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CLE - MDW

$60 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 6/5. 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
0 bags
Sat 6/29
Sat 7/6

Search 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
In the last 7 days travelers have searched 42,686,544 times on KAYAK, and here is why:

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Cheap flight deals from Cleveland to Midway (CLE-MDW)

 
These are the cheapest deals for flights from Cleveland to Midway currently on KAYAK along with options from the most popular airlines KAYAK users selected for this route. 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 Cleveland to Midway

Recommended round-trip deals departing in the coming months from the most popular airlines that fly from Cleveland to Midway.

Recent one-way flight deals from Cleveland to Midway

Only flying one-way? Below are some of the best one-way flight deals from Cleveland to Midway found on KAYAK recently.

Recent last minute flight deals from Cleveland to Midway

Leaving soon but still want a bargain? Check out these latest deals for last minute flights from Cleveland to Midway.

Recent direct flight deals from Cleveland to Midway

The latest deals for direct flights from Cleveland to Midway so you can sit back and relax without the need for a layover.

Cheap bus & train deals from Cleveland to Midway

Find recent round-trip train or bus tickets from Cleveland to Midway.

All round-trip flight deals to Midway

The cheapest plane tickets to Midway found on KAYAK recently.
Discover the best prices and deals for you by selecting your travel dates.
Choose your dates
9:35 am - 6:48 pmCLE-MDW
10h 13m1 stop
10:00 am - 9:11 pmMDW-CLE
10h 11m1 stop
$155Frontier
Find Deal
Wed, Aug 21 - Mon, Sep 23
9:35 am - 6:48 pmCLE-MDW
10h 13m1 stop
10:00 am - 10:32 pmMDW-CLE
11h 32m1 stop
$159Frontier
Find Deal
Wed, Aug 21 - Sun, Sep 22
1:49 pm - 6:58 pmCLE-MDW
6h 09m1 stop
7:00 am - 8:39 pmMDW-CLE
12h 39m1 stop
$160Frontier
Find Deal
Sat, Jul 13 - Tue, Jul 16
9:16 am - 6:48 pmCLE-MDW
10h 32m1 stop
12:34 pm - 12:29 amMDW-CLE
10h 55m1 stop
$163Frontier
Find Deal
Mon, Aug 26 - Mon, Sep 23
2:12 pm - 9:20 pmCLE-MDW
8h 08m2 stops
8:27 am - 11:01 pmMDW-CLE
13h 34m1 stop
$164Frontier
Find Deal
Tue, Jun 11 - Fri, Jun 14
6:00 am - 11:44 amCLE-MDW
6h 44m1 stop
1:10 pm - 5:11 pmMDW-CLE
3h 01m1 stop
$176Delta
Find Deal
Wed, Aug 21 - Tue, Sep 24
11:55 am - 6:36 pmCLE-MDW
7h 41m1 stop
9:29 am - 1:18 pmMDW-CLE
2h 49m1 stop
$205Delta
Find Deal
Tue, Jun 25 - Tue, Jul 2
7:05 am - 11:44 amCLE-MDW
5h 39m1 stop
2:24 pm - 11:54 pmMDW-CLE
8h 30m2 stops
$220Delta
Find Deal
Wed, Aug 28 - Fri, Aug 30
4:56 pm - 9:46 pmCLE-MDW
5h 50m1 stop
1:24 pm - 12:44 amMDW-CLE
10h 20m2 stops
$259Delta
Find Deal
Fri, Aug 9 - Tue, Aug 13
8:25 am - 8:18 pmCLE-MDW
12h 53m2 stops
2:14 pm - 1:09 amMDW-CLE
9h 55m2 stops
Fri, Jun 14 - Mon, Jun 17
5:18 pm - 11:08 amCLE-MDW
18h 50m1 stop
$60Frontier
Find Deal
Wed, Jun 5
6:00 am - 10:55 amCLE-MDW
5h 55m1 stop
$62Frontier
Find Deal
Sat, Jun 8
3:09 pm - 9:20 pmCLE-MDW
7h 11m1 stop
$80Frontier
Find Deal
Tue, Jun 18
1:49 pm - 6:58 pmCLE-MDW
6h 09m1 stop
$84Frontier
Find Deal
Sat, Aug 10
10:19 am - 6:36 pmCLE-MDW
9h 17m2 stops
$188Delta
Find Deal
Sat, Aug 10
5:00 am - 8:18 pmCLE-MDW
16h 18m3 stops
Fri, Jun 14
7:35 am - 5:06 pmCLE-MDW
10h 31m2 stops
$233Delta
Find Deal
Wed, Jun 5
5:00 am - 8:18 pmCLE-MDW
16h 18m3 stops
Mon, Jun 17
7:40 pm - 6:39 pmCLE-MDW
23h 59m3 stops
$632WestJet
Find Deal
Thu, Jul 18
1:58 pm - 1:44 pmCLE-MDW
24h 46m3 stops
$738WestJet
Find Deal
Sun, Jun 16
1:05 pm - 9:00 pmCLE-MDW
8h 55m1 stop
10:52 am - 9:07 pmMDW-CLE
9h 15m1 stop
$209Frontier
Find Deal
Sat, Jun 1 - Tue, Jun 4
8:46 pm - 5:50 amCLE-MDW
10h 04m1 stop
8:58 pm - 6:55 amMDW-CLE
8h 57m1 stop
$217Frontier
Find Deal
Mon, Jun 3 - Mon, Jun 10
8:15 am - 9:54 pmCLE-MDW
14h 39m1 stop
8:27 am - 11:01 pmMDW-CLE
13h 34m1 stop
$272Frontier
Find Deal
Mon, Jun 3 - Fri, Jun 7
7:56 pm - 5:50 amCLE-MDW
10h 54m1 stop
10:49 pm - 11:10 amMDW-CLE
11h 21m1 stop
$328Frontier
Find Deal
Sat, Jun 1 - Sun, Jun 2
1:05 pm - 9:00 pmCLE-MDW
8h 55m1 stop
10:49 pm - 11:10 amMDW-CLE
11h 21m1 stop
$333Frontier
Find Deal
Sat, Jun 1 - Sun, Jun 2
8:48 pm - 11:09 amCLE-MDW
15h 21m1 stop
10:52 am - 9:07 pmMDW-CLE
9h 15m1 stop
$336Frontier
Find Deal
Sun, Jun 2 - Tue, Jun 4
6:35 pm - 12:09 amCLE-MDW
6h 34m1 stop
8:56 pm - 10:09 amMDW-CLE
12h 13m1 stop
$376Frontier
Find Deal
Sat, Jun 1 - Mon, Jun 3
8:33 pm - 5:50 amCLE-MDW
10h 17m1 stop
10:49 pm - 11:10 amMDW-CLE
11h 21m1 stop
$388Frontier
Find Deal
Fri, May 31 - Sun, Jun 2
7:35 am - 4:13 pmCLE-MDW
9h 38m2 stops
6:48 pm - 12:44 amMDW-CLE
4h 56m1 stop
$476Delta
Find Deal
Sat, Jun 1 - Sun, Jun 2
7:00 am - 9:06 amCLE-MDW
3h 06m1 stop
1:21 pm - 6:17 pmMDW-CLE
3h 56m1 stop
$537Delta
Find Deal
Tue, Jun 4 - Tue, Jun 4

