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Cheap flights from Cleveland to Chicago Midway Airport from $85

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Cleveland to Chicago Midway Airport departing on 12/21. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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Find the cheapest flights from Cleveland to Chicago

Cheap round-trip flights

These are some of the best round-trip flight deals from Cleveland to Chicago that have been recently found on momondo from popular airlines, departing in the coming months.

Cheap one-way flights

Flying one-way? These are some of the best deals recently discovered on momondo for flights from Cleveland to Chicago.

Cheap last minute flights

Planning a quick getaway from Cleveland to Chicago? These are the last-minute flight deals available now.

Cheap direct flights

If you prefer a non-stop journey, check out our latest direct flight deals to Chicago, so you can enjoy a seamless trip without layovers.

Cheap bus & train deals from Cleveland to Chicago

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

All round-trip flight deals to Chicago

The cheapest plane tickets to Chicago found on KAYAK recently.
6:15 pm - 6:30 pmCLE-MDW
1h 15mnonstop
7:00 pm - 9:15 pmMDW-CLE
1h 15mnonstop
$158Southwest
Find Deal
Tue, Dec 17 - Wed, Dec 18
7:27 pm - 11:48 amCLE-MDW
17h 21m1 stop
5:15 am - 12:58 pmMDW-CLE
6h 43m1 stop
$168Frontier
Find Deal
Thu, Dec 12 - Sun, Dec 15
6:05 am - 8:50 amCLE-MDW
3h 45m1 stop
6:00 am - 12:41 pmMDW-CLE
5h 41m1 stop
$176Delta
Find Deal
Wed, Jan 1 - Wed, Jan 8
6:30 am - 11:41 amCLE-MDW
6h 11m1 stop
6:00 am - 8:24 pmMDW-CLE
13h 24m1 stop
$178Frontier
Find Deal
Mon, Dec 16 - Mon, Dec 23
7:27 pm - 11:48 amCLE-MDW
17h 21m1 stop
5:01 am - 9:22 pmMDW-CLE
15h 21m1 stop
$179Frontier
Find Deal
Thu, Dec 12 - Mon, Dec 16
6:30 am - 11:40 amCLE-MDW
6h 10m1 stop
6:49 pm - 5:24 pmMDW-CLE
21h 35m1 stop
$180Frontier
Find Deal
Sun, Dec 8 - Mon, Dec 23
10:04 am - 5:01 pmCLE-MDW
7h 57m2 stops
4:58 pm - 12:23 amMDW-CLE
6h 25m1 stop
$181Delta
Find Deal
Tue, Dec 17 - Wed, Dec 18
3:00 pm - 8:05 pmCLE-MDW
6h 05m1 stop
7:00 pm - 9:15 pmMDW-CLE
1h 15mnonstop
$182Southwest
Find Deal
Tue, Dec 17 - Wed, Dec 18
10:04 am - 5:01 pmCLE-MDW
7h 57m2 stops
1:30 pm - 12:23 amMDW-CLE
9h 53m2 stops
$186Delta
Find Deal
Tue, Dec 17 - Wed, Dec 18
6:20 am - 2:10 pmCLE-MDW
8h 50m2 stops
3:15 pm - 5:30 pmMDW-CLE
1h 15mnonstop
$187Southwest
Find Deal
Tue, Dec 31 - Wed, Jan 1
5:30 am - 10:33 pmCLE-MDW
18h 03m1 stop
$85Frontier
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Sat, Dec 21
12:01 pm - 4:10 pmCLE-MDW
5h 09m1 stop
$88Delta
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Wed, Dec 25
7:27 pm - 11:40 amCLE-MDW
17h 13m1 stop
$89Frontier
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Sat, Dec 7
10:00 pm - 10:21 amCLE-MDW
13h 21m1 stop
$90Frontier
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Sun, Dec 15
10:04 am - 5:01 pmCLE-MDW
7h 57m2 stops
$93Delta
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Tue, Dec 17
6:15 pm - 6:30 pmCLE-MDW
1h 15mnonstop
$94Southwest
