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$59+ 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 2/17. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — CLE
Feb 23 — Mar 21
Mon 2/23
Mon 3/2
1 adult, Economy
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Cheap 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 January 24, 2026.

This Priceline deal was found by Cheapflights users on 1/21. 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.
Mon 2/21:00 pm
MDW
-
CLE
1 stop10h 43m
Frontier
Mon 2/97:10 am
CLE
-
MDW
1 stop5h 35m
Frontier
Deal found 1/21$181
This Delta deal was found by Cheapflights users on 1/22. 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.
Tue 3/31:29 pm
MDW
-
CLE
2 stops10h 01m
Delta
Thu 3/56:00 am
CLE
-
MDW
2 stops7h 46m
Delta
Deal found 1/22$185
This Southwest deal was found by Cheapflights users on 1/23. 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 3/512:50 pm
MDW
-
CLE
2 stops5h 25m
Southwest
Sat 3/78:00 pm
CLE
-
MDW
Nonstop1h 20m
Southwest
Deal found 1/23$186
This Expedia deal was found by Cheapflights users on 1/23. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/1011:19 am
MDW
-
CLE
1 stop12h 54m
Frontier
Wed 3/111:38 pm
CLE
-
MDW
1 stop9h 41m
Frontier
Deal found 1/23$190
This Delta deal was found by Cheapflights users on 1/22. 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.
Thu 2/121:29 pm
MDW
-
CLE
1 stop4h 21m
Delta
Thu 2/1911:53 am
CLE
-
MDW
1 stop6h 52m
Delta
Deal found 1/22$191
This Priceline deal was found by Cheapflights users on 1/22. 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.
Thu 2/55:01 pm
MDW
-
CLE
1 stop5h 10m
Frontier
Sun 2/87:05 am
CLE
-
MDW
1 stop5h 40m
Frontier
Deal found 1/22$195
This Southwest deal was found by Cheapflights users on 1/22. 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.
Sat 2/212:10 pm
MDW
-
CLE
2 stops7h 50m
Southwest
Mon 2/234:20 pm
CLE
-
MDW
1 stop6h 05m
Southwest
Deal found 1/22$196
This Kiwi.com deal was found by Cheapflights users on 1/23. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 2/25:01 pm
MDW
-
CLE
1 stop13h 33m
Frontier
Wed 2/47:10 am
CLE
-
MDW
1 stop5h 55m
Frontier
Deal found 1/23$199
This Kiwi.com deal was found by Cheapflights users on 1/23. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/286:25 am
MDW
-
CLE
1 stop15h 56m
Frontier
Mon 3/25:44 pm
CLE
-
MDW
2 stops26h 23m
Frontier
Deal found 1/23$209
This Kiwi.com deal was found by Cheapflights users on 1/22. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 2/95:01 pm
MDW
-
CLE
2 stops16h 49m
Frontier
Thu 2/127:15 am
CLE
-
MDW
1 stop16h 19m
Frontier
Deal found 1/22$211
This Southwest deal was found by Cheapflights users on 1/22. 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 3/126:45 pm
MDW
-
CLE
Nonstop1h 10m
Southwest
Sun 3/157:55 am
CLE
-
MDW
Nonstop1h 25m
Southwest
Deal found 1/22$213

Find 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 January 24, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

Expedia
3 stars

Round-trip from

$181
(Priceline)

One-way from

$59
(Southwest)

Popular in

July

Cheapest in

August

Average price

$536

Good round-trip deal

$371 or less

Good one-way deal

$247 or less
Provider with most accurate pricing for Chicago Midway-Cleveland Hopkins Intl flight deals.
Search Deals
Provider most trusted by Cheapflights users for Chicago Midway-Cleveland Hopkins Intl flights.
Search Deals
From Chicago Midway to Cleveland Hopkins Intl
Search Deals
One-way flight from Chicago Midway to Cleveland Hopkins Intl
Search Deals
Highest demand for flights based on searches. 9% potential increase in price ($35 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 11% potential price decrease ($35 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in January 2026
Search Deals
Price to beat on a round-trip flight from Chicago Midway to Cleveland Hopkins Intl.
Search Deals
Price to beat on a one-way flight from Chicago Midway to Cleveland Hopkins Intl.
Search Deals

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 January 24, 2026.
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

