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Cheap flights from Chicago Midway Airport to Cleveland from $71

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 11/3. 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
2:25 pm - 8:25 pmMDW  Chicago Midway-CLE Cleveland Hopkins Intl
5h 00m1 stop Nashville Intl
Southwest Logo
7:00 pm - 7:15 pmCLE  Cleveland Hopkins Intl-MDW Chicago Midway
1h 15mnonstop
$127Southwest
Sat, Sep 5 - Sun, Sep 6
Southwest Logo
11:15 am - 4:45 pmMDW  Chicago Midway-CLE Cleveland Hopkins Intl
4h 30m1 stop Nashville Intl
Southwest Logo
7:00 pm - 7:15 pmCLE  Cleveland Hopkins Intl-MDW Chicago Midway
1h 15mnonstop
$127Southwest
Sat, Sep 5 - Sun, Sep 6
Southwest Logo
2:25 pm - 8:25 pmMDW  Chicago Midway-CLE Cleveland Hopkins Intl
5h 00m1 stop Nashville Intl
Southwest Logo
12:35 pm - 12:50 pmCLE  Cleveland Hopkins Intl-MDW Chicago Midway
1h 15mnonstop
$127Southwest
Sat, Sep 5 - Sun, Sep 6
Frontier Logo
11:50 am - 10:31 pmMDW  Chicago Midway-CLE Cleveland Hopkins Intl
9h 41m1 stop Atlanta Hartsfield-Jackson
Frontier Logo
3:45 pm - 11:44 pmCLE  Cleveland Hopkins Intl-MDW Chicago Midway
8h 59m1 stop Atlanta Hartsfield-Jackson
$142Frontier
Thu, Sep 3 - Thu, Sep 10
Frontier Logo
11:45 am - 10:31 pmMDW  Chicago Midway-CLE Cleveland Hopkins Intl
9h 46m1 stop Atlanta Hartsfield-Jackson
Frontier Logo
9:00 am - 8:31 pmCLE  Cleveland Hopkins Intl-MDW Chicago Midway
12h 31m1 stop Dallas/Fort Worth
$142Frontier
Sat, Aug 29 - Mon, Aug 31
Frontier Logo
12:03 pm - 8:37 pmMDW  Chicago Midway-CLE Cleveland Hopkins Intl
7h 34m1 stop Atlanta Hartsfield-Jackson
Frontier Logo
3:40 pm - 9:58 pmCLE  Cleveland Hopkins Intl-MDW Chicago Midway
7h 18m1 stop Atlanta Hartsfield-Jackson
$142Frontier
Tue, Oct 13 - Thu, Oct 15
Frontier Logo
11:50 am - 10:31 pmMDW  Chicago Midway-CLE Cleveland Hopkins Intl
9h 41m1 stop Atlanta Hartsfield-Jackson
Frontier Logo
5:15 pm - 10:47 pmCLE  Cleveland Hopkins Intl-MDW Chicago Midway
6h 32m1 stop Atlanta Hartsfield-Jackson
$142Frontier
Mon, Aug 24 - Wed, Aug 26
Frontier Logo
11:50 am - 10:31 pmMDW  Chicago Midway-CLE Cleveland Hopkins Intl
9h 41m1 stop Atlanta Hartsfield-Jackson
Frontier Logo
7:00 am - 5:51 pmCLE  Cleveland Hopkins Intl-MDW Chicago Midway
11h 51m1 stop Atlanta Hartsfield-Jackson
$142Frontier
Tue, Sep 8 - Sat, Sep 12
Frontier Logo
12:03 pm - 8:37 pmMDW  Chicago Midway-CLE Cleveland Hopkins Intl
7h 34m1 stop Atlanta Hartsfield-Jackson
Frontier Logo
3:40 pm - 9:58 pmCLE  Cleveland Hopkins Intl-MDW Chicago Midway
7h 18m1 stop Atlanta Hartsfield-Jackson
$142Frontier
Sat, Oct 10 - Tue, Oct 13
Frontier Logo
1:02 pm - 12:40 amMDW  Chicago Midway-CLE Cleveland Hopkins Intl
10h 38m1 stop Dallas/Fort Worth
Frontier Logo
6:15 am - 10:58 amCLE  Cleveland Hopkins Intl-MDW Chicago Midway
5h 43m1 stop Atlanta Hartsfield-Jackson
$142Frontier
Sat, Oct 10 - Mon, Oct 12

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Frontier flights from Chicago Midway Airport to Cleveland

Our best Frontier deals on Chicago Midway Airport to Cleveland flight tickets
Frontier
Oct 10
MDW1:02 pmChicago Midway
10h 38m
1 stop
CLE12:40 amCleveland Hopkins Intl
Oct 12
CLE3:40 pmCleveland Hopkins Intl
7h 18m
1 stop
MDW9:58 pmChicago Midway
$142
Frontier
Aug 27
MDW11:50 amChicago Midway
9h 41m
1 stop
CLE10:31 pmCleveland Hopkins Intl
Aug 31
CLE9:00 amCleveland Hopkins Intl
12h 31m
1 stop
MDW8:31 pmChicago Midway
$143
Frontier
Oct 29
MDW7:25 amChicago Midway
5h 04m
1 stop
CLE1:29 pmCleveland Hopkins Intl
Nov 2
CLE3:40 pmCleveland Hopkins Intl
7h 13m
1 stop
MDW9:53 pmChicago Midway
$162

