Cheap flights Cleveland (Hopkins) to Chicago

From

To

Depart

Return

Passengers

1 passenger, economy

Cheap flights Cleveland to Chicago

Compare prices, duration and stops

Filters

Stops

Direct only 1 stop

Price

S$62 S$200 S$200

Airlines

American Airlines Frontier Airlines Southwest Airlines United Airlines

F9 1056

23:59

Cleveland, Hopkins (CLE)

Sat, 19 sep

15h 21min

1 stop

15:20

Chicago, O'Hare International Airport (ORD)

Sun, 20 sep +1

S$171

WN 1401

21:25

Cleveland, Hopkins (CLE)

Mon, 21 sep

1h 15min

Direct

22:40

Chicago, Chicago Midway International Airport (MDW)

Mon, 21 sep

S$76

AA 3841

09:30

Cleveland, Hopkins (CLE)

Tue, 22 sep

1h 29min

Direct

10:59

Chicago, O'Hare International Airport (ORD)

Tue, 22 sep

S$191

F9 3916

23:59

Cleveland, Hopkins (CLE)

Tue, 22 sep

28h

1 stop

03:59

Chicago, O'Hare International Airport (ORD)

Thu, 24 sep +1

S$157

WN 1654

16:50

Cleveland, Hopkins (CLE)

Wed, 23 sep

1h 15min

Direct

18:05

Chicago, Chicago Midway International Airport (MDW)

Wed, 23 sep

S$77

WN 175

23:15

Cleveland, Hopkins (CLE)

Wed, 23 sep

1h 15min

Direct

00:30

Chicago, Chicago Midway International Airport (MDW)

Thu, 24 sep +1

S$76

WN 2097

17:50

Cleveland, Hopkins (CLE)

Thu, 24 sep

1h 15min

Direct

19:05

Chicago, Chicago Midway International Airport (MDW)

Thu, 24 sep

S$81

WN 1401 🔥 Hot deal

21:25

Cleveland, Hopkins (CLE)

Thu, 24 sep

1h 15min

Direct

22:40

Chicago, Chicago Midway International Airport (MDW)

Thu, 24 sep

S$76

F9 4895

16:23

Cleveland, Hopkins (CLE)

Fri, 25 sep

8h 12min

1 stop

00:35

Chicago, O'Hare International Airport (ORD)

Sat, 26 sep +1

S$188

F9 2409

19:45

Cleveland, Hopkins (CLE)

Fri, 25 sep

27h 38min

1 stop

23:23

Chicago, O'Hare International Airport (ORD)

Sat, 26 sep +1

S$100

F9 2467

11:00

Cleveland, Hopkins (CLE)

Sat, 26 sep

5h 51min

1 stop

16:51

Chicago, O'Hare International Airport (ORD)

Sat, 26 sep

S$163

F9 4895

16:23

Cleveland, Hopkins (CLE)

Sat, 26 sep

8h 18min

1 stop

00:41

Chicago, O'Hare International Airport (ORD)

Sun, 27 sep +1

S$80

WN 4949

20:35

Cleveland, Hopkins (CLE)

Sat, 26 sep

1h 20min

Direct

21:55

Chicago, Chicago Midway International Airport (MDW)

Sat, 26 sep

S$81

F9 2668

10:00

Cleveland, Hopkins (CLE)

Tue, 29 sep

17h 59min

1 stop

03:59

Chicago, O'Hare International Airport (ORD)

Wed, 30 sep +1

S$171

WN 175

23:15

Cleveland, Hopkins (CLE)

Tue, 29 sep

1h 15min

Direct

00:30

Chicago, Chicago Midway International Airport (MDW)

Wed, 30 sep +1

S$78

AA 4360

09:12

Cleveland, Hopkins (CLE)

Sat, 10 oct

1h 37min

Direct

10:49

Chicago, O'Hare International Airport (ORD)

Sat, 10 oct

S$79

F9 2409

19:46

Cleveland, Hopkins (CLE)

Sat, 10 oct

8h 57min

1 stop

04:43

Chicago, Chicago Midway International Airport (MDW)

Sun, 11 oct +1

S$119

F9 2467

11:00

Cleveland, Hopkins (CLE)

Thu, 15 oct

12h 31min

1 stop

23:31

Chicago, O'Hare International Airport (ORD)

Thu, 15 oct

S$109

WN 1207

12:20

Cleveland, Hopkins (CLE)

