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Cheap flights from Cleveland to Chicago Midway Airport from $54

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 1/23. 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.
1:09 pm - 9:05 pmCLE-MDW
8h 56m1 stop
7:15 am - 7:58 pmMDW-CLE
11h 43m1 stop
$111Frontier
Find Deal
Thu, Jan 9 - Mon, Jan 13
1:12 pm - 8:53 pmCLE-MDW
8h 41m1 stop
7:15 am - 7:57 pmMDW-CLE
11h 42m1 stop
$120Frontier
Find Deal
Thu, Jan 30 - Mon, Feb 3
6:46 pm - 11:14 pmCLE-MDW
5h 28m1 stop
7:15 am - 7:58 pmMDW-CLE
11h 43m1 stop
$128Frontier
Find Deal
Mon, Jan 6 - Mon, Jan 13
2:15 pm - 6:14 pmCLE-MDW
4h 59m1 stop
9:34 am - 1:35 pmMDW-CLE
3h 01m1 stop
$176Delta
Find Deal
Tue, Jan 14 - Wed, Jan 15
7:05 am - 1:08 pmCLE-MDW
7h 03m2 stops
5:07 pm - 12:39 amMDW-CLE
6h 32m1 stop
$181Delta
Find Deal
Tue, Jan 14 - Wed, Jan 15
12:05 pm - 12:20 pmCLE-MDW
1h 15mnonstop
3:15 pm - 5:30 pmMDW-CLE
1h 15mnonstop
$183Southwest
Find Deal
Mon, Jan 6 - Mon, Jan 6
10:28 am - 5:47 pmCLE-MDW
8h 19m2 stops
9:34 am - 8:39 pmMDW-CLE
10h 05m2 stops
$186Delta
Find Deal
Tue, Jan 14 - Wed, Jan 15
7:00 pm - 7:20 pmCLE-MDW
1h 20mnonstop
10:35 am - 12:50 pmMDW-CLE
1h 15mnonstop
$188Southwest
Find Deal
Thu, Jan 9 - Mon, Jan 13
6:25 pm - 6:50 pmCLE-MDW
1h 25mnonstop
7:25 pm - 9:40 pmMDW-CLE
1h 15mnonstop
$217Southwest
Find Deal
Thu, Jan 16 - Sun, Jan 19
7:20 am - 12:15 pmCLE-MDW
5h 55m1 stop
3:15 pm - 5:30 pmMDW-CLE
1h 15mnonstop
$222Southwest
Find Deal
Mon, Jan 6 - Mon, Jan 6
1:12 pm - 8:53 pmCLE-MDW
8h 41m1 stop
$54Frontier
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Thu, Jan 23
9:59 pm - 10:02 amCLE-MDW
13h 03m1 stop
$60Frontier
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Sat, Jan 25
7:27 pm - 11:44 amCLE-MDW
17h 17m1 stop
$61Frontier
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Wed, Jan 22
6:25 pm - 12:29 pmCLE-MDW
19h 04m1 stop
$64Frontier
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Mon, Jan 6
7:00 pm - 7:20 pmCLE-MDW
1h 20mnonstop
$79Southwest
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Wed, Jan 22
6:00 am - 11:59 amCLE-MDW
6h 59m1 stop
$88Delta
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Wed, Feb 19
6:00 am - 1:05 pmCLE-MDW
8h 05m2 stops
$93Delta
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Wed, Feb 19
6:55 am - 7:25 amCLE-MDW
1h 30mnonstop
$94Southwest
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Mon, Feb 24
4:57 pm - 5:30 pmCLE-MDW
25h 33m3 stops
Wed, Feb 26
4:57 pm - 5:32 pmCLE-MDW
25h 35m3 stops
Wed, Feb 19
6:20 am - 6:45 amCLE-MDW
