Latest deals
Insights
When to book
FAQs
Reviews
Price Alerts

Cheap flights from Chicago Midway Airport to Cleveland from $70

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 10/21. 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

Save money when you book flights with momondo

Big names and deals

Big names and deals

Search 100s of travel sites to compare prices.

Filter for what you want

Filter for what you want

Free Wi-Fi? Stopover? Instantly customize your results.

Trusted and free

Trusted and free

We’re completely free to use - no hidden charges or fees.

Price Alerts

Price Alerts

Not ready to book? to track prices.
Search flight deals

Find the cheapest flights from Chicago Midway Airport to Cleveland

Cheap round-trip flights

Frontier Logo
4:56 pm - 12:43 amMDW-CLE
6h 47m1 stop
Frontier Logo
7:19 pm - 11:41 pmCLE-MDW
5h 22m1 stop
$143Frontier
Find Deal
Thu, Oct 2 - Sat, Oct 4
Frontier Logo
11:49 am - 12:44 amMDW-CLE
11h 55m1 stop
Frontier Logo
7:39 pm - 11:46 pmCLE-MDW
5h 07m1 stop
$144Frontier
Find Deal
Thu, Oct 16 - Sun, Oct 19
Frontier Logo
6:20 am - 12:22 pmMDW-CLE
5h 02m1 stop
Frontier Logo
6:48 pm - 12:30 amCLE-MDW
6h 42m1 stop
$145Frontier
Find Deal
Fri, Oct 31 - Mon, Nov 3
Frontier Logo
6:20 am - 12:22 pmMDW-CLE
5h 02m1 stop
Frontier Logo
6:48 pm - 12:30 amCLE-MDW
6h 42m1 stop
$146Frontier
Find Deal
Fri, Oct 31 - Mon, Nov 3
Frontier Logo
5:15 pm - 12:43 amMDW-CLE
6h 28m1 stop
Frontier Logo
6:00 am - 12:44 pmCLE-MDW
7h 44m1 stop
$151Frontier
Find Deal
Fri, Oct 3 - Sun, Oct 5
Multiple Airlines Logo
8:05 am - 6:51 pmMDW-CLE
33h 46m2 stops
Multiple Airlines Logo
7:44 pm - 11:38 amCLE-MDW
16h 54m1 stop
$182Multiple Airlines
Find Deal
Wed, Oct 22 - Mon, Oct 27
Southwest Logo
3:25 pm - 5:35 pmMDW-CLE
1h 10mnonstop
Southwest Logo
4:35 pm - 4:50 pmCLE-MDW
1h 15mnonstop
$231Southwest
Find Deal
Sat, Oct 11 - Sat, Oct 18
Southwest Logo
7:15 pm - 9:30 pmMDW-CLE
1h 15mnonstop
Southwest Logo
4:35 pm - 4:55 pmCLE-MDW
1h 20mnonstop
$235Southwest
Find Deal
Fri, Oct 31 - Mon, Nov 3
Delta Logo
10:35 am - 5:18 pmMDW-CLE
5h 43m1 stop
Delta Logo
4:59 pm - 10:14 pmCLE-MDW
6h 15m1 stop
$251Delta
Find Deal
Sat, Oct 11 - Sat, Oct 18
Delta Logo
1:06 pm - 12:36 amMDW-CLE
10h 30m2 stops
Delta Logo
8:20 am - 12:31 pmCLE-MDW
5h 11m1 stop
$256Delta
Find Deal
Sat, Oct 11 - Sat, Oct 18

Frontier flights from Chicago Midway Airport to Cleveland

Our best Frontier deals on Chicago Midway Airport to Cleveland flight tickets
Frontier
Oct 2
MDW4:56 pmChicago Midway
6h 47m
1 stop
CLE12:43 amCleveland Hopkins Intl
Oct 4
CLE7:19 pmCleveland Hopkins Intl
5h 22m
1 stop
MDW11:41 pmChicago Midway
$143
Find similar
Frontier
Oct 16
MDW11:49 amChicago Midway
11h 55m
1 stop
CLE12:44 amCleveland Hopkins Intl
Oct 19
CLE7:39 pmCleveland Hopkins Intl
5h 07m
1 stop
MDW11:46 pmChicago Midway
$144
Find similar
Frontier
Oct 31
MDW6:20 amChicago Midway
5h 02m
1 stop
CLE12:22 pmCleveland Hopkins Intl
Nov 3
CLE6:48 pmCleveland Hopkins Intl
6h 42m
1 stop
MDW12:30 amChicago Midway
$145
Find similar

