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 August , September 2026

30 Aug - 12 Sep $ 353.00
CLE
Cleveland
United Airlines
DIRECT
CHI
Chicago
CHI
Chicago
United Airlines
DIRECT
CLE
Cleveland
Pick dates
26 Aug - 09 Sep $ 556.00
CLE
Cleveland
Alaska Airlines
1 STOPS
CHI
Chicago
CHI
Chicago
Alaska Airlines
2 STOPS
CLE
Cleveland
Pick dates
26 Aug - 05 Sep $ 686.00
CLE
Cleveland
Alaska Airlines
1 STOPS
CHI
Chicago
CHI
Chicago
Alaska Airlines
1 STOPS
CLE
Cleveland
Pick dates

Last minute flights from Cleveland to Chicago

31 Aug - 31 Aug $ 514.00
CLE
Cleveland
United Airlines
DIRECT
CHI
Chicago
CHI
Chicago
United Airlines
DIRECT
CLE
Cleveland
Pick dates
21 Aug - 31 Aug $ 526.00
CLE
Cleveland
United Airlines
DIRECT
CHI
Chicago
CHI
Chicago
United Airlines
DIRECT
CLE
Cleveland
Pick dates
19 Aug - 31 Aug $ 526.00
CLE
Cleveland
United Airlines
DIRECT
CHI
Chicago
CHI
Chicago
United Airlines
DIRECT
CLE
Cleveland
Pick dates

One-way flights to Chicago from Cleveland

7:25 AM - 9:55 AM
Frontier Airlines
1 Stops
7h 11m
CLE - CHI
$ 159
Kiwi
Pick dates
8:23 AM - 8:23 AM
United Airlines
0 Stops
1h 37m
CLE - CHI
$ 225
Kiwi
Pick dates
7:00 AM - 7:00 AM
United Airlines
0 Stops
1h 31m
CLE - CHI
$ 238
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.