1h 25mnonstop
7:00 pm - 9:15 pmMDW-CLE
1h 15mnonstop
$456Southwest
Find Deal
Sat, Dec 28 - Wed, Jan 1
3:50 pm - 11:10 pmCLE-MDW
8h 20m1 stop
3:15 pm - 5:30 pmMDW-CLE
1h 15mnonstop
$465Southwest
Find Deal
Sat, Dec 28 - Wed, Jan 1
3:50 pm - 9:35 pmCLE-MDW
6h 45m2 stops
3:15 pm - 5:30 pmMDW-CLE
1h 15mnonstop
$470Southwest
Find Deal
Sat, Dec 28 - Wed, Jan 1
12:12 pm - 9:17 pmCLE-MDW
10h 05m1 stop
8:00 am - 4:13 pmMDW-CLE
7h 13m1 stop
$473Frontier
Find Deal
Wed, Dec 25 - Thu, Jan 2
3:50 pm - 10:00 pmCLE-MDW
7h 10m2 stops
1:30 pm - 9:05 pmMDW-CLE
6h 35m1 stop
$509Southwest
Find Deal
Sat, Dec 28 - Wed, Jan 1
5:18 pm - 11:40 pmCLE-MDW
7h 22m1 stop
8:25 am - 5:43 pmMDW-CLE
8h 18m1 stop
$513Frontier
Find Deal
Sun, Dec 29 - Fri, Jan 3
5:18 pm - 11:40 pmCLE-MDW
7h 22m1 stop
10:50 am - 9:05 pmMDW-CLE
9h 15m1 stop
$533Frontier
Find Deal
Sun, Dec 29 - Wed, Jan 1
6:05 am - 8:50 amCLE-MDW
3h 45m1 stop
5:51 pm - 10:35 pmMDW-CLE
3h 44m1 stop
$580Delta
Find Deal
Sat, Dec 28 - Wed, Jan 1
6:00 am - 4:10 pmCLE-MDW
11h 10m2 stops
10:08 am - 5:13 pmMDW-CLE
6h 05m1 stop
$631Delta
Find Deal
Wed, Dec 25 - Thu, Jan 2
12:01 pm - 4:24 pmCLE-MDW
5h 23m1 stop
5:03 pm - 12:44 amMDW-CLE
6h 41m1 stop
$682Delta
Find Deal
Fri, Dec 27 - Sat, Dec 28
12:05 pm - 12:20 pmCLE-MDW
1h 15mnonstop
3:15 pm - 5:30 pmMDW-CLE
1h 15mnonstop
$183Southwest
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Mon, Jan 6 - Mon, Jan 6
7:00 pm - 7:20 pmCLE-MDW
1h 20mnonstop
10:35 am - 12:50 pmMDW-CLE
1h 15mnonstop
$188Southwest
Find Deal
Thu, Jan 9 - Mon, Jan 13
6:25 pm - 6:50 pmCLE-MDW
1h 25mnonstop
7:25 pm - 9:40 pmMDW-CLE
1h 15mnonstop
$217Southwest
Find Deal
Thu, Jan 16 - Sun, Jan 19
7:05 am - 7:35 amCLE-MDW
1h 30mnonstop
6:20 pm - 8:35 pmMDW-CLE
1h 15mnonstop
$228Southwest
Find Deal
Wed, Feb 5 - Fri, Feb 7
7:05 am - 7:35 amCLE-MDW
1h 30mnonstop
6:20 pm - 8:35 pmMDW-CLE
1h 15mnonstop
$243Southwest
Find Deal
Thu, Jan 23 - Sun, Jan 26
7:00 pm - 7:20 pmCLE-MDW
1h 20mnonstop
3:30 pm - 5:40 pmMDW-CLE
1h 10mnonstop
$254Southwest
Find Deal
Wed, Jan 8 - Sun, Jan 12
7:00 pm - 7:20 pmCLE-MDW
1h 20mnonstop
3:30 pm - 5:40 pmMDW-CLE
1h 10mnonstop
$275Southwest
Find Deal
Thu, Jan 9 - Sun, Jan 12
7:30 pm - 7:50 pmCLE-MDW
1h 20mnonstop
7:40 pm - 9:50 pmMDW-CLE
1h 10mnonstop
$298Southwest
Find Deal
Thu, Mar 6 - Mon, Mar 10
7:30 pm - 7:50 pmCLE-MDW
1h 20mnonstop
9:20 am - 11:35 amMDW-CLE
1h 15mnonstop
$318Southwest
Find Deal
Mon, Mar 10 - Sat, Mar 15
7:05 am - 7:35 amCLE-MDW
1h 30mnonstop
3:30 pm - 5:40 pmMDW-CLE
1h 10mnonstop
$325Southwest
Find Deal
Fri, Jan 10 - Sun, Jan 12

