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$76+ 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 12/16. Fares are subject to change and may not be available on all flights or dates of travel.
CLE — MDW
Oct 11 — Oct 181
Sat 10/11
Sat 10/18
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 September 11, 2025.

Round-trip from

$139
(Kiwi.com)

One-way from

$76
(Southwest)

Popular in

August

Cheapest in

January

Average price

$237

Good round-trip deal

$236 or less

Good one-way deal

$163 or less
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. 5% potential increase in price ($15 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($8 potential savings vs. average RT price).
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Average for round-trip flights in September 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 September 11, 2025.

This Kiwi.com deal was found by Cheapflights users on 9/9. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/36:48 pmCLE - MDW
1 stop6h 42mFrontier
Wed 11/52:06 pmMDW - CLE
1 stop21h 16mFrontier
Deal found 9/9$139
This Southwest deal was found by Cheapflights users on 9/9. 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.
Mon 11/34:35 pmCLE - MDW
Nonstop1h 20mSouthwest
Wed 11/55:35 amMDW - CLE
1 stop5h 50mSouthwest
Deal found 9/9$142
This Priceline deal was found by Cheapflights users on 9/10. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/2611:27 amCLE - MDW
1 stop10h 25mFrontier
Fri 10/35:15 pmMDW - CLE
1 stop6h 28mFrontier
Deal found 9/10$143
This Priceline deal was found by Cheapflights users on 9/10. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/207:19 pmCLE - MDW
1 stop4h 58mFrontier
Mon 9/225:15 pmMDW - CLE
1 stop6h 28mFrontier
Deal found 9/10$144
This Kiwi.com deal was found by Cheapflights users on 9/11. 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 10/177:46 pmCLE - MDW
1 stop28h 01mFrontier
Tue 10/218:05 amMDW - CLE
1 stop8h 21mFrontier
Deal found 9/11$146
This Southwest deal was found by Cheapflights users on 9/11. 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 11/112:55 pmCLE - MDW
Nonstop1h 15mSouthwest
Tue 11/45:35 amMDW - CLE
1 stop5h 50mSouthwest
Deal found 9/11$151
This Kiwi.com deal was found by Cheapflights users on 9/10. 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.
Thu 9/189:50 pmCLE - MDW
1 stop12h 03mFrontier
Fri 9/195:15 pmMDW - CLE
1 stop6h 28mFrontier
Deal found 9/10$152
This Frontier deal was found by Cheapflights users on 9/10. 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.
Fri 9/265:30 amCLE - MDW
1 stop11h 30mFrontier
Mon 9/295:15 pmMDW - CLE
1 stop6h 28mFrontier
Deal found 9/10$153
This Frontier deal was found by Cheapflights users on 9/10. 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.
Sat 10/47:19 pmCLE - MDW
1 stop5h 22mFrontier
Sun 10/56:21 amMDW - CLE
1 stop17h 14mFrontier
Deal found 9/10$155
This Southwest deal was found by Cheapflights users on 9/11. 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 10/288:50 amCLE - MDW
1 stop4h 10mSouthwest
Wed 10/298:35 pmMDW - CLE
Nonstop1h 10mSouthwest
Deal found 9/11$156
This Kiwi.com deal was found by Cheapflights users on 9/10. 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.
Thu 10/27:34 pmCLE - MDW
1 stop5h 07mFrontier
Sun 10/56:21 amMDW - CLE
1 stop17h 14mFrontier
Deal found 9/10$157

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 September 11, 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

Mon 10/6

11:57 am-8:52 pm

1 stop9h 55m

Chicago Midway

Tue 10/7

8:05 am-5:44 pm

1 stop8h 39m

$143

ClevelandChicago

CLE - MDW

CLEMDW

Cleveland Hopkins Intl

Sat 11/1

12:55 pm-1:10 pm

Nonstop1h 15m

Chicago Midway

Tue 11/4

5:35 am-12:25 pm

1 stop5h 50m

$151

ClevelandChicago

CLE - MDW

CLEMDW

Cleveland Hopkins Intl

Sat 12/6

6:10 am-11:45 am

1 stop6h 35m

Chicago Midway

Sat 12/6

4:45 pm-9:55 pm

1 stop4h 10m

$171

ClevelandChicago

CLE - MDW

CLEMDW

Cleveland Hopkins Intl

Thu 11/13

1:47 pm-6:18 pm

1 stop5h 31m

Chicago Midway

Mon 11/17

9:32 am-1:42 pm

1 stop3h 10m

$177

ClevelandChicago

CLE - MDW

CLEMDW

Cleveland Hopkins Intl

Tue 9/30

8:12 am-11:48 am

1 stop4h 36m

Chicago Midway

Wed 10/1

10:35 am-5:03 pm

1 stop5h 28m

$177

ClevelandChicago

CLE - MDW

CLEMDW

Cleveland Hopkins Intl

Fri 12/5

5:22 am-8:54 am

1 stop4h 32m

Chicago Midway

Sun 12/7

6:40 pm-11:53 pm

1 stop4h 13m

$177

ClevelandChicago

CLE - MDW

CLEMDW

Cleveland Hopkins Intl

Wed 10/29

5:09 pm-10:14 pm

1 stop6h 05m

Chicago Midway

Thu 10/30

9:35 am-1:46 pm

1 stop3h 11m

$177

ClevelandChicago

CLE - MDW

CLEMDW

Cleveland Hopkins Intl

Tue 9/30

4:30 pm-9:36 pm

1 stop6h 06m

Chicago Midway

Fri 10/3

1:08 pm-7:06 pm

1 stop4h 58m

$177

ClevelandChicago

CLE - MDW

CLEMDW

Cleveland Hopkins Intl

Wed 10/15

5:20 am-8:40 am

1 stop4h 20m

Chicago Midway

Thu 10/16

9:35 am-3:20 pm

1 stop4h 45m

$177

ClevelandChicago

CLE - MDW

CLEMDW

Cleveland Hopkins Intl

Tue 10/7

1:05 pm-1:20 pm

Nonstop1h 15m

Chicago Midway

Thu 10/9

9:55 pm-12:05 am

Nonstop1h 10m

$181

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/9

Showing 1-10 of 18 results
1
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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

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 September 11, 2025.

It’s optimal to fly from Cleveland to Chicago Midway Airport in the evening. By choosing this option you can save up to 12% 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 September 7, 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 at noon flights should be avoided if possible as fares are typically the most expensive at this time.

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 September 11, 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
4,248 reviews

Entertainment

7.5

Food

7.0

Overall

8.0

Comfort

8.0

Crew

8.6

Boarding

8.1

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
4,248 reviews
Southwest
8.0
Very good
4,248 reviews

Entertainment

7.5

Food

7.0

Overall

8.0

Comfort

8.0

Crew

8.6

Boarding

8.1

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 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 Frontier, Southwest, or Delta 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 $289, our data indicates the cheapest price to be $118. The most popular route (Cleveland Hopkins Intl - Chicago Midway), is priced around $101.

  • 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 Chicago Midway Airport?

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

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 September 11, 2025.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$141Average$277FlexibilityNo cancel feeOn-time63%

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