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Cheap flights from Cleveland to Chicago from $100

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 11/11. 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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Cheap round-trip flights

Enter your travel dates to find the best prices.
Multiple Airlines Logo
6:00 am - 10:47 pmCLE-MDW
17h 47m1 stop
Multiple Airlines Logo
5:56 pm - 2:14 pmMDW-CLE
19h 18m2 stops
$176Multiple Airlines
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Sat, Oct 25 - Tue, Oct 28
Frontier Logo
5:30 am - 11:05 pmCLE-MDW
18h 35m1 stop
Frontier Logo
8:42 pm - 11:33 amMDW-CLE
13h 51m1 stop
$177Frontier
Find Deal
Sat, Dec 13 - Mon, Dec 15
Frontier Logo
6:00 am - 4:09 pmCLE-MDW
11h 09m1 stop
Frontier Logo
12:30 pm - 11:51 pmMDW-CLE
10h 21m1 stop
$180Frontier
Find Deal
Mon, Oct 27 - Mon, Nov 3
Frontier Logo
7:51 pm - 6:39 pmCLE-MDW
23h 48m1 stop
Frontier Logo
6:20 am - 12:54 amMDW-CLE
17h 34m1 stop
$181Frontier
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Fri, Oct 31 - Mon, Nov 3
Frontier Logo
11:33 am - 5:15 pmCLE-MDW
6h 42m1 stop
Frontier Logo
12:30 pm - 11:51 pmMDW-CLE
10h 21m1 stop
$185Frontier
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Fri, Nov 14 - Mon, Nov 17
Multiple Airlines Logo
3:40 pm - 6:39 pmCLE-MDW
27h 59m1 stop
Multiple Airlines Logo
2:06 pm - 11:59 pmMDW-CLE
32h 53m2 stops
$203Multiple Airlines
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Wed, Nov 5 - Wed, Nov 12
Southwest Logo
6:15 am - 6:55 amCLE-MDW
1h 40mnonstop
Southwest Logo
9:55 am - 12:10 pmMDW-CLE
1h 15mnonstop
$215Southwest
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Wed, Jan 14 - Sat, Jan 17
Delta Logo
12:28 pm - 5:19 pmCLE-MDW
5h 51m1 stop
Delta Logo
6:08 pm - 10:31 pmMDW-CLE
3h 23m1 stop
$219Delta
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Wed, Dec 24 - Thu, Dec 25
Delta Logo
5:20 am - 8:40 amCLE-MDW
4h 20m1 stop
Delta Logo
1:08 pm - 10:12 pmMDW-CLE
8h 04m2 stops
$224Delta
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Fri, Oct 31 - Fri, Oct 31
Southwest Logo
3:05 pm - 3:30 pmCLE-MDW
1h 25mnonstop
Southwest Logo
5:35 pm - 7:50 pmMDW-CLE
1h 15mnonstop
$226Southwest
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Thu, Jan 15 - Sat, Jan 17

Frontier flights from Cleveland to Chicago Midway Airport

Our best Frontier deals on Cleveland to Chicago Midway Airport flight tickets
Frontier
Dec 13
CLE5:30 amCleveland Hopkins Intl
18h 35m
1 stop
MDW11:05 pmChicago Midway
Dec 15
MDW8:42 pmChicago Midway
13h 51m
1 stop
CLE11:33 amCleveland Hopkins Intl
$177
Find similar
Frontier
Oct 27
CLE6:00 amCleveland Hopkins Intl
11h 09m
1 stop
MDW4:09 pmChicago Midway
Nov 3
MDW12:30 pmChicago Midway
10h 21m
1 stop
CLE11:51 pmCleveland Hopkins Intl
$180
Find similar
Frontier
Oct 31
CLE7:51 pmCleveland Hopkins Intl
23h 48m
1 stop
MDW6:39 pmChicago Midway
Nov 3
MDW6:20 amChicago Midway
17h 34m
1 stop
CLE12:54 amCleveland Hopkins Intl
$181
Find similar

