MDW - CLE

$53 Find Cheap Flights from Chicago Midway Airport to Cleveland

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Midway to Cleveland departing on 8/19. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
1 adult, Economy

KAYAK searches hundreds of travel sites at once for deals on flights to Cleveland

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to Cleveland, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to Cleveland, as well as popular online travel agencies
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Flights Deals

Cheap Flights from Midway to Cleveland (MDW-CLE)

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Midway to Cleveland that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Midway to Cleveland

Thu, Sep 18 - Sun, Sep 21
Frontier Logo
5:04 pm - 12:43 amMDW-CLE
6h 39m1 stop
Frontier Logo
6:00 am - 12:44 pmCLE-MDW
7h 44m1 stop
$107Frontier
Find Deal
Fri, Oct 3 - Sun, Oct 5
Frontier Logo
5:04 pm - 12:43 amMDW-CLE
6h 39m1 stop
Frontier Logo
6:00 am - 12:44 pmCLE-MDW
7h 44m1 stop
$124Frontier
Find Deal
Sat, Aug 2 - Mon, Aug 4
Southwest Logo
3:30 pm - 5:40 pmMDW-CLE
1h 10mnonstop
Southwest Logo
8:00 pm - 8:20 pmCLE-MDW
1h 20mnonstop
$127Southwest
Find Deal
Tue, Aug 19 - Fri, Aug 22
Frontier Logo
9:16 am - 5:31 pmMDW-CLE
7h 15m1 stop
Frontier Logo
12:20 pm - 6:05 pmCLE-MDW
6h 45m1 stop
$130Frontier
Find Deal
Sat, Aug 2 - Mon, Aug 4
Southwest Logo
3:30 pm - 5:40 pmMDW-CLE
1h 10mnonstop
Southwest Logo
5:45 pm - 9:40 pmCLE-MDW
4h 55m1 stop
$137Southwest
Find Deal
Fri, Aug 8 - Wed, Aug 13
Southwest Logo
9:30 am - 11:45 amMDW-CLE
1h 15mnonstop
Southwest Logo
6:40 pm - 7:00 pmCLE-MDW
1h 20mnonstop
$139Southwest
Find Deal
Wed, Aug 6 - Sat, Aug 9
Southwest Logo
10:30 am - 6:20 pmMDW-CLE
6h 50m2 stops
Southwest Logo
7:15 am - 7:30 amCLE-MDW
1h 15mnonstop
$142Southwest
Find Deal
Sat, Aug 16 - Sat, Aug 23
Delta Logo
9:31 am - 1:36 pmMDW-CLE
3h 05m1 stop
Delta Logo
2:16 pm - 6:37 pmCLE-MDW
5h 21m1 stop
$177Delta
Find Deal
Sat, Aug 16 - Sat, Aug 23
Delta Logo
9:31 am - 1:36 pmMDW-CLE
3h 05m1 stop
Delta Logo
7:05 am - 12:28 pmCLE-MDW
6h 23m2 stops
$182Delta
Find Deal
Fri, Aug 15 - Fri, Aug 22
Delta Logo
7:17 pm - 12:30 amMDW-CLE
4h 13m1 stop
Delta Logo
8:30 am - 12:28 pmCLE-MDW
4h 58m1 stop
$208Delta
Find Deal
Expert advice

Expert advice for your flight from Midway to Cleveland

 
Snippets provided in this section are AI-generated based on a summarization of KAYAK-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.
KAYAK teamed up with top travel experts to share the best tips for your journey.
Airports
MDW

Midway offers a compact terminal with easy navigation, making it ideal for quick departures. Enjoy local dining like Billy Goat Tavern before your flight.

Read more about MDWby Stefanie Waldek
CLE

Use the RTA Red Line from CLE to reach downtown Cleveland in under 30 minutes. Trains depart every 15 minutes from the airport station.

Read more about CLEby Brandon Schultz
Our travel experts
Stefanie Waldek

Stefanie Waldek

Expert on MDW

Stefanie Waldek

Stefanie Waldek

Stefanie Waldek is a freelance space, travel, and design writer based in Saratoga Springs, NY. Her words have appeared in Space.com, Travel + Leisure, Condé Nast Traveler, Architectural Digest, and House Beautiful, among other publications. An expert in aviation and expedition cruising, Stefanie is frequently up in the air or on the sea, likely en route to Antarctica or the Arctic.

Read more
Brandon Schultz

Brandon Schultz

Expert on CLE

Brandon Schultz

Brandon Schultz

Brandon Schultz is an award-winning food and travel writer based in New York City. His work has appeared in Forbes, AAA, Thrillist, Travel + Leisure, and The Daily Meal, among many others, and he is the author of 6 books, including 3 cookbooks.

Read more
Useful Info

KAYAK's insights & trends for Midway to Cleveland flights

Get data-powered insights and trends into flights from Midway to Cleveland to help you find the cheapest flights, the best time to fly and much more.

What’s the cheapest day of the week to fly from Chicago Midway Airport to Cleveland?

The average price of all round-trip flights from Chicago Midway Airport to Cleveland clicked on KAYAK for each day over the last 12 months.

When flying from Chicago Midway Airport to Cleveland, you should consider leaving on a Saturday and avoid Sundays if you are looking for the best rates. For your return to Chicago Midway Airport, you’ll find the best rates on Saturdays and the most expensive ones on Sundays.

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

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Chicago Midway Airport to Cleveland, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.

The cheapest month for flights from Chicago Midway Airport to Cleveland is June, where tickets cost $237 (return) on average. On the other hand, the most expensive months are July and March, where the average cost of round-trip tickets is $679 and $561 respectively.

