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Direct flights from Cleveland to Chicago

Airlines Schedules

CLE - MDW route map All flights from CLE to MDW non-stop. There are direct flights from Cleveland Hopkins International (CLE), Ohio, USA to Chicago Midway International (MDW), Illinois, USA with Southwest Airlines. 20 weekly departures are currently scheduled on this route. Departure times range from 07:05 to 21:35 depending on the schedule period. The flight distance is 307 miles (494 km). Flight time ranges from 1 hour and 15 minutes to 1 hour and 40 minutes.

CLE
Cleveland Hopkins
USACleveland , USA
MDW
Chicago Midway
USAChicago , USA
CLE
Cleveland Hopkins
USACleveland , USA
Chicago Midway
USAChicago , USA
MDW
Flight time 1h 15min to 1h 40min
Updated Nov 9, 2026
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Airlines with non-stop routes:

Southwest Airlines Low-cost carrier

Departure times vary between 07:05 and 21:35
S
M
T
W
T
F
S
Sun
Mon
Tue
Wed
Thu
Fri
Sat
20 flights/week
20 flights/week
Weekday-labels: HAS FLIGHTS UPCOMING NO FLIGHTS
View all flight dates
Flight schedule from Cleveland to Chicago with Southwest Airlines

This is a weekly direct flight schedule for Southwest Airlines. Use the arrows or click on the date to change week. Click on any flight departure time to show more information and check availability.

 
Flight
Mon
Nov 16
Tue
Nov 17
Wed
Nov 18
Thu
Nov 19
Fri
Nov 20
Sat
Nov 21
Sun
Nov 22
WN1218
08:45
08:45
08:45
08:45
08:35
08:40
08:35
WN1219
13:55
13:55
13:55
13:55
12:35
----
12:35
WN1220
19:10
19:10
19:10
19:10
19:55
19:40
19:55

The timetable & schedule information was updated at 2026-11-09

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Cleveland to Chicago scheduled departures

Select a date to see every published non-stop departure between CLE and MDW.

Saturday
Sat
Dec 05
2 flights(2)
Sunday
Sun
Dec 06
3 flights(3)
Monday
Mon
Dec 07
3 flights(3)
Tuesday
Tue
Dec 08
3 flights(3)
Wednesday
Wed
Dec 09
3 flights(3)
Thursday
Thu
Dec 10
3 flights(3)
Friday
Fri
Dec 11
3 flights(3)
Time
Airline
Flight
08:35
Southwest Airlines Southwest Airlines
WN1218
16:35
Southwest Airlines Southwest Airlines
WN1220
08:35
Southwest Airlines Southwest Airlines
WN1218
12:35
Southwest Airlines Southwest Airlines
WN1219
19:55
Southwest Airlines Southwest Airlines
WN1220
08:45
Southwest Airlines Southwest Airlines
WN1218
13:55
Southwest Airlines Southwest Airlines
WN1219
19:10
Southwest Airlines Southwest Airlines
WN1220
08:45
Southwest Airlines Southwest Airlines
WN1218
13:55
Southwest Airlines Southwest Airlines
WN1219
19:10
Southwest Airlines Southwest Airlines
WN1220
08:45
Southwest Airlines Southwest Airlines
WN1218
13:55
Southwest Airlines Southwest Airlines
WN1219
19:10
Southwest Airlines Southwest Airlines
WN1220
08:45
Southwest Airlines Southwest Airlines
WN1218
13:55
Southwest Airlines Southwest Airlines
WN1219
19:10
Southwest Airlines Southwest Airlines
WN1220
08:35
Southwest Airlines Southwest Airlines
WN1218
12:35
Southwest Airlines Southwest Airlines
WN1219
19:55
Southwest Airlines Southwest Airlines
WN1220
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CLE-MDW flight route
Route map from Cleveland, CLE to Chicago, MDW. The distance is 307 miles or 494 km.
Cleveland - Chicago direct flight map
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CLE - MDW route facts

  • Distance
    307 miles (494 km)
  • Flight time
    1 hour and 15 minutes to 1 hour and 40 minutes
  • Airline
    Southwest Southwest
  • Airline alliances
    Low-cost carrier
  • Cabins
    Economy
  • Aircraft
    Boeing 737MAX 8 Passenger, Boeing 737-800 (winglets) Passenger/BBJ2 and Boeing 737-700 Passenger (Scimitar Winglets)

Route FAQ

Southwest Airlines operates non-stop flights from CLE to MDW with 20 weekly departures (Nov 16 – Nov 22, 2026).

Scheduled flight time from CLE to MDW ranges from 1 hour and 15 minutes to 1 hour and 40 minutes. The route covers 307 miles (494 km).

20 weekly departures (Nov 16 – Nov 22, 2026) are currently scheduled on this route, with published departure times ranging from 07:05 to 21:35 depending on the schedule period.

Economy are currently scheduled on non-stop flights for this route.
Direct flights from Cleveland to IL, USA
From Cleveland to Chicago

ORD Chicago O Hare International
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