Flight deals from Cleveland to Chicago

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Fare Guide

Estimated lowest fares found within 7 days

The cheapest airline(s) flying from Cleveland to Chicago is Frontier Airlines.

Travel Period: June 2024 - May 2025

The cheapest month(s) to fly from Cleveland to Chicago is June.

Jun 2024
Jul 2024
Aug 2024
Sep 2024
Oct 2024
Nov 2024
Dec 2024
Jan 2025
Feb 2025
Mar 2025
Apr 2025
May 2025

The cheapest day(s) of the week to fly from Cleveland to Chicago is Sunday.

Sun Sunday
Mon Monday
Tue Tuesday
Wed Wednesday
Thu Thursday
Fri Friday
Sat Saturday

The cheapest time of the day to fly from Cleveland to Chicago is in the early morning.

Early Morning 12:01am - 06:00am

Morning 6:01am - 12:00pm

Afternoon 12:01pm - 6:00pm

Evening 6:01pm to 12:00am

12am

6am

12pm

6pm

Flight Schedules

Last Updated: Thu, 2 May, 2024

Depart Earliest
- Earliest
- Latest
Arrive
- Earliest
- Latest
Airline Filter by Airline
All
Total Duration
- Shortest
- Longest
Stopover
All
Availability
- M
- T
- W
- T
- F
- S
- S

06:00 - 06:30

CLE - ORD
06:00 (CLE)Cleveland Hopkins International Airport
06:30 (ORD)Chicago O'Hare International Airport
United Airlines (UA 1503)Boeing 737 700
1h 30m
Direct
- M
- T
- W
- T
- F
- S
- S
Boeing 737 700

07:10 - 07:40

CLE - ORD
07:10 (CLE)Cleveland Hopkins International Airport
07:40 (ORD)Chicago O'Hare International Airport
American Airlines (AA 769)Boeing 737 800
1h 30m
Direct
- M
- T
- W
- T
- F
- S
- S
Boeing 737 800

07:20 - 07:35

CLE - MDW
07:20 (CLE)Cleveland Hopkins International Airport
07:35 (MDW)Chicago Midway Airport
(WN 179)Boeing 737 700
1h 15m
Direct
- M
- -
- -
- T
- F
- -
- -
Boeing 737 700

07:30 - 08:00

CLE - ORD
07:30 (CLE)Cleveland Hopkins International Airport
08:00 (ORD)Chicago O'Hare International Airport
United Airlines (UA 411)Boeing 737 800
1h 30m
Direct
- M
- T
- W
- T
- F
- S
- S
Boeing 737 800

07:55 - 08:10

CLE - MDW
07:55 (CLE)Cleveland Hopkins International Airport
08:10 (MDW)Chicago Midway Airport
(WN 179)Boeing 737 Max 8 Passenger
1h 15m
Direct
- -
- T
- W
- -
- -
- -
- -
Boeing 737 Max 8 Passenger

08:15 - 08:30

CLE - MDW
08:15 (CLE)Cleveland Hopkins International Airport
08:30 (MDW)Chicago Midway Airport
(WN 179)Boeing 737 Max 8 Passenger
1h 15m
Direct
- -
- -
- -
- -
- -
- S
- -
Boeing 737 Max 8 Passenger

08:25 - 08:40

CLE - MDW
08:25 (CLE)Cleveland Hopkins International Airport
08:40 (MDW)Chicago Midway Airport
(WN 179)Boeing 737 700
1h 15m
Direct
- -
- -
- -
- -
- -
- -
- S
Boeing 737 700

09:00 - 09:30

CLE - ORD
09:00 (CLE)Cleveland Hopkins International Airport
09:30 (ORD)Chicago O'Hare International Airport
United Airlines (UA 2112)Boeing 737 800
1h 30m
Direct
- M
- T
- W
- T
- F
- S
- S
Boeing 737 800

