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Cheap flights from Chicago Midway Airport to Cleveland from $83

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Chicago Midway Airport to Cleveland departing on 9/15. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
1 adult, Economy, 0 bags

Find the cheapest flights from Chicago Midway Airport to Cleveland

Cheap round-trip flights

Enter your travel dates to find the best prices.
Southwest Logo
1:00 pm - 9:25 pm
MDW
-
CLE
7h 25m
2 stops
Southwest Logo
8:45 am - 8:55 am
CLE
-
MDW
1h 10mnonstop
$192Southwest
Wed, Aug 5 - Wed, Aug 12
Southwest Logo
6:30 pm - 8:45 pm
MDW
-
CLE
1h 15mnonstop
Southwest Logo
5:40 am - 12:20 pm
CLE
-
MDW
7h 40m
2 stops
$193Southwest
Mon, Aug 24 - Thu, Aug 27
Southwest Logo
1:00 pm - 9:25 pm
MDW
-
CLE
7h 25m
2 stops
Southwest Logo
1:50 pm - 2:05 pm
CLE
-
MDW
1h 15mnonstop
$194Southwest
Wed, Aug 19 - Thu, Aug 20
Frontier Logo
6:05 am - 10:31 pm
MDW
-
CLE
15h 26m
1 stop
Frontier Logo
5:15 pm - 10:47 pm
CLE
-
MDW
6h 32m
1 stop
$196Frontier
Sun, Aug 23 - Sun, Aug 30
Delta Logo
6:42 pm - 11:56 pm
MDW
-
CLE
4h 14m
1 stop
Delta Logo
6:43 am - 9:17 am
CLE
-
MDW
3h 34m
1 stop
$197Delta
Mon, Aug 24 - Wed, Sep 2
Frontier Logo
11:06 am - 8:52 pm
MDW
-
CLE
8h 46m
1 stop
Frontier Logo
3:46 pm - 10:03 pm
CLE
-
MDW
7h 17m
1 stop
$198Frontier
Sat, Aug 8 - Mon, Aug 10
Frontier Logo
11:06 am - 8:52 pm
MDW
-
CLE
8h 46m
1 stop
Frontier Logo
3:46 pm - 9:51 am
CLE
-
MDW
19h 05m
1 stop
$200Frontier
Fri, Aug 7 - Fri, Aug 14
Frontier Logo
11:50 am - 10:31 pm
MDW
-
CLE
9h 41m
1 stop
Frontier Logo
5:15 pm - 10:50 am
CLE
-
MDW
18h 35m
1 stop
$201Frontier
Wed, Aug 26 - Fri, Aug 28
Southwest Logo
1:00 pm - 9:25 pm
MDW
-
CLE
7h 25m
2 stops
Southwest Logo
6:25 pm - 10:20 pm
CLE
-
MDW
4h 55m
1 stop
$202Southwest
Wed, Aug 5 - Wed, Aug 12
Southwest Logo
8:05 am - 10:25 am
MDW
-
CLE
1h 20mnonstop
Southwest Logo
5:25 pm - 5:40 pm
CLE
-
MDW
1h 15mnonstop
$203Southwest
Thu, Aug 27 - Fri, Aug 28

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Southwest flights from Chicago Midway Airport to Cleveland

Our best Southwest deals on Chicago Midway Airport to Cleveland flight tickets
Southwest
Dec 1
MDW1:55 pmChicago Midway
1h 15m
CLE4:10 pmCleveland Hopkins Intl
Dec 5
CLE1:25 pmCleveland Hopkins Intl
5h 00m
1 stop
MDW5:25 pmChicago Midway
$187
Southwest
Aug 5
MDW8:35 amChicago Midway
1h 25m
CLE11:00 amCleveland Hopkins Intl
Aug 10
CLE6:05 pmCleveland Hopkins Intl
5h 15m
1 stop
MDW10:20 pmChicago Midway
$188
Southwest
Aug 5
MDW1:00 pmChicago Midway
7h 25m
2 stops
CLE9:25 pmCleveland Hopkins Intl
Aug 10
CLE5:25 pmCleveland Hopkins Intl
1h 15m
MDW5:40 pmChicago Midway
$192

Frontier flights from Chicago Midway Airport to Cleveland

Our best Frontier deals on Chicago Midway Airport to Cleveland flight tickets
Frontier
Aug 23
MDW6:05 amChicago Midway
15h 26m
1 stop
CLE10:31 pmCleveland Hopkins Intl
Aug 30
CLE5:15 pmCleveland Hopkins Intl
6h 32m
1 stop
MDW10:47 pmChicago Midway
$196
Frontier
Aug 5
MDW11:06 amChicago Midway
8h 46m
1 stop
CLE8:52 pmCleveland Hopkins Intl
Aug 9
CLE5:51 pmCleveland Hopkins Intl
17h 00m
1 stop
MDW9:51 amChicago Midway
$198
Frontier
Sep 11
MDW12:03 pmChicago Midway
7h 34m
1 stop
CLE8:37 pmCleveland Hopkins Intl
Sep 13
CLE3:40 pmCleveland Hopkins Intl
7h 18m
1 stop
MDW9:58 pmChicago Midway
$199

momondo Fare Finder

 
Customize your flight search to find flights from Chicago Midway Airport to Cleveland that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, momondo users made 832,500 searches. Data last updated July 10, 2026.
Use the filters below to find and compare flights from Chicago Midway Airport to Cleveland that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

