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Cheap flights from Chicago Midway Airport to Cleveland from $72

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 10/24. 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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Find the cheapest flights from Chicago Midway Airport to Cleveland

Cheap round-trip flights

Frontier Logo
5:15 pm - 12:43 amMDW-CLE
6h 28m1 stop
Frontier Logo
6:00 am - 12:44 pmCLE-MDW
7h 44m1 stop
$143Frontier
Find Deal
Fri, Sep 19 - Sun, Sep 21
Frontier Logo
8:19 am - 8:55 pmMDW-CLE
11h 36m1 stop
Frontier Logo
8:00 am - 3:11 pmCLE-MDW
8h 11m1 stop
$144Frontier
Find Deal
Mon, Oct 6 - Sat, Oct 11
Frontier Logo
4:56 pm - 12:43 amMDW-CLE
6h 47m1 stop
Frontier Logo
6:00 am - 12:44 pmCLE-MDW
7h 44m1 stop
$146Frontier
Find Deal
Thu, Sep 18 - Sun, Sep 21
Frontier Logo
5:15 pm - 12:43 amMDW-CLE
6h 28m1 stop
Frontier Logo
6:00 am - 12:44 pmCLE-MDW
7h 44m1 stop
$147Frontier
Find Deal
Fri, Sep 19 - Sun, Sep 21
Delta Logo
9:30 am - 1:32 pmMDW-CLE
3h 02m1 stop
Delta Logo
5:30 am - 8:35 amCLE-MDW
4h 05m1 stop
$217Delta
Find Deal
Thu, Sep 4 - Sat, Sep 6
Delta Logo
9:30 am - 1:32 pmMDW-CLE
3h 02m1 stop
Delta Logo
6:00 am - 12:28 pmCLE-MDW
7h 28m2 stops
$222Delta
Find Deal
Thu, Sep 4 - Sat, Sep 6
Southwest Logo
8:35 pm - 10:45 pmMDW-CLE
1h 10mnonstop
Southwest Logo
7:55 pm - 8:15 pmCLE-MDW
1h 20mnonstop
$227Southwest
Find Deal
Wed, Oct 15 - Mon, Oct 20
Southwest Logo
7:10 pm - 9:25 pmMDW-CLE
1h 15mnonstop
Southwest Logo
5:20 pm - 5:40 pmCLE-MDW
1h 20mnonstop
$234Southwest
Find Deal
Thu, Nov 13 - Sat, Nov 15
Logo
6:20 am - 6:24 pmMDW-CLE
11h 04m2 stops
Logo
5:30 am - 4:00 pmCLE-MDW
11h 30m1 stop
$236
Find Deal
Fri, Sep 12 - Mon, Sep 15
Logo
6:20 am - 6:24 pmMDW-CLE
11h 04m2 stops
Logo
7:34 pm - 3:58 pmCLE-MDW
21h 24m1 stop
$251
Find Deal
Mon, Sep 22 - Mon, Sep 29

Delta flights from Chicago Midway Airport to Cleveland

Our best Delta deals on Chicago Midway Airport to Cleveland flight tickets
Delta
Aug 30
MDW6:17 pmChicago Midway
3h 55m
1 stop
CLE11:12 pmCleveland Hopkins Intl
Aug 31
CLE8:30 amCleveland Hopkins Intl
4h 58m
1 stop
MDW12:28 pmChicago Midway
$217
Find similar
Delta
Aug 30
MDW6:17 pmChicago Midway
3h 55m
1 stop
CLE11:12 pmCleveland Hopkins Intl
Aug 31
CLE8:30 amCleveland Hopkins Intl
10h 07m
2 stops
MDW5:37 pmChicago Midway
$222
Find similar
Delta
Sep 16
MDW6:30 pmChicago Midway
5h 09m
1 stop
CLE12:39 amCleveland Hopkins Intl
Sep 20
CLE5:30 amCleveland Hopkins Intl
4h 10m
1 stop
MDW8:40 amChicago Midway
$244
Find similar

