit20 May 2025Tickets from 43
Saint Louis26 June 2025Tickets from 43
Baltimore18 May 2025Tickets from 45
Miami30 July 2025Tickets from 47
Boston25 May 2025Tickets from 52
Los Angeles31 May 2025Tickets from 54
Fort Lauderdale10 June 2025Tickets from 56
Houston10 June 2025Tickets from 59
Tampa2 May 2025Tickets from 65
Las Vegas5 May 2025Tickets from 75
Portland13 June 2025Tickets from 77
Dallas18 August 2025Tickets from 82
San Francisco7 May 2025Tickets from 82
Washington18 May 2025Tickets from 83
Denver12 June 2025Tickets from 84
Philadelphia5 May 2025Tickets from 85
Toronto16 June 2025Tickets from 85

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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