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Get the cheapest flights to Chicago booking at the best possible time

Getting the cheapest flight to Chicago is possible, thanks to the Airlines Flight flight comparison engine.

We compare all the offers from over 300 airline companies to help you find the one that is most convenient to you, including low-cost flights, last-minute offers and the special promotions offered by the travel agencies we work with.

Discover how to get cheap flights to Chicago

The prices of plane tickets depend on a large quantity of factors. To find cheap flights you just need to indicate your preferences on the Airlines Flight comparison engine. Enter the city from which you wish to travel to Chicago, the dates and the number of passengers, and whether you want to travel in economy or business class. This way you will get more precise results.
When you get your search results you will be able to sort all the plane tickets found by departure time, return time, nearby airports, airlines, etcetera. Airlines Flight lets you save when you fly to Chicago taking your needs into account.

Find cheap flights in United States to Chicago

Flights Price Partner
Miami - International • Chicago From 05/15/2021 to 05/16/2021 Round trip Search date 15 days ago $1
Boston - Logan • Chicago From 06/21/2021 to 06/25/2021 Round trip Search date 15 days ago $3
Fort Myers - Southwest Florida International • Chicago On 06/22/2021 One way Search date 15 days ago $21
Los Angeles • Chicago On 05/22/2021 One way Search date 9 days ago $21
Atlanta - Hartsfield-Jackson • Chicago On 07/12/2021 One way Search date 5 days ago $28
Tampa • Chicago On 07/25/2021 One way Search date 5 days ago $29
Orlando - International • Chicago On 05/18/2021 One way Search date Yesterday $32
Houston - William P. Hobby • Chicago On 05/18/2021 One way Search date 6 days ago $35
Fort Lauderdale • Chicago On 05/22/2021 One way Search date 2 days ago $37
San Francisco • Chicago From 07/30/2021 to 08/10/2021 Round trip Search date Yesterday $37

Get cheap international flights to Chicago

Flights Price Partner
Montego Bay - Sangster • Chicago On 11/09/2021 One way Search date 4 days ago $60
San Juan - Luis Muñoz Marín • Chicago On 05/29/2021 One way Search date 12 days ago $87
Cancun • Chicago On 05/14/2021 One way Search date 4 days ago $89
Guatemala City • Chicago On 05/21/2021 One way Search date 12 days ago $116
Guadalajara - Miguel Hidalgo y Costilla • Chicago On 12/03/2021 One way Search date 12 days ago $119
Quito • Chicago From 06/08/2021 to 06/22/2021 Round trip Search date 3 days ago $126
Aguadilla - Rafael Hernández • Chicago On 05/21/2021 One way Search date Yesterday $134
Lima • Chicago From 06/16/2021 to 07/11/2021 Round trip Search date 2 days ago $137
Mexico City - International • Chicago On 06/24/2021 One way Search date 6 days ago $139
Toronto • Chicago On 07/27/2021 One way Search date 2 days ago $147
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