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$88+ 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 6/17. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — CLE
May 23 — May 301
Sat 5/23
Sat 5/30
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 April 23, 2026.

This Kiwi.com deal was found by Cheapflights users on 4/20. 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.
Tue 6/1612:27 pm
MDW
-
CLE
1 stop7h 28m
Frontier
Tue 6/235:51 pm
CLE
-
MDW
1 stop18h 18m
Frontier
Deal found 4/20$169
This Kiwi.com deal was found by Cheapflights users on 4/21. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/1012:04 pm
MDW
-
CLE
1 stop5h 25m
Frontier
Sat 6/203:46 pm
CLE
-
MDW
1 stop7h 25m
Frontier
Deal found 4/21$174
This Southwest deal was found by Cheapflights users on 4/19. 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 5/1912:45 pm
MDW
-
CLE
Nonstop1h 15m
Southwest
Wed 5/202:45 pm
CLE
-
MDW
Nonstop1h 20m
Southwest
Deal found 4/19$179
This Expedia deal was found by Cheapflights users on 4/19. 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.
Fri 5/84:52 pm
MDW
-
CLE
1 stop27h 00m
Frontier
Sun 5/107:00 am
CLE
-
MDW
1 stop8h 12m
Frontier
Deal found 4/19$180
This Kiwi.com deal was found by Cheapflights users on 4/20. 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 5/186:00 am
MDW
-
CLE
1 stop11h 27m
Frontier
Mon 5/257:24 pm
CLE
-
MDW
1 stop27h 38m
Frontier
Deal found 4/20$181
This Kiwi.com deal was found by Cheapflights users on 4/18. 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.
Fri 5/156:00 am
MDW
-
CLE
1 stop11h 27m
Frontier
Mon 5/189:57 pm
CLE
-
MDW
2 stops25h 05m
Frontier
Deal found 4/18$184
This Frontier deal was found by Cheapflights users on 4/20. 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.
Tue 5/2612:27 pm
MDW
-
CLE
1 stop5h 52m
Frontier
Wed 5/273:36 pm
CLE
-
MDW
1 stop7h 26m
Frontier
Deal found 4/20$185
This Kiwi.com deal was found by Cheapflights users on 4/18. 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.
Tue 5/1212:24 pm
MDW
-
CLE
2 stops9h 47m
Frontier
Wed 5/137:24 pm
CLE
-
MDW
1 stop16h 45m
Frontier
Deal found 4/18$193
This Southwest deal was found by Cheapflights users on 4/22. 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.
Wed 5/2012:45 pm
MDW
-
CLE
Nonstop1h 15m
Southwest
Wed 5/276:45 pm
CLE
-
MDW
Nonstop1h 15m
Southwest
Deal found 4/22$196

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 April 23, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$169
(Kiwi.com)

One-way from

$88
(Kiwi.com)

Popular in

July

Cheapest in

June

Average price

$436

Good round-trip deal

$237 or less

Good one-way deal

$138 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
High demand for flights, 2% potential price rise
Search Deals
Cheapest flight prices on average. 10% potential price decrease ($33 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in April 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 April 23, 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

Tue 5/26

12:45 pm-3:00 pm

Nonstop1h 15m

Cleveland Hopkins Intl

Wed 5/27

2:45 pm-3:05 pm

Nonstop1h 20m

$179

ChicagoCleveland

MDW - CLE

MDWCLE

Chicago Midway

Wed 9/23

12:45 pm-9:00 pm

2 stops7h 15m

Cleveland Hopkins Intl

Sun 9/27

8:55 am-9:05 am

Nonstop1h 10m

$243

ChicagoCleveland

MDW - CLE

MDWCLE

Chicago Midway

Sun 5/31

7:45 am-9:55 am

Nonstop1h 10m

Cleveland Hopkins Intl

Thu 6/4

4:45 pm-5:05 pm

Nonstop1h 20m

$246

ChicagoCleveland

MDW - CLE

MDWCLE

Chicago Midway

Wed 5/20

10:10 am-5:00 pm

2 stops5h 50m

Cleveland Hopkins Intl

Wed 5/27

6:40 am-3:45 pm

2 stops10h 05m

$260
Quickest round-trip

ChicagoCleveland

MDW - CLE

MDWCLE

Chicago Midway

Tue 5/12

7:45 am-9:55 am

Nonstop1h 10m

Cleveland Hopkins Intl

Wed 5/13

9:00 am-9:15 am

Nonstop1h 15m

$271

ChicagoCleveland

MDW - CLE

MDWCLE

Chicago Midway

Fri 7/17

7:55 am-10:10 am

Nonstop1h 15m

Cleveland Hopkins Intl

Tue 7/21

3:25 pm-3:40 pm

Nonstop1h 15m

$277

ChicagoCleveland

MDW - CLE

MDWCLE

Chicago Midway

Sun 5/31

4:05 pm-10:25 pm

1 stop5h 20m

Cleveland Hopkins Intl

Sun 6/21

8:20 am-8:35 am

Nonstop1h 15m

$287

ChicagoCleveland

MDW - CLE

MDWCLE

Chicago Midway

Sun 6/21

8:00 am-10:15 am

Nonstop1h 15m

Cleveland Hopkins Intl

Sun 6/28

7:15 am-10:10 am

1 stop3h 55m

$287

ChicagoCleveland

MDW - CLE

MDWCLE

Chicago Midway

Fri 6/26

7:35 pm-9:50 pm

Nonstop1h 15m

Cleveland Hopkins Intl

Mon 7/6

5:45 pm-10:00 pm

1 stop5h 15m

$287
Cheapest one-way
Quickest one-way

ChicagoCleveland

MDW - CLE

MDWCLE

Chicago Midway

Wed 6/10

3:45 pm-5:55 pm

Nonstop1h 10m

$89

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/22

Showing 1-10 of 21 resultsSorted by cheapest first
1
2
3

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 April.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars

*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 FlightHub the most. FlightHub 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 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 April 23, 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 27% versus a flight in the evening.

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 April 18, 2026.

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

How much does it cost to fly round-trip from Chicago Midway Airport to Cleveland?

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 April 23, 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
4,327 reviews

Boarding

8.1

Comfort

8.0

Entertainment

7.5

Food

7.0

Overall

8.0

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
Southwest
8.0
Very good
4,327 reviews
Southwest
8.0
Very good
4,327 reviews

Boarding

8.1

Comfort

8.0

Entertainment

7.5

Food

7.0

Overall

8.0

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.

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.

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

    Departing from Chicago Midway Airport to Cleveland will take you 1h 15m. The distance between Chicago Midway Airport and Cleveland is about 305 mi. Generally, flights for this route are nonstop.

  • 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 $97. Southwest is 72% 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 $291 for a flight from Chicago Midway Airport to Cleveland. The cheapest flight overall is $58 while the most popular route, (Chicago Midway - Cleveland Hopkins Intl) is currently priced at $189.

  • 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.

See more FAQs

Traveling to a place near Cleveland?

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

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 April 23, 2026.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$97Average$344FlexibilityNo cancel feeOn-time63%

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