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Cheap flights from Cleveland to Chicago from $64

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 1/21. 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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0 bags

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Cheap round-trip flights

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Multiple Airlines Logo
3:59 pm - 11:45 am
CLE
-
MDW
20h 46m2 stops
Multiple Airlines Logo
1:20 pm - 10:42 pm
MDW
-
CLE
8h 22m1 stop
$213Multiple Airlines
Wed, Jan 21 - Tue, Jan 27
Frontier Logo
7:45 am - 2:05 pm
CLE
-
MDW
7h 20m1 stop
Frontier Logo
3:10 pm - 11:51 pm
MDW
-
CLE
7h 41m1 stop
$214Frontier
Mon, Dec 29 - Wed, Dec 31
Frontier Logo
11:26 am - 5:38 pm
CLE
-
MDW
7h 12m1 stop
Frontier Logo
10:50 pm - 11:07 am
MDW
-
CLE
11h 17m1 stop
$218Frontier
Thu, Jan 1 - Sun, Jan 4
Multiple Airlines Logo
6:00 am - 11:09 pm
CLE
-
MDW
18h 09m2 stops
Multiple Airlines Logo
6:10 am - 5:13 pm
MDW
-
CLE
10h 03m1 stop
$219Multiple Airlines
Fri, Jan 9 - Sun, Jan 11
Southwest Logo
6:15 am - 6:55 am
CLE
-
MDW
1h 40mnonstop
Southwest Logo
9:55 am - 12:10 pm
MDW
-
CLE
1h 15mnonstop
$221Southwest
Wed, Jan 7 - Sat, Jan 10
Frontier Logo
8:00 am - 10:43 pm
CLE
-
MDW
15h 43m2 stops
Frontier Logo
6:20 am - 11:11 pm
MDW
-
CLE
15h 51m1 stop
$222Frontier
Mon, Jan 19 - Sun, Jan 25
Delta Logo
6:30 am - 12:51 pm
CLE
-
MDW
7h 21m2 stops
Delta Logo
9:32 am - 7:26 pm
MDW
-
CLE
8h 54m2 stops
$224Delta
Tue, Jan 20 - Tue, Jan 27
Multiple Airlines Logo
2:40 pm - 10:34 pm
CLE
-
MDW
8h 54m1 stop
Multiple Airlines Logo
9:04 pm - 5:20 pm
MDW
-
CLE
19h 16m2 stops
$225Multiple Airlines
Fri, Feb 20 - Sun, Feb 22
Frontier Logo
3:22 pm - 8:43 am
CLE
-
MDW
18h 21m2 stops
Frontier Logo
1:20 pm - 10:42 pm
MDW
-
CLE
8h 22m1 stop
$226Frontier
Fri, Jan 23 - Wed, Jan 28
Multiple Airlines Logo
4:54 pm - 8:03 am
CLE
-
MDW
16h 09m2 stops
Multiple Airlines Logo
9:38 am - 11:11 pm
MDW
-
CLE
12h 33m1 stop
$228Multiple Airlines
Sat, Jan 17 - Sat, Jan 24

Frontier flights from Cleveland to Chicago Midway Airport

Our best Frontier deals on Cleveland to Chicago Midway Airport flight tickets
Frontier
Dec 29
CLE7:45 amCleveland Hopkins Intl
7h 20m
1 stop
MDW2:05 pmChicago Midway
Dec 31
MDW3:10 pmChicago Midway
7h 41m
1 stop
CLE11:51 pmCleveland Hopkins Intl
$214
Find similar
Frontier
Dec 19
CLE11:26 amCleveland Hopkins Intl
11h 46m
1 stop
MDW10:12 pmChicago Midway
Jan 5
MDW8:15 amChicago Midway
7h 15m
1 stop
CLE4:30 pmCleveland Hopkins Intl
$217
Find similar
Frontier
Jan 1
CLE11:26 amCleveland Hopkins Intl
7h 12m
1 stop
MDW5:38 pmChicago Midway
Jan 4
MDW10:50 pmChicago Midway
11h 17m
1 stop
CLE11:07 amCleveland Hopkins Intl
$218
Find similar

Southwest flights from Cleveland to Chicago Midway Airport

Our best Southwest deals on Cleveland to Chicago Midway Airport flight tickets
Southwest
Jan 7
CLE6:15 amCleveland Hopkins Intl
1h 40m
MDW6:55 amChicago Midway
Jan 10
MDW9:55 amChicago Midway
1h 15m
CLE12:10 pmCleveland Hopkins Intl
$221
Find similar
Southwest
Jan 7
CLE5:35 amCleveland Hopkins Intl
7h 00m
1 stop
MDW11:35 amChicago Midway
Jan 10
MDW9:55 amChicago Midway
1h 15m
CLE12:10 pmCleveland Hopkins Intl
$231
Find similar
Southwest
Jan 13
CLE4:25 pmCleveland Hopkins Intl
1h 25m
MDW4:50 pmChicago Midway
Jan 15
MDW9:50 amChicago Midway
1h 15m
CLE12:05 pmCleveland Hopkins Intl
$234
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from Cleveland to Chicago Midway Airport that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, momondo users made 832,500 searches. Data last updated December 14, 2025.
Use the filters below to find and compare flights from Cleveland to Chicago Midway Airport that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

