Earn point on your loyalty program!arrow arc left

Cheap flights from Cleveland (CLE) to Chicago (CHI)

Know your dates, get live prices in seconds
airplane logo

pin logo

calendar
Departure
calendar backward
Return
airplane logo
1 Adults (11+)
0 Children (2~11)
0 Infants (0~2)
Save up to 31%
Book Flight + Hotel at the same time

How to find the cheapest flight from Cleveland (CLE) to Chicago (CHI)

How to find the cheapest flight from Cleveland (CLE) to Chicago (CHI)
Some placeholder content for the first accordion panel. This panel is shown by default, thanks to the .show class.
How to find the cheapest flight from Cleveland (CLE) to Chicago (CHI)
Some placeholder content for the first accordion panel. This panel is shown by default, thanks to the .show class.
How to find the cheapest flight from Cleveland (CLE) to Chicago (CHI)
Some placeholder content for the first accordion panel. This panel is shown by default, thanks to the .show class.

Cheap flights from Cleveland to Chicago in December 2025 , January 2026

31 Dec - 18 Jan $ 248.00
CLE
Cleveland
United Airlines
DIRECT
CHI
Chicago
CHI
Chicago
United Airlines
DIRECT
CLE
Cleveland
Pick dates
16 Dec - 20 Jan $ 413.00
CLE
Cleveland
United Airlines
DIRECT
CHI
Chicago
CHI
Chicago
United Airlines
DIRECT
CLE
Cleveland
Pick dates
16 Dec - 20 Jan $ 413.00
CLE
Cleveland
United Airlines
DIRECT
CHI
Chicago
CHI
Chicago
United Airlines
DIRECT
CLE
Cleveland
Pick dates

Last minute flights from Cleveland to Chicago

24 Dec - 31 Dec $ 250.00
CLE
Cleveland
United Airlines
DIRECT
CHI
Chicago
CHI
Chicago
United Airlines
DIRECT
CLE
Cleveland
Pick dates
25 Dec - 31 Dec $ 250.00
CLE
Cleveland
United Airlines
DIRECT
CHI
Chicago
CHI
Chicago
United Airlines
DIRECT
CLE
Cleveland
Pick dates
25 Dec - 31 Dec $ 250.00
CLE
Cleveland
United Airlines
DIRECT
CHI
Chicago
CHI
Chicago
United Airlines
DIRECT
CLE
Cleveland
Pick dates

One-way flights to Chicago from Cleveland

10:55 AM - 10:55 AM
United Airlines
0 Stops
1h 38m
CLE - CHI
$ 125
Kiwi
Pick dates
5:53 PM - 5:53 PM
United Airlines
0 Stops
1h 41m
CLE - CHI
$ 125
Kiwi
Pick dates
10:55 AM - 10:55 AM
United Airlines
0 Stops
1h 32m
CLE - CHI
$ 295
Kiwi
Pick dates

How to find the cheapest flight from Cleveland (CLE) to Chicago (CHI)

Related info for your journey
Some placeholder content for the first accordion panel. This panel is shown by default, thanks to the .show class.
How to find the cheapest flight from Cleveland (CLE) to Chicago (CHI)
Some placeholder content for the first accordion panel. This panel is shown by default, thanks to the .show class.
How to find the cheapest flight from Cleveland (CLE) to Chicago (CHI)
Some placeholder content for the first accordion panel. This panel is shown by default, thanks to the .show class.