Flights from Cleveland to Midway - Travel Insights & Trends

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 flights from Cleveland to Chicago Midway Airport clicked on KAYAK for each day over the last 12 months.
For Cleveland to Chicago Midway Airport, Tuesday is the cheapest day to fly on average and Friday is the most expensive. Flying from Chicago Midway Airport back to Cleveland, the best deals are generally found on Tuesday, with Monday being the most expensive.

Which airlines provide the cheapest flights from Cleveland to Chicago Midway Airport?

The cheapest price for the route for each airline clicked by KAYAK users in the last 72 hours.
The cheapest return flight ticket from Cleveland to Chicago Midway Airport found by KAYAK users in the last 72 hours was for $155 on Frontier, followed by Delta ($176). One-way flight deals have also been found from as low as $60 on Frontier and from $188 on Delta.

How many flights are there between Cleveland and Chicago Midway Airport per day?

Each day, there are between 3 and 4 nonstop flights that take off from Cleveland and land in Chicago Midway Airport, with an average flight time of 1h 16m. The most common departure time is 1:00 pm and most flights take off in the morning. Each week, there are 24 flights. The most frequent day of departure is Thursday, when 17% of all weekly flights depart. The fewest flights depart on a Saturday.

Which cabin class options are there for flights between Cleveland and Chicago Midway Airport?

