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Cheap flights from Chicago Midway Airport to Cleveland from $86

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 7/25. 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

Find the cheapest flights from Chicago Midway Airport to Cleveland

Cheap round-trip flights

Enter your travel dates to find the best prices.
Delta Logo
1:22 pm - 12:39 am
MDW
-
CLE
10h 17m
2 stops
Delta Logo
6:35 am - 1:19 pm
CLE
-
MDW
7h 44m
2 stops
$194Delta
Sat, May 23 - Wed, May 27
Southwest Logo
4:40 pm - 9:15 pm
MDW
-
CLE
3h 35m
1 stop
Southwest Logo
6:40 am - 3:45 pm
CLE
-
MDW
10h 05m
2 stops
$195Southwest
Tue, May 26 - Wed, May 27
Frontier Logo
6:00 am - 6:27 pm
MDW
-
CLE
11h 27m
1 stop
Frontier Logo
6:54 am - 10:02 pm
CLE
-
MDW
16h 08m
1 stop
$197Frontier
Mon, May 25 - Mon, Jun 1
Frontier Logo
6:00 am - 6:27 pm
MDW
-
CLE
11h 27m
1 stop
Frontier Logo
6:54 am - 11:09 am
CLE
-
MDW
5h 15m
1 stop
$201Frontier
Mon, May 11 - Thu, May 14
Frontier Logo
6:00 am - 6:29 pm
MDW
-
CLE
11h 29m
1 stop
Frontier Logo
7:24 pm - 10:08 pm
CLE
-
MDW
27h 44m
1 stop
$204Frontier
Wed, Jul 1 - Fri, Jul 24
Frontier Logo
12:27 pm - 7:34 pm
MDW
-
CLE
6h 07m
1 stop
Frontier Logo
7:00 am - 2:12 pm
CLE
-
MDW
8h 12m
1 stop
$205Frontier
Sun, May 24 - Sun, May 31
Frontier Logo
6:00 am - 7:29 pm
MDW
-
CLE
12h 29m
2 stops
Frontier Logo
3:46 pm - 10:02 pm
CLE
-
MDW
7h 16m
1 stop
$206Frontier
Thu, May 28 - Fri, May 29
Frontier Logo
6:00 am - 6:27 pm
MDW
-
CLE
11h 27m
1 stop
Frontier Logo
8:49 pm - 11:09 am
CLE
-
MDW
15h 20m
1 stop
$207Frontier
Fri, May 22 - Tue, May 26
Southwest Logo
5:20 pm - 10:15 pm
MDW
-
CLE
3h 55m
1 stop
Southwest Logo
8:25 am - 8:40 am
CLE
-
MDW
1h 15mnonstop
$209Southwest
Tue, Jun 9 - Tue, Jun 16
Frontier Logo
6:00 am - 6:26 pm
MDW
-
CLE
11h 26m
1 stop
Frontier Logo
3:46 pm - 10:08 pm
CLE
-
MDW
7h 22m
1 stop
$210Frontier
Wed, Jul 15 - Fri, Jul 17

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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
May 26
MDW4:40 pmChicago Midway
3h 35m
1 stop
CLE9:15 pmCleveland Hopkins Intl
May 27
CLE6:40 amCleveland Hopkins Intl
10h 05m
2 stops
MDW3:45 pmChicago Midway
$195
Southwest
May 18
MDW7:55 amChicago Midway
1h 15m
CLE10:10 amCleveland Hopkins Intl
May 19
CLE6:45 pmCleveland Hopkins Intl
1h 15m
MDW7:00 pmChicago Midway
$196
Southwest
Jun 9
MDW5:20 pmChicago Midway
3h 55m
1 stop
CLE10:15 pmCleveland Hopkins Intl
Jun 16
CLE8:25 amCleveland Hopkins Intl
1h 15m
MDW8:40 amChicago Midway
$209