Thu 3/5

5:40 pm-10:55 pm

1 stop4h 15m

Cleveland Hopkins Intl

Sat 3/7

8:00 pm-8:20 pm

Nonstop1h 20m

$181

ChicagoCleveland

MDW - CLE

MDWCLE

Chicago Midway

Tue 3/3

1:29 pm-12:30 am

2 stops10h 01m

Cleveland Hopkins Intl

Thu 3/5

6:00 am-12:46 pm

2 stops7h 46m

$185

ChicagoCleveland

MDW - CLE

MDWCLE

Chicago Midway

Tue 3/10

6:00 am-6:42 pm

1 stop11h 42m

Cleveland Hopkins Intl

Tue 3/17

1:38 pm-8:54 pm

1 stop8h 16m

$191

ChicagoCleveland

MDW - CLE

MDWCLE

Chicago Midway

Tue 2/17

6:20 pm-11:54 pm

1 stop4h 34m

Cleveland Hopkins Intl

Wed 2/18

10:32 am-12:46 pm

1 stop3h 14m

$191

ChicagoCleveland

MDW - CLE

MDWCLE

Chicago Midway

Thu 3/12

7:45 am-12:55 pm

1 stop4h 10m

Cleveland Hopkins Intl

Mon 3/16

8:45 pm-12:05 am

1 stop4h 20m

$191

ChicagoCleveland

MDW - CLE

MDWCLE

Chicago Midway

Mon 3/9

5:40 pm-12:29 am

1 stop5h 49m

Cleveland Hopkins Intl

Mon 3/16

4:43 pm-10:31 pm

1 stop6h 48m

$191

ChicagoCleveland

MDW - CLE

MDWCLE

Chicago Midway

Sat 2/28

7:45 am-12:40 pm

1 stop3h 55m

Cleveland Hopkins Intl

Mon 3/2

4:20 pm-9:25 pm

1 stop6h 05m

$191

ChicagoCleveland

MDW - CLE

MDWCLE

Chicago Midway

Thu 2/12

1:29 pm-6:50 pm

1 stop4h 21m

Cleveland Hopkins Intl

Thu 2/19

11:53 am-5:45 pm

1 stop6h 52m

$191

ChicagoCleveland

MDW - CLE

MDWCLE

Chicago Midway

Sat 2/21

6:00 pm-8:15 pm

Nonstop1h 15m

Cleveland Hopkins Intl

Mon 2/23

7:05 pm-7:40 pm

Nonstop1h 35m

$201

ChicagoCleveland

MDW - CLE

MDWCLE

Chicago Midway

Tue 2/24

2:35 pm-4:45 pm

Nonstop1h 10m

$59

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/23

Showing 1-10 of 19 results
1
2

Compare providers for flights from Midway to Cleveland

Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Midway to Cleveland in January.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*1 star

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: When it comes to deals on Chicago Midway Airport-Cleveland flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Chicago Midway Airport-Cleveland flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Chicago Midway Airport-Cleveland flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Chicago Midway Airport-Cleveland flights, Cheapflights users trust Expedia the most. Expedia has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Chicago Midway Airport-Cleveland flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

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, August is the cheapest month in which you can book a flight from Chicago Midway Airport to Cleveland (average of $93). Flying from Chicago Midway Airport to Cleveland in April is currently the most expensive (average of $239). 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 January 24, 2026.

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 3% versus a flight in the evening.

The best insider tips for Chicago Midway Airport to Cleveland flights

AI-powered summary based on content written by travel experts. AI can make mistakes.
Cheapflights partnered with top experts to bring you the best recommendations for your Chicago Midway Airport to Cleveland trip
Our travel experts
Ramsey Qubein

Ramsey Qubein

Expert on MDW and CLE

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

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 January 24, 2026.
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
4,268 reviews

Comfort

8.0

Food

7.0

Crew

8.6

Entertainment

7.5

Boarding

8.1

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
Southwest
8.0
Very good
4,268 reviews
Southwest
8.0
Very good
4,268 reviews

Comfort

8.0

Food

7.0

Crew

8.6

Entertainment

7.5

Boarding

8.1

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am

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 is 1 daily inbound flight from Chicago Midway from 1 airline.

  • How long is the flight from Chicago Midway Airport to Cleveland?

    Departing from Chicago Midway Airport to Cleveland will take you 4h 15m. The distance between Chicago Midway Airport and Cleveland is about 305 mi. Both multi-stop and nonstop flights can be found to your destination and back.

  • 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 $157. Southwest is 52% 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 $317 for a flight from Chicago Midway Airport to Cleveland. The cheapest flight overall is $128 while the most popular route, (Chicago Midway - Cleveland Hopkins Intl) is currently priced at $117.

  • 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, August is the cheapest month in which you can book a flight from Chicago Midway Airport to Cleveland (average of $93). Flying from Chicago Midway Airport to Cleveland in April is currently the most expensive (average of $239). 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
Mansfield
Avon
Independence
Wooster
Beachwood
Lakewood
Willoughby
Streetsboro
Cleveland Heights
North Olmsted
Cuyahoga Falls
Macedonia
Kent
Medina
Strongsville
Elyria

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

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 January 24, 2026.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$157Average$297FlexibilityNo cancel feeOn-time63%

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