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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 12/31. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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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.
Southwest Logo
9:55 am - 12:10 pm
MDW
-
CLE
1h 15mnonstop
Southwest Logo
6:35 am - 7:10 am
CLE
-
MDW
1h 35mnonstop
$233Southwest
Sat, Jan 10 - Sun, Jan 11
Southwest Logo
1:35 pm - 3:45 pm
MDW
-
CLE
1h 10mnonstop
Southwest Logo
5:55 pm - 10:30 pm
CLE
-
MDW
5h 35m1 stop
$236Southwest
Fri, Jan 16 - Mon, Jan 19
Frontier Logo
8:15 am - 4:30 pm
MDW
-
CLE
7h 15m1 stop
Frontier Logo
2:30 pm - 11:21 pm
CLE
-
MDW
9h 51m1 stop
$238Frontier
Sat, Dec 20 - Sun, Dec 21
Frontier Logo
6:12 am - 4:30 pm
MDW
-
CLE
9h 18m1 stop
Frontier Logo
11:26 am - 10:12 pm
CLE
-
MDW
11h 46m1 stop
$242Frontier
Fri, Dec 19 - Thu, Dec 25
Frontier Logo
8:15 am - 4:30 pm
MDW
-
CLE
7h 15m1 stop
Frontier Logo
9:30 pm - 10:12 pm
CLE
-
MDW
25h 42m2 stops
$245Frontier
Wed, Dec 24 - Tue, Dec 30
Southwest Logo
4:20 pm - 11:20 pm
MDW
-
CLE
6h 00m1 stop
Southwest Logo
6:15 am - 6:55 am
CLE
-
MDW
1h 40mnonstop
$252Southwest
Mon, Dec 29 - Tue, Jan 6
Multiple Airlines Logo
6:12 am - 4:30 pm
MDW
-
CLE
9h 18m1 stop
Multiple Airlines Logo
11:43 am - 9:58 pm
CLE
-
MDW
11h 15m2 stops
$255Multiple Airlines
Thu, Dec 18 - Wed, Dec 31
Frontier Logo
6:12 am - 4:30 pm
MDW
-
CLE
9h 18m1 stop
Frontier Logo
2:30 pm - 11:21 pm
CLE
-
MDW
9h 51m1 stop
$257Frontier
Thu, Dec 18 - Sun, Dec 21
Frontier Logo
6:14 am - 4:30 pm
MDW
-
CLE
9h 16m1 stop
Frontier Logo
11:26 am - 5:38 pm
CLE
-
MDW
7h 12m1 stop
$258Frontier
Tue, Dec 30 - Thu, Jan 1
Frontier Logo
8:15 am - 4:30 pm
MDW
-
CLE
7h 15m1 stop
Frontier Logo
6:59 pm - 9:58 pm
CLE
-
MDW
27h 59m1 stop
$265Frontier
Fri, Dec 19 - Mon, Dec 22

Frontier flights from Chicago Midway Airport to Cleveland

Our best Frontier deals on Chicago Midway Airport to Cleveland flight tickets
Frontier
Dec 11
MDW6:15 amChicago Midway
8h 33m
1 stop
CLE3:48 pmCleveland Hopkins Intl
Dec 14
CLE12:06 pmCleveland Hopkins Intl
7h 06m
1 stop
MDW6:12 pmChicago Midway
$225
Find similar
Frontier
Dec 20
MDW8:15 amChicago Midway
7h 15m
1 stop
CLE4:30 pmCleveland Hopkins Intl
Dec 21
CLE2:30 pmCleveland Hopkins Intl
9h 51m
1 stop
MDW11:21 pmChicago Midway
$238
Find similar
Frontier
Dec 19
MDW6:12 amChicago Midway
9h 18m
1 stop
CLE4:30 pmCleveland Hopkins Intl
Dec 25
CLE11:26 amCleveland Hopkins Intl
11h 46m
1 stop
MDW10:12 pmChicago Midway
$242
Find similar

