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Cheap flights from Cleveland to Chicago Midway Airport from $39

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 6/25. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
0 bags

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Find the cheapest flights from Cleveland to Chicago

Cheap round-trip flights

KAYAK's recommended round-trip deals from the most popular airlines that fly from Cleveland to Chicago.
Southwest Logo
7:20 pm - 7:40 pmCLE-MDW
1h 20mnonstop
Southwest Logo
6:10 pm - 8:20 pmMDW-CLE
1h 10mnonstop
$77Southwest
Find Deal
Tue, Jul 1 - Thu, Jul 3
Southwest Logo
3:50 pm - 4:10 pmCLE-MDW
1h 20mnonstop
Southwest Logo
5:05 am - 12:35 pmMDW-CLE
6h 30m1 stop
$87Southwest
Find Deal
Tue, Jul 1 - Thu, Jul 3
Southwest Logo
4:50 pm - 11:00 pmCLE-MDW
7h 10m1 stop
Southwest Logo
5:05 am - 12:35 pmMDW-CLE
6h 30m1 stop
$97Southwest
Find Deal
Tue, Jul 1 - Thu, Jul 3
Southwest Logo
5:50 am - 9:00 amCLE-MDW
4h 10m1 stop
Southwest Logo
11:10 am - 11:10 pmMDW-CLE
11h 00m2 stops
$108Southwest
Find Deal
Thu, Sep 18 - Mon, Sep 22
Frontier Logo
1:20 pm - 11:39 pmCLE-MDW
11h 19m1 stop
Frontier Logo
1:19 pm - 12:36 amMDW-CLE
10h 17m1 stop
$160Frontier
Find Deal
Thu, May 15 - Mon, May 19
Frontier Logo
2:21 pm - 11:54 pmCLE-MDW
10h 33m1 stop
Frontier Logo
1:19 pm - 12:36 amMDW-CLE
10h 17m1 stop
$170Frontier
Find Deal
Sun, May 11 - Fri, May 16
Delta Logo
11:49 am - 5:45 pmCLE-MDW
6h 56m1 stop
Delta Logo
6:30 pm - 11:57 pmMDW-CLE
4h 27m1 stop
$177Delta
Find Deal
Wed, Jun 4 - Sat, Jun 7
Delta Logo
6:00 am - 12:30 pmCLE-MDW
7h 30m2 stops
Delta Logo
6:00 am - 1:25 pmMDW-CLE
6h 25m1 stop
$182Delta
Find Deal
Wed, Jul 30 - Tue, Aug 19
Delta Logo
6:05 am - 8:40 amCLE-MDW
3h 35m1 stop
Delta Logo
4:15 pm - 9:41 pmMDW-CLE
4h 26m1 stop
$185Delta
Find Deal
Mon, May 26 - Fri, May 30
Frontier Logo
5:30 am - 12:24 pmCLE-MDW
7h 54m1 stop
Frontier Logo
1:19 pm - 12:36 amMDW-CLE
10h 17m1 stop
$190Frontier
Find Deal
Fri, May 16 - Mon, May 19

Frontier flights from Cleveland to Chicago Midway Airport

Our best Frontier deals on Cleveland to Chicago Midway Airport flight tickets
Frontier
May 15
CLE1:20 pmCleveland Hopkins Intl
11h 19m
1 stop
MDW11:39 pmChicago Midway
May 19
MDW1:19 pmChicago Midway
10h 17m
1 stop
CLE12:36 amCleveland Hopkins Intl
Frontier
May 11
CLE2:21 pmCleveland Hopkins Intl
10h 33m
1 stop
MDW11:54 pmChicago Midway
May 16
MDW1:19 pmChicago Midway
10h 17m
1 stop
CLE12:36 amCleveland Hopkins Intl
Frontier
May 1
CLE2:05 pmCleveland Hopkins Intl
9h 35m
1 stop
MDW10:40 pmChicago Midway
May 8
MDW8:30 amChicago Midway
6h 17m
1 stop
CLE3:47 pmCleveland Hopkins Intl

Delta flights from Cleveland to Chicago Midway Airport

Our best Delta deals on Cleveland to Chicago Midway Airport flight tickets
Delta
Jun 4
CLE11:49 amCleveland Hopkins Intl
6h 56m
1 stop
MDW5:45 pmChicago Midway
Jun 7
MDW6:30 pmChicago Midway
4h 27m
1 stop
CLE11:57 pmCleveland Hopkins Intl
Delta
Jul 30
CLE6:00 amCleveland Hopkins Intl
7h 30m
2 stops
MDW12:30 pmChicago Midway
Aug 19
MDW6:00 amChicago Midway
6h 25m
1 stop
CLE1:25 pmCleveland Hopkins Intl
Delta
May 26
CLE6:05 amCleveland Hopkins Intl
3h 35m
1 stop
MDW8:40 amChicago Midway
May 30
MDW4:15 pmChicago Midway
4h 26m
1 stop
CLE9:41 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 typical price of a round-trip flight between Cleveland and Chicago Midway Airport?

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 $188. If you are unable to visit Chicago Midway Airport during the month of January, then departing from Cleveland during the month May is also very affordable. Most momondo users find prices during this month for around $252.

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

According to our data, Saturday is the cheapest day to fly to Chicago Midway Airport from Cleveland. The lowest ticket price found for a Saturday departure recently was $377. 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 $466.

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 $373 when looking at flights departing in the evening. Try not to purchase tickets in the morning because they tend to be around $413. 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.

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

$39

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 $39. The best round-trip flight deal from Cleveland to Chicago Midway Airport found on momondo in the last 72 hours is $77.
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
7,920 reviews
Search Delta flights
SouthwestPriceFrom $172Free CancellationRating
8.0
4,287 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 $172. Generally, Southwest has 15 flights on this route every week with an average price of $281. Southwest is rated 8.0/10 by our users.


Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
New Buffalo
Hammond
Benton Harbor
Portage
Lansing
Saint Joseph
Schererville
Valparaiso
Munster
Crown Point
Monticello
Chesterton
Griffith
Porter
Saint John

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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