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 York18 November 2025Tickets from 25
Charlotte25 January 2026Tickets from 31
Tampa3 December 2025Tickets from 31
Miami3 December 2025Tickets from 33
Baltimore22 November 2025Tickets from 34
Boston17 January 2026Tickets from 35
Fort Lauderdale3 December 2025Tickets from 38
Los Angeles16 December 2025Tickets from 40
New Haven25 November 2025Tickets from 41
Atlanta20 December 2025Tickets from 45
Las Vegas27 November 2025Tickets from 45
Philadelphia3 December 2025Tickets from 52
Minneapolis9 December 2025Tickets from 52
San Francisco12 January 2026Tickets from 59
Washington1 January 2026Tickets from 63
Ontario8 January 2026Tickets from 65
New Orleans1 January 2026Tickets from 69
Seattle24 November 2025Tickets from 72
Omaha9 January 2026Tickets from 80
Orlando12 March 2026Tickets from 99

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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