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:

$116 Spirit Airlines
From To Departure Time
Tampa, FL (TPA) Chicago, IL (ORD) 01/11/2025 12:10 pm
Chicago, IL (ORD) Tampa, FL (TPA) 01/20/2025 07:20 am
cheapoair.com check price
$123 Multiple Airlines
From To Departure Time
Fort Worth/Dallas, TX (DFW) Chicago, IL (ORD) 12/07/2024 03:10 pm
Chicago, IL (ORD) Fort Worth/Dallas, TX (DFW) 12/12/2024 03:51 pm
cheapoair.com check price
$138 Frontier Airlines
From To Departure Time
Orlando, FL (MCO) Chicago, IL (MDW) 02/04/2025 06:20 am
Chicago, IL (MDW) Orlando, FL (MCO) 02/12/2025 10:00 am
cheapoair.com check price
$141 Multiple Airlines
From To Departure Time
Boston, MA (BOS) Chicago, IL (ORD) 12/31/2024 06:27 am
Chicago, IL (ORD) Boston, MA (BOS) 01/08/2025 12:42 pm
cheapoair.com check price
$142 Multiple Airlines
From To Departure Time
Minneapolis, MN (MSP) Chicago, IL (MDW) 12/08/2024 11:51 am
Chicago, IL (MDW) Minneapolis, MN (MSP) 12/17/2024 11:33 am
cheapoair.com check price

From	To	Departure	Time
Tampa, FL (TPA)	Chicago, IL (ORD)	01/11/2025	12:10 pm
Chicago, IL (ORD)	Tampa, FL (TPA)	01/20/2025	07:20 am

From	To	Departure	Time
Fort Worth/Dallas, TX (DFW)	Chicago, IL (ORD)	12/07/2024	03:10 pm
Chicago, IL (ORD)	Fort Worth/Dallas, TX (DFW)	12/12/2024	03:51 pm

From	To	Departure	Time
Orlando, FL (MCO)	Chicago, IL (MDW)	02/04/2025	06:20 am
Chicago, IL (MDW)	Orlando, FL (MCO)	02/12/2025	10:00 am

From	To	Departure	Time
Boston, MA (BOS)	Chicago, IL (ORD)	12/31/2024	06:27 am
Chicago, IL (ORD)	Boston, MA (BOS)	01/08/2025	12:42 pm

From	To	Departure	Time
Minneapolis, MN (MSP)	Chicago, IL (MDW)	12/08/2024	11:51 am
Chicago, IL (MDW)	Minneapolis, MN (MSP)	12/17/2024	11:33 am

Chicago travel guides

Travel information that may interest you

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Chicago Nightlife

Charlie Trotter’s. Located at 816 W. Armitage Avenue at Halsted Street, this restaurant is open from Tuesdays to Saturdays from 6:00 to 10:00 PM. Named after Chicago’s first celebrity chef, it offers you fine dining in a very creative way. The place is a bit expensive though. You need not worry since the dining pleasure is worth your money [...]

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$1781 Depart: 11/23/2024
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$683 Depart: 12/07/2024
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$248 Depart: 10/01/2019
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$2942 Depart: 11/25/2024
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