Thu, 15 oct

1h 20min

Direct

13:40

Chicago, Chicago Midway International Airport (MDW)

Thu, 15 oct

S$148

F9 2409

19:46

Cleveland, Hopkins (CLE)

Fri, 16 oct

20h 46min

1 stop

16:32

Chicago, O'Hare International Airport (ORD)

Sat, 17 oct +1

S$128

AA 3429

16:51

Cleveland, Hopkins (CLE)

Sat, 17 oct

1h 44min

Direct

18:35

Chicago, O'Hare International Airport (ORD)

Sat, 17 oct

S$113

F9 2409

19:46

Cleveland, Hopkins (CLE)

Sat, 17 oct

8h 57min

1 stop

04:43

Chicago, Chicago Midway International Airport (MDW)

Sun, 18 oct +1

S$124

UA 2315

20:23

Cleveland, Hopkins (CLE)

Sat, 17 oct

1h 39min

Direct

22:02

Chicago, O'Hare International Airport (ORD)

Sat, 17 oct

S$72

WN 850 Best price

21:25

Cleveland, Hopkins (CLE)

Sat, 17 oct

1h 20min

Direct

22:45

Chicago, Chicago Midway International Airport (MDW)

Sat, 17 oct

S$62

F9 2668

10:00

Cleveland, Hopkins (CLE)

Sun, 18 oct

26h 31min

1 stop

12:31

Chicago, O'Hare International Airport (ORD)

Mon, 19 oct +1

S$178

F9 2280

01:59

Cleveland, Hopkins (CLE)

Mon, 19 oct

10h 32min

1 stop

12:31

Chicago, O'Hare International Airport (ORD)

Mon, 19 oct

S$177

F9 2409

19:46

Cleveland, Hopkins (CLE)

Mon, 19 oct

43h 28min

2 stops

15:14

Chicago, Chicago Rockford International Airport (RFD)

Wed, 21 oct +1

S$159

WN 2068

00:20

Cleveland, Hopkins (CLE)

Tue, 20 oct

1h 15min

Direct

01:35

Chicago, Chicago Midway International Airport (MDW)

Tue, 20 oct

S$66

AA 4784

00:43

Cleveland, Hopkins (CLE)

Tue, 20 oct

1h 46min

Direct

02:29

Chicago, O'Hare International Airport (ORD)

Tue, 20 oct

S$113

F9 2280

01:59

Cleveland, Hopkins (CLE)

Tue, 20 oct

10h 52min

1 stop

12:51

Chicago, O'Hare International Airport (ORD)

Tue, 20 oct

S$138

WN 1209

18:20

Cleveland, Hopkins (CLE)

Tue, 20 oct

1h 15min

Direct

19:35

Chicago, Chicago Midway International Airport (MDW)

Tue, 20 oct

S$73

F9 2409

19:46

Cleveland, Hopkins (CLE)

Tue, 20 oct

19h 28min

2 stops

15:14

Chicago, Chicago Rockford International Airport (RFD)

Wed, 21 oct +1

S$132

F9 4639

20:50

Cleveland, Hopkins (CLE)

Tue, 20 oct

8h 34min

1 stop

05:24

Chicago, O'Hare International Airport (ORD)

Wed, 21 oct +1

S$149

F9 2409

19:46

Cleveland, Hopkins (CLE)

Wed, 21 oct

8h 57min

1 stop

04:43

Chicago, Chicago Midway International Airport (MDW)

Thu, 22 oct +1

S$154

F9 2467

11:00

Cleveland, Hopkins (CLE)

Thu, 22 oct

12h 31min

1 stop

23:31

Chicago, O'Hare International Airport (ORD)

Thu, 22 oct

S$162

WN 2068

00:20

Cleveland, Hopkins (CLE)

Sat, 24 oct

1h 15min

Direct

01:35

Chicago, Chicago Midway International Airport (MDW)

Sat, 24 oct

S$99

AA 5010

15:17

Cleveland, Hopkins (CLE)

Thu, 12 nov

1h 52min

Direct

17:09

Chicago, O'Hare International Airport (ORD)

Thu, 12 nov

S$74

AA 5005

21:59

Cleveland, Hopkins (CLE)

Fri, 13 nov

2h

Direct

23:59

Chicago, O'Hare International Airport (ORD)

Fri, 13 nov

S$96

AA 5010

15:17

Cleveland, Hopkins (CLE)

Wed, 16 dec

1h 52min

Direct

17:09

Chicago, O'Hare International Airport (ORD)

