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Cheap flights from Cleveland to Chicago from $40

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 departing on 8/9. 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

Southwest Logo
7:05 am - 7:20 amCLE-MDW
1h 15mnonstop
Southwest Logo
7:30 pm - 9:45 pmMDW-CLE
1h 15mnonstop
$79Southwest
Find Deal
Wed, Aug 27 - Sat, Aug 30
Southwest Logo
3:50 pm - 4:05 pmCLE-MDW
1h 15mnonstop
Southwest Logo
4:35 pm - 6:50 pmMDW-CLE
1h 15mnonstop
$85Southwest
Find Deal
Sat, Aug 9 - Mon, Aug 11
Southwest Logo
11:40 am - 4:25 pmCLE-MDW
5h 45m1 stop
Southwest Logo
7:30 pm - 9:45 pmMDW-CLE
1h 15mnonstop
$89Southwest
Find Deal
Wed, Aug 27 - Sat, Aug 30
Southwest Logo
3:30 pm - 3:50 pmCLE-MDW
1h 20mnonstop
Southwest Logo
4:35 pm - 6:50 pmMDW-CLE
1h 15mnonstop
$91Southwest
Find Deal
Thu, Aug 7 - Mon, Aug 18
Southwest Logo
11:40 am - 7:10 pmCLE-MDW
8h 30m2 stops
Southwest Logo
7:30 pm - 9:45 pmMDW-CLE
1h 15mnonstop
$94Southwest
Find Deal
Wed, Aug 27 - Sat, Aug 30
Southwest Logo
3:30 pm - 3:50 pmCLE-MDW
1h 20mnonstop
Southwest Logo
2:05 pm - 9:20 pmMDW-CLE
6h 15m1 stop
$95Southwest
Find Deal
Thu, Aug 7 - Tue, Aug 12
Southwest Logo
3:30 pm - 3:50 pmCLE-MDW
1h 20mnonstop
Southwest Logo
8:35 pm - 10:50 pmMDW-CLE
1h 15mnonstop
$97Southwest
Find Deal
Fri, Aug 8 - Tue, Aug 12
Southwest Logo
3:30 pm - 3:50 pmCLE-MDW
1h 20mnonstop
Southwest Logo
10:30 am - 6:20 pmMDW-CLE
6h 50m2 stops
$100Southwest
Find Deal
Thu, Aug 7 - Tue, Aug 12
Southwest Logo
6:40 pm - 7:00 pmCLE-MDW
1h 20mnonstop
Southwest Logo
6:35 am - 4:55 pmMDW-CLE
9h 20m1 stop
$101Southwest
Find Deal
Wed, Aug 13 - Sat, Aug 16
Southwest Logo
3:30 pm - 3:50 pmCLE-MDW
1h 20mnonstop
Southwest Logo
9:30 am - 11:45 amMDW-CLE
1h 15mnonstop
$103Southwest
Find Deal
Fri, Aug 29 - Mon, Sep 1

Southwest flights from Cleveland to Chicago Midway Airport

Our best Southwest deals on Cleveland to Chicago Midway Airport flight tickets
Southwest
Aug 27
CLE7:05 amCleveland Hopkins Intl
1h 15m
MDW7:20 amChicago Midway
Aug 30
MDW7:30 pmChicago Midway
1h 15m
CLE9:45 pmCleveland Hopkins Intl
$79
Find similar
Southwest
Aug 9
CLE3:50 pmCleveland Hopkins Intl
1h 15m
MDW4:05 pmChicago Midway
Aug 11
MDW4:35 pmChicago Midway
1h 15m
CLE6:50 pmCleveland Hopkins Intl
$85
Find similar
Southwest
Aug 27
CLE11:40 amCleveland Hopkins Intl
5h 45m
1 stop
MDW4:25 pmChicago Midway
Aug 30
MDW7:30 pmChicago Midway
1h 15m
CLE9:45 pmCleveland Hopkins Intl
$89
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Frontier flights from Cleveland to Chicago Midway Airport

Our best Frontier deals on Cleveland to Chicago Midway Airport flight tickets
Frontier
Jul 19
CLE6:25 pmCleveland Hopkins Intl
5h 10m
1 stop
MDW10:35 pmChicago Midway
Jul 27
MDW8:35 amChicago Midway
6h 37m
1 stop
CLE4:12 pmCleveland Hopkins Intl
$176
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Frontier
Jul 12
CLE6:25 pmCleveland Hopkins Intl
5h 10m
1 stop
MDW10:35 pmChicago Midway
Jul 14
MDW8:35 amChicago Midway
7h 26m
1 stop
CLE5:01 pmCleveland Hopkins Intl
$178
Find similar
Frontier
Jul 19
CLE6:25 pmCleveland Hopkins Intl
5h 10m
1 stop
MDW10:35 pmChicago Midway
Jul 22
MDW11:39 amChicago Midway
5h 24m
1 stop
CLE6:03 pmCleveland Hopkins Intl
$179
Find similar

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 $188. 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, Saturday is the cheapest day to fly to Chicago Midway Airport from Cleveland. The lowest ticket price found for a Saturday departure recently was $376. 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 $430.

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 $364 when looking at flights departing in the evening. Try not to purchase tickets in the morning because they tend to be around $407. 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 10% 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

$40

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 $40. The best round-trip flight deal from Cleveland to Chicago Midway Airport found on momondo in the last 72 hours is $79.
The fastest flight from Cleveland to Chicago Midway Airport takes 1h 15m
Direct flights go from Cleveland to Chicago Midway Airport every day.
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  • 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
8.0
4,250 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 $151. Generally, Southwest has 20 flights on this route every week with an average price of $275. 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
Saint Joseph
Portage
Lansing
Schererville
Valparaiso
Crown Point
Munster
Monticello
Chesterton
Porter
Griffith
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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