Good to know

Low seasonFebruary
High seasonNovember
Cheapest flight$53
Best time to beat the crowds with an average 20% drop in price.
Most popular time to fly and prices are also 29% lower on average.
Flight from Chicago Midway Airport to Cleveland

When to book flights from Midway to Cleveland

Are your dates flexible? Find out the best times to travel from Midway to Cleveland based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated round-trip price
KAYAK looks at all historical flight data for each date to provide a predicted price for one-way trips or round-trips with a duration up to 40 days. While we try to provide actual minimum prices for each date, some prices are predictions and actual prices may differ.

FAQs for booking Chicago Midway Airport to Cleveland flights

  • What is the cheapest flight from Chicago Midway Airport to Cleveland?

    In the last 3 days, the lowest price for a flight from Chicago Midway Airport to Cleveland was $53 for a one-way ticket and $107 for a round-trip.

  • Do I need a passport to fly between Chicago Midway Airport and Cleveland?

    Even though you are not required to have a passport, keep in mind that an official ID is needed to board the airplane.

  • Which airports will I be using when flying from Chicago Midway Airport to Cleveland?

    Chicago Midway Airport airport is called Chicago Midway and the only airport in Cleveland is Cleveland Hopkins Intl.

  • Which airlines offer Wi-Fi service onboard planes from Chicago Midway Airport to Cleveland?

    Only American Airlines offers inflight Wi-Fi service on the Chicago Midway Airport to Cleveland flight route.

  • Which aircraft models fly most regularly from Chicago Midway Airport to Cleveland?

    The Boeing 737 MAX 8 is the aircraft model that flies most regularly on the Chicago Midway Airport to Cleveland flight route.

  • On which days can I fly direct from Chicago Midway Airport to Cleveland?

    There are nonstop flights from Chicago Midway Airport to Cleveland on a daily basis.

  • How does KAYAK find such low prices on flights from Chicago Midway Airport to Cleveland?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Chicago Midway Airport to Cleveland.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Chicago Midway Airport to Cleveland?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Cleveland from Chicago Midway Airport is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Chicago Midway Airport to Cleveland?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Cleveland with an airline and back to Chicago Midway Airport with another airline. Booking your flights between Chicago Midway Airport and CLE can sometimes prove cheaper using this method.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Chicago Midway Airport to Cleveland?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Cleveland from Chicago Midway Airport up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

KAYAK’s top tips for finding a cheap flight from Chicago Midway Airport to Cleveland

  • Looking for a cheap flight? 25% of our users found flights on this route for $118 or less one-way and $247 or less round-trip.

Prefer to fly direct from Chicago Midway Airport to Cleveland?

 
Direct data is based off flight results for the next 60 days. Find direct flights from all airlines flying direct from Chicago Midway to Cleveland Hopkins Intl.
Find which airlines fly direct from Chicago Midway Airport to Cleveland Hopkins Intl Airport, which days they fly and book direct flights.

Direct departures

Chicago Midway to Cleveland Hopkins Intl

Monday

Southwest

Southwest

Tuesday

Southwest

Southwest

Wednesday

Southwest

Southwest

Thursday

Southwest

Southwest

Friday

Southwest

Southwest

Saturday

Southwest

Southwest

Sunday

Southwest

Southwest

See more direct flights

Direct returns

Cleveland Hopkins Intl to Chicago Midway

Monday

Southwest

Southwest

Tuesday

Southwest

Southwest

Wednesday

Southwest

Southwest

Thursday

Southwest

Southwest

Friday

Southwest

Southwest

Saturday

Southwest

Southwest

Sunday

Southwest

Southwest

See more direct flights

Reviews of the top airline flying from Midway to Cleveland

 
See real verified KAYAK customer reviews for airlines flying from Chicago to Cleveland. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with from Midway to Cleveland? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
8.0
SouthwestOverall score based on 4266 reviews
8.0Comfort
7.0Food
8.6Crew
7.6Entertainment
8.2Boarding
Airline reviews

Delayed flight. Nicest crew member was a SW pilot flying seated next to me who kindly move to seat the final passenger. Flight extra delayed. My cup of refreshment of ginger ale was so packed with ice it was literally 2 sips.

4.0 OkayTraci, Jun 2025OAK - SEA
Read more Southwest reviews

Delayed flight. Nicest crew member was a SW pilot flying seated next to me who kindly move to seat the final passenger. Flight extra delayed. My cup of refreshment of ginger ale was so packed with ice it was literally 2 sips.

For my birthday trip this was my second time ever flying, this trip was the best.

after landing, we stay 2 hours on the taxi way before reaching the gate The airline and the crew were good though

No trays in our seats, we sat in first row, purchased a business class fare. Had to hold our drinks and snack in our hands. No plugs for our cell phones. Had to pay for it a drink cocktail each. Seats so uncomfortable.

Flight wasn’t even full, but too many carry-ons caused us to run out of bin space. New bag fee has folks who would usually check their bags carrying on. Watching Southwest morph into Spirit/Frontier is so sad to watch

Sat on tarmac for 2 hours and then missed my connecting flight

First time traveling on Southwest since bag fees were implemented. Usual good service. Just more expensive now.

Everything was on time. I was disappointed by the front section female, African American flight attendant. I did not see her name tag or would have identified by name not race. As passengers moved to the bathroom early in flight, she would say with a disdainful tone “I have to say the seat belt light is on” then go back to her book. Better trained flight attendants say something like be careful the seat belt light is on.

Cluster mess boarding. Can't wait for SWA reserved seating. Internet didn't seem to work on the plane.

Flights delayed by 4-6 hours. Boarding was a mess and unclear. Bags were not at arrival airport and had never even been put on the plane. No idea when I’ll get them. Don’t fly into Denver!

Everything you need to know for your flight from Midway to Cleveland

Information on your arrival and departure airports

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