Delta flights from Chicago Midway Airport to Cleveland

Our best Delta deals on Chicago Midway Airport to Cleveland flight tickets
Delta
Sep 5
MDW4:52 pmChicago Midway
4h 51m
1 stop
CLE10:43 pmCleveland Hopkins Intl
Sep 6
CLE10:52 amCleveland Hopkins Intl
6h 05m
1 stop
MDW3:57 pmChicago Midway
$157
Delta
Sep 5
MDW4:52 pmChicago Midway
4h 51m
1 stop
CLE10:43 pmCleveland Hopkins Intl
Sep 6
CLE10:52 amCleveland Hopkins Intl
6h 05m
1 stop
MDW3:57 pmChicago Midway
$158
Delta
Sep 5
MDW9:24 amChicago Midway
3h 16m
1 stop
CLE1:40 pmCleveland Hopkins Intl
Sep 7
CLE8:18 amCleveland Hopkins Intl
5h 21m
1 stop
MDW12:39 pmChicago Midway
$164

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 6, 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 Chicago Midway - CLE Cleveland Hopkins Intl

MDWCLE

Chicago Midway

Sat 9/5

2:25 pm-8:25 pm

1 stop5h 00m

Cleveland Hopkins Intl

Sun 9/6

7:00 pm-7:15 pm

Nonstop1h 15m

$127
Quickest round-trip

ChicagoCleveland

MDW Chicago Midway - CLE Cleveland Hopkins Intl

MDWCLE

Chicago Midway

Sat 9/5

11:15 am-4:45 pm

1 stop4h 30m

Cleveland Hopkins Intl

Sun 9/6

7:00 pm-7:15 pm

Nonstop1h 15m

$127

ChicagoCleveland

MDW Chicago Midway - CLE Cleveland Hopkins Intl

MDWCLE

Chicago Midway

Sat 9/5

2:25 pm-8:25 pm

1 stop5h 00m

Cleveland Hopkins Intl

Sun 9/6

12:35 pm-12:50 pm

Nonstop1h 15m

$127

ChicagoCleveland

MDW Chicago Midway - CLE Cleveland Hopkins Intl

MDWCLE

Chicago Midway

Thu 9/3

11:50 am-10:31 pm

1 stop9h 41m

Cleveland Hopkins Intl

Thu 9/10

3:45 pm-11:44 pm

1 stop8h 59m

$142

ChicagoCleveland

MDW Chicago Midway - CLE Cleveland Hopkins Intl

MDWCLE

Chicago Midway

Sat 8/29

11:45 am-10:31 pm

1 stop9h 46m

Cleveland Hopkins Intl

Mon 8/31

9:00 am-8:31 pm

1 stop12h 31m

$142

ChicagoCleveland

MDW Chicago Midway - CLE Cleveland Hopkins Intl

MDWCLE

Chicago Midway

Tue 10/13

12:03 pm-8:37 pm

1 stop7h 34m

Cleveland Hopkins Intl

Thu 10/15

3:40 pm-9:58 pm

1 stop7h 18m

$142

ChicagoCleveland

MDW Chicago Midway - CLE Cleveland Hopkins Intl

MDWCLE

Chicago Midway

Mon 8/24

11:50 am-10:31 pm

1 stop9h 41m

Cleveland Hopkins Intl

Wed 8/26

5:15 pm-10:47 pm

1 stop6h 32m

$142

ChicagoCleveland

MDW Chicago Midway - CLE Cleveland Hopkins Intl

MDWCLE

Chicago Midway

Tue 9/8

11:50 am-10:31 pm

1 stop9h 41m

Cleveland Hopkins Intl

Sat 9/12

7:00 am-5:51 pm

1 stop11h 51m

$142

ChicagoCleveland

MDW Chicago Midway - CLE Cleveland Hopkins Intl

MDWCLE

Chicago Midway

Sat 10/10

12:03 pm-8:37 pm

1 stop7h 34m

Cleveland Hopkins Intl

Tue 10/13

3:40 pm-9:58 pm

1 stop7h 18m

$142

ChicagoCleveland

MDW Chicago Midway - CLE Cleveland Hopkins Intl

MDWCLE

Chicago Midway

Sat 10/10

1:02 pm-12:40 am

1 stop10h 38m

Cleveland Hopkins Intl

Mon 10/12

6:15 am-10:58 am

1 stop5h 43m

$142

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, 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 May is your next best option. Flight prices from Chicago Midway Airport to Cleveland during May average around $234.

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 $274. 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 $543.

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 evening when prices are around $484.

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?

You could potentially save up to 32% on your flight if you consider stops on a Chicago Midway Airport to Cleveland flight.

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

$232

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 $232. The best round-trip flight deal from Chicago Midway Airport to Cleveland found on momondo in the last 72 hours is $265.
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
8.0
4,218 reviews
Search Southwest flights

  • Southwest Flights From Chicago Midway Airport to Cleveland

    Across 8 Southwest flights from Chicago Midway Airport to Cleveland this week, the average price was $509, with the best Southwest deals starting from $137 round-trip. 4,218 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
Westlake
Independence
Mentor
Elyria
Kent
Willoughby
Painesville
Geneva-on-the-Lake
Medina
Wooster
Streetsboro
Macedonia
Lakewood
North Olmsted
Ashland
Avon
Cuyahoga Falls

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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