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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Check our newest flight offers to Chicago:

$129 Spirit Airlines
From To Departure Time
New York, NY (LGA) Chicago, IL (ORD) 08/25/2019 09:59 am
Chicago, IL (ORD) New York, NY (LGA) 09/08/2019 05:44 am
cheapoair.com check price
$149 Spirit Airlines
From To Departure Time
Boston, MA (BOS) Chicago, IL (ORD) 09/03/2019 12:35 pm
Chicago, IL (ORD) Boston, MA (BOS) 09/17/2019 01:46 pm
cheapoair.com check price
$175 Southwest Airlines
From To Departure Time
Cincinnati, OH (CVG) Chicago, IL (MDW) 08/10/2019 07:30 am
Chicago, IL (MDW) Cincinnati, OH (CVG) 08/23/2019 10:35 pm
flightnetwork.com check price
$178 Multiple Airlines
From To Departure Time
Fort Myers, FL (RSW) Chicago, IL (MDW) 08/05/2019 06:05 am
Chicago, IL (MDW) Fort Myers, FL (RSW) 08/17/2019 11:35 am
flightnetwork.com check price
$205 Southwest Airlines
From To Departure Time
Detroit, MI (DTW) Chicago, IL (MDW) 08/05/2019 05:55 am
Chicago, IL (MDW) Detroit, MI (DTW) 08/19/2019 06:40 am
flightnetwork.com check price

From	To	Departure	Time
New York, NY (LGA)	Chicago, IL (ORD)	08/25/2019	09:59 am
Chicago, IL (ORD)	New York, NY (LGA)	09/08/2019	05:44 am

From	To	Departure	Time
Boston, MA (BOS)	Chicago, IL (ORD)	09/03/2019	12:35 pm
Chicago, IL (ORD)	Boston, MA (BOS)	09/17/2019	01:46 pm

From	To	Departure	Time
Cincinnati, OH (CVG)	Chicago, IL (MDW)	08/10/2019	07:30 am
Chicago, IL (MDW)	Cincinnati, OH (CVG)	08/23/2019	10:35 pm

From	To	Departure	Time
Fort Myers, FL (RSW)	Chicago, IL (MDW)	08/05/2019	06:05 am
Chicago, IL (MDW)	Fort Myers, FL (RSW)	08/17/2019	11:35 am

From	To	Departure	Time
Detroit, MI (DTW)	Chicago, IL (MDW)	08/05/2019	05:55 am
Chicago, IL (MDW)	Detroit, MI (DTW)	08/19/2019	06:40 am

Chicago travel guides

Travel information that may interest you

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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 [...]

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