Southwest flights from Cleveland to Chicago Midway Airport

Our best Southwest deals on Cleveland to Chicago Midway Airport flight tickets
Southwest
Jan 14
CLE6:15 amCleveland Hopkins Intl
1h 40m
MDW6:55 amChicago Midway
Jan 17
MDW9:55 amChicago Midway
1h 15m
CLE12:10 pmCleveland Hopkins Intl
$215
Find similar
Southwest
Jan 15
CLE3:05 pmCleveland Hopkins Intl
1h 25m
MDW3:30 pmChicago Midway
Jan 17
MDW5:35 pmChicago Midway
1h 15m
CLE7:50 pmCleveland Hopkins Intl
$226
Find similar
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
$231
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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 October 13, 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

Sat 10/25

6:00 am-10:47 pm

1 stop17h 47m

Chicago Midway

Tue 10/28

5:56 pm-2:14 pm

2 stops19h 18m

$176

ClevelandChicago

CLE - MDW

CLEMDW

Cleveland Hopkins Intl

Sat 12/13

5:30 am-11:05 pm

1 stop18h 35m

Chicago Midway

Mon 12/15

8:42 pm-11:33 am

1 stop13h 51m

$177

ClevelandChicago

CLE - MDW

CLEMDW

Cleveland Hopkins Intl

Mon 10/27

6:00 am-4:09 pm

1 stop11h 09m

Chicago Midway

Mon 11/3

12:30 pm-11:51 pm

1 stop10h 21m

$180

ClevelandChicago

CLE - MDW

CLEMDW

Cleveland Hopkins Intl

Fri 10/31

7:51 pm-6:39 pm

1 stop23h 48m

Chicago Midway

Mon 11/3

6:20 am-12:54 am

1 stop17h 34m

$181

ClevelandChicago

CLE - MDW

CLEMDW

Cleveland Hopkins Intl

Fri 11/14

11:33 am-5:15 pm

1 stop6h 42m

Chicago Midway

Mon 11/17

12:30 pm-11:51 pm

1 stop10h 21m

$185

ClevelandChicago

CLE - MDW

CLEMDW

Cleveland Hopkins Intl

Wed 11/5

3:40 pm-6:39 pm

1 stop27h 59m

Chicago Midway

Wed 11/12

2:06 pm-11:59 pm

2 stops32h 53m

$203

ClevelandChicago

CLE - MDW

CLEMDW

Cleveland Hopkins Intl

Wed 1/14

6:15 am-6:55 am

Nonstop1h 40m

Chicago Midway

Sat 1/17

9:55 am-12:10 pm

Nonstop1h 15m

$215

ClevelandChicago

CLE - MDW

CLEMDW

Cleveland Hopkins Intl

Wed 12/24

12:28 pm-5:19 pm

1 stop5h 51m

Chicago Midway

Thu 12/25

6:08 pm-10:31 pm

1 stop3h 23m

$219

ClevelandChicago

CLE - MDW

CLEMDW

Cleveland Hopkins Intl

Fri 10/31

5:20 am-8:40 am

1 stop4h 20m

Chicago Midway

Fri 10/31

1:08 pm-10:12 pm

2 stops8h 04m

$224

ClevelandChicago

CLE - MDW

CLEMDW

Cleveland Hopkins Intl

Thu 1/15

3:05 pm-3:30 pm

Nonstop1h 25m

Chicago Midway

Sat 1/17

5:35 pm-7:50 pm

Nonstop1h 15m

$226

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 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 $225.

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 $361. 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 $420.

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 $338 when looking at flights departing in the afternoon. Try not to purchase tickets in the morning because they tend to be around $404. 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.

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

$169

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 $169. The best round-trip flight deal from Cleveland to Chicago Midway Airport found on momondo in the last 72 hours is $282.
The fastest flight from Cleveland to Chicago Midway Airport takes 1h 15m
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 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 $142Free CancellationRating
8.0
4,235 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 $142. Generally, Southwest has 15 flights on this route every week with an average price of $280. 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
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.

An easier way to manage your Chicago Midway Airport trip

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