The average price of flights for each cabin class for the route found by users searching on KAYAK over the last 2 weeks.
There is only one cabin class option available for the route, which is Economy. Perform a search on KAYAK to find the latest prices and availability for all cabin fares, which differ across airlines.

What’s the earliest departure time from Cleveland to Chicago Midway Airport?

Early birds can take the earliest flight from Cleveland at 6:20 am and will be landing in Chicago Midway Airport at 6:35 am.

What’s the latest departure time from Cleveland to Chicago Midway Airport?

If you prefer to fly at night, the latest flight from Cleveland to Chicago Midway Airport jets off at 8:35 pm and lands at 8:55 pm.

Good to know

Low season

October

High season

March

Cheapest flight

$60
Best time to beat the crowds with an average 64% drop in price.
Most popular time to fly with an average 30% increase in price.
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 $60 for a one-way ticket and $155 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?

    Only American Airlines offers 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 737-800 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.

  • Which is the best airline for flights from Cleveland to Chicago, Delta or Frontier?

    The two airlines most popular with KAYAK users for flights from Cleveland to Chicago are Delta and Frontier. With an average price for the route of $364 and an overall rating of 8.0, Delta is the most popular choice. Frontier is also a great choice for the route, with an average price of $175 and an overall rating of 6.2.

  • 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.

See more FAQs

Prefer to fly non-stop from Cleveland to Chicago Midway Airport?

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

Nonstop 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

Nonstop 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 airlines 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
DeltaOverall score based on 10457 reviews
8.2Boarding
7.9Comfort
8.6Crew
7.4Food
8.0Entertainment
Airline reviews

Flew first class so everything was great. But maybe because the flights were red eye, no meals were served, just chips. I flew Alaska Air 1st class at 9PM (2 hour flight) and they served beef short rib sliders!

10.0 ExcellentMichael, May 2024SJC - ATL
Read more about Delta reviews

Flew first class so everything was great. But maybe because the flights were red eye, no meals were served, just chips. I flew Alaska Air 1st class at 9PM (2 hour flight) and they served beef short rib sliders!

Had to change aircraft due to a faulty door. Surprisingly it only caused about an hour and a half of delay. Delta handled this situation as well as can be expected.

Awful. Flight was continuously getting delayed and gates kept changing without any reason. Flight was delayed for more then 3 hours

Paid premium for Delta only to be on safe but tired old 767 with ancient cabin in mediocre condition. Poor wifi and horrible inflight entertainment. Hardly a premium experience. Should have flown SW and had fun flight crew and no pretense

Our flight to Zurich was delayed by almost 3 hours, so we missed our next flight. There was no indication it would be delayed this much. We were told the gate had changed and then it apparently took over 2 hours to load the "catering" on the plane. We were not compensated in any way for the trouble.

Rated entertainment as Mediocre as there were major problems with the Infotainment system that took probably a half hour for them to fix.

Your crew could maybe answer the call bell at least one of the times I pressed it. I pressed it first time with 2.5 hours left in our flight bc my partner was hungry and wanted a sandwich. We finally got the sandwich with 40 mins left in the flight.

Delta crushed it. Flight attendant in first was attentive and just never stopped. Honestly one of the best domestic flights I’ve been on.

They were an hour late and they didn’t have my wheelchair for me

The Flight crew didn’t serve us until about 1.5 hours into the flight because of turbulence but after it ended it was fine to move around. They served us water only and snacks and then NEVER, NOT ONE TIME came through to collect trash until right before landing about 1.5 hours later. There was absolutely no need for that. They crew was just standing around talking and visiting with each other and really never tried to see if we might want something besides water or even try to come pick up trash. This is VERY unusual for a Delta flight but it was not what I would have expected for a 4 hour flight.

It was delayed 9 hours for operational reasons, despite the plane arriving to the airport on time.

I am very disappointed with Frontier Airlines. They cancelled our flight because they couldn't find a crew member, and then didn't get us to our connecting flight. We had to cancel our whole vacation. We were promised flight and hotel vouchers, but they never sent them.

9hrs delay and didn’t provided anything until after flight landed $75 voucher for fiuture travel no meals or anything.

It was ridiculously hard to check in for the flight, and Frontier charged us a LOT of money to have a carry on suitcase, and then told everyone we could not carry on bags and had to check them through at the gate, and didn't refund the extra money we paid to have the suitcase as carry on.

