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$97+ Cheap flights from Cleveland (CLE) to Midway (MDW)

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 5/14. Fares are subject to change and may not be available on all flights or dates of travel.
CLE — MDW
may. 6 — may. 131
mar. 5/6
mar. 5/13
1 adult, Economy
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Cheap flight deals from Cleveland to Midway

Discover tips and strategies to find the most affordable flight options for your journey from Cleveland (CLE) to Midway (MDW). 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 mayo 1, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$190
(Frontier)

One-way from

$97
(CheapOair)

Popular in

August

Cheapest in

January

Average price

$252

Good round-trip deal

$311 or less

Good one-way deal

$148 or less
Provider with most accurate pricing for Cleveland Hopkins Intl-Chicago Midway flight deals.
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Provider most trusted by Cheapflights users for Cleveland Hopkins Intl-Chicago Midway flights.
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From Cleveland Hopkins Intl to Chicago Midway
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One-way flight from Cleveland Hopkins Intl to Chicago Midway
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Highest demand for flights based on searches. 11% potential increase in price ($37 potential increase over avg. RT price).
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Cheapest flight prices on average. 5% potential price decrease ($16 potential savings vs. average RT price).
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Average for round-trip flights in May 2025
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Price to beat on a round-trip flight from Cleveland Hopkins Intl to Chicago Midway.
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Price to beat on a one-way flight from Cleveland Hopkins Intl to Chicago Midway.
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Find flight deals from Cleveland to Midway

Cheapest flights from Cleveland to Midway
Explore the most affordable flight options available from Cleveland to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on mayo 1, 2025.

This Booking.com deal was found by Cheapflights users on 4/30. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 5/152:05 pmCLE - MDW
1 stop9h 35mFrontier
dom. 5/184:00 pmMDW - CLE
1 stop14h 40mFrontier
Deal found 4/30$191
This Southwest deal was found by Cheapflights users on 4/30. 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.
sáb. 5/243:20 pmCLE - MDW
Nonstop1h 20mSouthwest
sáb. 5/317:00 pmMDW - CLE
Nonstop1h 10mSouthwest
Deal found 4/30$197
This Delta deal was found by Cheapflights users on 4/29. 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.
sáb. 5/2410:30 amCLE - MDW
1 stop2h 58mDelta
dom. 5/259:16 amMDW - CLE
1 stop4h 38mDelta
Deal found 4/29$217

Cheapflights Fare Finder

Customize your flight search to find flights from Cleveland to Midway 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 mayo 1, 2025.
Use the filters below to find and compare flights from Cleveland to Chicago Midway Airport that are best for you.

Fly from

Cleveland

Fly to

Midway

Route

Depart

Return

Price

ClevelandChicago

CLE - MDW

CLEMDW

Cleveland Hopkins Intl

jue. 5/15

2:05 pm-10:40 pm

1 stop9h 35m

Chicago Midway

dom. 5/18

4:00 pm-7:40 am

1 stop14h 40m

$191

ClevelandChicago

CLE - MDW

CLEMDW

Cleveland Hopkins Intl

sáb. 5/24

3:20 pm-3:40 pm

Nonstop1h 20m

Chicago Midway

sáb. 5/31

7:00 pm-9:10 pm

Nonstop1h 10m

$197

ClevelandChicago

CLE - MDW

CLEMDW

Cleveland Hopkins Intl

sáb. 5/24

10:30 am-12:28 pm

1 stop2h 58m

Chicago Midway

dom. 5/25

9:16 am-2:54 pm

1 stop4h 38m

$217

ClevelandChicago

CLE - MDW

CLEMDW

Cleveland Hopkins Intl

mié. 5/14

9:17 pm-10:40 pm

1 stop26h 23m

$97

ClevelandChicago

CLE - MDW

CLEMDW

Cleveland Hopkins Intl

vie. 5/30

6:50 pm-7:05 pm

Nonstop1h 15m

$99

ClevelandChicago

CLE - MDW

CLEMDW

Cleveland Hopkins Intl

sáb. 7/5

2:11 pm-6:41 pm

1 stop5h 30m

$109

ClevelandChicago

CLE - MDW

CLEMDW

Cleveland Hopkins Intl

jue. 5/29

6:15 pm-7:14 pm

3 stops25h 59m

$184

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/29

Compare providers for flights from Cleveland to Midway

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 Cleveland to Midway in May.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*2 stars
eDreamsPrice Accuracy3 starsTrust Score*3 stars
PricelinePrice Accuracy2 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 Cleveland-Chicago Midway Airport flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Cleveland-Chicago Midway Airport flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Cleveland-Chicago Midway Airport flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Cleveland-Chicago Midway Airport 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 Cleveland-Chicago Midway Airport 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 Cleveland to Midway

Have a flexible travel schedule? Discover the best time to fly to Midway from Cleveland 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 Cleveland to Chicago Midway Airport

What is the cheapest month to book a flight from Cleveland to Chicago Midway Airport?

