MDW - CLE

$68 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 3/2. 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, 0 bags

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
Travelers love KAYAK
41 299 237 searches in the past 7 days on KAYAK

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Everything you should know

Cheapest round-trip
$128
Frontier
Tue 2/3Wed 2/4
MDW - CLE • 1 stop
Cheapest non-stop
$207
Typical prices: $456-$617
Southwest
Sat 1/17Sun 1/18
MDW - CLE • Non-stop
Our travelers' advice
AI-powered summary based on content written by travel experts. AI can make mistakes.
Midway's compact terminal allows for quick departures.
Use the RTA Red Line to reach downtown Cleveland fast.
Expert advice
Expert advice
Expert advice
Expert advice
Start a new search
KAYAK searches 100s of sites at once to find you the best travel deals.
We hope you love your trip to Cleveland!
Flight Deals
Booking Insights
Expert advice
Flight 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

Tue, Feb 3 - Wed, Feb 4
Frontier Logo
1:20 pm - 10:42 pm
MDW
-
CLE
8h 22m1 stop
Frontier Logo
7:10 am - 12:05 pm
CLE
-
MDW
5h 55m1 stop
$128Frontier
Thu, Feb 19 - Tue, Feb 24
Frontier Logo
3:21 pm - 1:59 am
MDW
-
CLE
9h 38m1 stop
Frontier Logo
9:30 am - 7:07 pm
CLE
-
MDW
10h 37m1 stop
$146Frontier
Wed, Jan 21 - Thu, Jan 22
Frontier Logo
1:20 pm - 10:42 pm
MDW
-
CLE
8h 22m1 stop
Frontier Logo
7:10 am - 11:45 am
CLE
-
MDW
5h 35m1 stop
$178Frontier
Mon, Feb 16 - Fri, Feb 20
Frontier Logo
2:19 pm - 7:34 am
MDW
-
CLE
16h 15m1 stop
Frontier Logo
4:55 pm - 2:55 pm
CLE
-
MDW
23h 00m1 stop
$196Frontier
Sat, Jan 17 - Sun, Jan 18
Delta Logo
5:00 pm - 10:54 pm
MDW
-
CLE
4h 54m1 stop
Delta Logo
2:00 pm - 5:34 pm
CLE
-
MDW
4h 34m1 stop
$197Delta
Sat, Jan 17 - Sun, Jan 18
Delta Logo
1:28 pm - 10:54 pm
MDW
-
CLE
8h 26m2 stops
Delta Logo
6:30 am - 8:52 am
CLE
-
MDW
3h 22m1 stop
$202Delta
Sat, Jan 17 - Sun, Jan 18
Southwest Logo
9:55 am - 12:10 pm
MDW
-
CLE
1h 15mnonstop
Southwest Logo
6:15 am - 6:55 am
CLE
-
MDW
1h 40mnonstop
$207Southwest
Sun, Jan 25 - Fri, Jan 30
Frontier Logo
5:01 pm - 11:11 pm
MDW
-
CLE
29h 10m1 stop
Frontier Logo
11:53 am - 7:52 pm
CLE
-
MDW
8h 59m1 stop
$208Frontier
Sun, Jan 25 - Fri, Jan 30
Frontier Logo
5:01 pm - 2:50 pm
MDW
-
CLE
20h 49m2 stops
Frontier Logo
11:53 am - 7:52 pm
CLE
-
MDW
8h 59m1 stop
$212Frontier
Tue, Feb 3 - Wed, Feb 4
Multiple Airlines Logo
1:20 pm - 10:42 pm
MDW
-
CLE
8h 22m1 stop
Multiple Airlines Logo
7:02 pm - 10:19 pm
CLE
-
MDW
28h 17m2 stops
$214Multiple Airlines
Booking Insights

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 Mondays if you are looking for the best rates. For your return to Chicago Midway Airport, you’ll find the best rates on Tuesdays and the most expensive ones on Sundays.

Can I save money by flying with a layover from Chicago Midway Airport to Cleveland?

The average round-trip price for all non-stop flights, flights with one layover, and flights with two layovers for the route found by users searching on KAYAK in the last 2 weeks.

Yes, flying with a layover may cost you more time, but you can also save money on the route, with a 1 stop layover the cheapest option at $244 on average.

Find deals
Expert advice

Expert advice for your flight from Midway to Cleveland

 
AI-powered summary based on content written by travel experts. AI can make mistakes.
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

Good to know

Low seasonAugust
Cheapest flight$68
Best time to beat the crowds with an average 43% drop in price.
Most popular time to fly with an average 65% increase in price.
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 $68 for a one-way ticket and $128 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 737-700 Passenger/BBJ1 (winglets) 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 $209 or less one-way and $244 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 4257 reviews
8.6Crew
7.0Food
7.5Entertainment
8.0Comfort
8.1Boarding
Airline reviews

Flight was fine other than there was a gate change that I was not notified of. By chance I happened to check my phone and saw the change, otherwise, we would have missed our connecting flight.

8.0 ExcellentMaggie, Dec 2025
BWI - LAS
Read more Southwest reviews

Flight was fine other than there was a gate change that I was not notified of. By chance I happened to check my phone and saw the change, otherwise, we would have missed our connecting flight.

Haven’t flown on SW in years. Flight was on time departing and arriving. Served vegan butter onion flavored pretzels which were bad. Coke served was in a tiny paper cup. Crew was not engaging. Felt like they were going through the motions. Old plane, tight seats and no leg room.

Check-in, Boarding and flight were smooth. All the employees and crew was very nice and funny. They gave the kids crayons and workbooks to keep them occupied which was a big win. I’ve flown Southwest many times and that’s the first time I’ve seen that and it is a great addition.

Flight was on time. Wi-fi was a little spotty/slow. Boarding and exit were efficient.

Okay, not wonderful. Short flight. Wi-fi didn't work properly. Stuck waiting for a gate to open upon arrival for 20 or so minutes.

They sent a notice that they were boarding an hour early. We had to leave the club and run to the gate. They said sorry, that came from corporate and was a mistake. They did not have enough seating because the flight before it had not taken off on time. They moved our gate and delayed it for an hour.

The boarding and seat assignment system no longer works for me, but I know it is being replaced. Otherwise, I am good with the overall experience.

The lead steward kept singing about "San Francisco" and hotel California---more annoying than humorous....needs work. Flight was smooth and on time.

Still a fan of open seating. Flight was on schedule and arrived on time. The 737 MAX is very comfortable.

Airline travel is always too cramped to really be pleasant, but the cabin crew on this flight did a pretty good job of making up for it by putting on some music during boarding and sprinkling a few funny remarks into the safety briefing and announcements, and just generally being friendly and helpful. It definitely reminded me of why I prefer the in-flight experience on Southwest!

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

Information on your arrival and departure airports

Chicago Midway Airport (MDW)
Cleveland (CLE)