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$73+ Cheap flights from Midway (MDW) to Cleveland (CLE)

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 9/15. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — CLE
Aug 19 — Aug 261
Tue 8/19
Tue 8/26
1 adult, Economy
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Cheap flight deals from Midway to Cleveland

Discover tips and strategies to find the most affordable flight options for your journey from Midway (MDW) to Cleveland (CLE). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated August 14, 2025.

Round-trip from

$149
(Priceline)

One-way from

$73
(Priceline)

Popular in

July

Cheapest in

June

Average price

$489

Good round-trip deal

$151 or less

Good one-way deal

$75 or less
From Chicago Midway to Cleveland Hopkins Intl
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One-way flight from Chicago Midway to Cleveland Hopkins Intl
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Highest demand for flights based on searches. 19% potential increase in price ($91 potential increase over avg. RT price).
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Cheapest flight prices on average. 7% potential price decrease ($27 potential savings vs. average RT price).
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Average for round-trip flights in August 2025
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Price to beat on a round-trip flight from Chicago Midway to Cleveland Hopkins Intl.
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Price to beat on a one-way flight from Chicago Midway to Cleveland Hopkins Intl.
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Find flight deals from Midway to Cleveland

Cheapest flights from Midway to Cleveland
Explore the most affordable flight options available from Midway to Cleveland. Find the lowest fares from popular airlines and budget airlines, with prices last updated on August 14, 2025.

This Priceline deal was found by Cheapflights users on 8/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/195:15 pmMDW - CLE
1 stop6h 28mFrontier
Sun 9/216:00 amCLE - MDW
1 stop7h 44mFrontier
Deal found 8/14$149
This Frontier deal was found by Cheapflights users on 8/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/38:15 amMDW - CLE
1 stop10h 20mFrontier
Sat 10/47:19 pmCLE - MDW
1 stop4h 58mFrontier
Deal found 8/14$153
This Frontier deal was found by Cheapflights users on 8/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/44:56 pmMDW - CLE
1 stop6h 47mFrontier
Mon 9/86:00 amCLE - MDW
1 stop7h 44mFrontier
Deal found 8/14$159
This FlightHub deal was found by Cheapflights users on 8/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/198:15 amMDW - CLE
1 stop10h 20mFrontier
Mon 9/225:30 amCLE - MDW
1 stop18h 50mFrontier
Deal found 8/14$160
This FlightHub deal was found by Cheapflights users on 8/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/106:20 amMDW - CLE
1 stop17h 27mFrontier
Mon 10/136:00 amCLE - MDW
1 stop10h 24mFrontier
Deal found 8/14$165
This Southwest deal was found by Cheapflights users on 8/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/84:35 pmMDW - CLE
Nonstop1h 15mSouthwest
Wed 9/107:05 amCLE - MDW
Nonstop1h 15mSouthwest
Deal found 8/13$166
This Frontier deal was found by Cheapflights users on 8/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/278:00 amMDW - CLE
1 stop6h 02mFrontier
Thu 8/286:00 amCLE - MDW
1 stop8h 10mFrontier
Deal found 8/14$168
This FlightHub deal was found by Cheapflights users on 8/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/226:15 amMDW - CLE
1 stop17h 43mFrontier
Thu 8/286:00 amCLE - MDW
1 stop8h 10mFrontier
Deal found 8/14$176
This Southwest deal was found by Cheapflights users on 8/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/41:00 pmMDW - CLE
Nonstop1h 15mSouthwest
Mon 9/87:35 pmCLE - MDW
Nonstop1h 15mSouthwest
Deal found 8/14$177

Cheapflights Fare Finder

 
Customize your flight search to find flights from Midway 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, Cheapflights users made 2,558,603 searches. Data last updated August 14, 2025.
Use the filters below to find and compare flights from Chicago Midway Airport to Cleveland that are best for you.