Currently, April is the cheapest month in which you can book a flight from Cleveland to Chicago Midway Airport (average of $160). Flying from Cleveland to Chicago Midway Airport in November is currently the most expensive (average of $249). 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 CLE to MDW?

Find hourly flight availability from Cleveland to Midway. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated mayo 1, 2025.

It’s optimal to fly from Cleveland to Chicago Midway Airport in the evening. By choosing this option you can save up to 10% on the cost of your flight, compared to a flight in the morning.

What is the cheapest day to fly from Cleveland to Chicago Midway Airport?

Use this chart to determine the cheapest time to fly round-trip from Cleveland to Midway. Price data was last updated on March 30, 2025.

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

Rainfall in Midway by month

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

In terms of precipitation, rainfall in Chicago Midway Airport ranges from 1.7 - 4.9 inches per month. August is typically the wettest month, when rainfall can reach 4.9 in. January is typically the driest time to visit Chicago Midway Airport when rainfall is around 1.7 in.

Temperature in Midway by month

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

If weather is an important factor for your trip to Chicago Midway Airport, 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 23.0 F).

Reviews of airlines servicing Midway

Get insights into the airlines that provide service to Midway. 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 Midway. Reviews last updated mayo 1, 2025.
Peruse reviews from past customers who have flown with Southwest, Delta and Frontier from Cleveland to Chicago to help guide your decision. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,294 reviews

Boarding

8.2

Comfort

8.0

Food

7.1

Entertainment

7.6

Crew

8.6

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
Southwest
8.0
Very good
4,294 reviews
Southwest
8.0
Very good
4,294 reviews

Boarding

8.2

Comfort

8.0

Food

7.1

Entertainment

7.6

Crew

8.6

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
Delta
8.0
Very good
7,934 reviews
Southwest
8.0
Very good
4,294 reviews

Boarding

8.2

Comfort

8.0

Food

7.1

Entertainment

7.6

Crew

8.6

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
Frontier
6.0
Okay
3,287 reviews
Southwest
8.0
Very good
4,294 reviews

Boarding

8.2

Comfort

8.0

Food

7.1

Entertainment

7.6

Crew

8.6

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!

Related info for your journey

Find useful and relevant information for your journey from Cleveland to Midway. 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 from for flights from Cleveland to Chicago Midway?

    Cleveland Hopkins Intl (CLE) is the airport you will fly out of if you book a flight from Cleveland to Chicago Midway. You should not have trouble finding flights to Chicago Midway from Hopkins Intl; the airport handles an average of 2 outbound flights to Chicago Midway per day. You should also have plenty of airline options to choose from since 1 airline has flights from the Cleveland airport to Chicago Midway. It is only a 10.1 mi journey to Hopkins Intl (CLE) from Cleveland’s city center.

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

    Flying on Frontier is currently your cheapest option to Chicago Midway Airport, with prices starting at $190. Additional round-trip tickets that might be worth considering are offered by Southwest and Delta, with the lowest prices starting at $197 and $217, respectively. Users have found that Frontier is 36% cheaper than the other options available to this destination.

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

    To fly one-way, consider booking your trip with Frontier, which is currently one of the cheapest options available, starting at $97. Southwest flights start at $99 while deals on Delta start at $109 one-way.

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

    Looking for the cheapest flight from Cleveland to Chicago Midway Airport? While on average our users pay $289, our data indicates the cheapest price to be $109. The most popular route (Cleveland Hopkins Intl - Chicago Midway), is priced around $197.

  • Can I find deals for flights from Cleveland to Midway that include hotel bookings?

    Yes. In addition to deals on Cleveland to Midway flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Cleveland to Midway?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Cleveland to Midway.

  • Can I find deals for business class flights from Cleveland to Midway?

    Yes. Cheapflights offers flight deals from Cleveland to Midway 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 Cleveland to Chicago Midway Airport?

    Currently, April is the cheapest month in which you can book a flight from Cleveland to Chicago Midway Airport (average of $160). Flying from Cleveland to Chicago Midway Airport in November is currently the most expensive (average of $249). 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
Merrillville
Hammond
Benton Harbor
Porter
Lansing
Valparaiso
Chesterton

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Top airline flying from Cleveland to Midway

Discover the top airline that operate flights from Cleveland to Midway. 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 mayo 1, 2025.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$172Average$281FlexibilityNo cancel feeOn-time63%

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