Cheap flights to Chicago

Travel > North America > United States > Chicago flights

Though residents complain about the cold weather that lasts almost through the whole year, at least on a winter day, they can duck into such popular clubs as Andy's, where there's hot jazz even at noon. The best time to visit is between May and October when the weather is the most predictable. Then you could head out to ivy-covered Wrigley Field to catch baseball's Cubs in action, or take a cruise boat under the bridges of the Chicago River at sunset.... (read more in our Chicago Travel Guide)

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Cheapest flights found for the next 6 months

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Didn't have an exact departure location, just looking for the cheapest price? Browse our cheap flights state directory:

Check our newest flight offers to Chicago:

$270 Porter Airlines
From To Departure Time
Montreal, QC (YUL) Chicago, IL (MDW) 05/20/2025 10:45 am
Chicago, IL (MDW) Montreal, QC (YUL) 05/27/2025 09:15 am
cheapoair.com check price
$376 Westjet
From To Departure Time
Saskatoon, SK (YXE) Chicago, IL (ORD) 05/20/2025 07:55 am
Chicago, IL (ORD) Saskatoon, SK (YXE) 06/04/2025 01:40 pm
cheapoair.com check price
$512 Spirit Airlines
From To Departure Time
Atlantic City, NJ (ACY) Chicago, IL (ORD) 06/04/2025 05:20 am
Chicago, IL (ORD) Atlantic City, NJ (ACY) 06/11/2025 05:05 am
cheapoair.com check price
$611 Spirit Airlines
From To Departure Time
Philadelphia, PA (PHL) Chicago, IL (ORD) 07/02/2025 06:10 am
Chicago, IL (ORD) Philadelphia, PA (PHL) 07/16/2025 05:05 am
cheapoair.com check price
$700 Frontier Airlines
From To Departure Time
Cincinnati, OH (CVG) Chicago, IL (ORD) 05/28/2025 07:35 pm
Chicago, IL (ORD) Cincinnati, OH (CVG) 06/03/2025 06:15 am
cheapoair.com check price

From	To	Departure	Time
Montreal, QC (YUL)	Chicago, IL (MDW)	05/20/2025	10:45 am
Chicago, IL (MDW)	Montreal, QC (YUL)	05/27/2025	09:15 am

From	To	Departure	Time
Saskatoon, SK (YXE)	Chicago, IL (ORD)	05/20/2025	07:55 am
Chicago, IL (ORD)	Saskatoon, SK (YXE)	06/04/2025	01:40 pm

From	To	Departure	Time
Atlantic City, NJ (ACY)	Chicago, IL (ORD)	06/04/2025	05:20 am
Chicago, IL (ORD)	Atlantic City, NJ (ACY)	06/11/2025	05:05 am

From	To	Departure	Time
Philadelphia, PA (PHL)	Chicago, IL (ORD)	07/02/2025	06:10 am
Chicago, IL (ORD)	Philadelphia, PA (PHL)	07/16/2025	05:05 am

From	To	Departure	Time
Cincinnati, OH (CVG)	Chicago, IL (ORD)	05/28/2025	07:35 pm
Chicago, IL (ORD)	Cincinnati, OH (CVG)	06/03/2025	06:15 am

Chicago travel guides

Travel information that may interest you

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Chicago Nightlife

A lot of foodies could select from dining alternatives in Chicago. Whether you are craving for a taste of American dishes and other regional specialties, the city is your place to be. Some of the famous Chicago restaurants are: [...]

cheap domestic and international flights

Recently found cheap flight deals

New York City To Georgetown Caribbean Airlines airfares from New York City in January
$724 Depart: 01/16/2025
Return: 01/26/2025
provided by Cheapoair.com

Saint Louis To Las Vegas Frontier Airlines airfares from Saint Louis in June
$336 Depart: 06/11/2025
Return: 06/17/2025
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Chicago To Orlando Multiple Airlines airfares from Chicago in April
$204 Depart: 04/13/2025
Return: 04/18/2025
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Dallas To Washington DC Sun Country Airlines airfares from Dallas in June
$472 Depart: 06/12/2024
Return: 06/26/2024
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Edmonton To Toronto Westjet airfares from Edmonton in July
$380 Depart: 07/21/2025
Return: 07/26/2025
provided by Cheapoair.com

Kelowna To Las Vegas Alaska Airlines airfares from Kelowna in February
$1318 Depart: 02/24/2024
Return: 03/09/2024
provided by Cheapoair.com

Atlanta To Toluco Frontier Airlines airfares from Atlanta in March
$558 Depart: 03/04/2025
Return: 03/12/2025
provided by Cheapoair.com

Philadelphia To San Jose Multiple Airlines airfares from Philadelphia in March
$862 Depart: 03/31/2023
Return: 04/11/2023
provided by Cheapoair.com

Moline To Atlanta Alaska Airlines airfares from Moline in December
$2698 Depart: 12/31/2019
Return: 01/08/2020
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