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Cheap flights from Chicago Midway Airport to Cleveland from $88

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 5/10. 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
0 bags

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Find the cheapest flights from Chicago Midway Airport to Cleveland

Cheap round-trip flights

Enter your travel dates to find the best prices.
Frontier Logo
6:00 am - 2:49 pm
MDW
-
CLE
7h 49m
1 stop
Frontier Logo
8:25 pm - 1:00 pm
CLE
-
MDW
17h 35m
1 stop
$123Frontier
Thu, Apr 16 - Mon, Apr 20
Frontier Logo
6:00 am - 5:55 pm
MDW
-
CLE
10h 55m
1 stop
Frontier Logo
8:25 pm - 1:00 pm
CLE
-
MDW
17h 35m
1 stop
$138Frontier
Sat, Apr 18 - Mon, Apr 20
Frontier Logo
7:34 pm - 7:44 am
MDW
-
CLE
11h 10m
1 stop
Frontier Logo
8:25 pm - 1:00 pm
CLE
-
MDW
17h 35m
1 stop
$139Frontier
Sat, Apr 18 - Mon, Apr 20
Frontier Logo
6:10 am - 2:26 pm
MDW
-
CLE
7h 16m
1 stop
Frontier Logo
11:46 am - 10:14 pm
CLE
-
MDW
11h 28m
1 stop
$140Frontier
Tue, Apr 28 - Wed, Apr 29
Frontier Logo
6:00 am - 7:32 pm
MDW
-
CLE
12h 32m
1 stop
Frontier Logo
6:54 am - 10:02 pm
CLE
-
MDW
16h 08m
1 stop
$141Frontier
Thu, May 7 - Tue, May 12
Frontier Logo
6:00 am - 2:49 pm
MDW
-
CLE
7h 49m
1 stop
Frontier Logo
8:25 pm - 1:00 pm
CLE
-
MDW
17h 35m
1 stop
$147Frontier
Thu, Apr 16 - Mon, Apr 20
Frontier Logo
6:00 am - 2:49 pm
MDW
-
CLE
7h 49m
1 stop
Frontier Logo
10:44 am - 10:19 pm
CLE
-
MDW
12h 35m
1 stop
$151Frontier
Thu, Apr 16 - Mon, Apr 20
Frontier Logo
7:30 am - 12:43 am
MDW
-
CLE
16h 13m
1 stop
Frontier Logo
11:46 am - 7:31 pm
CLE
-
MDW
8h 45m
1 stop
$158Frontier
Mon, Apr 20 - Wed, Apr 22
Frontier Logo
7:34 pm - 7:44 am
MDW
-
CLE
11h 10m
1 stop
Frontier Logo
1:33 pm - 10:19 pm
CLE
-
MDW
9h 46m
1 stop
$160Frontier
Sat, May 2 - Mon, May 4
Frontier Logo
6:00 am - 6:27 pm
MDW
-
CLE
11h 27m
1 stop
Frontier Logo
8:47 pm - 11:09 am
CLE
-
MDW
15h 22m
1 stop
$163Frontier
Fri, May 8 - Sun, May 10

Delta flights from Chicago Midway Airport to Cleveland

Our best Delta deals on Chicago Midway Airport to Cleveland flight tickets
Delta
May 27
MDW9:22 amChicago Midway
3h 01m
1 stop
CLE1:23 pmCleveland Hopkins Intl
Jun 2
CLE1:44 pmCleveland Hopkins Intl
5h 12m
1 stop
MDW5:56 pmChicago Midway
$197
Delta
Apr 20
MDW1:24 pmChicago Midway
8h 41m
2 stops
CLE11:05 pmCleveland Hopkins Intl
Apr 22
CLE5:50 amCleveland Hopkins Intl
5h 06m
1 stop
MDW9:56 amChicago Midway
$209
Delta
Apr 20
MDW5:21 pmChicago Midway
4h 44m
1 stop
CLE11:05 pmCleveland Hopkins Intl
Apr 23
CLE4:54 pmCleveland Hopkins Intl
6h 34m
1 stop
MDW10:28 pmChicago Midway
$211

