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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 12/31. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — CLE
ene. 11 — ene. 181
dom. 1/11
dom. 1/18
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 diciembre 12, 2025.

This Frontier deal was found by Cheapflights users on 12/10. 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.
lun. 12/228:15 amMDW - CLE
1 stop7h 15mFrontier
jue. 1/111:26 amCLE - MDW
1 stop11h 46mFrontier
Deal found 12/10$243
This Frontier deal was found by Cheapflights users on 12/10. 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.
jue. 12/256:12 amMDW - CLE
1 stop9h 18mFrontier
mié. 12/3111:26 amCLE - MDW
1 stop11h 46mFrontier
Deal found 12/10$288
This Trip.com deal was found by Cheapflights users on 12/10. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 12/186:12 amMDW - CLE
1 stop9h 18mFrontier
sáb. 12/2011:26 amCLE - MDW
1 stop11h 46mFrontier
Deal found 12/10$294
This Southwest deal was found by Cheapflights users on 12/9. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 12/241:40 pmMDW - CLE
Nonstop1h 10mSouthwest
lun. 12/299:05 pmCLE - MDW
Nonstop1h 20mSouthwest
Deal found 12/9$298
This Frontier deal was found by Cheapflights users on 12/10. 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.
lun. 12/228:15 amMDW - CLE
1 stop7h 15mFrontier
mié. 12/316:20 amCLE - MDW
1 stop8h 01mFrontier
Deal found 12/10$317
This Delta deal was found by Cheapflights users on 12/10. 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.
mié. 12/246:08 pmMDW - CLE
1 stop3h 23mDelta
lun. 12/296:29 amCLE - MDW
1 stop3h 20mDelta
Deal found 12/10$318
This Southwest deal was found by Cheapflights users on 12/10. 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.
mié. 12/248:40 pmMDW - CLE
Nonstop1h 15mSouthwest
mar. 12/309:05 pmCLE - MDW
Nonstop1h 20mSouthwest
Deal found 12/10$328
This Kiwi.com deal was found by Cheapflights users on 12/10. 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.
mié. 12/2410:21 amMDW - CLE
2 stops36h 34mFrontier
mié. 12/316:20 amCLE - MDW
1 stop16h 52mFrontier
Deal found 12/10$335
This Southwest deal was found by Cheapflights users on 12/10. 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.
lun. 12/295:25 pmMDW - CLE
2 stops5h 40mSouthwest
mié. 12/316:45 amCLE - MDW
Nonstop1h 35mSouthwest
Deal found 12/10$336
This Frontier deal was found by Cheapflights users on 12/10. 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.
jue. 12/116:15 amMDW - CLE
1 stop8h 33mFrontier
vie. 12/124:48 pmCLE - MDW
1 stop6h 51mFrontier
Deal found 12/10$342

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 diciembre 12, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$221
(Southwest)

One-way from

$88
(Frontier)

Popular in

July

Cheapest in

August

Average price

$352

Good round-trip deal

$257 or less

Good one-way deal

$195 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. 6% potential increase in price ($25 potential increase over avg. RT price).
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 December 2025
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 diciembre 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

lun. 2/23

6:15 pm-8:30 pm

Nonstop1h 15m

Cleveland Hopkins Intl

mié. 2/25

4:25 pm-4:50 pm

Nonstop1h 25m

$224

ChicagoCleveland

MDW - CLE

MDWCLE

Chicago Midway

mié. 1/7

5:31 pm-12:39 am

1 stop6h 08m

Cleveland Hopkins Intl

mié. 1/14

2:00 pm-5:34 pm

1 stop4h 34m

$231

ChicagoCleveland

MDW - CLE

MDWCLE

Chicago Midway

mar. 1/6

2:35 pm-8:50 pm

1 stop5h 15m

Cleveland Hopkins Intl

mié. 1/7

5:35 am-1:55 pm

2 stops9h 20m

$236

ChicagoCleveland

MDW - CLE

MDWCLE

Chicago Midway

vie. 1/16

5:31 pm-12:39 am

1 stop6h 08m

Cleveland Hopkins Intl

dom. 1/18

6:30 am-8:52 am

1 stop3h 22m

$237

ChicagoCleveland

MDW - CLE

MDWCLE

Chicago Midway

sáb. 2/14

11:00 am-1:10 pm

Nonstop1h 10m

Cleveland Hopkins Intl

dom. 2/15

6:35 am-7:10 am

Nonstop1h 35m

$244

ChicagoCleveland

MDW - CLE

MDWCLE

Chicago Midway

sáb. 1/17

2:40 pm-7:20 pm

1 stop3h 40m

Cleveland Hopkins Intl

dom. 1/18

4:25 pm-4:50 pm

Nonstop1h 25m

$244

ChicagoCleveland

MDW - CLE

MDWCLE

Chicago Midway

sáb. 1/10

8:40 am-3:10 pm

1 stop5h 30m

Cleveland Hopkins Intl

mar. 1/13

5:35 am-1:55 pm

2 stops9h 20m

$246

ChicagoCleveland

MDW - CLE

MDWCLE

Chicago Midway

vie. 1/23

3:00 pm-5:10 pm

Nonstop1h 10m

Cleveland Hopkins Intl

lun. 1/26

6:15 am-6:55 am

Nonstop1h 40m

$247

ChicagoCleveland

MDW - CLE

MDWCLE

Chicago Midway

sáb. 5/9

3:40 pm-5:50 pm

Nonstop1h 10m

Cleveland Hopkins Intl

dom. 5/10

4:10 pm-4:30 pm

Nonstop1h 20m

$257

ChicagoCleveland

MDW - CLE

MDWCLE

Chicago Midway

vie. 1/9

7:55 pm-10:10 pm

Nonstop1h 15m

Cleveland Hopkins Intl

lun. 1/12

8:40 am-2:15 pm

1 stop6h 35m

$257

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/11

Showing 1-10 of 23 results
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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 December.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*1 star
eDreamsPrice 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 eDreams to be most consistent on Cheapflights vs. eDreams Users can find the same prices on Chicago Midway Airport-Cleveland flight deals on Cheapflights vs. eDreams >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 eDreams the most. eDreams 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 diciembre 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 in the evening, which can drop the price by up to 8% 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 December 6, 2025.

Travelers seeking maximum savings on their Chicago Midway Airport to Cleveland flight should consider departing on Friday evenings 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.

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
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

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 diciembre 12, 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
7.9
Good
4,253 reviews

Boarding

8.1

Comfort

8.0

Food

7.0

Overall

7.9

Crew

8.6

Entertainment

7.5

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
7.9
Good
4,253 reviews
Southwest
7.9
Good
4,253 reviews

Boarding

8.1

Comfort

8.0

Food

7.0

Overall

7.9

Crew

8.6

Entertainment

7.5

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 1h 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 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 $395 for a flight from Chicago Midway Airport to Cleveland. The cheapest flight overall is $107 while the most popular route, (Chicago Midway - Cleveland Hopkins Intl) is currently priced at $128.

  • 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
Beachwood
Wooster
Independence
Willoughby
Lakewood
Streetsboro
Medina
Cleveland Heights
North Olmsted
Cuyahoga Falls
Macedonia
Kent
Strongsville
Elyria
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 diciembre 12, 2025.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$157Average$301FlexibilityNo cancel feeOn-time63%

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