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$69+ 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 17 — Aug 241
Mon 8/17
Mon 8/24
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 July 18, 2026.

This Southwest deal was found by Cheapflights users on 7/13. 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.
Tue 8/412:45 pm
MDW
-
CLE
2 stops7h 15m
Southwest
Sat 8/83:15 pm
CLE
-
MDW
1 stop6h 15m
Southwest
Deal found 7/13$181
This Southwest deal was found by Cheapflights users on 7/14. 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.
Wed 8/194:40 pm
MDW
-
CLE
1 stop4h 15m
Southwest
Sat 8/225:40 am
CLE
-
MDW
2 stops8h 25m
Southwest
Deal found 7/14$185
This Southwest deal was found by Cheapflights users on 7/15. 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 8/297:55 am
MDW
-
CLE
2 stops7h 50m
Southwest
Sat 9/55:40 am
CLE
-
MDW
2 stops8h 25m
Southwest
Deal found 7/15$186
This KAYAK deal was found by Cheapflights users on 7/15. 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.
Mon 8/106:30 pm
MDW
-
CLE
Nonstop1h 15m
Southwest
Wed 8/1212:50 pm
CLE
-
MDW
Nonstop1h 15m
Southwest
Deal found 7/15$187
This Delta deal was found by Cheapflights users on 7/16. 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 8/89:24 am
MDW
-
CLE
1 stop3h 16m
Delta
Mon 8/103:49 pm
CLE
-
MDW
1 stop3h 44m
Delta
Deal found 7/16$188
This Southwest deal was found by Cheapflights users on 7/17. 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 8/87:40 am
MDW
-
CLE
Nonstop1h 15m
Southwest
Mon 8/107:15 pm
CLE
-
MDW
Nonstop1h 15m
Southwest
Deal found 7/17$195
This Southwest deal was found by Cheapflights users on 7/17. 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 9/57:40 am
MDW
-
CLE
Nonstop1h 15m
Southwest
Sun 9/612:35 pm
CLE
-
MDW
Nonstop1h 15m
Southwest
Deal found 7/17$197
This Delta deal was found by Cheapflights users on 7/13. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/109:29 am
MDW
-
CLE
1 stop3h 11m
Delta
Mon 10/1210:34 am
CLE
-
MDW
1 stop3h 14m
Delta
Deal found 7/13$198

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 July 18, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$181
(Southwest)

One-way from

$69
(Southwest)

Popular in

April

Cheapest in

May

Average price

$573

Good round-trip deal

$207 or less

Good one-way deal

$222 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. 6% potential price decrease ($25 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in July 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 July 18, 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 8/11

12:45 pm-9:00 pm

2 stops7h 15m

Cleveland Hopkins Intl

Wed 8/12

7:15 pm-7:30 pm

Nonstop1h 15m

$210

ChicagoCleveland

MDW - CLE

MDWCLE

Chicago Midway

Thu 10/15

1:28 pm-6:36 pm

1 stop4h 08m

Cleveland Hopkins Intl

Sat 10/17

6:00 am-9:18 am

1 stop4h 18m

$215

ChicagoCleveland

MDW - CLE

MDWCLE

Chicago Midway

Sat 10/17

1:28 pm-6:37 pm

1 stop4h 09m

Cleveland Hopkins Intl

Mon 10/19

6:00 am-9:18 am

1 stop4h 18m

$218

ChicagoCleveland

MDW - CLE

MDWCLE

Chicago Midway

Sat 8/15

7:55 am-4:45 pm

2 stops7h 50m

Cleveland Hopkins Intl

Sat 8/22

7:15 am-9:30 am

1 stop3h 15m

$220

ChicagoCleveland

MDW - CLE

MDWCLE

Chicago Midway

Fri 10/23

4:20 pm-11:45 pm

2 stops6h 25m

Cleveland Hopkins Intl

Mon 10/26

5:50 pm-10:00 pm

1 stop5h 10m

$222

ChicagoCleveland

MDW - CLE

MDWCLE

Chicago Midway

Thu 9/3

10:10 am-4:45 pm

2 stops5h 35m

Cleveland Hopkins Intl

Mon 9/7

11:00 am-4:15 pm

1 stop6h 15m

$222

ChicagoCleveland

MDW - CLE

MDWCLE

Chicago Midway

Fri 8/28

5:50 pm-10:10 pm

1 stop3h 20m

Cleveland Hopkins Intl

Sat 8/29

4:35 pm-4:55 pm

Nonstop1h 20m

$246

ChicagoCleveland

MDW - CLE

MDWCLE

Chicago Midway

Fri 10/16

9:29 am-1:40 pm

1 stop3h 11m

Cleveland Hopkins Intl

Sat 10/17

10:34 am-12:48 pm

1 stop3h 14m

$256

ChicagoCleveland

MDW - CLE

MDWCLE

Chicago Midway

Mon 11/30

8:00 am-4:10 pm

1 stop7h 10m

Cleveland Hopkins Intl

Tue 12/1

8:40 am-9:05 am

Nonstop1h 25m

$256
Quickest round-trip

ChicagoCleveland

MDW - CLE

MDWCLE

Chicago Midway

Fri 8/28

8:05 am-10:25 am

Nonstop1h 20m

Cleveland Hopkins Intl

Fri 9/4

7:15 pm-7:30 pm

Nonstop1h 15m

$277

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/17

Showing 1-10 of 20 resultsSorted by cheapest first
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 July.
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 July 18, 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 40% 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 July 11, 2026.

Travelers seeking maximum savings on their Chicago Midway Airport to Cleveland flight should consider departing on Wednesday evenings 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 July 18, 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
4,241 reviews

Boarding

8.1

Overall

8.0

Entertainment

7.5

Crew

8.6

Comfort

8.0

Food

7.0

Reviews

1 / 20
10.0
Excellent

Sarah,Aug 2024

MDW - AUS

My first time, surprisingly good! It was a good ride overall. Coming from Singapore, this budget flight is better than the budget airline for our national carrier Singapore Airlines.
Southwest
8.0
Very good
4,241 reviews
Southwest
8.0
Very good
4,241 reviews

Boarding

8.1

Overall

8.0

Entertainment

7.5

Crew

8.6

Comfort

8.0

Food

7.0

Reviews

1 / 20
10.0
Excellent

Sarah,Aug 2024

MDW - AUS

My first time, surprisingly good! It was a good ride overall. Coming from Singapore, this budget flight is better than the budget airline for our national carrier Singapore Airlines.

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 4h 08m. 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 $137. Southwest is 67% 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 $281 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 $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.

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
Independence
Mansfield
Avon
Strongsville
Lakewood
Streetsboro
Medina
Cuyahoga Falls
North Olmsted
Macedonia
Kent
Westlake
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 July 18, 2026.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$137Average$503FlexibilityNo cancel feeOn-time63%

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