Fly from

Midway

Fly to

Cleveland

Route

Depart

Return

Price

ChicagoCleveland

MDW - CLE

MDWCLE

Chicago Midway

Fri 9/12

5:15 pm-12:43 am

1 stop6h 28m

Cleveland Hopkins Intl

Sun 9/14

6:00 am-12:44 pm

1 stop7h 44m

$149

ChicagoCleveland

MDW - CLE

MDWCLE

Chicago Midway

Fri 9/26

5:15 pm-12:43 am

1 stop6h 28m

Cleveland Hopkins Intl

Mon 9/29

6:00 am-12:44 pm

1 stop7h 44m

$149

ChicagoCleveland

MDW - CLE

MDWCLE

Chicago Midway

Fri 10/3

8:15 am-7:35 pm

1 stop10h 20m

Cleveland Hopkins Intl

Sat 10/4

7:19 pm-11:17 pm

1 stop4h 58m

$153

ChicagoCleveland

MDW - CLE

MDWCLE

Chicago Midway

Tue 9/9

3:30 pm-5:45 pm

Nonstop1h 15m

Cleveland Hopkins Intl

Tue 9/16

1:35 pm-1:50 pm

Nonstop1h 15m

$155

ChicagoCleveland

MDW - CLE

MDWCLE

Chicago Midway

Thu 9/4

4:56 pm-12:43 am

1 stop6h 47m

Cleveland Hopkins Intl

Mon 9/8

6:00 am-12:44 pm

1 stop7h 44m

$159

ChicagoCleveland

MDW - CLE

MDWCLE

Chicago Midway

Wed 10/22

8:05 am-2:55 pm

1 stop5h 50m

Cleveland Hopkins Intl

Sun 10/26

6:33 pm-12:36 am

1 stop7h 03m

$160

ChicagoCleveland

MDW - CLE

MDWCLE

Chicago Midway

Fri 9/19

8:15 am-7:35 pm

1 stop10h 20m

Cleveland Hopkins Intl

Mon 9/22

5:30 am-11:20 pm

1 stop18h 50m

$160

ChicagoCleveland

MDW - CLE

MDWCLE

Chicago Midway

Fri 10/10

9:44 am-12:47 am

1 stop14h 03m

Cleveland Hopkins Intl

Sun 10/12

5:30 am-11:44 am

1 stop7h 14m

$165

ChicagoCleveland

MDW - CLE

MDWCLE

Chicago Midway

Sat 9/6

6:15 am-6:24 pm

1 stop11h 09m

Cleveland Hopkins Intl

Mon 9/8

6:00 am-12:44 pm

1 stop7h 44m

$165

ChicagoCleveland

MDW - CLE

MDWCLE

Chicago Midway

Tue 9/9

12:50 pm-3:05 pm

Nonstop1h 15m

Cleveland Hopkins Intl

Thu 9/11

3:30 pm-3:50 pm

Nonstop1h 20m

$166

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/14

Showing 1-10 of 23 results
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The best insider tips for Chicago Midway Airport to Cleveland flights

Snippets provided in this section are AI-generated based on a summarization of Cheapflights-commissioned articles. The articles are presented as-is, for general informational purposes only, and may not be up-to-date. The opinions contained in the articles are original to the author and reflect their authentic experience, which may vary significantly from the experience of others.
Cheapflights partnered with top experts to bring you the best recommendations for your Chicago Midway Airport to Cleveland trip
Airports
MDW

Order food via the airport’s mobile system directly to your gate to save time and avoid missing boarding for Southwest flights.

Read more about MDWby Ramsey Qubein
CLE

Take the Red line train from CLE to downtown Cleveland in under 30 minutes, with departures every 15 minutes.

Read more about CLEby Ramsey Qubein
Our travel experts
Ramsey Qubein

Ramsey Qubein

Expert on MDW and CLE

Ramsey Qubein

Ramsey Qubein

An avid traveler and aviation expert who has visited 173 countries, all 50 states and seven continents, Ramsey Qubein flies nearly 400,000 miles a year. As a North Carolina-based freelance journalist for publications including Conde Nast Traveler, Forbes, USA Today and Bloomberg among others, he explores the latest trends in aviation, hospitality, cruises and business.

Read more

Best time to book a flight from Midway to Cleveland

Have a flexible travel schedule? Discover the best time to fly to Cleveland from Midway with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Chicago Midway Airport to Cleveland

What is the cheapest month to book a flight from Chicago Midway Airport to Cleveland?

Currently, April is the cheapest month in which you can book a flight from Chicago Midway Airport to Cleveland (average of $250). Flying from Chicago Midway Airport to Cleveland in June is currently the most expensive (average of $290). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

What is the cheapest time of day to fly from MDW to CLE?

