Cheap flights to Chicago

Travel > North America > United States > Chicago flights

If you want to visit a vibrant, energetic city that's rich in heritage, culture, entertainment, and commerce, Chicago runs right up there with the big dogs. You could start by visiting downtown which is the center for government, finance, and commerce of Chicago and is encircled by The Loop, named for the elevated train tracks that loop around the central area. Tall skyscrapers such as the world's second-tallest building, the Sears Tower, and the Chicago Board of Trade are landmarks... (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:

  • $129Spirit Airlines flight Spirit Airlines 
    FromToDepartureTime
    New York, NY (LGA)Chicago, IL (ORD)08/25/201909:59 am
    Chicago, IL (ORD)New York, NY (LGA)09/08/201905:44 am
    cheapoair.com check price
  • $149Spirit Airlines flight Spirit Airlines 
    FromToDepartureTime
    Boston, MA (BOS)Chicago, IL (ORD)09/03/201912:35 pm
    Chicago, IL (ORD)Boston, MA (BOS)09/17/201901:46 pm
    cheapoair.com check price
  • $175Southwest Airlines flight Southwest Airlines 
    FromToDepartureTime
    Cincinnati, OH (CVG)Chicago, IL (MDW)08/10/201907:30 am
    Chicago, IL (MDW)Cincinnati, OH (CVG)08/23/201910:35 pm
    flightnetwork.com check price
  • $178Multiple Airlines flight Multiple Airlines 
    FromToDepartureTime
    Fort Myers, FL (RSW)Chicago, IL (MDW)08/05/201906:05 am
    Chicago, IL (MDW)Fort Myers, FL (RSW)08/17/201911:35 am
    flightnetwork.com check price
  • $205Southwest Airlines flight Southwest Airlines 
    FromToDepartureTime
    Detroit, MI (DTW)Chicago, IL (MDW)08/05/201905:55 am
    Chicago, IL (MDW)Detroit, MI (DTW)08/19/201906:40 am
    flightnetwork.com check price
Chicago travel guides

Travel information that may interest you

Chicago History

The Great Chicago Fire was considered one of the most tragic points in the history of Chicago.  The fact that firefighters were sent to a wrong neighborhood lead the fire to crumble up the walls of wooden houses and other properties found near the area.  It even reached the north and the east of DeKoven Street leaving a lot of infrastructures to ashes.  This left the city embarked to a rebuilding program replacing wooden buildings with stone.  They even created the first modern fire department in America [...]

cheap domestic and international flights

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Frontier AirlinesOntario To New York City Frontier Airlines airfares from Ontario in July
$460 Depart: 07/31/2019
Return: 08/09/2019

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$719 Depart: 08/07/2019
Return: 08/18/2019

provided by FlyFar

Multiple AirlinesKey West To Milwaukee Multiple Airlines airfares from Key West in July
$918 Depart: 07/28/2019
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$386 Depart: 09/18/2019
Return: 10/08/2019

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Spirit AirlinesPhiladelphia To Cleveland Spirit Airlines airfares from Philadelphia in July
$329 Depart: 07/23/2019
Return: 07/30/2019

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Alaska AirlinesOntario, CA To San Francisco Alaska Airlines airfares from Ontario, CA in August
$358 Depart: 08/21/2019
Return: 09/03/2019

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Spirit AirlinesTampa To Newark Spirit Airlines airfares from Tampa in October
$504 Depart: 10/22/2019
Return: 11/06/2019

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Spirit AirlinesSan Diego To San Juan Spirit Airlines airfares from San Diego in August
$427 Depart: 08/13/2019
Return: 08/21/2019

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Multiple AirlinesBoston To Thessaloniki Multiple Airlines airfares from Boston in June
$1584 Depart: 06/24/2019
Return: 07/05/2019

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