11:09 - 11:37

CLE - ORD
11:09 (CLE)Cleveland Hopkins International Airport
11:37 (ORD)Chicago O'Hare International Airport
United Airlines (UA 609)Boeing 737 800
1h 28m
Direct
- M
- T
- W
- T
- F
- S
- S
Boeing 737 800

12:10 - 12:45

CLE - ORD
12:10 (CLE)Cleveland Hopkins International Airport
12:45 (ORD)Chicago O'Hare International Airport
American Airlines (AA 6074)Crj Canadair Regional
1h 35m
Direct
- M
- T
- W
- T
- F
- S
- S
Crj Canadair Regional

12:15 - 12:30

CLE - MDW
12:15 (CLE)Cleveland Hopkins International Airport
12:30 (MDW)Chicago Midway Airport
(WN 3063)Boeing 737 700
1h 15m
Direct
- M
- -
- -
- T
- F
- -
- -
Boeing 737 700

13:25 - 13:40

CLE - MDW
13:25 (CLE)Cleveland Hopkins International Airport
13:40 (MDW)Chicago Midway Airport
(WN 2969)Boeing 737 Max 8 Passenger
1h 15m
Direct
- -
- -
- -
- -
- -
- -
- S
Boeing 737 Max 8 Passenger

14:08 - 14:42

CLE - ORD
14:08 (CLE)Cleveland Hopkins International Airport
14:42 (ORD)Chicago O'Hare International Airport
United Airlines (UA 1654)Boeing 737 800
1h 34m
Direct
- M
- T
- W
- T
- F
- S
- S
Boeing 737 800

14:45 - 15:00

CLE - MDW
14:45 (CLE)Cleveland Hopkins International Airport
15:00 (MDW)Chicago Midway Airport
(WN 2969)Boeing 737 700
1h 15m
Direct
- -
- T
- W
- -
- -
- -
- -
Boeing 737 700

15:35 - 15:45

CLE - MDW
15:35 (CLE)Cleveland Hopkins International Airport
15:45 (MDW)Chicago Midway Airport
(WN 3064)Boeing 737 700
1h 10m
Direct
- M
- -
- -
- T
- F
- -
- -
Boeing 737 700

15:43 - 16:15

CLE - ORD
15:43 (CLE)Cleveland Hopkins International Airport
16:15 (ORD)Chicago O'Hare International Airport
American Airlines (AA 3412)Embraer 170
1h 32m
Direct
- M
- T
- W
- T
- F
- S
- S
Embraer 170

17:50 - 18:28

CLE - ORD
17:50 (CLE)Cleveland Hopkins International Airport
18:28 (ORD)Chicago O'Hare International Airport
United Airlines (UA 1673)Boeing 737 800
1h 38m
Direct
- M
- T
- W
- T
- F
- S
- S
Boeing 737 800

17:55 - 18:20

CLE - MDW
17:55 (CLE)Cleveland Hopkins International Airport
18:20 (MDW)Chicago Midway Airport
(WN 2774)Boeing 737 800
1h 25m
Direct
- -
- -
- -
- -
- -
- S
- -
Boeing 737 800

19:13 - 19:45

CLE - ORD
19:13 (CLE)Cleveland Hopkins International Airport
19:45 (ORD)Chicago O'Hare International Airport
American Airlines (AA 4170)Embraer 170
1h 32m
Direct
- M
- T
- W
- T
- F
- S
- S
Embraer 170

19:25 - 19:40

CLE - MDW
19:25 (CLE)Cleveland Hopkins International Airport
19:40 (MDW)Chicago Midway Airport
(WN 2774)Boeing 737 700
1h 15m
Direct
- M
- -
- -
- T
- F
- -
- -
Boeing 737 700

19:35 - 19:50

CLE - MDW
19:35 (CLE)Cleveland Hopkins International Airport
19:50 (MDW)Chicago Midway Airport
(WN 2774)Boeing 737 Max 8 Passenger
1h 15m
Direct
- -
- T
- W
- -
- -
- -
- -
Boeing 737 Max 8 Passenger