I had a terrible experience with Frontier. I arrived before the 60 minute cut off and was told that Frontier has a two hour window for bags. I was then told the next available flight wasn’t until the end of the day (I had booked a 6am flight). I took a look around and saw other people being told that they could not board their flights or that they had to pay additional fees. I opted to rebook on American Airlines. There’s absolutely no straightforward way to contact Frontier, so this ticket was a complete waste of money. Oh - and the kicker is that the lady lied about the two hour cut off.

Frontier won’t help you at the airport without paying $25. Carry on was $75. Then you get on the plain and every beverage or snack is also a charge. Seats are hard and real packed in. I would never fly them again.

Worst experience I have seen. The flight was cancelled without any reason.

My experience with frontier staff at the Denver airport was absolutely horrible. The manager on duty was even worst if was the worst experience I have ever had, I have never been treated so poorly as a customer in my life! The staff was extremely rude, eye rolls and attitude and then refusal to help me at all. I wish I could never fly frontier again that’s how horrible it was!

The Frontier app wasn’t working. So I could not pay for a carry on the week prior to flying. They charged me 99$ at the gate to carry on a duffle bag.

Good for the price. My only complaint is that the pilot should keep the air flowing while passengers are waiting to getting out of airplane.

Book cheap flights from Cleveland to Chicago

Recent one-way flight deals

 
Only flying one-way? Below are some of the best one-way flight deals from Cleveland to Chicago found on KAYAK in the last 72 hours.
6/5Wed
1 stopFrontier
18h 50mCLE-MDW
$60
6/8Sat
1 stopFrontier
5h 55mCLE-MDW
$62
6/18Tue
1 stopFrontier
7h 11mCLE-MDW
$80
8/10Sat
1 stopFrontier
6h 09mCLE-MDW
$84
8/10Sat
2 stopsDelta
9h 17mCLE-MDW
$188
6/14Fri
3 stops
16h 18mCLE-MDW
$225
6/5Wed
2 stopsDelta
10h 31mCLE-MDW
$233
6/17Mon
3 stops
16h 18mCLE-MDW
$246
7/18Thu
3 stopsWestJet
23h 59mCLE-MDW
$632
6/16Sun
3 stopsWestJet
24h 46mCLE-MDW
$738

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Last minute flights from Cleveland to Midway

Last minute flight, train and bus deals

 
These last-minute flight deals are the cheapest flights found on KAYAK in the last 72 hours for flights from Cleveland to Chicago that are departing in the next 10 days.
6/1Sat
multi-stopFrontier
8h 55mCLE-MDW
6/4Tue
multi-stopFrontier
9h 15mMDW-CLE
$209
6/3Mon
multi-stopFrontier
10h 04mCLE-MDW
6/10Mon
multi-stopFrontier
8h 57mMDW-CLE
$217
6/3Mon
multi-stopFrontier
14h 39mCLE-MDW
6/7Fri
multi-stopFrontier
13h 34mMDW-CLE
$272
6/1Sat
multi-stopFrontier
10h 54mCLE-MDW
6/2Sun
multi-stopFrontier
11h 21mMDW-CLE
$328
6/1Sat
multi-stopFrontier
8h 55mCLE-MDW
6/2Sun
multi-stopFrontier
11h 21mMDW-CLE
$333
6/2Sun
multi-stopFrontier
15h 21mCLE-MDW
6/4Tue
multi-stopFrontier
9h 15mMDW-CLE
$336
6/1Sat
multi-stopFrontier
6h 34mCLE-MDW
6/3Mon
multi-stopFrontier
12h 13mMDW-CLE
$376
5/31Fri
multi-stopFrontier
10h 17mCLE-MDW
6/2Sun
multi-stopFrontier
11h 21mMDW-CLE
$388
6/1Sat
multi-stopDelta
9h 38mCLE-MDW
6/2Sun
multi-stopDelta
4h 56mMDW-CLE
$476
6/4Tue
multi-stopDelta
3h 06mCLE-MDW
6/4Tue
multi-stopDelta
3h 56mMDW-CLE
$537

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Cleveland - Chicago Midway Airport Flights

Departure:

Cleveland (CLE)United States

Destination:

Chicago Midway Airport (MDW)United States

Return flight deals:

Chicago Midway Airport - Cleveland

Cabin classes:

$572