Southwest flights from Cleveland to Chicago Midway Airport

Our best Southwest deals on Cleveland to Chicago Midway Airport flight tickets
Southwest
Jan 6
CLE12:05 pmCleveland Hopkins Intl
1h 15m
MDW12:20 pmChicago Midway
Jan 6
MDW3:15 pmChicago Midway
1h 15m
CLE5:30 pmCleveland Hopkins Intl
Southwest
Jan 9
CLE7:00 pmCleveland Hopkins Intl
1h 20m
MDW7:20 pmChicago Midway
Jan 13
MDW10:35 amChicago Midway
1h 15m
CLE12:50 pmCleveland Hopkins Intl
Southwest
Jan 16
CLE6:25 pmCleveland Hopkins Intl
1h 25m
MDW6:50 pmChicago Midway
Jan 19
MDW7:25 pmChicago Midway
1h 15m
CLE9:40 pmCleveland Hopkins Intl

Frontier flights from Cleveland to Chicago Midway Airport

Our best Frontier deals on Cleveland to Chicago Midway Airport flight tickets
Frontier
Jan 9
CLE1:09 pmCleveland Hopkins Intl
8h 56m
1 stop
MDW9:05 pmChicago Midway
Jan 13
MDW7:15 amChicago Midway
11h 43m
1 stop
CLE7:58 pmCleveland Hopkins Intl
Frontier
Jan 30
CLE1:12 pmCleveland Hopkins Intl
8h 41m
1 stop
MDW8:53 pmChicago Midway
Feb 3
MDW7:15 amChicago Midway
11h 42m
1 stop
CLE7:57 pmCleveland Hopkins Intl
Frontier
Jan 6
CLE6:46 pmCleveland Hopkins Intl
5h 28m
1 stop
MDW11:14 pmChicago Midway
Jan 13
MDW7:15 amChicago Midway
11h 43m
1 stop
CLE7:58 pmCleveland Hopkins Intl

See travel insights to Chicago from

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 to Chicago Midway Airport?

The month of January is, on average, the cheapest month to fly to Chicago Midway Airport from Cleveland, with most prices found around $220. If you are unable to visit Chicago Midway Airport during the month of January, then departing from Cleveland during the month September is also very affordable. Most momondo users find prices during this month for around $242.

What is the cheapest day to depart on your flight to Chicago Midway Airport?

According to our data, Monday is the cheapest day to fly to Chicago Midway Airport from Cleveland. The lowest ticket price found for a Monday departure recently was $245. Keep in mind that prices can always vary depending on your route and whether or not you are flying domestic or international. On the other hand, Sunday is the most expensive day to depart from Cleveland because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $402.

What is the cheapest time of day to depart on your flight to Chicago Midway Airport?

Flying to Chicago Midway Airport from Cleveland in the evening is the least expensive time of day to depart. momondo users have found prices as low as $255 when looking at flights departing in the evening. Try not to purchase tickets at noon because they tend to be around $298. Of course, these prices can vary depending on the time of year and what airport you fly to.

What is the cheapest Cleveland Hopkins Intl to Chicago Midway flight route?

Fly from Cleveland Hopkins Intl to Chicago Midway for the best Cleveland Hopkins Intl - Chicago Midway flight prices

What cabin class options are available on Cleveland Hopkins Intl to Chicago Midway flights?

There are 1 cabin classes available to choose from on Cleveland Hopkins Intl to Chicago Midway flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

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

$54

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 $54. The best round-trip flight deal from Cleveland to Chicago Midway Airport found on momondo in the last 72 hours is $111.
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
DeltaPriceFrom $156Free CancellationRating
8.0
8,580 reviews
Search Delta flights
SouthwestPriceFrom $168Free CancellationRating
8.1
4,765 reviews
Search Southwest 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 $168. Generally, Southwest has 16 flights on this route every week with an average price of $280. 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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