Southwest Airlines
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United States
Cleveland Hopkins International Airport
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United States
Midway International Airport
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Scan through all non-stop flights from Cleveland to Chicago. The full flight schedule below gives an overview of all non-stop flights from CLE to MDW, which includes the daily timetable of every operating airline for the upcoming 12 months.
Note: for airline-specific flight schedules, please scroll further down.
Known for its continental climate, Chicago features hot, humid summers with temperatures above 30°C (86°F) and cold, snowy winters that often drop below 0°C (32°F). This striking seasonal contrast offers travelers a variety of activities, from summer hiking to winter sports, ensuring year-round appeal.
The best time to visit Chicago is from March to November, covering spring, summer, and fall. While summer can be hot, it also sees slightly more rainfall than other seasons.
Currently, there is only one airline operating non-stop flights from Cleveland CLE to Chicago MDW, which is Southwest Airlines. This section gives an overview of the flight schedules and timetables of every airline with direct flights for this route.
Click an airline below to view their CLE MDW flight schedule.
Flights from CLE to MDW are operated 11 times a week, with an average of 2 flights per day. Departure times vary between 07:15 - 20:30. The earliest flight departs at 07:15, the last flight departs at 20:30. However, this depends on the date you are flying so please check with the full flight schedule above to see which departure times are available on your preferred date(s) of travel.
On this non-stop route, you can fly in Economy only.
The fastest direct flight from Cleveland to Chicago takes 1 hour and 15 minutes. The flight distance between Cleveland and Chicago is 305 miles (or 491 km).
There are 2 airports in Chicago: Midway International Airport (MDW) and O'Hare International Airport (ORD).
There are 11 flights per week flying from Cleveland to Chicago (as of March 2026).
1 hour and 15 minutes is the average flight time from Cleveland to Chicago.
The distance from Cleveland to Chicago is 305 miles (491 kilometers).
Southwest Airlines is the only airline flying nonstop from Cleveland to Chicago.
There are no alliances flying direct from Cleveland to Chicago at the moment.
You can fly non-stop in Economy only.
Aircraft types that fly from Cleveland to Chicago:
The earliest flight departs at 07:15 from Cleveland and arrives at 07:45 at Chicago.
The latest flight departs at 20:30 from Cleveland and arrives at 20:50 at Chicago.
305 miles (491 km) · 1h 15m
07:15
07:45
Southwest Airlines
WN 1875
Southwest Airlines
Boeing 757
Y
W
J
F
07:55
08:20
Southwest Airlines
WN 1086
Southwest Airlines
Boeing 757
Y
W
J
F
08:35
09:00
Southwest Airlines
WN 1875
Southwest Airlines
Boeing 757
Y
W
J
F
08:40
09:05
Southwest Airlines
WN 1875
Southwest Airlines
Boeing 757
Y
W
J
F
11:05
11:25
Southwest Airlines
WN 1514
Southwest Airlines
Boeing 757
Y
W
J
F
14:30
14:50
Southwest Airlines
WN 878
Southwest Airlines
Boeing 757
Y
W
J
F
14:40
15:00
Southwest Airlines
WN 878
Southwest Airlines
Boeing 737-800 (winglets)
Y
W
J
F
19:15
19:40
Southwest Airlines
WN 648
Southwest Airlines
Boeing 737 MAX 8
Y
W
J
F
19:50
20:10
Southwest Airlines
WN 2211
Southwest Airlines
Boeing 757
Y
W
J
F
20:30
20:50
Southwest Airlines
WN 2841
Southwest Airlines
Boeing 737 MAX 8
Y
W
J
F
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