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Flights from Cleveland to Chicago – Direct & connecting routes

Non-stop airlines Connecting flights Show map Price search

CLE to MDW flights and routes map CLE to MDW – All flight route options from Cleveland Hopkins International, Ohio, USA to Chicago Midway International, Illinois, USA. These flights are operated by 2 airlines. Fly non-stop with Southwest Airlines or choose from 1 different transit flights. The shortest flight time is 1 hour and 20 minutes. See the full flight schedule and time table, including departure times, airlines and stopover details to find the best option for you.

From
To
USA CLE Cleveland Hopkins Cleveland, OH, USA
USA MDW Chicago Midway , IL, USA
CLE
Cleveland Hopkins
USACleveland, OH, USA
Chicago Midway
USAChicago, IL, USA
MDW
1 direct route found »
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1 routes with 1 stop found »
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Non-stop route options:

Duration

Southwest Airlines
Non-stop with Southwest Airlines. 3-4 flights per day.

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1h 20m

Southwest Airlines
Non-stop with Southwest Airlines.
1h 20m
3-4 flights per day.
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1 stop route options with the same airline:

Duration

Via Detroit DTW
1 stop with Delta Air Lines. 3-4 flights per day.

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3h 41m

Via Detroit DTW
1 stop with Delta Air Lines.
3h 41m
3-4 flights per day.
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Cleveland to Chicago flights

With over 48 flights every week and 2 different airlines you have a wide range of options. You can fly non-stop to Chicago (MDW) from Cleveland (CLE) with Southwest Airlines or opt for a connecting flight via Detroit (DTW).

Cleveland to Chicago with Southwest Airlines

You can fly non-stop every weekday with flights departing from 6:00 am to 9:00 pm.

With Delta Air Lines

If you fly from Cleveland with Delta Air Lines you will do a stopover in Detroit, DTW before reaching Chicago. This flight trip will take 3 hours and 41 minutes and you can fly every weekday with departures between 5:00 am and 4:00 pm. Delta Air Lines is a member of SkyTeam.

Distance & flight times: Cleveland Hopkins International to Midway International Airport

The shortest flight time between CLE and MDW is 1 hour and 20 minutes.

ViaTotal flight timeLayover timeDistance
Direct1h 20m-307 miles (494 km)
DTW Detroit3h 41m1h 56m324 miles (521 km)
The flight times and layover times in the table above are approximate and may vary depending on flight number, aircraft, airline, weather, and time of day.CLE-MDW flight routesCleveland to Chicago flight routes illustrated on a map.
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Cleveland - Chicago route map and flight paths
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You can fly non-stop from Cleveland (CLE) to Chicago (MDW) with Southwest Airlines. The flight takes approximately 1 hour and 20 minutes. If you travel with a connecting flight instead, for example via Detroit, the total flight time will be 3 hours and 41 minutes.

If you're interested in direct flights, Southwest Airlines is available. For flights with stopovers, Delta Air Lines is also an option.

The flight time between Cleveland Hopkins (CLE) and Chicago Midway International (MDW) is approximately 1 hour and 20 minutes. The distance between the two airports is 324 miles (or 521 kilometers).

Yes, you can fly non-stop to MDW from CLE with Southwest Airlines.

A codeshare agreement means that cooperating airlines are able to sell seats on each other’s flights. This means that you are able to travel to more destinations than your airline of choice normally offers. Codeshare flights are also beneficial because of the seamless transits you can get with connecting flights from the same airline. The downside of choosing a codeshare flight can be that you in some cases can’t upgrade codeshare flights or use elite benefits.

A connecting or transit flight means that you reach your final destination through two or more flights – in other words a non-direct flight. You will change to a new aircraft after your first flight, this may include moving to another terminal at the airport aswell. The time required to transfer passengers and luggage between flights is called Minimum Connecting Time (MCT) and are always taken into account here on Flightroutes.com.

If you bought your whole flight on a single ticket, the airline will book you on the next available connecting flight.

With connecting flights, checked in luggage is most commonly forwarded to your final destination when buying a single ticket for both flights.

If you miss your connecting flight due to circumstances outside your control such as your first flight being delayed, you should turn to your airline who will provide you with a seat on the next available flight. This is usually done free of charge, and only applies if you purchased your trip as one ticket. If the next connecting flight is the following day, the airline usually provides accommodation and meals.
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