MDW - CLE

$55 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 11/15. 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
$227
Overall average: $305
Delta
Thu 12/11Thu 12/18
MDW - CLE • 1 stop
Cheapest non-stop
$252
Typical prices: $361-$509
Southwest
Sat 12/27Mon 1/5
MDW - CLE • Non-stop
Our travelers' advice
AI-generated summary based on content written by travel experts
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
Top airlines
Delta
Cheapest • from $227 (round-trip)
Southwest
Best reviews • 8.0 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
When to travel
November
Cheapest • 41% price drop
November
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
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

Thu, Dec 11 - Thu, Dec 18
Delta Logo
6:00 am - 1:07 pmMDW-CLE
6h 07m1 stop
Delta Logo
10:30 am - 12:34 pmCLE-MDW
3h 04m1 stop
$227Delta
Find Deal
Thu, Dec 11 - Thu, Dec 18
Delta Logo
1:50 pm - 11:53 pmMDW-CLE
9h 03m2 stops
Delta Logo
10:30 am - 12:34 pmCLE-MDW
3h 04m1 stop
$232Delta
Find Deal
Tue, Nov 18 - Wed, Nov 19
Southwest Logo
8:40 pm - 10:55 pmMDW-CLE
1h 15mnonstop
Southwest Logo
3:50 pm - 9:05 pmCLE-MDW
6h 15m1 stop
$241Southwest
Find Deal
Tue, Nov 18 - Sat, Nov 22
Frontier Logo
1:56 pm - 2:14 pmMDW-CLE
23h 18m1 stop
Frontier Logo
9:13 am - 5:07 pmCLE-MDW
8h 54m1 stop
$242Frontier
Find Deal
Wed, Nov 19 - Sat, Nov 22
Frontier Logo
1:56 pm - 10:32 amMDW-CLE
19h 36m1 stop
Frontier Logo
5:30 am - 2:40 pmCLE-MDW
10h 10m1 stop
$246Frontier
Find Deal
Thu, Jan 8 - Sun, Jan 11
Southwest Logo
1:25 pm - 8:50 pmMDW-CLE
6h 25m2 stops
Southwest Logo
7:05 pm - 7:40 pmCLE-MDW
1h 35mnonstop
$247Southwest
Find Deal
Sat, Nov 15 - Sun, Nov 16
Frontier Logo
6:15 am - 11:57 pmMDW-CLE
16h 42m2 stops
Frontier Logo
5:45 pm - 8:32 amCLE-MDW
15h 47m1 stop
$248Frontier
Find Deal
Mon, Nov 10 - Wed, Nov 12
Frontier Logo
6:27 pm - 1:31 pmMDW-CLE
18h 04m2 stops
Frontier Logo
1:46 pm - 9:12 amCLE-MDW
20h 26m1 stop
$249Frontier
Find Deal
Wed, Nov 19 - Sat, Nov 22
Multiple Airlines Logo
1:56 pm - 10:32 amMDW-CLE
19h 36m1 stop
Multiple Airlines Logo
7:51 pm - 4:30 pmCLE-MDW
21h 39m2 stops
$253Multiple Airlines
Find Deal
Sat, Nov 8 - Fri, Nov 14
Multiple Airlines Logo
6:15 am - 11:59 pmMDW-CLE
16h 44m2 stops
Multiple Airlines Logo
5:45 pm - 10:26 amCLE-MDW
17h 41m1 stop
$284Multiple Airlines
Find Deal
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 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 Tuesdays 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 November, where tickets cost $192 (return) on average. On the other hand, the most expensive months are July and March, where the average cost of round-trip tickets is $673 and $561 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 $267 on average.

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

Good to know

Low seasonFebruary
Cheapest flight$55
Best time to beat the crowds with an average 10% drop in price.
Most popular time to fly and prices are also 42% 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 $55 for a one-way ticket and $227 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 $75 or less one-way and $253 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 4240 reviews
8.1Boarding
8.6Crew
8.0Comfort
7.5Entertainment
7.0Food
Airline reviews

Full cans of soda would be nice. A choice between two snacks would be appreciated.

8.0 ExcellentMargaret, Oct 2025SAV - HOU
Read more Southwest reviews

Full cans of soda would be nice. A choice between two snacks would be appreciated.

Tried watching free movie and it kept freezing so I couldn’t finish.

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

Sacrament staff are always polite and helpful. Airport is easy to maneuver and boarding is straightforward.

Great flight. Outstanding Service. Southwest was able to put us on a direct flight to Denver when the connection could have been affected by a later arrival to Baltimore. The direct flight was less expensive that the flight with the connection in Baltimore.

Delays delays delays. Late taking off, late landing, wait for a gate, etc.

Boarded on time but once we were ready for take off, the crew determined that, although every seat was taken, somehow someone was on the wrong flight. Delay, delay delay, announcements and ended up with one person checking EVERY ID against their passenger Manifest only to figure out it was a "clerical error." We departed 54 minutes late causing me to run in the St. Louis Airport to make my connection and lose the priority boarding spot I had paid for. Unnecessary delay.

I was re-booked onto another flight because my original flight was delayed and I would have missed my connector. I ended up in the “C” group after paying extra to be in the “A “ group on the original flight. At least if you’re going to re-book people, re-book them into the same group.

Flight was delayed due to plane not passing inspection And one of the crew had to time out and we had to wait for another one A 3 hour delay

mandatory demand customer to check their carry on because not enough people check bags.

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

Information on your arrival and departure airports

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