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Wed, Dec 18
7:30 pm - 10:20 pmCLE-MDW
3h 50m1 stop
$103Southwest
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Tue, Dec 31
2:05 pm - 7:35 pmCLE-MDW
6h 30m2 stops
$108Southwest
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Tue, Dec 24
6:07 pm - 12:46 pmCLE-MDW
19h 39m3 stops
$451WestJet
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Thu, Jan 30
4:00 pm - 5:47 pmCLE-MDW
26h 47m3 stops
$455WestJet
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Wed, Jan 22
6:05 am - 1:10 pmCLE-MDW
8h 05m1 stop
3:53 pm - 12:09 amMDW-CLE
7h 16m1 stop
$288Frontier
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Fri, Nov 22 - Mon, Nov 25
7:13 pm - 1:12 amCLE-MDW
6h 59m1 stop
1:31 pm - 8:24 amMDW-CLE
17h 53m1 stop
$298Frontier
Find Deal
Sat, Nov 23 - Sun, Nov 24
9:20 pm - 9:40 pmCLE-MDW
1h 20mnonstop
8:25 am - 10:40 amMDW-CLE
1h 15mnonstop
$305Southwest
Find Deal
Sat, Nov 23 - Mon, Dec 2
9:33 am - 5:38 pmCLE-MDW
9h 05m1 stop
6:30 am - 6:53 pmMDW-CLE
11h 23m1 stop
$308Frontier
Find Deal
Thu, Nov 21 - Sat, Nov 23
9:20 pm - 9:40 pmCLE-MDW
1h 20mnonstop
6:25 am - 12:10 pmMDW-CLE
4h 45m1 stop
$314Southwest
Find Deal
Sat, Nov 23 - Mon, Dec 2
6:48 pm - 1:36 pmCLE-MDW
19h 48m1 stop
6:30 am - 6:53 pmMDW-CLE
11h 23m1 stop
$318Frontier
Find Deal
Wed, Nov 20 - Sat, Nov 23
10:24 am - 6:32 pmCLE-MDW
9h 08m2 stops
6:49 pm - 12:50 amMDW-CLE
5h 01m1 stop
$358Delta
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Sat, Nov 23 - Mon, Dec 2
2:18 pm - 5:54 pmCLE-MDW
4h 36m1 stop
1:30 pm - 12:45 amMDW-CLE
10h 15m2 stops
$509Delta
Find Deal
Wed, Nov 20 - Sat, Nov 23
5:12 am - 8:45 amCLE-MDW
28h 33m3 stops
7:55 pm - 11:02 pmMDW-CLE
26h 07m3 stops
$1,638
Find Deal
Fri, Nov 22 - Mon, Nov 25
5:12 am - 8:45 amCLE-MDW
28h 33m3 stops
7:55 pm - 11:02 pmMDW-CLE
26h 07m3 stops
$2,126
Find Deal
Fri, Nov 22 - Sun, Nov 24
6:15 pm - 6:30 pmCLE-MDW
1h 15mnonstop
7:00 pm - 9:15 pmMDW-CLE
1h 15mnonstop
$158Southwest
Find Deal
Tue, Dec 17 - Wed, Dec 18
4:15 pm - 4:35 pmCLE-MDW
1h 20mnonstop
7:00 pm - 9:15 pmMDW-CLE
1h 15mnonstop
$188Southwest
Find Deal
Sat, Dec 7 - Tue, Dec 10
6:15 pm - 6:30 pmCLE-MDW
1h 15mnonstop
7:00 pm - 9:15 pmMDW-CLE
1h 15mnonstop
$218Southwest
Find Deal
Mon, Dec 9 - Wed, Dec 11
7:00 pm - 7:20 pmCLE-MDW
1h 20mnonstop
10:35 am - 12:50 pmMDW-CLE
1h 15mnonstop
$228Southwest
Find Deal
Tue, Jan 7 - Fri, Jan 10
2:00 pm - 2:15 pmCLE-MDW
1h 15mnonstop
9:35 am - 11:50 amMDW-CLE
1h 15mnonstop
$239Southwest
Find Deal
Sun, Dec 15 - Tue, Dec 17
6:15 pm - 6:30 pmCLE-MDW
1h 15mnonstop
8:25 am - 10:40 amMDW-CLE
1h 15mnonstop
$243Southwest
Find Deal
Mon, Dec 16 - Mon, Dec 23
6:15 pm - 6:30 pmCLE-MDW
1h 15mnonstop
4:35 pm - 6:45 pmMDW-CLE
1h 10mnonstop
$248Southwest
Find Deal
Wed, Dec 25 - Sun, Dec 29
2:00 pm - 2:15 pmCLE-MDW
1h 15mnonstop
7:00 pm - 9:15 pmMDW-CLE
1h 15mnonstop
$254Southwest
Find Deal
Fri, Dec 13 - Mon, Dec 16
7:30 pm - 7:45 pmCLE-MDW
1h 15mnonstop
3:15 pm - 5:30 pmMDW-CLE
1h 15mnonstop
$263Southwest
Find Deal
Fri, Dec 27 - Tue, Dec 31
12:05 pm - 12:20 pmCLE-MDW
1h 15mnonstop
10:40 am - 12:50 pmMDW-CLE
1h 10mnonstop
$264Southwest
Find Deal
Thu, Dec 12 - Sat, Dec 14

