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

(click city name to see more / use right arrow to view later 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:

  • $270Porter Airlines flight Porter Airlines 
    FromToDepartureTime
    Montreal, QC (YUL)Chicago, IL (MDW)05/20/202510:45 am
    Chicago, IL (MDW)Montreal, QC (YUL)05/27/202509:15 am
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  • $376Westjet flight Westjet 
    FromToDepartureTime
    Saskatoon, SK (YXE)Chicago, IL (ORD)05/20/202507:55 am
    Chicago, IL (ORD)Saskatoon, SK (YXE)06/04/202501:40 pm
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  • $512Spirit Airlines flight Spirit Airlines 
    FromToDepartureTime
    Atlantic City, NJ (ACY)Chicago, IL (ORD)06/04/202505:20 am
    Chicago, IL (ORD)Atlantic City, NJ (ACY)06/11/202505:05 am
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  • $611Spirit Airlines flight Spirit Airlines 
    FromToDepartureTime
    Philadelphia, PA (PHL)Chicago, IL (ORD)07/02/202506:10 am
    Chicago, IL (ORD)Philadelphia, PA (PHL)07/16/202505:05 am
    cheapoair.com check price
  • $700Frontier Airlines flight Frontier Airlines 
    FromToDepartureTime
    Cincinnati, OH (CVG)Chicago, IL (ORD)05/28/202507:35 pm
    Chicago, IL (ORD)Cincinnati, OH (CVG)06/03/202506:15 am
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Chicago travel guides

Travel information that may interest you

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

Caribbean AirlinesNew 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

Frontier AirlinesSaint 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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Multiple AirlinesChicago To Orlando Multiple Airlines airfares from Chicago in April
$204 Depart: 04/13/2025
Return: 04/18/2025

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Sun Country AirlinesDallas To Washington DC Sun Country Airlines airfares from Dallas in June
$472 Depart: 06/12/2024
Return: 06/26/2024

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WestjetEdmonton To Toronto Westjet airfares from Edmonton in July
$380 Depart: 07/21/2025
Return: 07/26/2025

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Alaska AirlinesKelowna To Las Vegas Alaska Airlines airfares from Kelowna in February
$1318 Depart: 02/24/2024
Return: 03/09/2024

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Frontier AirlinesAtlanta To Toluco Frontier Airlines airfares from Atlanta in March
$558 Depart: 03/04/2025
Return: 03/12/2025

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Multiple AirlinesPhiladelphia To San Jose Multiple Airlines airfares from Philadelphia in March
$862 Depart: 03/31/2023
Return: 04/11/2023

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

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