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$100+ 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 12/9. Fares are subject to change and may not be available on all flights or dates of travel.
CLE — MDW
Nov 26 — Dec 31
Wed 11/26
Wed 12/3
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 October 27, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$175
(Kiwi.com)

One-way from

$100
(Kiwi.com)

Popular in

November

Cheapest in

January

Average price

$277

Good round-trip deal

$292 or less

Good one-way deal

$193 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. 9% potential increase in price ($29 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($7 potential savings vs. average RT price).
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Average for round-trip flights in October 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 October 27, 2025.

This Kiwi.com deal was found by Cheapflights users on 10/26. 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 12/512:06 pmCLE - MDW
1 stop11h 06mFrontier
Sun 12/76:37 pmMDW - CLE
2 stops19h 51mFrontier
Deal found 10/26$175
This Kiwi.com deal was found by Cheapflights users on 10/26. 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 12/54:38 pmCLE - MDW
2 stops22h 21mFrontier
Mon 12/88:42 pmMDW - CLE
1 stop14h 29mFrontier
Deal found 10/26$178
This Booking.com deal was found by Cheapflights users on 10/26. 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.
Thu 11/134:15 pmCLE - MDW
1 stop20h 15mFrontier
Sun 11/1612:30 pmMDW - CLE
1 stop10h 21mFrontier
Deal found 10/26$181
This Kiwi.com deal was found by Cheapflights users on 10/26. 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.
Thu 12/48:20 pmCLE - MDW
1 stop15h 48mFrontier
Sun 12/76:37 pmMDW - CLE
2 stops19h 51mFrontier
Deal found 10/26$182
This Priceline deal was found by Cheapflights users on 10/26. 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 11/66:00 amCLE - MDW
1 stop6h 30mFrontier
Mon 11/1012:30 pmMDW - CLE
1 stop10h 21mFrontier
Deal found 10/26$183
This Kiwi.com deal was found by Cheapflights users on 10/27. 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.
Thu 12/115:33 pmCLE - MDW
1 stop5h 39mFrontier
Thu 12/186:12 amMDW - CLE
1 stop9h 18mFrontier
Deal found 10/27$184
This Kiwi.com deal was found by Cheapflights users on 10/25. 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 11/87:20 amCLE - MDW
1 stop15h 15mMultiple Airlines
Tue 11/111:56 pmMDW - CLE
2 stops33h 03mMultiple Airlines
Deal found 10/25$185
This Kiwi.com deal was found by Cheapflights users on 10/26. 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.
Thu 12/118:20 pmCLE - MDW
2 stops24h 22mFrontier
Mon 12/156:15 amMDW - CLE
1 stop10h 03mFrontier
Deal found 10/26$186
This Booking.com deal was found by Cheapflights users on 10/26. 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.
Thu 11/136:00 amCLE - MDW
1 stop6h 30mFrontier
Fri 12/58:05 amMDW - CLE
1 stop7h 02mFrontier
Deal found 10/26$187
This Booking.com deal was found by Cheapflights users on 10/24. 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.
Fri 10/315:45 pmCLE - MDW
1 stop17h 41mFrontier
Fri 11/712:14 pmMDW - CLE
1 stop4h 24mFrontier
Deal found 10/24$188

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 October 27, 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

