MDW - CLE

$69 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 8/28. 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
Travelers love KAYAK
41,299,237 searches in the past 7 days on KAYAK

Save 20% or moreCompare multiple travel sites with one search.

Track pricesNot ready to book? Create a price alert for when prices drop.

Bundle and saveSave money when you bundle your flight + hotel.

Filter your dealsChoose cabin class, free Wi-Fi and more.

Flights Deals
Expert advice
Useful Info
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, Aug 7 - Mon, Aug 11
Southwest Logo
4:35 pm - 6:50 pmMDW-CLE
1h 15mnonstop
Southwest Logo
7:35 pm - 7:50 pmCLE-MDW
1h 15mnonstop
$137Southwest
Find Deal
Wed, Aug 13 - Sat, Aug 16
Southwest Logo
3:30 pm - 5:45 pmMDW-CLE
1h 15mnonstop
Southwest Logo
7:15 am - 7:30 amCLE-MDW
1h 15mnonstop
$144Southwest
Find Deal
Thu, Aug 7 - Mon, Aug 11
Southwest Logo
9:30 am - 11:45 amMDW-CLE
1h 15mnonstop
Southwest Logo
4:00 pm - 8:35 pmCLE-MDW
5h 35m1 stop
$147Southwest
Find Deal
Thu, Aug 7 - Mon, Aug 11
Southwest Logo
9:30 am - 11:45 amMDW-CLE
1h 15mnonstop
Southwest Logo
5:50 am - 1:30 pmCLE-MDW
8h 40m2 stops
$152Southwest
Find Deal
Tue, Aug 12 - Tue, Aug 19
Delta Logo
6:04 am - 11:23 amMDW-CLE
4h 19m1 stop
Delta Logo
8:10 am - 11:48 amCLE-MDW
4h 38m1 stop
$177Delta
Find Deal
Wed, Jul 9 - Sun, Jul 13
Frontier Logo
11:39 am - 6:03 pmMDW-CLE
5h 24m1 stop
Frontier Logo
11:37 am - 10:24 pmCLE-MDW
11h 47m1 stop
$180Frontier
Find Deal
Wed, Aug 13 - Sat, Aug 16
Delta Logo
9:31 am - 1:32 pmMDW-CLE
3h 01m1 stop
Delta Logo
7:06 am - 12:28 pmCLE-MDW
6h 22m2 stops
$182Delta
Find Deal
Thu, Jun 26 - Sun, Jun 29
Frontier Logo
2:55 pm - 12:36 amMDW-CLE
8h 41m1 stop
Frontier Logo
7:10 am - 10:32 pmCLE-MDW
16h 22m1 stop
$190Frontier
Find Deal
Fri, Jun 27 - Sun, Jun 29
Logo
10:34 am - 9:49 amMDW-CLE
22h 15m2 stops
Logo
1:00 pm - 9:44 amCLE-MDW
21h 44m2 stops
$413
Find Deal
Fri, Jul 11 - Sun, Jul 13
Logo
10:31 am - 11:32 amMDW-CLE
24h 01m3 stops
Logo
12:37 pm - 9:41 amCLE-MDW
22h 04m2 stops
$427
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.

Find deals

Good to know

Low seasonFebruary
High seasonNovember
Cheapest flight$69
Best time to beat the crowds with an average 20% drop in price.
Most popular time to fly and prices are also 30% 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 $69 for a one-way ticket and $137 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 737-800 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 $121 or less one-way and $214 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

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 4278 reviews
8.6Crew
7.6Entertainment
8.0Comfort
7.1Food
8.2Boarding
Airline reviews

Southwest is Southwest. No frills. If you're luck enough to get a happy crew (we did), then it makes for a nicer flight.

10.0 ExcellentMichael, Jun 2025SMF - SEA
Read more Southwest reviews

Southwest is Southwest. No frills. If you're luck enough to get a happy crew (we did), then it makes for a nicer flight.

Southwest is typically delayed, and it gets wearisome. It is no longer a discount airline and you get way less than you pay for when it comes to comfort and Ce.

We sat on the plane on the tarmac for 4 hours.

I'm not a fan of Southwest's model. I don't like the herding style of boarding.

Flight crew and cabin crew were great. I had to rearrange flights because my original flight was 3hrs delayed for weather, the rub is the flight I moved to boarded on time then we sat at the gate for 2 hours because scheduling stole our first officer for another flight, TWICE. Then our actual FO was an hour delayed. To make it worse my original flight went from a 3 hour delay to departing 15min EARLY. Just poor scheduling operations all around.

Bring back peanuts Take our drink orders when were all seated, especially after you switch to assigned seating.

Staff was far less than helpful at all times. Departure and arrival times mean nothing to Southwest. Extremely disappointed, will never fly with them again, and I’ll be sure to share my experience with all.

It is southwest seat was ok. Not the most comfortable seat

I’ve always loved Southwest. No issues at all. I was flying standby and the gate agent was extremely friendly and helpful. Boarding was smooth and I was able to get a window seat in the emergency exit row. Crew was fantastic! They were very professional and accommodating. We had to divert from our destination due to weather but the flight crew kept everyone at ease and informed us of all pertinent information. Excellent flight

The price of the tickets isn't matching the flight experience. No matter how long the flight is, you're only getting pretzels. The flight attendants looked unkept and over it.

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)

Not what you’re looking for? Find thousands of other hotels, flights, car rentals and package deals with KAYAK.