Find hourly flight availability from Midway to Cleveland. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated August 14, 2025.

When flying from Chicago Midway Airport to Cleveland, the time of day you fly usually plays a role in the price. Save by searching for a flight in the evening, which can drop the price by up to 25% versus a flight in the afternoon.

What is the cheapest day to fly from Chicago Midway Airport to Cleveland?

Use this chart to determine the cheapest time to fly round-trip from Midway to Cleveland. Price data was last updated on August 10, 2025.

Travelers seeking maximum savings on their Chicago Midway Airport to Cleveland flight should consider departing on Thursday at noon when fares are most often at their lowest. Monday evenings flights should be avoided if possible as fares are typically the most expensive at this time.

Reviews of airlines servicing Cleveland

Get insights into the airlines that provide service to Cleveland. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Cleveland. Reviews last updated August 14, 2025.
See what other customers who have flown with Southwest from Chicago Midway Airport to Cleveland have to say. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,244 reviews

Entertainment

7.5

Crew

8.6

Overall

8.0

Boarding

8.1

Comfort

8.0

Food

7.0

Reviews

1 / 20
8.0
Excellent

Walter,Aug 2025

OAK - SAN

Dozens of flights and I've never seen a row's beverages forgotten. I even went back and asked the attendant to check on them and nothing. I really hope it didn't have something to do with the Black mother with her kid in the row. Otherwise it was a typical Southwest flight, rapid boarding, tolerable leg room.
Southwest
8.0
Very good
4,244 reviews
Southwest
8.0
Very good
4,244 reviews

Entertainment

7.5

Crew

8.6

Overall

8.0

Boarding

8.1

Comfort

8.0

Food

7.0

Reviews

1 / 20
8.0
Excellent

Walter,Aug 2025

OAK - SAN

Dozens of flights and I've never seen a row's beverages forgotten. I even went back and asked the attendant to check on them and nothing. I really hope it didn't have something to do with the Black mother with her kid in the row. Otherwise it was a typical Southwest flight, rapid boarding, tolerable leg room.

Related info for your journey

Find useful and relevant information for your journey from Midway to Cleveland. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly into for flights to Cleveland from Chicago Midway?

    Located just 10.1 mi from the city center, Cleveland Hopkins Intl is the airport most travelers will use when flying to Cleveland from Chicago Midway. Booking flights from Chicago Midway to Hopkins Intl (CLE) should be relatively easy as there are 2 daily inbound flights from Chicago Midway from 1 airline.

  • What is the cheapest airline to fly from Chicago Midway Airport to Cleveland round-trip?

    Flying on Southwest is currently your cheapest option to Cleveland, with prices starting at $172. Southwest is 54% cheaper than the average price of flights available within the next 90 days to this destination.

  • What are the cheapest flights from Chicago Midway Airport to Cleveland?

    On average you can expect to pay $182 for a flight from Chicago Midway Airport to Cleveland. The cheapest flight overall is $45 while the most popular route, (Chicago Midway - Cleveland Hopkins Intl) is currently priced at $165.

  • Can I find deals for flights from Midway to Cleveland that include hotel bookings?

    Yes. In addition to deals on Midway to Cleveland flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Midway to Cleveland?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Midway to Cleveland.

  • Can I find deals for business class flights from Midway to Cleveland?

    Yes. Cheapflights offers flight deals from Midway to Cleveland by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Chicago Midway Airport to Cleveland?

    Currently, April is the cheapest month in which you can book a flight from Chicago Midway Airport to Cleveland (average of $250). Flying from Chicago Midway Airport to Cleveland in June is currently the most expensive (average of $290). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

Traveling to a place near Cleveland?

Book flights to Cleveland if you plan to visit one of these locations
Sandusky
Mentor
Beachwood
Mansfield
Wooster
Avon
Independence
Willoughby
Elyria
Streetsboro
Kent
Cleveland Heights
North Olmsted
Cuyahoga Falls
Macedonia
Strongsville
Medina
Westlake

Browse thousands of different options on Cheapflights for your next trip

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Top airline flying from Midway to Cleveland

Discover the top airline that operate flights from Midway to Cleveland. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated August 14, 2025.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$172Average$316FlexibilityNo cancel feeOn-time63%

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