Thu 12/11

1:10 pm-1:35 pm

Nonstop1h 25m

Chicago Midway

Mon 12/15

1:40 pm-3:50 pm

Nonstop1h 10m

$207

ClevelandChicago

CLE - MDW

CLEMDW

Cleveland Hopkins Intl

Thu 12/4

6:20 am-9:55 am

1 stop4h 35m

Chicago Midway

Mon 12/8

8:40 pm-10:55 pm

Nonstop1h 15m

$217

ClevelandChicago

CLE - MDW

CLEMDW

Cleveland Hopkins Intl

Fri 12/5

1:10 pm-1:35 pm

Nonstop1h 25m

Chicago Midway

Mon 12/8

10:05 am-12:30 pm

Nonstop1h 25m

$232

ClevelandChicago

CLE - MDW

CLEMDW

Cleveland Hopkins Intl

Wed 12/24

6:20 am-10:12 pm

1 stop16h 52m

Chicago Midway

Mon 12/29

3:10 pm-7:43 am

1 stop15h 33m

$239

ClevelandChicago

CLE - MDW

CLEMDW

Cleveland Hopkins Intl

Thu 12/4

7:20 pm-10:35 pm

1 stop4h 15m

Chicago Midway

Sun 12/7

7:10 pm-9:25 pm

Nonstop1h 15m

$242

ClevelandChicago

CLE - MDW

CLEMDW

Cleveland Hopkins Intl

Fri 12/12

5:30 am-8:50 am

1 stop4h 20m

Chicago Midway

Mon 12/15

10:05 am-12:30 pm

Nonstop1h 25m

$242

ClevelandChicago

CLE - MDW

CLEMDW

Cleveland Hopkins Intl

Sat 12/6

6:45 am-7:20 am

Nonstop1h 35m

Chicago Midway

Sun 12/7

9:40 am-11:55 am

Nonstop1h 15m

$244

ClevelandChicago

CLE - MDW

CLEMDW

Cleveland Hopkins Intl

Mon 11/24

3:43 pm-6:08 pm

1 stop3h 25m

Chicago Midway

Mon 12/1

1:15 pm-6:58 pm

1 stop4h 43m

$253

ClevelandChicago

CLE - MDW

CLEMDW

Cleveland Hopkins Intl

Mon 11/24

7:05 am-11:52 am

1 stop5h 47m

Chicago Midway

Sun 11/30

9:34 am-1:42 pm

1 stop3h 08m

$253

ClevelandChicago

CLE - MDW

CLEMDW

Cleveland Hopkins Intl

Mon 12/1

6:15 pm-9:55 pm

1 stop4h 40m

Chicago Midway

Mon 12/8

10:05 am-12:30 pm

Nonstop1h 25m

$262

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/25

Showing 1-10 of 19 results
1
2

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 October.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*1 star
eDreamsPrice Accuracy3 starsTrust Score*3 stars
PricelinePrice Accuracy1 starTrust 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 eDreams to be most consistent on Cheapflights vs. eDreams Users can find the same prices on Cleveland-Chicago Midway Airport flight deals on Cheapflights vs. eDreams >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, August is the cheapest month in which you can book a flight from Cleveland to Chicago Midway Airport (average of $94). Flying from Cleveland to Chicago Midway Airport in December is currently the most expensive (average of $191). 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 October 27, 2025.

It’s optimal to fly from Cleveland to Chicago Midway Airport in the afternoon. By choosing this option you can save up to 16% 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 October 26, 2025.

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

The best insider tips for Cleveland to Chicago Midway Airport flights

Snippets provided in this section are AI-generated based on a summarization of Cheapflights-commissioned articles. The articles are presented as-is, for general informational purposes only, and may not be up-to-date. The opinions contained in the articles are original to the author and reflect their authentic experience, which may vary significantly from the experience of others.
Cheapflights partnered with top experts to bring you the best recommendations for your Cleveland to Chicago Midway Airport trip
Airports
CLE

Reserve a parking spot at CLE to ensure availability, especially for early flights. Over 6,000 spots are available, with closer spots costing more.

Read more about CLEby Ramsey Qubein
MDW

Use the Orange Line train from MDW for a quick, 30-minute ride to downtown Chicago. It's affordable and operates almost 24 hours.

Read more about MDWby 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 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 October 27, 2025.
Get a feel of what it's like to fly with Southwest from Cleveland to Chicago Midway Airport by reading reviews from past customers. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,236 reviews

Food

7.0

Entertainment

7.5

Boarding

8.1

Comfort

8.0

Crew

8.6

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Southwest
8.0
Very good
4,236 reviews
Southwest
8.0
Very good
4,236 reviews

Food

7.0

Entertainment

7.5

Boarding

8.1

Comfort

8.0

Crew

8.6

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines

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 1 outbound flight 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.

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

    There are many flights that can get you from Cleveland to Chicago Midway Airport in 1h 25m. Fly via Southwest or Frontier to get the fastest option. Cleveland and Chicago Midway Airport are separated by a distance of 305 mi. This flight may include one or multiple stops.

  • What is the cheapest airline to fly from Cleveland to Chicago Midway Airport round-trip?

    Flying on Southwest is currently your cheapest option to Chicago Midway Airport, with prices starting at $141. Users have found that Southwest is 49% cheaper than the other options available to this destination.

  • 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 $319, our data indicates the cheapest price to be $119. The most popular route (Cleveland Hopkins Intl - Chicago Midway), is priced around $174.

  • 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, August is the cheapest month in which you can book a flight from Cleveland to Chicago Midway Airport (average of $94). Flying from Cleveland to Chicago Midway Airport in December is currently the most expensive (average of $191). 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 Chicago Midway Airport?

Book flights to Chicago Midway Airport if you plan to visit one of these locations
Merrillville
Lansing
Hammond
Porter
Benton Harbor

Browse thousands of different options on Cheapflights for your next trip

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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 October 27, 2025.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$141Average$283FlexibilityNo cancel feeOn-time63%

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