19:50 - 20:05

CLE - MDW
19:50 (CLE)Cleveland Hopkins International Airport
20:05 (MDW)Chicago Midway Airport
(WN 2774)Boeing 737 700
1h 15m
Direct
- -
- -
- -
- -
- -
- -
- S
Boeing 737 700

Connecting Flights

20:30 - 21:00

CLE - BNA

21:50 - 23:25

BNA - MDW
20:30 (CLE)Cleveland Hopkins International Airport

21:50 (BNA)Nashville Airport
21:00 (BNA)Nashville Airport

23:25 (MDW)Chicago Midway Airport
(WN 2202)Boeing 737 700

(WN 3046)Boeing 737 700
3h 55m (50m)
BNA Nashville 50m
- M
- -
- -
- T
- F
- -
- -

21:15 - 21:50

CLE - STL

22:50 - 23:55

STL - MDW
21:15 (CLE)Cleveland Hopkins International Airport

22:50 (STL)St Louis Lambert Intl Airport
21:50 (STL)St Louis Lambert Intl Airport

23:55 (MDW)Chicago Midway Airport
(WN 4621)Boeing 737 Max 8 Passenger

(WN 3244)Boeing 737 800
3h 40m (1h)
STL Saint Louis 1h
- -
- -
- -
- -
- -
- -
- S

21:25 - 21:55+ 1

CLE - BNA

22:40 - 00:10+ 1

BNA - MDW
21:25 (CLE)Cleveland Hopkins International Airport

22:40 (BNA)Nashville Airport
21:55 (BNA)Nashville Airport + 1

00:10 (MDW)Chicago Midway Airport
(WN 2202)Boeing 737 Max 8 Passenger

(WN 5212)Boeing 737 700
3h 45m (45m)
BNA Nashville 45m
- -
- -
- -
- -
- -
- -
- S

11:15 - 11:50

CLE - STL

12:35 - 13:40

STL - MDW
11:15 (CLE)Cleveland Hopkins International Airport

12:35 (STL)St Louis Lambert Intl Airport
11:50 (STL)St Louis Lambert Intl Airport

13:40 (MDW)Chicago Midway Airport
(WN 1643)Boeing 737 700

(WN 3241)Boeing 737 700
3h 25m (45m)
STL Saint Louis 45m
- M
- -
- -
- T
- F
- -
- -

12:55 - 13:30

CLE - STL

14:20 - 15:25

STL - MDW
12:55 (CLE)Cleveland Hopkins International Airport

14:20 (STL)St Louis Lambert Intl Airport
13:30 (STL)St Louis Lambert Intl Airport

15:25 (MDW)Chicago Midway Airport
(WN 1643)Boeing 737 700

(WN 2732)Boeing 737 700
3h 30m (50m)
STL Saint Louis 50m
- -
- -
- -
- -
- -
- -
- S

Sorry, there are no schedules matching your filters. Try removing one. reset

What’s the fastest flight time from Cleveland to Chicago?

The fastest flight time for direct flights from Cleveland to Chicago is 1 hour 10 minutes. Check latest flight schedules & prices on Wego.

What’s the most popular airline flying from Cleveland to Chicago?

The most popular airline flying from Cleveland to Chicago is United Airlines. Find the latest flight deals on Wego.

How far is Chicago from Cleveland?

The flight distance between Cleveland and Chicago is 495km. Check all available flights on Wego.

When is the earliest and latest flight of the day?

The earliest flight of the day departs at 06:00. The last flight of the day departs at 20:30. See the full list of flight times on Wego.

How many airlines offer direct flights from Cleveland to Chicago?

There are 3 airlines that offer direct flights from Cleveland to Chicago. Find out the list of airlines on Wego.

Flight deals from Cleveland to Chicago

Fare Guide

Estimated lowest fares found within 7 days

Flight Schedules

Last Updated: Thu, 2 May, 2024

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