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$64+ 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 8/29. Fares are subject to change and may not be available on all flights or dates of travel.
CLE — MDW
Aug 22 — Aug 291
Sat 8/22
Sat 8/29
1 adult, Economy
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Cheap 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 July 23, 2026.

This Southwest deal was found by Cheapflights users on 7/20. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/15:25 pm
CLE
-
MDW
Nonstop1h 15m
Southwest
Sun 9/69:25 am
MDW
-
CLE
Nonstop1h 15m
Southwest
Deal found 7/20$156
This Delta deal was found by Cheapflights users on 7/23. 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.
Wed 8/126:43 am
CLE
-
MDW
1 stop3h 34m
Delta
Sat 8/159:24 am
MDW
-
CLE
1 stop3h 16m
Delta
Deal found 7/23$157
This Delta deal was found by Cheapflights users on 7/22. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/136:43 am
CLE
-
MDW
1 stop3h 34m
Delta
Sat 8/159:24 am
MDW
-
CLE
1 stop3h 16m
Delta
Deal found 7/22$167
This Southwest deal was found by Cheapflights users on 7/18. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/288:35 am
CLE
-
MDW
Nonstop1h 20m
Southwest
Fri 10/304:20 pm
MDW
-
CLE
2 stops6h 25m
Southwest
Deal found 7/18$171
This Southwest deal was found by Cheapflights users on 7/20. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/76:15 am
CLE
-
MDW
2 stops6h 50m
Southwest
Wed 10/72:45 pm
MDW
-
CLE
2 stops5h 15m
Southwest
Deal found 7/20$176
This Southwest deal was found by Cheapflights users on 7/23. 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.
Thu 8/208:50 am
CLE
-
MDW
Nonstop1h 10m
Southwest
Thu 8/2010:30 am
MDW
-
CLE
1 stop6h 00m
Southwest
Deal found 7/23$177
This Delta deal was found by Cheapflights users on 7/20. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/52:20 pm
CLE
-
MDW
1 stop3h 39m
Delta
Sun 9/69:24 am
MDW
-
CLE
1 stop3h 16m
Delta
Deal found 7/20$178
This Delta deal was found by Cheapflights users on 7/20. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/306:00 am
CLE
-
MDW
1 stop4h 18m
Delta
Sat 11/149:30 am
MDW
-
CLE
1 stop3h 05m
Delta
Deal found 7/20$186
This Southwest deal was found by Cheapflights users on 7/21. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/38:50 am
CLE
-
MDW
Nonstop1h 10m
Southwest
Sun 9/69:25 am
MDW
-
CLE
Nonstop1h 15m
Southwest
Deal found 7/21$187

Find 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 July 23, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$156
(Southwest)

One-way from

$64
(Southwest)

Popular in

January

Cheapest in

September

Average price

$277

Good round-trip deal

$256 or less

Good one-way deal

$200 or less
Provider with most accurate pricing for Cleveland Hopkins Intl-Chicago Midway flight deals.
Search Deals
Provider most trusted by Cheapflights users for Cleveland Hopkins Intl-Chicago Midway flights.
Search Deals
From Cleveland Hopkins Intl to Chicago Midway
Search Deals
One-way flight from Cleveland Hopkins Intl to Chicago Midway
Search Deals
Highest demand for flights based on searches. 26% potential increase in price ($110 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 9% potential price decrease ($26 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 Cleveland Hopkins Intl to Chicago Midway.
Search Deals
Price to beat on a one-way flight from Cleveland Hopkins Intl to Chicago Midway.
Search Deals

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 July 23, 2026.
Use the filters below to find and compare flights from Cleveland to Chicago Midway Airport that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