ChicagoCleveland

MDW - CLE

MDWCLE

Chicago Midway

Wed 8/5

1:00 pm-9:25 pm

2 stops7h 25m

Cleveland Hopkins Intl

Wed 8/12

8:45 am-8:55 am

Nonstop1h 10m

$192

ChicagoCleveland

MDW - CLE

MDWCLE

Chicago Midway

Mon 8/24

6:30 pm-8:45 pm

Nonstop1h 15m

Cleveland Hopkins Intl

Thu 8/27

5:40 am-12:20 pm

2 stops7h 40m

$193

ChicagoCleveland

MDW - CLE

MDWCLE

Chicago Midway

Wed 8/19

1:00 pm-9:25 pm

2 stops7h 25m

Cleveland Hopkins Intl

Thu 8/20

1:50 pm-2:05 pm

Nonstop1h 15m

$194

ChicagoCleveland

MDW - CLE

MDWCLE

Chicago Midway

Sun 8/23

6:05 am-10:31 pm

1 stop15h 26m

Cleveland Hopkins Intl

Sun 8/30

5:15 pm-10:47 pm

1 stop6h 32m

$196

ChicagoCleveland

MDW - CLE

MDWCLE

Chicago Midway

Mon 8/24

6:42 pm-11:56 pm

1 stop4h 14m

Cleveland Hopkins Intl

Wed 9/2

6:43 am-9:17 am

1 stop3h 34m

$197

ChicagoCleveland

MDW - CLE

MDWCLE

Chicago Midway

Sat 8/8

11:06 am-8:52 pm

1 stop8h 46m

Cleveland Hopkins Intl

Mon 8/10

3:46 pm-10:03 pm

1 stop7h 17m

$198

ChicagoCleveland

MDW - CLE

MDWCLE

Chicago Midway

Fri 8/7

11:06 am-8:52 pm

1 stop8h 46m

Cleveland Hopkins Intl

Fri 8/14

3:46 pm-9:51 am

1 stop19h 05m

$200

ChicagoCleveland

MDW - CLE

MDWCLE

Chicago Midway

Wed 8/26

11:50 am-10:31 pm

1 stop9h 41m

Cleveland Hopkins Intl

Fri 8/28

5:15 pm-10:50 am

1 stop18h 35m

$201

ChicagoCleveland

MDW - CLE

MDWCLE

Chicago Midway

Wed 8/5

1:00 pm-9:25 pm

2 stops7h 25m

Cleveland Hopkins Intl

Wed 8/12

6:25 pm-10:20 pm

1 stop4h 55m

$202
Quickest round-trip

ChicagoCleveland

MDW - CLE

MDWCLE

Chicago Midway

Thu 8/27

8:05 am-10:25 am

Nonstop1h 20m

Cleveland Hopkins Intl

Fri 8/28

5:25 pm-5:40 pm

Nonstop1h 15m

$203

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
1
2

See travel insights to Cleveland from

How to get the cheapest flight ticket from Chicago Midway Airport to Cleveland

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

What is the typical price of a round-trip flight between Chicago Midway Airport and Cleveland?

What is the cheapest month to fly to Cleveland?

In general, November is the cheapest month to fly from Chicago Midway Airport to Cleveland. Due to it being the ‘off-season’ during this time, you can expect flight prices to be around $0. If you’re not able to fly to Cleveland in November, then August is your next best option. Flight prices from Chicago Midway Airport to Cleveland during August average around $0.

What is the cheapest day to depart on your flight to Cleveland?

The cheapest day to depart from Chicago Midway Airport to Cleveland is on a Saturday when prices can be found for as low as $276. Be sure to avoid booking your departure on a Sunday as prices are generally higher than usual. According to our data, the average ticket price to Cleveland on Sunday is $538.

What is the cheapest time of day to depart on your flight to Cleveland?

Our data shows that the cheapest Chicago Midway Airport to Cleveland flights are usually those with departure times at noon. Our users have found flights to Cleveland at noon for as low as $328. In contrast, the most expensive time of day to depart to Cleveland is in the afternoon when prices are around $424.

What is the cheapest Chicago Midway to Cleveland Hopkins Intl flight route?

Fly from Chicago Midway to Cleveland Hopkins Intl for the best Chicago Midway - Cleveland Hopkins Intl flight prices

What cabin class options are available on Chicago Midway Airport to Cleveland flights?