Southwest flights from Chicago Midway Airport to Cleveland

Our best Southwest deals on Chicago Midway Airport to Cleveland flight tickets
Southwest
Oct 11
MDW3:25 pmChicago Midway
1h 10m
CLE5:35 pmCleveland Hopkins Intl
Oct 18
CLE4:35 pmCleveland Hopkins Intl
1h 15m
MDW4:50 pmChicago Midway
$231
Find similar
Southwest
Oct 31
MDW7:15 pmChicago Midway
1h 15m
CLE9:30 pmCleveland Hopkins Intl
Nov 3
CLE4:35 pmCleveland Hopkins Intl
1h 20m
MDW4:55 pmChicago Midway
$235
Find similar
Southwest
Oct 11
MDW3:25 pmChicago Midway
1h 10m
CLE5:35 pmCleveland Hopkins Intl
Oct 18
CLE5:50 pmCleveland Hopkins Intl
4h 00m
1 stop
MDW8:50 pmChicago Midway
$241
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 September 17, 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

Thu 10/2

4:56 pm-12:43 am

1 stop6h 47m

Cleveland Hopkins Intl

Sat 10/4

7:19 pm-11:41 pm

1 stop5h 22m

$143

ChicagoCleveland

MDW - CLE

MDWCLE

Chicago Midway

Thu 10/16

11:49 am-12:44 am

1 stop11h 55m

Cleveland Hopkins Intl

Sun 10/19

7:39 pm-11:46 pm

1 stop5h 07m

$144

ChicagoCleveland

MDW - CLE

MDWCLE

Chicago Midway

Fri 10/31

6:20 am-12:22 pm

1 stop5h 02m

Cleveland Hopkins Intl

Mon 11/3

6:48 pm-12:30 am

1 stop6h 42m

$145

ChicagoCleveland

MDW - CLE

MDWCLE

Chicago Midway

Fri 10/31

6:20 am-12:22 pm

1 stop5h 02m

Cleveland Hopkins Intl

Mon 11/3

6:48 pm-12:30 am

1 stop6h 42m

$146

ChicagoCleveland

MDW - CLE

MDWCLE

Chicago Midway

Fri 10/3

5:15 pm-12:43 am

1 stop6h 28m

Cleveland Hopkins Intl

Sun 10/5

6:00 am-12:44 pm

1 stop7h 44m

$151

ChicagoCleveland

MDW - CLE

MDWCLE

Chicago Midway

Wed 10/22

8:05 am-6:51 pm

2 stops33h 46m

Cleveland Hopkins Intl

Mon 10/27

7:44 pm-11:38 am

1 stop16h 54m

$182

ChicagoCleveland

MDW - CLE

MDWCLE

Chicago Midway

Sat 10/11

3:25 pm-5:35 pm

Nonstop1h 10m

Cleveland Hopkins Intl

Sat 10/18

4:35 pm-4:50 pm

Nonstop1h 15m

$231

ChicagoCleveland

MDW - CLE

MDWCLE

Chicago Midway

Fri 10/31

7:15 pm-9:30 pm

Nonstop1h 15m

Cleveland Hopkins Intl

Mon 11/3

4:35 pm-4:55 pm

Nonstop1h 20m

$235

ChicagoCleveland

MDW - CLE

MDWCLE

Chicago Midway

Sat 10/11

10:35 am-5:18 pm

1 stop5h 43m

Cleveland Hopkins Intl

Sat 10/18

4:59 pm-10:14 pm

1 stop6h 15m

$251

ChicagoCleveland

MDW - CLE

MDWCLE

Chicago Midway

Sat 10/11

1:06 pm-12:36 am

2 stops10h 30m

Cleveland Hopkins Intl

Sat 10/18

8:20 am-12:31 pm

1 stop5h 11m

$256

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
1
2

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 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 $261. 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 $437.

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 $297. 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.

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

$108

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 $108. The best round-trip flight deal from Chicago Midway Airport to Cleveland found on momondo in the last 72 hours is $278.
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
4,242 reviews
Search Southwest flights

  • Southwest Flights From Chicago Midway Airport to Cleveland

    Across 20 Southwest flights from Chicago Midway Airport to Cleveland this week, the average price was $300, with the best Southwest deals starting from $158 round-trip. 4,242 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
Elyria
Geneva-on-the-Lake
Mentor
Independence
Wooster
Westlake
Streetsboro
Kent
North Olmsted
Willoughby
Ashland
Cuyahoga Falls
Medina
Painesville
Avon
Kelleys Island
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.

An easier way to manage your Cleveland trip

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.
Start using Trips
Find my bookings

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.
1 adult
Fri 10/17
Fri 10/24
By creating a price alert you accept our terms of use and privacy policy.

Find better results for your trip to the United States