ClevelandChicago

CLE - MDW

CLEMDW

Cleveland Hopkins Intl

Fri 9/11

6:30 am-9:07 am

1 stop3h 37m

Chicago Midway

Mon 9/14

7:01 pm-11:54 pm

1 stop3h 53m

$167

ClevelandChicago

CLE - MDW

CLEMDW

Cleveland Hopkins Intl

Fri 10/30

6:00 am-9:18 am

1 stop4h 18m

Chicago Midway

Sat 11/14

9:30 am-1:35 pm

1 stop3h 05m

$186
Quickest round-trip

ClevelandChicago

CLE - MDW

CLEMDW

Cleveland Hopkins Intl

Wed 9/9

12:50 pm-1:05 pm

Nonstop1h 15m

Chicago Midway

Sun 9/13

3:20 pm-5:30 pm

Nonstop1h 10m

$192

ClevelandChicago

CLE - MDW

CLEMDW

Cleveland Hopkins Intl

Sun 9/27

8:55 am-9:05 am

Nonstop1h 10m

Chicago Midway

Tue 9/29

6:05 pm-8:20 pm

Nonstop1h 15m

$192

ClevelandChicago

CLE - MDW

CLEMDW

Cleveland Hopkins Intl

Mon 8/10

7:15 pm-7:30 pm

Nonstop1h 15m

Chicago Midway

Tue 8/11

8:35 am-11:00 am

Nonstop1h 25m

$195

ClevelandChicago

CLE - MDW

CLEMDW

Cleveland Hopkins Intl

Fri 9/25

1:15 pm-4:55 pm

1 stop4h 40m

Chicago Midway

Mon 9/28

4:25 pm-6:40 pm

Nonstop1h 15m

$202

ClevelandChicago

CLE - MDW

CLEMDW

Cleveland Hopkins Intl

Wed 8/19

7:25 pm-9:50 pm

1 stop3h 25m

Chicago Midway

Fri 8/21

6:30 pm-8:45 pm

Nonstop1h 15m

$202

ClevelandChicago

CLE - MDW

CLEMDW

Cleveland Hopkins Intl

Thu 9/3

6:05 pm-10:20 pm

1 stop5h 15m

Chicago Midway

Mon 9/7

6:30 pm-8:45 pm

Nonstop1h 15m

$205

ClevelandChicago

CLE - MDW

CLEMDW

Cleveland Hopkins Intl

Fri 8/21

6:40 am-12:15 pm

2 stops6h 35m

Chicago Midway

Mon 8/24

8:05 am-10:25 am

Nonstop1h 20m

$207

ClevelandChicago

CLE - MDW

CLEMDW

Cleveland Hopkins Intl

Fri 8/28

7:20 pm-9:55 pm

1 stop3h 35m

Chicago Midway

Mon 8/31

2:35 pm-9:55 pm

2 stops6h 20m

$217

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/23

Showing 1-10 of 20 resultsSorted by cheapest first
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 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 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 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 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, September is the cheapest month in which you can book a flight from Cleveland to Chicago Midway Airport (average of $205). Flying from Cleveland to Chicago Midway Airport in January is currently the most expensive (average of $591). 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 July 23, 2026.

It’s optimal to fly from Cleveland to Chicago Midway Airport in the afternoon. By choosing this option you can save up to 21% 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 July 18, 2026.

Travelers seeking maximum savings on their Cleveland to Chicago Midway Airport flight should consider departing on Wednesday at noon when fares are most often at their lowest. Saturday at noon 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 Cleveland to Chicago Midway Airport?

Airfare is below average for this route at the moment.

Cleveland to Chicago Midway Airport flights typically cost between $188 and $424 in September.
The cheapest round-trip price found within the last 5 days was $156 on Southwest (Sep 1-Sep 6).

The best insider tips for Cleveland to Chicago Midway Airport 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 Cleveland to Chicago Midway Airport 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 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 July 23, 2026.
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
4,238 reviews

Crew

8.6

Food

7.0

Entertainment

7.5

Boarding

8.1

Overall

8.0

Comfort

8.0

Reviews

1 / 20
6.0
Good

Reza,Jun 2026

TPA - MDW

The seats were super cramped and couldn’t move without hitting other passengers
Southwest
8.0
Very good
4,238 reviews
Southwest
8.0
Very good
4,238 reviews

Crew

8.6

Food

7.0

Entertainment

7.5

Boarding

8.1

Overall

8.0

Comfort

8.0

Reviews

1 / 20
6.0
Good

Reza,Jun 2026

TPA - MDW

The seats were super cramped and couldn’t move without hitting other passengers

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.

  • 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 15m. Fly via Delta or Southwest 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 $137. Users have found that Southwest is 55% 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 $317, our data indicates the cheapest price to be $108. The most popular route (Cleveland Hopkins Intl - Chicago Midway), is priced around $97.

  • 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, September is the cheapest month in which you can book a flight from Cleveland to Chicago Midway Airport (average of $205). Flying from Cleveland to Chicago Midway Airport in January is currently the most expensive (average of $591). 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
Benton Harbor
Lansing
Merrillville
Valparaiso
Hammond
Saint Joseph
Porter

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 July 23, 2026.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$137Average$259FlexibilityNo cancel feeOn-time63%

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