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CLE - MDW

$49 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 5/21. 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
Fri 6/7
Fri 6/14

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 43,968,530 times on KAYAK, and here is why:

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Cheap flight deals 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 and deals for you by selecting your travel dates.
Choose your dates
8:15 am - 10:04 pmCLE-MDW
14h 49m1 stop
6:07 pm - 7:40 amMDW-CLE
12h 33m1 stop
$133Frontier
Find Deal
Mon, May 20 - Tue, May 21
9:36 pm - 5:35 pmCLE-MDW
20h 59m1 stop
6:07 pm - 7:40 amMDW-CLE
12h 33m1 stop
$137Frontier
Find Deal
Sun, May 19 - Tue, May 21
8:32 am - 9:55 pmCLE-MDW
14h 23m1 stop
10:00 am - 9:11 pmMDW-CLE
10h 11m1 stop
$140Frontier
Find Deal
Wed, Aug 21 - Wed, Sep 18
4:32 pm - 5:21 amCLE-MDW
13h 49m1 stop
1:50 pm - 8:09 pmMDW-CLE
5h 19m1 stop
$150Frontier
Find Deal
Sat, Jun 22 - Tue, Jun 25
11:10 am - 9:38 pmCLE-MDW
11h 28m1 stop
6:17 pm - 7:45 amMDW-CLE
12h 28m1 stop
$154Frontier
Find Deal
Sat, May 18 - Sun, May 19
10:10 am - 6:06 pmCLE-MDW
8h 56m2 stops
5:59 pm - 11:49 pmMDW-CLE
4h 50m1 stop
$190Delta
Find Deal
Sat, Sep 7 - Mon, Sep 9
7:00 am - 8:49 amCLE-MDW
2h 49m1 stop
1:24 pm - 7:19 pmMDW-CLE
4h 55m1 stop
$215Delta
Find Deal
Fri, Jul 5 - Mon, Jul 8
7:25 pm - 7:40 pmCLE-MDW
1h 15mnonstop
7:45 pm - 9:55 pmMDW-CLE
1h 10mnonstop
$349Southwest
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Mon, May 20 - Tue, May 21
8:30 pm - 11:25 pmCLE-MDW
3h 55m1 stop
7:45 pm - 9:55 pmMDW-CLE
1h 10mnonstop
$358Southwest
Find Deal
Mon, May 20 - Tue, May 21
5:00 am - 9:47 amCLE-MDW
29h 47m3 stops
8:45 pm - 5:34 pmMDW-CLE
19h 49m2 stops
$1,022
Find Deal
Sat, May 18 - Sun, May 19

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 $133 on Frontier, followed by Delta ($190). One-way flight deals have also been found from as low as $49 on Frontier and from $78 on Delta.

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

Each day, there are between 5 and 8 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 afternoon. Each week, there are 46 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

$49
Best time to beat the crowds with an average 65% drop in price.
Most popular time to fly with an average 28% 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 $49 for a one-way ticket and $133 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 $381 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 $173 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 10789 reviews
8.2Boarding
7.9Comfort
8.6Crew
7.4Food
8.0Entertainment
Airline reviews

The gate area was incredibly short staffed, with one representative manning 4-5 flights, which caused a 3 hr delay in boarding even though the plane was all ready to leave. Other flights also were delayed because of this. The flight crew was awesome and I feel bad for the only gate worker on call, but Delta needs to hire more employees.

2.0 MediocreAnonymous, May 2024AVL - LGA
Read more about Delta reviews

The gate area was incredibly short staffed, with one representative manning 4-5 flights, which caused a 3 hr delay in boarding even though the plane was all ready to leave. Other flights also were delayed because of this. The flight crew was awesome and I feel bad for the only gate worker on call, but Delta needs to hire more employees.

Very frustrated with boarding gate crew. She announced the plane was small and they would be limiting us to one item to carry on. Not a problem for me as I understand the tiny planes have limited space!! Not the case here! It was a rather large plane and had plenty of room for bags! So because I don’t want to be one of “those people” who ignores the request to check a carry on I did so asking if I would be able to pick it up at the bottom of the ramp on arrival in Knoxville to which she responded “yes”! Then I watched as every other passenger held onto their 2 items and boarded!! Then when we arrived in Knoxville our 2 carry ons had been put with all the other luggage and we had to go to baggage pick up and wait for all the big checked bags to come off the carousel! So she lied!! Frustrating. Next time I won’t be so nice!

It was a good experience except when boarding a female flight attendant did not go out of her way to assist my teenage daughters in finding space for their carry-ons after their compartments were full.

On time departure, smooth trip, flight attendant told through passengers the gate we would arrive at and the gate our outbound flight was departing from. Early arrival

Checking in at the airport the agent only booked the first keg of my trip and had my checked luggage going to the airport with a layover! Never was issued a boarding pass for the second leg or received sticker fir my checked bag. All was well in the end! Delta agents helped to resolve the situation!!!

Delayed due to an ill passenger after loading. Not preventable on Delta's part. Was in first class. The seats are becoming worn and detaching from their velcro attachments. Only got snacks on flight. The attendant was not the friendliest.

I would fly again the whole experience was great. The only feed back I can give that they don't do that American Airlines does is the crew there is more humorous with boarding and thank their passengers. It makes it more fun to fly with them. I would however fly Delta again.

From Atlanta to Cabo I would have hoped on a plane that size I would have been able to breathe and wiggle my feet a little! The leg room in that plane is non existent and I am only 5”4’. And the air vent either wasn’t working very well or just could not blow air from the ceiling to the seat area as I was suffocating through the entire flight! And please don’t say I would have been more comfortable in first class because I cannot afford those rates and have always travelled Main Cabin without issues !