Frontier flights from Chicago Midway Airport to Cleveland

Our best Frontier deals on Chicago Midway Airport to Cleveland flight tickets
Frontier
Apr 16
MDW6:00 amChicago Midway
7h 49m
1 stop
CLE2:49 pmCleveland Hopkins Intl
Apr 20
CLE8:25 pmCleveland Hopkins Intl
17h 35m
1 stop
MDW1:00 pmChicago Midway
$123
Frontier
Apr 18
MDW6:00 amChicago Midway
10h 55m
1 stop
CLE5:55 pmCleveland Hopkins Intl
Apr 20
CLE8:25 pmCleveland Hopkins Intl
17h 35m
1 stop
MDW1:00 pmChicago Midway
$138
Frontier
Apr 18
MDW7:34 pmChicago Midway
11h 10m
1 stop
CLE7:44 amCleveland Hopkins Intl
Apr 20
CLE8:25 pmCleveland Hopkins Intl
17h 35m
1 stop
MDW1:00 pmChicago Midway
$139

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 March 29, 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

Thu 4/16

6:00 am-2:49 pm

1 stop7h 49m

Cleveland Hopkins Intl

Mon 4/20

8:25 pm-1:00 pm

1 stop17h 35m

$123

ChicagoCleveland

MDW - CLE

MDWCLE

Chicago Midway

Sat 4/18

6:00 am-5:55 pm

1 stop10h 55m

Cleveland Hopkins Intl

Mon 4/20

8:25 pm-1:00 pm

1 stop17h 35m

$138

ChicagoCleveland

MDW - CLE

MDWCLE

Chicago Midway

Sat 4/18

7:34 pm-7:44 am

1 stop11h 10m

Cleveland Hopkins Intl

Mon 4/20

8:25 pm-1:00 pm

1 stop17h 35m

$139
Quickest round-trip

ChicagoCleveland

MDW - CLE

MDWCLE

Chicago Midway

Tue 4/28

6:10 am-2:26 pm

1 stop7h 16m

Cleveland Hopkins Intl

Wed 4/29

11:46 am-10:14 pm

1 stop11h 28m

$140

ChicagoCleveland

MDW - CLE

MDWCLE

Chicago Midway

Thu 5/7

6:00 am-7:32 pm

1 stop12h 32m

Cleveland Hopkins Intl

Tue 5/12

6:54 am-10:02 pm

1 stop16h 08m

$141

ChicagoCleveland

MDW - CLE

MDWCLE

Chicago Midway

Thu 4/16

6:00 am-2:49 pm

1 stop7h 49m

Cleveland Hopkins Intl

Mon 4/20

8:25 pm-1:00 pm

1 stop17h 35m

$147

ChicagoCleveland

MDW - CLE

MDWCLE

Chicago Midway

Thu 4/16

6:00 am-2:49 pm

1 stop7h 49m

Cleveland Hopkins Intl

Mon 4/20

10:44 am-10:19 pm

1 stop12h 35m

$151

ChicagoCleveland

MDW - CLE

MDWCLE

Chicago Midway

Mon 4/20

7:30 am-12:43 am

1 stop16h 13m

Cleveland Hopkins Intl

Wed 4/22

11:46 am-7:31 pm

1 stop8h 45m

$158

ChicagoCleveland

MDW - CLE

MDWCLE

Chicago Midway

Sat 5/2

7:34 pm-7:44 am

1 stop11h 10m

Cleveland Hopkins Intl

Mon 5/4

1:33 pm-10:19 pm

1 stop9h 46m

$160

ChicagoCleveland

MDW - CLE

MDWCLE

Chicago Midway

Fri 5/8

6:00 am-6:27 pm

1 stop11h 27m

Cleveland Hopkins Intl

Sun 5/10

8:47 pm-11:09 am

1 stop15h 22m

$163

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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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 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 $256. Be sure to avoid booking your departure on a Monday as prices are generally higher than usual. According to our data, the average ticket price to Cleveland on Monday is $435.

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 in the morning. Our users have found flights to Cleveland in the morning for as low as $299. In contrast, the most expensive time of day to depart to Cleveland is in the afternoon when prices are around $357.

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 to Cleveland Hopkins Intl flights?

There is only 1 cabin class available to choose from on Chicago Midway to Cleveland Hopkins Intl 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

$138

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 $138. The best round-trip flight deal from Chicago Midway Airport to Cleveland found on momondo in the last 72 hours is $287.
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

  • 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 $97Free CancellationRating
8.0
4,331 reviews
Search Southwest flights

  • Southwest Flights From Chicago Midway Airport to Cleveland

    Across 16 Southwest flights from Chicago Midway Airport to Cleveland this week, the average price was $344, with the best Southwest deals starting from $97 round-trip. 4,331 users have rated Southwest on momondo, with an average score of 8.0/10.

Traveling to a place near Cleveland?

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