Latest deals
Insights
When to book
FAQs
Reviews
Price Alerts

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 8/1. 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

Enter your travel dates to find the best prices.
Southwest Logo
8:05 am - 10:25 am
MDW
-
CLE
1h 20mnonstop
Southwest Logo
4:35 pm - 4:55 pm
CLE
-
MDW
1h 20mnonstop
$191Southwest
Thu, Sep 3 - Sat, Sep 5
Southwest Logo
3:45 pm - 5:55 pm
MDW
-
CLE
1h 10mnonstop
Southwest Logo
4:45 pm - 5:05 pm
CLE
-
MDW
1h 20mnonstop
$197Southwest
Tue, Jun 9 - Mon, Jun 15
Frontier Logo
6:00 am - 12:32 pm
MDW
-
CLE
5h 32m
1 stop
Frontier Logo
3:36 pm - 10:02 pm
CLE
-
MDW
7h 26m
1 stop
$200Frontier
Tue, May 26 - Wed, May 27
Southwest Logo
12:50 pm - 3:05 pm
MDW
-
CLE
1h 15mnonstop
Southwest Logo
5:00 pm - 10:20 pm
CLE
-
MDW
6h 20m
1 stop
$201Southwest
Thu, May 28 - Mon, Jun 1
Frontier Logo
12:04 pm - 12:44 am
MDW
-
CLE
11h 40m
2 stops
Frontier Logo
3:46 pm - 10:11 pm
CLE
-
MDW
7h 25m
1 stop
$202Frontier
Wed, Aug 26 - Sat, Aug 29
Frontier Logo
12:04 pm - 6:27 pm
MDW
-
CLE
5h 23m
1 stop
Frontier Logo
3:46 pm - 10:02 pm
CLE
-
MDW
7h 16m
1 stop
$204Frontier
Wed, Jun 3 - Sat, Jun 6
Frontier Logo
6:00 am - 6:29 pm
MDW
-
CLE
11h 29m
1 stop
Frontier Logo
7:24 pm - 11:12 am
CLE
-
MDW
16h 48m
1 stop
$205Frontier
Fri, Jun 12 - Mon, Jun 15
Southwest Logo
7:55 am - 10:10 am
MDW
-
CLE
1h 15mnonstop
Southwest Logo
12:40 pm - 8:05 pm
CLE
-
MDW
8h 25m
2 stops
$206Southwest
Mon, Jun 1 - Mon, Jun 1
Southwest Logo
3:45 pm - 5:55 pm
MDW
-
CLE
1h 10mnonstop
Southwest Logo
8:10 pm - 8:25 pm
CLE
-
MDW
1h 15mnonstop
$207Southwest
Wed, Jul 8 - Mon, Jul 13
Frontier Logo
12:27 pm - 8:55 pm
MDW
-
CLE
7h 28m
1 stop
Frontier Logo
3:46 pm - 10:11 pm
CLE
-
MDW
7h 25m
1 stop
$208Frontier
Thu, Jul 2 - Sat, Jul 4

Delta flights from Chicago Midway Airport to Cleveland

Our best Delta deals on Chicago Midway Airport to Cleveland flight tickets
Delta
Sep 5
MDW9:30 amChicago Midway
3h 04m
1 stop
CLE1:34 pmCleveland Hopkins Intl
Sep 24
CLE4:00 pmCleveland Hopkins Intl
3h 31m
1 stop
MDW6:31 pmChicago Midway
$211
Delta
Aug 27
MDW1:27 pmChicago Midway
4h 09m
1 stop
CLE6:36 pmCleveland Hopkins Intl
Aug 31
CLE8:29 amCleveland Hopkins Intl
5h 01m
1 stop
MDW12:30 pmChicago Midway
$221
Delta
May 30
MDW5:10 pmChicago Midway
6h 29m
1 stop
CLE12:39 amCleveland Hopkins Intl
Jun 1
CLE10:51 amCleveland Hopkins Intl
2h 51m
1 stop
MDW12:42 pmChicago Midway
$222

