Cheap Flight Tickets from Cleveland (CLE) to Chicago (MDW), Starting at $109

Good to Know: Cheapest and Fastest CLE - MDW Flights

Useful information for finding best airline tickets from Cleveland Hopkins International to Chicago Midway International on your next trip.

Cheapest Round Trip Flight

$408

AA American Airlines • nonstop • 2h 28m

Aug 20 – Aug 20

The cheapest round trip flight from Cleveland to Chicago (CLE-MDW-CLE) is currently $408

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Cheapest One way Flight

$109

WN Southwest Airlines • 2 stops • 10h 40m

Sep 27

The cheapest one way flight from Cleveland to Chicago (CLE-MDW) is currently $109

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Cheapest Direct Flight

$483

AA American Airlines • nonstop • 2h 11m

Aug 20

The cheapest nonstop flight from Cleveland to Chicago (CLE-MDW) is currently $483

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Fastest Flight

1h 50m

The fastest nonstop flight from Cleveland to Chicago (CLE-MDW) takes 1h 50m

Top Airlines Flying from Cleveland to Chicago

Southwest Airlines-WN

Southwest Airlines

Delta Airline, DL

Delta Airlines

United Airlines, UA

United Airlines

American Airlines, AA

American Airlines

Latest Flight Deals from Cleveland (CLE) to Chicago (MDW)

Compare and book low fare round-trip air tickets from Cleveland to Chicago. Ideal for travelers with confirmed return itineraries.

Aug 20 - Aug 20, Economy
AA
Cleveland → Chicago
2h 28m
9:43 AM - 10:31 AM • nonstop
F9
Cleveland → Chicago
39h 18m
7:44 PM - 8:42 PM • 1 stop
$408
American Airlines
Aug 20 - Aug 20, Economy
AA
Cleveland → Chicago
2h 24m
1:11 PM - 1:55 PM • nonstop
F9
Cleveland → Chicago
25h 48m
7:44 PM - 12:32 PM • 1 stop
$408
American Airlines
Aug 20 - Aug 20, Economy
AA
Cleveland → Chicago
2h 11m
5:15 AM - 5:46 AM • nonstop
AA
Cleveland → Chicago
2h 9m
1:24 PM - 3:53 PM • nonstop
$483
American Airlines
Aug 20 - Aug 20, Economy
WN
Cleveland → Chicago
1h 50m
8:50 AM - 9:00 AM • nonstop
WN
Cleveland → Chicago
10h
3:10 PM - 10:10 PM • 1 stop
$509
Southwest Airlines
Aug 20 - Aug 20, Economy
WN
Cleveland → Chicago
8h 40m
6:40 AM - 11:00 AM • 1 stop
WN
Cleveland → Chicago
25h 35m
7:40 PM - 12:15 PM • 2 stops
$524
Southwest Airlines
Aug 20 - Aug 20, Economy
WN
Cleveland → Chicago
10h 35m
6:40 AM - 12:15 PM • 2 stops
WN
Cleveland → Chicago
10h 5m
4:25 PM - 11:30 PM • 1 stop
$524
Southwest Airlines

Fly from Cleveland to Chicago with the Best Airfare Deals on FareLeaders

Looking for a cheap last-minute deal or the best round-trip flight from Cleveland to Chicago? Find the biggest savings on one-way and round-trip tickets right here.

FAQs on Cleveland to Chicago Flights

What are the airports in Cleveland?
CLE
What’s the most popular airline flying from CLE to MDW?
The most popular airline flying from Cleveland to Chicago are
Can I fly from CLE to MDW non-stop?
Yes, you can fly CLE to MDW non-stop on
Which airlines fly nonstop between Cleveland and Chicago?
The non-stop flights between Cleveland and Chicago are .
What’s the earliest departure time from CLE to MDW Airport?
The earliest flight leaves CLE at 5:15 am and lands in MDW - Chicago Midway International
What are the airports in Chicago?
ORD,MDW
Can I make changes to my Cleveland to Chicago flight tickets or cancel them on FareLeaders.com?
No. We are an airfare comparison site. All the tickets are booked by the travel agent offering the flight deal and any changes or cancellations to be made are directly done directly by them or the airlines.
Can I cancel my flight tickets from CLE to MDW?
Read the fare rules of the Cleveland to Chicago air tickets booked. Some airlines allow you to cancel the tickets within a stipulated time period with a cancellation fee.
Which airline alliances offer flights from Cleveland and Chicago?
operate flights between Cleveland and Chicago
How long does a flight from Cleveland to Chicago take?
It takes approximately 1 hour to fly non-stop from CLE to MDW, which is 306.8 miles by air.
Which airlines provide the cheapest flights from Cleveland (CLE) to Chicago (MDW) ?
In the past couple of days, the cheapest tickets to MDW from CLE were found on WN : USD 110
Do I need a passport to fly between CLE and MDW?
No
What’s the latest departure time from CLE to MDW ?
The last flight leaves CLE at 3:05 pm

Cleveland (CLE) to Chicago (MDW): Airport Information

Origin Airport Cleveland Hopkins International , Cleveland, US
Destination Airport Chicago Midway International , Chicago, US
Distance 307 miles

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