ClevelandChicago

CLE - MDW

CLEMDW

Cleveland Hopkins Intl

Wed 1/21

3:59 pm-11:45 am

2 stops20h 46m

Chicago Midway

Tue 1/27

1:20 pm-10:42 pm

1 stop8h 22m

$213

ClevelandChicago

CLE - MDW

CLEMDW

Cleveland Hopkins Intl

Mon 12/29

7:45 am-2:05 pm

1 stop7h 20m

Chicago Midway

Wed 12/31

3:10 pm-11:51 pm

1 stop7h 41m

$214

ClevelandChicago

CLE - MDW

CLEMDW

Cleveland Hopkins Intl

Thu 1/1

11:26 am-5:38 pm

1 stop7h 12m

Chicago Midway

Sun 1/4

10:50 pm-11:07 am

1 stop11h 17m

$218

ClevelandChicago

CLE - MDW

CLEMDW

Cleveland Hopkins Intl

Fri 1/9

6:00 am-11:09 pm

2 stops18h 09m

Chicago Midway

Sun 1/11

6:10 am-5:13 pm

1 stop10h 03m

$219

ClevelandChicago

CLE - MDW

CLEMDW

Cleveland Hopkins Intl

Wed 1/7

6:15 am-6:55 am

Nonstop1h 40m

Chicago Midway

Sat 1/10

9:55 am-12:10 pm

Nonstop1h 15m

$221

ClevelandChicago

CLE - MDW

CLEMDW

Cleveland Hopkins Intl

Mon 1/19

8:00 am-10:43 pm

2 stops15h 43m

Chicago Midway

Sun 1/25

6:20 am-11:11 pm

1 stop15h 51m

$222

ClevelandChicago

CLE - MDW

CLEMDW

Cleveland Hopkins Intl

Tue 1/20

6:30 am-12:51 pm

2 stops7h 21m

Chicago Midway

Tue 1/27

9:32 am-7:26 pm

2 stops8h 54m

$224

ClevelandChicago

CLE - MDW

CLEMDW

Cleveland Hopkins Intl

Fri 2/20

2:40 pm-10:34 pm

1 stop8h 54m

Chicago Midway

Sun 2/22

9:04 pm-5:20 pm

2 stops19h 16m

$225

ClevelandChicago

CLE - MDW

CLEMDW

Cleveland Hopkins Intl

Fri 1/23

3:22 pm-8:43 am

2 stops18h 21m

Chicago Midway

Wed 1/28

1:20 pm-10:42 pm

1 stop8h 22m

$226

ClevelandChicago

CLE - MDW

CLEMDW

Cleveland Hopkins Intl

Sat 1/17

4:54 pm-8:03 am

2 stops16h 09m

Chicago Midway

Sat 1/24

9:38 am-11:11 pm

1 stop12h 33m

$228

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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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 September is, on average, the cheapest month to fly to Chicago Midway Airport from Cleveland, with most prices found around $225. If you are unable to visit Chicago Midway Airport during the month of September, then departing from Cleveland during the month January is also very affordable. Most momondo users find prices during this month for around $243.

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

According to our data, Wednesday is the cheapest day to fly to Chicago Midway Airport from Cleveland. The lowest ticket price found for a Wednesday departure recently was $365. 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 $413.

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 afternoon is the least expensive time of day to depart. momondo users have found prices as low as $335 when looking at flights departing in the afternoon. Try not to purchase tickets in the morning because they tend to be around $403. 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 is only 1 cabin class 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 54% 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

$183

Fastest flight time

1h 20m

Direct flights

Every day
The best one-way flight to Chicago Midway Airport from Cleveland in the past 72 hours is $183. The best round-trip flight deal from Cleveland to Chicago Midway Airport found on momondo in the last 72 hours is $346.
The fastest flight from Cleveland to Chicago Midway Airport takes 1h 20m
Direct flights go from Cleveland to Chicago Midway Airport every day.
Search flight deals

  • 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 20m, 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 $140Free CancellationRating
7.9
4,251 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 $140. Generally, Southwest has 9 flights on this route every week with an average price of $272. Southwest is rated 7.9/10 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
Chesterton
Monticello
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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