CLE - MDW

$55 Find Cheap Flights from Cleveland to Chicago Midway Airport

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Cleveland to Midway departing on 8/4. 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 Chicago Midway Airport

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

Cheap Flights from Cleveland to Midway (CLE-MDW)

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Cleveland to Midway 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 Cleveland to Midway

Wed, Aug 13 - Mon, Aug 18
Southwest Logo
11:35 am - 11:50 amCLE-MDW
1h 15mnonstop
Southwest Logo
4:35 pm - 6:50 pmMDW-CLE
1h 15mnonstop
$109Southwest
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Wed, Aug 13 - Mon, Aug 18
Southwest Logo
7:15 pm - 9:55 pmCLE-MDW
3h 40m1 stop
Southwest Logo
1:00 pm - 3:15 pmMDW-CLE
1h 15mnonstop
$119Southwest
Find Deal
Thu, Oct 2 - Mon, Oct 6
Southwest Logo
6:35 am - 6:50 amCLE-MDW
1h 15mnonstop
Southwest Logo
4:35 pm - 11:45 pmMDW-CLE
6h 10m2 stops
$124Southwest
Find Deal
Wed, Aug 13 - Mon, Aug 18
Southwest Logo
3:50 pm - 8:25 pmCLE-MDW
5h 35m1 stop
Southwest Logo
2:35 pm - 9:55 pmMDW-CLE
6h 20m1 stop
$129Southwest
Find Deal
Tue, Aug 5 - Wed, Aug 6
Delta Logo
6:00 pm - 9:42 pmCLE-MDW
4h 42m1 stop
Delta Logo
9:25 am - 1:29 pmMDW-CLE
3h 04m1 stop
$177Delta
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Sat, Aug 30 - Tue, Sep 2
Delta Logo
4:33 pm - 9:12 pmCLE-MDW
5h 39m1 stop
Delta Logo
9:30 am - 1:32 pmMDW-CLE
3h 02m1 stop
$208Delta
Find Deal
Sun, Aug 17 - Thu, Aug 21
Delta Logo
6:00 am - 9:16 amCLE-MDW
4h 16m1 stop
Delta Logo
9:31 am - 1:32 pmMDW-CLE
3h 01m1 stop
$211Delta
Find Deal
Sat, Jul 19 - Wed, Jul 23
Frontier Logo
6:25 pm - 10:35 pmCLE-MDW
5h 10m1 stop
Frontier Logo
11:39 am - 6:03 pmMDW-CLE
5h 24m1 stop
$232Frontier
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Mon, Jul 7 - Wed, Jul 9
Frontier Logo
7:26 pm - 10:40 amCLE-MDW
16h 14m1 stop
Frontier Logo
11:39 am - 6:03 pmMDW-CLE
5h 24m1 stop
$259Frontier
Find Deal
Sat, Oct 11 - Mon, Oct 13
Frontier Logo
6:58 pm - 7:44 amCLE-MDW
13h 46m1 stop
Frontier Logo
7:23 pm - 12:22 pmMDW-CLE
15h 59m1 stop
$260Frontier
Find Deal
Expert advice

Expert advice for your flight from Cleveland to Midway

 
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
CLE

Arrive 90 minutes before your flight at CLE for a smooth security experience, even during peak times.

Read more about CLEby Brandon Schultz
MDW

Take the CTA Orange Line from MDW to downtown Chicago in about 25-30 minutes for a hassle-free arrival.

Read more about MDWby Stefanie Waldek
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 Cleveland to Midway flights

Get data-powered insights and trends into flights from Cleveland to Midway 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 Cleveland to Chicago Midway Airport?

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

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

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

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Cleveland to Chicago Midway Airport, 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 Cleveland to Chicago Midway Airport is January, where tickets cost $188 (return) on average. On the other hand, the most expensive months are August and November, where the average cost of round-trip tickets is $435 and $389 respectively.

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

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.

No, with an average price for the route of $237, prices are generally cheapest when you fly direct.

Find deals

Good to know

Low seasonFebruary
High seasonSeptember
Cheapest flight$55
Best time to beat the crowds but there is an average 1% increase in price.
Most popular time to fly and prices are also 17% lower on average.
Flight from Cleveland to Chicago Midway Airport

When to book flights from Cleveland to Midway

Are your dates flexible? Find out the best times to travel from Cleveland to Midway 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 Cleveland to Chicago Midway Airport flights

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

    In the last 3 days, the lowest price for a flight from Cleveland to Chicago Midway Airport was $55 for a one-way ticket and $109 for a round-trip.

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

    No

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

    Cleveland and Chicago Midway Airport are both served by 1 main airport. You will leave Cleveland from Cleveland Hopkins Intl and will be arriving at Chicago Midway.

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

    American Airlines, Delta, and Alaska Airlines offer inflight Wi-Fi service on the Cleveland to Chicago Midway Airport flight route.

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

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

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

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

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

    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 Cleveland to Chicago Midway Airport.

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Chicago Midway Airport from Cleveland 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 Cleveland to Chicago Midway Airport?

    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 Chicago Midway Airport with an airline and back to Cleveland with another airline. Booking your flights between Cleveland and MDW 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 Cleveland to Chicago Midway Airport?

    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 Chicago Midway Airport from Cleveland 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 Cleveland to Chicago Midway Airport

  • Looking for a cheap flight? 25% of our users found flights on this route for $149 or less one-way and $253 or less round-trip.

Prefer to fly direct from Cleveland to Chicago Midway Airport?

Find which airlines fly direct from Cleveland Hopkins Intl Airport to Chicago Midway Airport, which days they fly and book direct flights.

Direct departures

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

Direct returns

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
See more direct flights

Top airline flying from Cleveland to Midway

 
See real verified KAYAK customer reviews for airlines flying from Cleveland to Chicago. 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 Cleveland to Midway? 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 4287 reviews
7.1Food
8.2Boarding
8.0Comfort
7.6Entertainment
8.6Crew
Airline reviews

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.

6.0 GoodDavid, Jun 2025BWI - COS
Read more Southwest reviews

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.

Plz don't take away free bags and free seating

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

Information on your arrival and departure airports

Cleveland (CLE)
Midway (MDW)

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