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$86+ 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 8/23. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — CLE
Jun 17 — Jun 241
Tue 6/17
Tue 6/24
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 June 12, 2025.

Round-trip from

$197
(Southwest)

One-way from

$86
(Southwest)

Popular in

July

Cheapest in

June

Average price

$237

Good round-trip deal

$214 or less

Good one-way deal

$121 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. 23% potential increase in price ($112 potential increase over avg. RT price).
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Cheapest flight prices on average. 8% potential price decrease ($28 potential savings vs. average RT price).
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Average for round-trip flights in June 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 June 12, 2025.

This Southwest deal was found by Cheapflights users on 6/11. 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.
Tue 8/1210:05 amMDW - CLE
2 stops7h 15mSouthwest
Fri 8/155:50 amCLE - MDW
2 stops8h 40mSouthwest
Deal found 6/11$197
This Delta deal was found by Cheapflights users on 6/9. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/169:31 amMDW - CLE
1 stop4h 32mDelta
Sun 8/178:30 amCLE - MDW
1 stop4h 58mDelta
Deal found 6/9$211
This KAYAK deal was found by Cheapflights users on 6/12. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/1611:39 amMDW - CLE
1 stop5h 24mFrontier
Sat 7/196:25 pmCLE - MDW
1 stop5h 10mFrontier
Deal found 6/12$236

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 June 12, 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

Tue 8/12

10:05 am-6:20 pm

2 stops7h 15m

Cleveland Hopkins Intl

Fri 8/15

5:50 am-1:30 pm

2 stops8h 40m

$197

ChicagoCleveland

MDW - CLE

MDWCLE

Chicago Midway

Sat 8/16

9:31 am-3:03 pm

1 stop4h 32m

Cleveland Hopkins Intl

Sun 8/17

8:30 am-12:28 pm

1 stop4h 58m

$211

ChicagoCleveland

MDW - CLE

MDWCLE

Chicago Midway

Wed 7/16

11:39 am-6:03 pm

1 stop5h 24m

Cleveland Hopkins Intl

Sat 7/19

6:25 pm-10:35 pm

1 stop5h 10m

$236

ChicagoCleveland

MDW - CLE

MDWCLE

Chicago Midway

Sat 8/23

7:00 am-12:05 pm

1 stop4h 05m

$86

ChicagoCleveland

MDW - CLE

MDWCLE

Chicago Midway

Sat 8/16

6:17 pm-10:43 pm

1 stop3h 26m

$89

ChicagoCleveland

MDW - CLE

MDWCLE

Chicago Midway

Wed 6/18

11:39 am-6:01 pm

1 stop5h 22m

$93

ChicagoCleveland

MDW - CLE

MDWCLE

Chicago Midway

Fri 8/15

7:07 pm-12:19 am

2 stops28h 12m

$154

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/11

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 June 12, 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 at noon, which can drop the price by up to 18% 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 June 8, 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. Wednesday afternoons flights should be avoided if possible as fares are typically the most expensive at this time.

Rainfall in Cleveland by month

Plan your trip to Cleveland by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Cleveland ranges from 2.3 - 3.8 inches per month. September is typically the wettest month, when rainfall can reach 3.8 in. February is typically the driest time to visit Cleveland when rainfall is around 2.3 in.

Temperature in Cleveland by month

Plan your trip to Cleveland by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Cleveland, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 28.4 F).

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 June 12, 2025.
See what other customers who have flown with Southwest, Delta and Frontier from Chicago to Cleveland have to say. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,287 reviews

Overall

8.0

Food

7.1

Boarding

8.2

Comfort

8.0

Entertainment

7.6

Crew

8.6

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
Southwest
8.0
Very good
4,287 reviews
Southwest
8.0
Very good
4,287 reviews

Overall

8.0

Food

7.1

Boarding

8.2

Comfort

8.0

Entertainment

7.6

Crew

8.6

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
Delta
8.0
Very good
7,946 reviews
Southwest
8.0
Very good
4,287 reviews

Overall

8.0

Food

7.1

Boarding

8.2

Comfort

8.0

Entertainment

7.6

Crew

8.6

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
Frontier
6.0
Okay
3,295 reviews
Southwest
8.0
Very good
4,287 reviews

Overall

8.0

Food

7.1

Boarding

8.2

Comfort

8.0

Entertainment

7.6

Crew

8.6

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.

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 are the cheapest airlines flying from Chicago Midway Airport to Cleveland round-trip?

    Flying on Southwest is currently your cheapest option to Cleveland, with prices starting at $197. Additional round-trip tickets that might be worth considering are offered by Delta and Frontier, with the lowest prices starting at $211 and $244, respectively. Southwest is 46% cheaper than the average price of flights available within the next 90 days to this destination.

  • What are the cheapest airlines to fly from Chicago Midway Airport to Cleveland one-way?

    To fly one-way, consider booking your trip with Southwest, which is currently one of the cheapest options available, starting at $86. Delta flights start at $89 while deals on Frontier start at $93 one-way.

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

    On average you can expect to pay $259 for a flight from Chicago Midway Airport to Cleveland. The cheapest flight overall is $98 while the most popular route, (Chicago Midway - Cleveland Hopkins Intl) is currently priced at $109.

  • 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 Chicago Midway Airport?

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

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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 June 12, 2025.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$172Average$314FlexibilityNo cancel feeOn-time63%

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