The pilots were good. Disappointing when planes don't have electrical ports

I liked the piloting of the aircraft. Very disappointed about lack of electrical ports. Also, although a short flight. there was enough time to hand out snacks to comfort + seats as was done for first class.

I checked a bag because it was $5 less than carry on. They managed to lose my bag on a 2.5 hr direct flight! Frontier has no airport staff at baggage claim to help. As soon as I got home around 11 pm I tried to use their online system to file the claim for lost bag - system wouldn't take the # on my baggage claim ticket - said it was not the correct number. Also said that I had not checked a bag, which wasn't true - even my online boarding pass showed that I had checked a bag. Wasted about an hour on that process with no luck. Tried again in the morning - same thing. So tried online chat with Frontier bot - waited 35-40" twice to be connected to a baggage agent and it never happened. Eventually drove to PDX after work and waited 2 hrs for the Frontier ticket agents to arrive prior to the next Frontier flight out of PDX and FINALLY got some help from one of them, to take me to lost luggage area where I was able to retrive my bag. Probably took 4-5 hrs. of my time and endless frustration to get my bag. This was my first -- and LAST -- experience flying Frontier Airlines. Check-in was also extremely difficult and time consuming. The flight itself (and staff) were fine but everything else about the experience was a total disaster! The fact that Frontier literally has NO WAY to connect to a human voice for customer service (in this case for lost luggage) is the WORST!!!!!

Frontier is a crappy airline nothing about it is honest

I didn't get to do this flight l, hard to review

Not good 😐 Over priced baggage fees Small hard seats No wifi or entertainment options 😕

Didn't like anything!! Horrible flight. Small seating area and hard seats. Butt was sore after 2 hour flight to Seattle No entertainment or free refreshments No wifi or USB charging receptacles to charge phone entoute like other airliners Luggage rates were 3 times as much as competitors. Difficult to navigate online luggue process to pre pay before flight Overall bad experience WILL NEVER RIDE OR RECOMMEND FRONTIER TO FRIENDS OR FAMILY MEMBERS!!! THIS IS A SHAME!! MOST MESERIBLE FLIGHT OF MY LIFE!! AND I THOUGHT SPIRIT WAS 👎 YOU GOT THEM BEAD HANDS DOWN!!

Flight was a little late taking off. Seats are too upright, no ports to charge devices, no wifi, no entertainment

Six hour delay. Poor customer service. No voucher. Bad communication. Missed important appointments.

Our flight was delayed an hour, then when we got to board our flight finally, we were waiting in our seats for take off for 45 minutes before it was communicated that there was a maintenance issue therefore we waited on the plane for over an hour while that was resolved. We did not get to Phoenix until almost 3 hours after we were originally supposed to. This was the first and last time I will be flying Frontier.

Flight was canceled with little warning. Flight was rebooked through Ontario, California and connecting flight was delayed by over three hours. Frontier is living up to their Greyhound of the skies reputation for sure.

I purchased a carry on bag online…was supposed to cost $72 but after a whole slew of bs charges, the total was over $175.00. Because of these hidden charges, I will not even consider flying Frontier ever again. It’s just not worth the hassle. I’m scratching this company off my list forever.

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.
5/21Tue
1 stopFrontier
7h 01mCLE-MDW
$49
9/11Wed
1 stopFrontier
10h 08mCLE-MDW
$75
5/29Wed
1 stopDelta
3h 06mCLE-MDW
$78
8/23Fri
1 stopFrontier
10h 08mCLE-MDW
$79
5/14Tue
1 stopFrontier
7h 46mCLE-MDW
$80
5/15Wed
1 stopFrontier
13h 21mCLE-MDW
$81
5/29Wed
2 stopsDelta
6h 30mCLE-MDW
$112
8/19Mon
2 stops
12h 00mCLE-MDW
$186
8/9Fri
2 stops
12h 15mCLE-MDW
$265
6/9Sun
3 stopsWestJet
23h 56mCLE-MDW
$548

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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.
5/13Mon
multi-stopFrontier
11h 29mCLE-MDW
5/15Wed
multi-stopFrontier
12h 43mMDW-CLE
$234
5/13Mon
multi-stopFrontier
11h 29mCLE-MDW
5/17Fri
multi-stopFrontier
20h 50mMDW-CLE
$247
5/12Sun
multi-stopFrontier
15h 50mCLE-MDW
5/15Wed
multi-stopFrontier
12h 43mMDW-CLE
$254
5/12Sun
multi-stopFrontier
15h 50mCLE-MDW
6/2Sun
multi-stopFrontier
12h 19mMDW-CLE
$301
5/11Sat
multi-stopFrontier
18h 06mCLE-MDW
5/14Tue
multi-stopFrontier
16h 29mMDW-CLE
$328
5/10Fri
multi-stopFrontier
11h 17mCLE-MDW
5/13Mon
multi-stopFrontier
21h 47mMDW-CLE
$358
5/9Thu
multi-stopFrontier
15h 50mCLE-MDW
5/13Mon
multi-stopFrontier
20h 36mMDW-CLE
$377
5/9Thu
multi-stopFrontier
15h 50mCLE-MDW
5/10Fri
multi-stopFrontier
15h 50mMDW-CLE
$387
5/12Sun
multi-stopDelta
7h 40mCLE-MDW
6/2Sun
multi-stopDelta
4h 37mMDW-CLE
$437
5/12Sun
multi-stopDelta
4h 05mCLE-MDW
5/15Wed
multi-stopDelta
7h 03mMDW-CLE
$452

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Cleveland - Chicago Midway Airport Flights

Departure:

Cleveland (undefined)United States

Destination:

Chicago Midway Airport (MDW)United States

Return flight deals:

Chicago Midway Airport - Cleveland

Cabin classes:

$225