There is only 1 cabin class available to choose from on Chicago Midway Airport to Cleveland flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

Can stopping save me money on Chicago Midway Airport to Cleveland flights?

No. A direct flight is the cheapest option for a flight between Chicago Midway Airport to Cleveland.

When to book flights from Chicago Midway Airport to Cleveland

Are you open to changing your travel dates? Check out the ideal times to fly from Chicago Midway Airport to Cleveland according to our flight data. Find out which month and days have the cheapest flights.
Estimated round-trip price

Cheap Chicago Midway Airport to Cleveland (MDW to CLE) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Chicago Midway Airport to Cleveland

Best Price Found

$103

Fastest flight time

1h 10m

Direct flights

Every day

Airports in Cleveland

1 airport
The best one-way flight to Cleveland from Chicago Midway Airport in the past 72 hours is $103. The best round-trip flight deal from Chicago Midway Airport to Cleveland found on momondo in the last 72 hours is $252.
The fastest flight from Chicago Midway Airport to Cleveland takes 1h 10m
Direct flights go from Chicago Midway Airport to Cleveland every day.
There is 1 airport in Cleveland. From Chicago Midway Airport there are direct flights to Cleveland Hopkins Intl (CLE).
Search flight deals

Frequently asked questions about flying from Chicago Midway Airport to Cleveland

  • How far is Chicago Midway to Cleveland Hopkins Intl by plane?

    Cleveland Hopkins Intl is 312.8 mi away from Chicago Midway. Typically, this will take 1h 10m by plane in normal conditions.

  • When did momondo last update prices for flights from Chicago Midway Airport to Cleveland Hopkins Intl Airport?

    Prices for flights from Chicago Midway Airport to Cleveland Hopkins Intl Airport are updated daily.

  • How many operators does momondo search for flights from Chicago Midway Airport to Cleveland Hopkins Intl Airport?

  • How old do you have to be to fly from Chicago Midway Airport to Cleveland Hopkins Intl Airport?

    The minimum age for a child to fly alone is five, but airlines that offer an unaccompanied minor (UNMR) service may have their own age limitations. Flight duration, scheduling, and layovers are among the considerations that may influence age limits. We recommend that you double-check with the airline you are booking with for travel from Chicago Midway Airport to Cleveland Hopkins Intl Airport.

  • What documentation or ID do you need to fly to Cleveland Hopkins Intl Airport?

    The required travel and health documents for your Cleveland Hopkins Intl Airport trip may vary depending on your itinerary and personal circumstances. As a general rule, you should carry multiple documents, including a national ID card or driver's license and a passport valid for six months after your intended arrival at Cleveland Hopkins Intl Airport. We recommend that you seek guidance from your airline or a reliable third party such as IATA.

  • What is the most popular plane model from Chicago Midway Airport to Cleveland?

  • What is the most popular airline from Chicago Midway Airport to Cleveland?

Best airlines flying from Chicago Midway Airport to Cleveland

Compare and see reviews for airlines that fly from Chicago Midway Airport to Cleveland with momondo
Airline
Rating
Free Cancellation
Price
SouthwestPriceFrom $137Free CancellationRating
7.9
4,248 reviews
Search Southwest flights

  • Southwest Flights From Chicago Midway Airport to Cleveland

    Across 20 Southwest flights from Chicago Midway Airport to Cleveland this week, the average price was $503, with the best Southwest deals starting from $137 round-trip. 4,248 users have rated Southwest on momondo, with an average score of 7.9/10.

Traveling to a place near Cleveland?

Book flights to Cleveland if you plan to visit one of these locations
Sandusky
Mansfield
Beachwood
Westlake
Independence
Mentor
Elyria
Kent
Willoughby
Geneva-on-the-Lake
Painesville
Streetsboro
Medina
Macedonia
Wooster
Cuyahoga Falls
Ashland
North Olmsted
Lakewood
Strongsville

Why use momondo?

Why should I use momondo to find a flight deal from Chicago to Cleveland?

It is quick and easy to find Chicago to Cleveland flights on momondo. We search and return numerous flight options from various airlines and agents. You can then use our filters to narrow your search until you have found the most convenient flight to Cleveland that suits you.

Can I find flights from Chicago to Cleveland with flexible booking policies on momondo?

Yes. All flights to Cleveland from Chicago on momondo can be compared and filtered by various policies on offer, including flexible booking.

How can momondo help me find flights from Chicago to Cleveland?

momondo offers useful filters to help you find the right flight. Choose specific flight times, airports or even what payment method you prefer. We have numerous options to help you book your ideal flight from Chicago to Cleveland.

I’m not ready to book a flight from Chicago to Cleveland right now. Can momondo alert me if prices change?

Price alerts on flights to Cleveland from Chicago are quick and easy to set up on momondo. Simply perform a search and select the price alert feature. It is as simple as that.

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