Delta flights from Chicago Midway Airport to Cleveland

Our best Delta deals on Chicago Midway Airport to Cleveland flight tickets
Delta
Jan 10
MDW9:32 amChicago Midway
10h 09m
2 stops
CLE8:41 pmCleveland Hopkins Intl
Jan 11
CLE6:00 amCleveland Hopkins Intl
7h 48m
2 stops
MDW12:48 pmChicago Midway
$269
Find similar
Delta
Apr 3
MDW6:35 pmChicago Midway
4h 15m
1 stop
CLE11:50 pmCleveland Hopkins Intl
Apr 6
CLE8:00 amCleveland Hopkins Intl
5h 29m
1 stop
MDW12:29 pmChicago Midway
$277
Find similar
Delta
Apr 3
MDW6:35 pmChicago Midway
4h 15m
1 stop
CLE11:50 pmCleveland Hopkins Intl
Apr 6
CLE8:00 amCleveland Hopkins Intl
5h 29m
1 stop
MDW12:29 pmChicago Midway
$319
Find similar

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 December 5, 2025.
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

ChicagoCleveland

MDW - CLE

MDWCLE

Chicago Midway

Sat 1/10

9:55 am-12:10 pm

Nonstop1h 15m

Cleveland Hopkins Intl

Sun 1/11

6:35 am-7:10 am

Nonstop1h 35m

$233

ChicagoCleveland

MDW - CLE

MDWCLE

Chicago Midway

Fri 1/16

1:35 pm-3:45 pm

Nonstop1h 10m

Cleveland Hopkins Intl

Mon 1/19

5:55 pm-10:30 pm

1 stop5h 35m

$236

ChicagoCleveland

MDW - CLE

MDWCLE

Chicago Midway

Sat 12/20

8:15 am-4:30 pm

1 stop7h 15m

Cleveland Hopkins Intl

Sun 12/21

2:30 pm-11:21 pm

1 stop9h 51m

$238

ChicagoCleveland

MDW - CLE

MDWCLE

Chicago Midway

Fri 12/19

6:12 am-4:30 pm

1 stop9h 18m

Cleveland Hopkins Intl

Thu 12/25

11:26 am-10:12 pm

1 stop11h 46m

$242

ChicagoCleveland

MDW - CLE

MDWCLE

Chicago Midway

Wed 12/24

8:15 am-4:30 pm

1 stop7h 15m

Cleveland Hopkins Intl

Tue 12/30

9:30 pm-10:12 pm

2 stops25h 42m

$245

ChicagoCleveland

MDW - CLE

MDWCLE

Chicago Midway

Mon 12/29

4:20 pm-11:20 pm

1 stop6h 00m

Cleveland Hopkins Intl

Tue 1/6

6:15 am-6:55 am

Nonstop1h 40m

$252

ChicagoCleveland

MDW - CLE

MDWCLE

Chicago Midway

Thu 12/18

6:12 am-4:30 pm

1 stop9h 18m

Cleveland Hopkins Intl

Wed 12/31

11:43 am-9:58 pm

2 stops11h 15m

$255

ChicagoCleveland

MDW - CLE

MDWCLE

Chicago Midway

Thu 12/18

6:12 am-4:30 pm

1 stop9h 18m

Cleveland Hopkins Intl

Sun 12/21

2:30 pm-11:21 pm

1 stop9h 51m

$257

ChicagoCleveland

MDW - CLE

MDWCLE

Chicago Midway

Tue 12/30

6:14 am-4:30 pm

1 stop9h 16m

Cleveland Hopkins Intl

Thu 1/1

11:26 am-5:38 pm

1 stop7h 12m

$258

ChicagoCleveland

MDW - CLE

MDWCLE

Chicago Midway

Fri 12/19

8:15 am-4:30 pm

1 stop7h 15m

Cleveland Hopkins Intl

Mon 12/22

6:59 pm-9:58 pm

1 stop27h 59m

$265

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 cheapest month to fly to Cleveland?

In general, August 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 $197. If you’re not able to fly to Cleveland in August, then September is your next best option. Flight prices from Chicago Midway Airport to Cleveland during September average around $229.

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 Monday as prices are generally higher than usual. According to our data, the average ticket price to Cleveland on Monday is $393.

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 $296. In contrast, the most expensive time of day to depart to Cleveland is in the afternoon when prices are around $327.

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

$285

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 $285. The best round-trip flight deal from Chicago Midway Airport to Cleveland found on momondo in the last 72 hours is $281.
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 near Cleveland: 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 $157Free CancellationRating
8.0
4,250 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 $301, with the best Southwest deals starting from $157 round-trip. 4,250 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
Elyria
Mentor
Geneva-on-the-Lake
Independence
Westlake
Kent
Wooster
North Olmsted
Streetsboro
Willoughby
Ashland
Cuyahoga Falls
Lakewood
Painesville
Medina
Kelleys Island
Avon

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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