Frontier flights from Chicago Midway Airport to Cleveland

Our best Frontier deals on Chicago Midway Airport to Cleveland flight tickets
Frontier
May 26
MDW6:00 amChicago Midway
5h 32m
1 stop
CLE12:32 pmCleveland Hopkins Intl
May 27
CLE3:36 pmCleveland Hopkins Intl
7h 26m
1 stop
MDW10:02 pmChicago Midway
$200
Frontier
Aug 26
MDW12:04 pmChicago Midway
11h 40m
2 stops
CLE12:44 amCleveland Hopkins Intl
Aug 29
CLE3:46 pmCleveland Hopkins Intl
7h 25m
1 stop
MDW10:11 pmChicago Midway
$202
Frontier
Jun 12
MDW6:00 amChicago Midway
11h 29m
1 stop
CLE6:29 pmCleveland Hopkins Intl
Jun 15
CLE7:24 pmCleveland Hopkins Intl
16h 48m
1 stop
MDW11:12 amChicago Midway
$205

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 May 9, 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

Thu 9/3

8:05 am-10:25 am

Nonstop1h 20m

Cleveland Hopkins Intl

Sat 9/5

4:35 pm-4:55 pm

Nonstop1h 20m

$191

ChicagoCleveland

MDW - CLE

MDWCLE

Chicago Midway

Tue 6/9

3:45 pm-5:55 pm

Nonstop1h 10m

Cleveland Hopkins Intl

Mon 6/15

4:45 pm-5:05 pm

Nonstop1h 20m

$197

ChicagoCleveland

MDW - CLE

MDWCLE

Chicago Midway

Tue 5/26

6:00 am-12:32 pm

1 stop5h 32m

Cleveland Hopkins Intl

Wed 5/27

3:36 pm-10:02 pm

1 stop7h 26m

$200

ChicagoCleveland

MDW - CLE

MDWCLE

Chicago Midway

Thu 5/28

12:50 pm-3:05 pm

Nonstop1h 15m

Cleveland Hopkins Intl

Mon 6/1

5:00 pm-10:20 pm

1 stop6h 20m

$201

ChicagoCleveland

MDW - CLE

MDWCLE

Chicago Midway

Wed 8/26

12:04 pm-12:44 am

2 stops11h 40m

Cleveland Hopkins Intl

Sat 8/29

3:46 pm-10:11 pm

1 stop7h 25m

$202

ChicagoCleveland

MDW - CLE

MDWCLE

Chicago Midway

Wed 6/3

12:04 pm-6:27 pm

1 stop5h 23m

Cleveland Hopkins Intl

Sat 6/6

3:46 pm-10:02 pm

1 stop7h 16m

$204

ChicagoCleveland

MDW - CLE

MDWCLE

Chicago Midway

Fri 6/12

6:00 am-6:29 pm

1 stop11h 29m

Cleveland Hopkins Intl

Mon 6/15

7:24 pm-11:12 am

1 stop16h 48m

$205

ChicagoCleveland

MDW - CLE

MDWCLE

Chicago Midway

Mon 6/1

7:55 am-10:10 am

Nonstop1h 15m

Cleveland Hopkins Intl

Mon 6/1

12:40 pm-8:05 pm

2 stops8h 25m

$206
Quickest round-trip

ChicagoCleveland

MDW - CLE

MDWCLE

Chicago Midway

Wed 7/8

3:45 pm-5:55 pm

Nonstop1h 10m

Cleveland Hopkins Intl

Mon 7/13

8:10 pm-8:25 pm

Nonstop1h 15m

$207

ChicagoCleveland

MDW - CLE

MDWCLE

Chicago Midway

Thu 7/2

12:27 pm-8:55 pm

1 stop7h 28m

Cleveland Hopkins Intl

Sat 7/4

3:46 pm-10:11 pm

1 stop7h 25m

$208

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 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 $262. 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 $484.

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 $309. In contrast, the most expensive time of day to depart to Cleveland is in the evening when prices are around $362.

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

$68

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 $68. The best round-trip flight deal from Chicago Midway Airport to Cleveland found on momondo in the last 72 hours is $234.
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
4,302 reviews
Search Southwest flights

  • Southwest Flights From Chicago Midway Airport to Cleveland

    Across 11 Southwest flights from Chicago Midway Airport to Cleveland this week, the average price was $457, with the best Southwest deals starting from $97 round-trip. 4,302 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
Mentor
Westlake
Geneva-on-the-Lake
Kent
Willoughby
Painesville
Cuyahoga Falls
Streetsboro
Lakewood
North Olmsted
Wooster
Ashland
Kelleys Island
Strongsville
Medina

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
Mon 6/8
Mon 6/15
By creating a price alert you accept our terms of use and privacy policy.

Find better results for your trip to the United States