MDW - CLE

$91 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 7/2. 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

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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Flights Deals

Cheap Flights from Midway to Cleveland

 
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.

Recent round-trip flight deals from Midway to Cleveland

KAYAK's recommended round-trip deals from the most popular airlines that fly from Midway to Cleveland.
Discover the best prices for you by selecting your travel dates on KAYAK.
Frontier Logo
2:45 pm - 12:59 amMDW-CLE
9h 14m1 stop
Frontier Logo
9:56 pm - 2:48 pmCLE-MDW
17h 52m1 stop
$190Frontier
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Fri, May 16 - Sun, May 18
Frontier Logo
1:19 pm - 12:36 amMDW-CLE
10h 17m1 stop
Frontier Logo
6:40 am - 10:40 pmCLE-MDW
17h 00m1 stop
$191Frontier
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Thu, May 15 - Sun, May 18
Southwest Logo
6:20 pm - 8:35 pmMDW-CLE
1h 15mnonstop
Southwest Logo
7:20 pm - 7:35 pmCLE-MDW
1h 15mnonstop
$207Southwest
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Tue, May 27 - Wed, May 28
Frontier Logo
8:30 am - 3:47 pmMDW-CLE
6h 17m1 stop
Frontier Logo
6:09 pm - 12:24 pmCLE-MDW
19h 15m1 stop
$210Frontier
Find Deal
Sun, May 11 - Sun, May 11
Southwest Logo
2:40 pm - 9:10 pmMDW-CLE
5h 30m1 stop
Southwest Logo
12:45 pm - 1:00 pmCLE-MDW
1h 15mnonstop
$217Southwest
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Tue, May 27 - Wed, May 28
Southwest Logo
6:35 am - 1:15 pmMDW-CLE
5h 40m1 stop
Southwest Logo
5:45 pm - 6:05 pmCLE-MDW
1h 20mnonstop
$224Southwest
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Sat, May 24 - Sun, May 25
Delta Logo
9:16 am - 1:29 pmMDW-CLE
3h 13m1 stop
Delta Logo
6:00 am - 11:53 amCLE-MDW
6h 53m1 stop
$227Delta
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Tue, May 27 - Wed, May 28
Southwest Logo
6:20 am - 10:35 amMDW-CLE
3h 15m1 stop
Southwest Logo
3:20 pm - 3:40 pmCLE-MDW
1h 20mnonstop
$230Southwest
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Mon, May 26 - Sat, May 31
Delta Logo
9:16 am - 1:29 pmMDW-CLE
3h 13m1 stop
Delta Logo
6:00 am - 12:28 pmCLE-MDW
7h 28m2 stops
$232Delta
Find Deal
Tue, May 27 - Wed, May 28
Delta Logo
1:08 pm - 6:50 pmMDW-CLE
4h 42m1 stop
Delta Logo
1:38 pm - 5:40 pmCLE-MDW
5h 02m1 stop
$237Delta
Find Deal
Tue, Jun 3 - Tue, Jun 10
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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 $212 (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.

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Good to know

Low seasonFebruary
High seasonNovember
Cheapest flight$91
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 $91 for a one-way ticket and $190 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 $148 or less one-way and $243 or less round-trip.

Prefer to fly direct from Chicago Midway Airport to Cleveland?

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
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 4294 reviews
8.0Comfort
8.2Boarding
7.6Entertainment
8.6Crew
7.1Food
Airline reviews

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

8.0 ExcellentJohn, Apr 2025PVD - FLL
Read more Southwest reviews

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

The seats were a bit cramped and worn, but otherwise okay.

I would have liked to arrive on time - not 5 hours late!

After a 3 hour layover in Denver my flight was delayed over 5 hours! No explanation; no assistance; no offer to provide compensation; no one at Southwest was willing to offer any assistance. 8 hours in the Denver airport - ridiculous!

It was a perfect flight in all aspects! Both legs!

Only one drink pass through the cabin for a 4 hour flight. Quite rough and bumpy landing.

Boarding process, crew were good. But the seats were so uncomfortable that was all I could focus on. I literally had to sit forward so that all 3 of us could fit in row. I will try to avoid Southwest in the future for any flights over 60 minutes.

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

Information on your arrival and departure airports

Cleveland (CLE)
Chicago Midway Airport (MDW)

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