Delta flights from Cleveland to Chicago Midway Airport

Our best Delta deals on Cleveland to Chicago Midway Airport flight tickets
Delta
Jan 1
CLE6:05 amCleveland Hopkins Intl
3h 45m
1 stop
MDW8:50 amChicago Midway
Jan 8
MDW6:00 amChicago Midway
5h 41m
1 stop
CLE12:41 pmCleveland Hopkins Intl
Delta
Dec 17
CLE10:04 amCleveland Hopkins Intl
7h 57m
2 stops
MDW5:01 pmChicago Midway
Dec 18
MDW4:58 pmChicago Midway
6h 25m
1 stop
CLE12:23 amCleveland Hopkins Intl
Delta
Dec 17
CLE10:04 amCleveland Hopkins Intl
7h 57m
2 stops
MDW5:01 pmChicago Midway
Dec 18
MDW1:30 pmChicago Midway
9h 53m
2 stops
CLE12:23 amCleveland Hopkins Intl

Southwest flights from Cleveland to Chicago Midway Airport

Our best Southwest deals on Cleveland to Chicago Midway Airport flight tickets
Southwest
Dec 17
CLE6:15 pmCleveland Hopkins Intl
1h 15m
MDW6:30 pmChicago Midway
Dec 18
MDW7:00 pmChicago Midway
1h 15m
CLE9:15 pmCleveland Hopkins Intl
Southwest
Dec 17
CLE3:00 pmCleveland Hopkins Intl
6h 05m
1 stop
MDW8:05 pmChicago Midway
Dec 18
MDW7:00 pmChicago Midway
1h 15m
CLE9:15 pmCleveland Hopkins Intl
Southwest
Dec 31
CLE6:20 amCleveland Hopkins Intl
8h 50m
2 stops
MDW2:10 pmChicago Midway
Jan 1
MDW3:15 pmChicago Midway
1h 15m
CLE5:30 pmCleveland Hopkins Intl

How to get the cheapest flight ticket from Cleveland to Chicago Midway Airport

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

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

January. The cheapest time of year to fly to Chicago Midway Airport from Cleveland is January. Most expensive is August

What is the cheapest day to depart Cleveland for Chicago Midway Airport?

Wednesday. The cheapest day of the week is typically Wednesday. The most expensive is typically Sunday

When is the cheapest time to fly from Cleveland to Chicago Midway Airport?

In the evening. Cleveland to Chicago Midway Airport flights are approximately 14% more expensive at noon than in the evening

What is the cheapest airline that flies to Chicago Midway Airport from Cleveland?

Southwest. Southwest and Delta are the most popular carriers operating from Cleveland to Chicago Midway Airport

How many flights depart from Cleveland to Chicago Midway Airport on average per day?

As of November 2024, there are 1 flights per week flying from Cleveland to Chicago Midway Airport. The most common time of day flights depart is 6:00AM, with 36% of flights taking off at noon.

How many flights depart from Cleveland to Chicago Midway Airport on average per week?

The number of flights available between Cleveland and Chicago Midway Airport is 12 per week as of November 2024. The most frequent departure day is Mon, with 25% of weekly flights leaving on this day.