Frontier flights from Chicago Midway Airport to Cleveland

Our best Frontier deals on Chicago Midway Airport to Cleveland flight tickets
Frontier
May 25
MDW6:00 amChicago Midway
11h 27m
1 stop
CLE6:27 pmCleveland Hopkins Intl
Jun 1
CLE6:54 amCleveland Hopkins Intl
16h 08m
1 stop
MDW10:02 pmChicago Midway
$197
Frontier
May 8
MDW6:00 amChicago Midway
11h 27m
1 stop
CLE6:27 pmCleveland Hopkins Intl
May 11
CLE3:49 pmCleveland Hopkins Intl
7h 13m
1 stop
MDW10:02 pmChicago Midway
$201
Frontier
Jul 1
MDW6:00 amChicago Midway
11h 29m
1 stop
CLE6:29 pmCleveland Hopkins Intl
Jul 24
CLE7:24 pmCleveland Hopkins Intl
27h 44m
1 stop
MDW10:08 pmChicago Midway
$204

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 April 28, 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

Sat 5/23

1:22 pm-12:39 am

2 stops10h 17m

Cleveland Hopkins Intl

Wed 5/27

6:35 am-1:19 pm

2 stops7h 44m

$194

ChicagoCleveland

MDW - CLE

MDWCLE

Chicago Midway

Tue 5/26

4:40 pm-9:15 pm

1 stop3h 35m

Cleveland Hopkins Intl

Wed 5/27

6:40 am-3:45 pm

2 stops10h 05m

$195

ChicagoCleveland

MDW - CLE

MDWCLE

Chicago Midway

Mon 5/25

6:00 am-6:27 pm

1 stop11h 27m

Cleveland Hopkins Intl

Mon 6/1

6:54 am-10:02 pm

1 stop16h 08m

$197

ChicagoCleveland

MDW - CLE

MDWCLE

Chicago Midway

Mon 5/11

6:00 am-6:27 pm

1 stop11h 27m

Cleveland Hopkins Intl

Thu 5/14

6:54 am-11:09 am

1 stop5h 15m

$201

ChicagoCleveland

MDW - CLE

MDWCLE

Chicago Midway

Wed 7/1

6:00 am-6:29 pm

1 stop11h 29m

Cleveland Hopkins Intl

Fri 7/24

7:24 pm-10:08 pm

1 stop27h 44m

$204

ChicagoCleveland

MDW - CLE

MDWCLE

Chicago Midway

Sun 5/24

12:27 pm-7:34 pm

1 stop6h 07m

Cleveland Hopkins Intl

Sun 5/31

7:00 am-2:12 pm

1 stop8h 12m

$205

ChicagoCleveland

MDW - CLE

MDWCLE

Chicago Midway

Thu 5/28

6:00 am-7:29 pm

2 stops12h 29m

Cleveland Hopkins Intl

Fri 5/29

3:46 pm-10:02 pm

1 stop7h 16m

$206

ChicagoCleveland

MDW - CLE

MDWCLE

Chicago Midway

Fri 5/22

6:00 am-6:27 pm

1 stop11h 27m

Cleveland Hopkins Intl

Tue 5/26

8:49 pm-11:09 am

1 stop15h 20m

$207
Quickest round-trip

ChicagoCleveland

MDW - CLE

MDWCLE

Chicago Midway

Tue 6/9

5:20 pm-10:15 pm

1 stop3h 55m

Cleveland Hopkins Intl

Tue 6/16

8:25 am-8:40 am

Nonstop1h 15m

$209

ChicagoCleveland

MDW - CLE

MDWCLE

Chicago Midway

Wed 7/15

6:00 am-6:26 pm

1 stop11h 26m

Cleveland Hopkins Intl

Fri 7/17

3:46 pm-10:08 pm

1 stop7h 22m

$210

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 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 June is your next best option. Flight prices from Chicago Midway Airport to Cleveland during June average around $157.

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 $258. 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 $469.

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 $301. In contrast, the most expensive time of day to depart to Cleveland is in the evening when prices are around $348.

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

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 $237.
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 $97Free CancellationRating
8.0
4,314 reviews
Search Southwest flights

  • Southwest Flights From Chicago Midway Airport to Cleveland

    Across 15 Southwest flights from Chicago Midway Airport to Cleveland this week, the average price was $503, with the best Southwest deals starting from $97 round-trip. 4,314 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
Westlake
Mentor
Geneva-on-the-Lake
Kent
Willoughby
Painesville
Cuyahoga Falls
Streetsboro
Lakewood
Wooster
North Olmsted
Kelleys Island
Avon
Ashland
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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