MDW - CLE

$69 Find Cheap Flights from Chicago Midway Airport to Cleveland - Compare and Save

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 7/22. 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
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Everything you should know

Cheapest round-trip
$204
Southwest
Sat 8/8Sat 8/15
MDW - CLE • 1 stop
Cheapest non-stop
$217
Southwest
Wed 8/5Sun 8/9
MDW - CLE • Non-stop
Top airlines
Southwest
Cheapest • from $204 (round-trip)
Southwest
Best reviews • 7.9 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
Nonstop flights
Every day
You can fly direct with Southwest. Average duration is 1h 12m
Direct flights
Direct flights
+1
+1
Direct flights
Direct flights
+1
Top layover airports
Detroit (DTW)
Cheapest • Avg $236 (round-trip)
Detroit (DTW)
Shortest trip • 3h 23m (one-way)
Insights
Insights
Insights
Insights
When to travel
November
Cheapest • 100% price drop
March
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
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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

Sat, Aug 8 - Sat, Aug 15
Southwest Logo
2:25 pm - 8:20 pm
MDW
-
CLE
4h 55m
1 stop
Southwest Logo
5:40 am - 1:05 pm
CLE
-
MDW
8h 25m
2 stops
$204Southwest
Mon, Aug 10 - Mon, Aug 17
Southwest Logo
8:05 am - 10:25 am
MDW
-
CLE
1h 20mnonstop
Southwest Logo
11:00 am - 4:15 pm
CLE
-
MDW
6h 15m
1 stop
$205Southwest
Sat, Aug 1 - Sun, Aug 2
Southwest Logo
7:50 am - 10:05 am
MDW
-
CLE
1h 15mnonstop
Southwest Logo
5:45 pm - 11:45 pm
CLE
-
MDW
7h 00m
1 stop
$207Southwest
Tue, Sep 1 - Wed, Sep 2
Frontier Logo
11:50 am - 10:31 pm
MDW
-
CLE
9h 41m
1 stop
Frontier Logo
5:15 pm - 10:47 pm
CLE
-
MDW
6h 32m
1 stop
$210Frontier
Wed, Jul 29 - Mon, Aug 3
Southwest Logo
7:50 am - 10:05 am
MDW
-
CLE
1h 15mnonstop
Southwest Logo
6:50 am - 1:35 pm
CLE
-
MDW
7h 45m
2 stops
$212Southwest
Thu, Sep 24 - Thu, Oct 1
Delta Logo
9:29 am - 1:40 pm
MDW
-
CLE
3h 11m
1 stop
Delta Logo
10:27 am - 12:39 pm
CLE
-
MDW
3h 12m
1 stop
$215Delta
Wed, Jul 29 - Thu, Jul 30
Southwest Logo
11:50 am - 6:35 pm
MDW
-
CLE
5h 45m
1 stop
Southwest Logo
5:45 pm - 10:00 pm
CLE
-
MDW
5h 15m
1 stop
$217Southwest
Mon, Aug 10 - Mon, Aug 17
Southwest Logo
5:55 am - 12:35 pm
MDW
-
CLE
5h 40m
1 stop
Southwest Logo
6:40 am - 12:15 pm
CLE
-
MDW
6h 35m
2 stops
$220Southwest
Wed, Aug 5 - Wed, Aug 5
Southwest Logo
8:45 am - 5:00 pm
MDW
-
CLE
7h 15m
2 stops
Southwest Logo
7:25 pm - 9:50 pm
CLE
-
MDW
3h 25m
1 stop
$222Southwest
Thu, Sep 17 - Sat, Sep 19
Southwest Logo
4:25 pm - 6:40 pm
MDW
-
CLE
1h 15mnonstop
Southwest Logo
4:35 pm - 4:55 pm
CLE
-
MDW
1h 20mnonstop
$226Southwest
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.

How much is a round-trip flight from Chicago Midway Airport to Cleveland?

This analysis is based on the cheapest round-trip price found on KAYAK in the last 12 months by searching for a flight from Chicago Midway Airport to Cleveland departing in August.

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 Wednesday 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 Mondays.

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 November, where tickets cost $0 (return) on average. On the other hand, the most expensive months are July and April, where the average cost of round-trip tickets is $673 and $629 respectively.

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 $277 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.
Our travel experts
Stefanie Waldek

Stefanie Waldek

Expert on MDW

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 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$69
Best time to beat the crowds with an average 52% drop in price.
Most popular time to fly and prices are also 15% 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 5 days, the lowest price for a flight from Chicago Midway Airport to Cleveland was $69 for a one-way ticket and $204 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?

    American Airlines, and JetBlue offer 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 $103 or less one-way and $277 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.
7.9
SouthwestOverall score based on 4246 reviews
8.6Crew
8.1Boarding
8.0Comfort
7.5Entertainment
7.0Food
Airline reviews

OKay. I sat in the back of the plane and it was really loud between babies and little kids, and adults who.like to talk a lot and loudly most of the flight.

6.0 GoodAnonymous, Jun 2026
MDW - BDL
Read more Southwest reviews

OKay. I sat in the back of the plane and it was really loud between babies and little kids, and adults who.like to talk a lot and loudly most of the flight.

The first time I flew in the extra legroom section. It was difficult to notice a difference. I had bad luck with my neighbors. The crew was okay. Southwest has reduced the live TV options.

I flew twice this week on Southwest, was delayed over 2 hours both ways. From Pittsburgh to Chicago it was due to weather but the gate agents, pilot etc were great at updating everyone. Today from Midway to Pittsburgh the plane had come from an international location, kept getting delayed, no information was given until we were delayed for the third time. It was ridiculous, whoever scheduled that plane to fly to Pittsburgh after didn’t consider a lot of things.

The staff was very friendly, professional, and courteous. The overall flight was a great experience.

All was good. I just had a hard time getting connected to the WiFi/internet during the flight

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

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

My flight to Chicago left and landed early. My return flight left two minutes late and arrived 2 minutes late. My seat selections were ideal! There were no snacks going to Chicago and no snacks on the return trip. There are no charging outlets on board.

Excellent experience. WiFi worked on this leg of My trip

My experience with Southwest as a whole was good but coming out of Cancun to Chicago it was terrible. Not only was it a language barrier with customer service we stood there to ask questions and they act like they didn't even see you. So the first come approach is not all that great anymore.

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)