Frontier flights from Chicago Midway Airport to Cleveland

Our best Frontier deals on Chicago Midway Airport to Cleveland flight tickets
Frontier
Sep 8
MDW5:15 pmChicago Midway
6h 28m
1 stop
CLE12:43 amCleveland Hopkins Intl
Sep 12
CLE6:00 amCleveland Hopkins Intl
7h 44m
1 stop
MDW12:44 pmChicago Midway
$143
Find similar
Frontier
Oct 6
MDW8:19 amChicago Midway
11h 36m
1 stop
CLE8:55 pmCleveland Hopkins Intl
Oct 11
CLE8:00 amCleveland Hopkins Intl
8h 11m
1 stop
MDW3:11 pmChicago Midway
$144
Find similar
Frontier
Sep 18
MDW4:56 pmChicago Midway
6h 47m
1 stop
CLE12:43 amCleveland Hopkins Intl
Sep 21
CLE6:00 amCleveland Hopkins Intl
7h 44m
1 stop
MDW12:44 pmChicago Midway
$146
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 August 25, 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

Fri 9/19

5:15 pm-12:43 am

1 stop6h 28m

Cleveland Hopkins Intl

Sun 9/21

6:00 am-12:44 pm

1 stop7h 44m

$143

ChicagoCleveland

MDW - CLE

MDWCLE

Chicago Midway

Mon 10/6

8:19 am-8:55 pm

1 stop11h 36m

Cleveland Hopkins Intl

Sat 10/11

8:00 am-3:11 pm

1 stop8h 11m

$144

ChicagoCleveland

MDW - CLE

MDWCLE

Chicago Midway

Thu 9/18

4:56 pm-12:43 am

1 stop6h 47m

Cleveland Hopkins Intl

Sun 9/21

6:00 am-12:44 pm

1 stop7h 44m

$146

ChicagoCleveland

MDW - CLE

MDWCLE

Chicago Midway

Fri 9/19

5:15 pm-12:43 am

1 stop6h 28m

Cleveland Hopkins Intl

Sun 9/21

6:00 am-12:44 pm

1 stop7h 44m

$147

ChicagoCleveland

MDW - CLE

MDWCLE

Chicago Midway

Thu 9/4

9:30 am-1:32 pm

1 stop3h 02m

Cleveland Hopkins Intl

Sat 9/6

5:30 am-8:35 am

1 stop4h 05m

$217

ChicagoCleveland

MDW - CLE

MDWCLE

Chicago Midway

Thu 9/4

9:30 am-1:32 pm

1 stop3h 02m

Cleveland Hopkins Intl

Sat 9/6

6:00 am-12:28 pm

2 stops7h 28m

$222

ChicagoCleveland

MDW - CLE

MDWCLE

Chicago Midway

Wed 10/15

8:35 pm-10:45 pm

Nonstop1h 10m

Cleveland Hopkins Intl

Mon 10/20

7:55 pm-8:15 pm

Nonstop1h 20m

$227

ChicagoCleveland

MDW - CLE

MDWCLE

Chicago Midway

Thu 11/13

7:10 pm-9:25 pm

Nonstop1h 15m

Cleveland Hopkins Intl

Sat 11/15

5:20 pm-5:40 pm

Nonstop1h 20m

$234

ChicagoCleveland

MDW - CLE

MDWCLE

Chicago Midway

Fri 9/12

6:20 am-6:24 pm

2 stops11h 04m

Cleveland Hopkins Intl

Mon 9/15

5:30 am-4:00 pm

1 stop11h 30m

$236

ChicagoCleveland

MDW - CLE

MDWCLE

Chicago Midway

Mon 9/22

6:20 am-6:24 pm

2 stops11h 04m

Cleveland Hopkins Intl

Mon 9/29

7:34 pm-3:58 pm

1 stop21h 24m

$251

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, September 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 $229. If you’re not able to fly to Cleveland in September, then June is your next best option. Flight prices from Chicago Midway Airport to Cleveland during June average around $237.

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 $255. 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 $430.

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 $294. In contrast, the most expensive time of day to depart to Cleveland is in the afternoon when prices are around $356.

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 are 1 cabin classes 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.

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

$77

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 $77. The best round-trip flight deal from Chicago Midway Airport to Cleveland found on momondo in the last 72 hours is $151.
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 $158Free CancellationRating
8.0
4,243 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 $307, with the best Southwest deals starting from $158 round-trip. 4,243 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
Beachwood
Mansfield
Geneva-on-the-Lake
Elyria
Mentor
Independence
Westlake
Wooster
Kent
Streetsboro
Willoughby
North Olmsted
Ashland
Cuyahoga Falls
Kelleys Island
Medina
Avon
Painesville
Lakewood

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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