Wed, 16 dec

S$155

AA 5570

17:06

Cleveland, Hopkins (CLE)

Thu, 17 dec

1h 54min

Direct

19:00

Chicago, O'Hare International Airport (ORD)

Thu, 17 dec

S$155

AA 3566

22:49

Cleveland, Hopkins (CLE)

Fri, 18 dec

1h 47min

Direct

00:36

Chicago, O'Hare International Airport (ORD)

Sat, 19 dec +1

S$200

Low price calendar

September 2026

Price chart (September 2026)

min: S$76 · max: S$188

Mon

Tue

Wed

Thu

Fri

Sat

Sun

1

placeholder

no data

2

placeholder

no data

3

placeholder

no data

4

placeholder

no data

5

placeholder

no data

6

placeholder

no data

7

placeholder

no data

8

placeholder

no data

9

placeholder

no data

10

placeholder

no data

11

placeholder

no data

12

placeholder

no data

13

placeholder

no data

14

placeholder

no data

15

placeholder

no data

16

placeholder

no data

17

placeholder

no data

18

placeholder

S$185

19

placeholder

S$171

20

placeholder

no data

21

Good deal

S$76

22

placeholder

S$157

23

Good deal

S$77

24

placeholder

S$81

25

placeholder

S$188

26

placeholder

S$163

27

placeholder

no data

28

placeholder

no data

29

placeholder

S$171

30

placeholder

no data

Cheap flights Cleveland to Chicago

Southwest Airlines

Mon, Tue, Wed, Thu, Sat

Price from

S$62

United Airlines

Sat

Price from

S$72

American Airlines

Tue, Wed, Thu, Fri, Sat

Price from

S$113

Frontier Airlines

Mon, Tue, Wed, Thu, Fri, Sat, Sun

Price from

S$119

Popular destinations from Cleveland

All →

CLE

Cleveland — Orlando

United States → United States

ORL

from

S$40

CLE

Cleveland — Orlando

United States → United States

MCO

from

S$46

CLE

Cleveland — Tampa

United States → United States

TPA

from

S$46

CLE

Cleveland — Fort Lauderdale

United States → United States

FLL

from

S$46

CLE

Cleveland — Houston

United States → United States

HOU

from

S$69

CLE

Cleveland — Las Vegas

United States → United States

LAS

from

S$69

CLE

Cleveland — Atlanta

United States → United States

ATL

from

S$70

CLE

Cleveland — Miami

United States → United States

MIA

from

S$76

CLE

Cleveland — Cincinnati

United States → United States

CVG

from

S$78

Popular destinations to Chicago

All →

HOU

Houston — Chicago

United States → United States

CHI

from

S$27

NYC

New York — Chicago

United States → United States

CHI

from

S$29

PHX

Phoenix — Chicago

United States → United States

CHI

from

S$31

FLL

Fort Lauderdale — Chicago

United States → United States

CHI

from

S$33

ATL

Atlanta — Chicago

United States → United States

CHI

from

S$35

BNA

Nashville — Chicago

United States → United States

CHI

from

S$35

LAX

Los Angeles — Chicago

United States → United States

CHI

from

S$39

ORL

Orlando — Chicago

United States → United States

CHI

from

S$40

MIA

Miami — Chicago

United States → United States

CHI

from

S$41

Cheap flights Cleveland to Chicago

Interesting facts about the route

Flight time

1h 53min

Distance

507 km

Average price

S$116

Most frequent flight

F9 2409

Passenger reviews

No reviews for this route yet

Internet abroad

eSIM · United States

change

3 GB

data

30

days

S$11

change

2 GB

data

15

days

S$16

change

5 GB

data

30

days

S$18

change

3 GB

data

30

days

S$20

change

5 GB

data

30

days

S$29

Frequently Asked Questions

The average ticket price Cleveland Chicago is S$116. The cheapest ticket costs S$76, operated by Southwest Airlines, flight 1401, departing Cleveland on 21 September at 21:25, arriving Chicago on 21 September at 22:40.

The average flight time is 1 hour 29 minutes.The fastest flight takes 1 hour 15 minutes, flight 1401operated by Southwest Airlines, departing Cleveland on 21 September at 21:25, arriving Chicago on 21 September at 22:40.

Flights on the Cleveland - Chicago route are operated by the following airlines: American Airlines, Frontier Airlines, United Airlines, Southwest Airlines.

The distance from Cleveland to Chicago is 507 km.