Cheap Flight Tickets from Cleveland (CLE) to Chicago (MDW), Starting at $183

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

$583

WN Southwest Airlines • nonstop • 1h 55m

Oct 11 – Oct 15

The cheapest round trip flight from Cleveland to Chicago (CLE-MDW-CLE) is currently $583

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Cheapest Direct Flight

$183

WN Southwest Airlines • nonstop • 2h

Oct 05

The cheapest nonstop flight from Cleveland to Chicago (CLE-MDW) is currently $183

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Fastest Flight

1h 55m

The fastest nonstop flight from Cleveland to Chicago (CLE-MDW) takes 1h 55m

Top Airlines Flying from Cleveland to Chicago

Southwest Airlines-WN

Southwest Airlines

Delta Airline, DL

Delta 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.

Oct 11 - Oct 15, Economy
WN
Cleveland → Chicago
1h 55m
1:25 PM - 1:40 PM • nonstop
WN
Cleveland → Chicago
10h
5:00 AM - 12:00 PM • 1 stop
$583
Southwest Airlines
Oct 11 - Oct 15, Economy
WN
Cleveland → Chicago
1h 55m
1:25 PM - 1:40 PM • nonstop
WN
Cleveland → Chicago
13h 30m
8:00 AM - 5:10 PM • 2 stops
$588
Southwest Airlines
Oct 11 - Oct 15, Economy
WN
Cleveland → Chicago
17h 5m
5:25 AM - 2:50 PM • 2 stops
WN
Cleveland → Chicago
1h 55m
7:45 AM - 10:00 AM • nonstop
$588
Southwest Airlines
Oct 11 - Oct 15, Economy
WN
Cleveland → Chicago
12h
5:25 AM - 11:45 AM • 1 stop
WN
Cleveland → Chicago
8h 30m
11:00 AM - 5:10 PM • 1 stop
$592
Southwest Airlines
Oct 11 - Oct 15, Economy
WN
Cleveland → Chicago
11h 55m
5:25 PM - 11:40 PM • 1 stop
WN
Cleveland → Chicago
7h 35m
7:05 AM - 1:00 PM • 1 stop
$592
Southwest Airlines
Oct 11 - Oct 15, Economy
WN
Cleveland → Chicago
5h 50m
9:20 PM - 12:10 AM • 1 stop
WN
Cleveland → Chicago
16h 45m
12:45 PM - 11:50 PM • 1 stop
$592
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 5:25 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 592
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 9:20 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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