Can stopping save me money on Cleveland to Chicago Midway Airport flights?

You could potentially save up to 31% on your flight if you consider stops on a Cleveland to Chicago Midway Airport flight.

When to book flights from Cleveland to Chicago Midway Airport

Are you open to changing your travel dates? Check out the ideal times to fly from Cleveland to Chicago Midway Airport according to our flight data. Find out which month and days have the cheapest flights.
Estimated round-trip price

Cheap Cleveland to Chicago Midway Airport (CLE to MDW) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Cleveland to Chicago Midway Airport

Best Price Found

$85

Fastest flight time

1h 15m

Direct flights

Every day
The best one-way flight to Chicago Midway Airport from Cleveland in the past 72 hours is $85. The best round-trip flight deal from Cleveland to Chicago Midway Airport found on momondo in the last 72 hours is $158.
The fastest flight from Cleveland to Chicago Midway Airport takes 1h 15m
Direct flights go from Cleveland to Chicago Midway Airport every day.

  • How far is Cleveland Hopkins Intl to Chicago Midway by plane?

    Cleveland Hopkins Intl and Chicago Midway are 312.8 mi apart from one another. Flights usually cover this in 1h 15m, depending on flying conditions and air traffic around both airports.

  • When did momondo last update prices for flights from Cleveland Hopkins Intl Airport to Chicago Midway Airport?

    Prices for flights from Cleveland Hopkins Intl Airport to Chicago Midway Airport are updated daily.

  • How many operators does momondo search for flights from Cleveland Hopkins Intl Airport to Chicago Midway Airport?

  • How old do you have to be to fly from Cleveland Hopkins Intl Airport to Chicago Midway Airport?

    Although the minimum age for a child to fly alone is five, airlines that offer an unaccompanied minor (UMNR) service may have their own age limits, which could be impacted by factors such as flight length, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Cleveland Hopkins Intl Airport to Chicago Midway Airport.

  • What documentation or ID do you need to fly to Chicago Midway Airport?

    The travel and health documents you'll need for your trip to Chicago Midway Airport may differ based on your itinerary and personal situation. Typically, you should have several documents on hand, such as a national ID card or driver's license and a passport that is valid for six months after your intended arrival at Chicago Midway Airport. It is always advisable to seek advice from your airline or a trusted third party, such as IATA.

  • What is the most popular plane model from Cleveland to Chicago Midway Airport?

  • What is the most popular airline from Cleveland to Chicago Midway Airport?


Best airlines flying from Cleveland to Chicago Midway Airport

Compare and see reviews for airlines that fly from Cleveland to Chicago Midway Airport with momondo
Airline
Rating
Free Cancellation
Price
SouthwestPriceFrom $151Free CancellationRating
8.1
5,022 reviews
Search Southwest flights
DeltaPriceFrom $156Free CancellationRating
8.0
8,766 reviews
Search Delta flights
  • Southwest Flights From Cleveland to Chicago Midway Airport

    The lowest priced Southwest flight from Cleveland to Chicago Midway Airport from the last 72 hours was $151. Generally, Southwest has 12 flights on this route every week with an average price of $252. Southwest is rated 8.1/10 by our users.


Why use momondo?

Why should I use momondo to find a flight deal from Cleveland to Chicago?

Finding the right flight to Chicago from Cleveland is quick and easy when you have a range of options in front of you, from reputable agents and recognisable airlines. Options that can then be filtered down to find the best fit. That is what momondo does. We make finding flights to Chicago quick and easy, saving you time and money.

Can I find flights from Cleveland to Chicago with flexible booking policies on momondo?

Yes. All flights to Chicago from Cleveland on momondo can be compared and filtered by various policies on offer, including flexible booking.

How can momondo help me find flights from Cleveland to Chicago?

Once all potential Cleveland to Chicago flight options are in front of you, momondo lets you sort and filter flights based on preferences such as airline, price and flight times amongst many other options.

I’m not ready to book a flight from Cleveland to Chicago right now. Can momondo alert me if prices change?

If you are not ready to book a flight from Cleveland to Chicago now, use our insights above to find helpful tips or alternatively set up a price alert, where momondo will track prices on flights to Chicago and let you know when they change.


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