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Cheap flights from Cleveland to Chicago from $76

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 10/11. 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

Frontier Logo
6:48 pm - 12:30 amCLE-MDW
6h 42m1 stop
Frontier Logo
2:06 pm - 12:22 pmMDW-CLE
21h 16m1 stop
$139Frontier
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Mon, Nov 3 - Wed, Nov 5
Southwest Logo
4:35 pm - 4:55 pmCLE-MDW
1h 20mnonstop
Southwest Logo
5:35 am - 12:25 pmMDW-CLE
5h 50m1 stop
$142Southwest
Find Deal
Mon, Nov 3 - Wed, Nov 5
Frontier Logo
11:27 am - 8:52 pmCLE-MDW
10h 25m1 stop
Frontier Logo
5:15 pm - 12:43 amMDW-CLE
6h 28m1 stop
$143Frontier
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Fri, Sep 26 - Fri, Oct 3
Frontier Logo
6:33 pm - 12:36 amCLE-MDW
7h 03m1 stop
Frontier Logo
12:11 pm - 1:59 amMDW-CLE
12h 48m1 stop
$144Frontier
Find Deal
Sun, Oct 26 - Mon, Oct 27
Southwest Logo
12:55 pm - 1:10 pmCLE-MDW
1h 15mnonstop
Southwest Logo
5:35 am - 12:25 pmMDW-CLE
5h 50m1 stop
$151Southwest
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Sat, Nov 1 - Tue, Nov 4
Frontier Logo
5:30 am - 4:00 pmCLE-MDW
11h 30m1 stop
Frontier Logo
5:15 pm - 12:43 amMDW-CLE
6h 28m1 stop
$153Frontier
Find Deal
Fri, Sep 26 - Fri, Oct 3
Frontier Logo
11:27 am - 8:52 pmCLE-MDW
10h 25m1 stop
Frontier Logo
6:21 am - 8:17 pmMDW-CLE
12h 56m1 stop
$154Frontier
Find Deal
Fri, Sep 26 - Sun, Sep 28
Frontier Logo
7:19 pm - 11:41 pmCLE-MDW
5h 22m1 stop
Frontier Logo
6:21 am - 12:35 amMDW-CLE
17h 14m1 stop
$155Frontier
Find Deal
Sat, Oct 4 - Sun, Oct 5
Delta Logo
8:12 am - 11:48 amCLE-MDW
4h 36m1 stop
Delta Logo
10:35 am - 5:03 pmMDW-CLE
5h 28m1 stop
$177Delta
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Tue, Sep 30 - Wed, Oct 1
Delta Logo
6:24 pm - 10:14 pmCLE-MDW
4h 50m1 stop
Delta Logo
1:08 pm - 11:21 pmMDW-CLE
9h 13m2 stops
$182Delta
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Fri, Oct 24 - Mon, Oct 27

Frontier flights from Cleveland to Chicago Midway Airport

Our best Frontier deals on Cleveland to Chicago Midway Airport flight tickets
Frontier
Nov 3
CLE6:48 pmCleveland Hopkins Intl
6h 42m
1 stop
MDW12:30 amChicago Midway
Nov 5
MDW2:06 pmChicago Midway
21h 16m
1 stop
CLE12:22 pmCleveland Hopkins Intl
$139
Find similar
Frontier
Sep 26
CLE11:27 amCleveland Hopkins Intl
10h 25m
1 stop
MDW8:52 pmChicago Midway
Oct 3
MDW5:15 pmChicago Midway
6h 28m
1 stop
CLE12:43 amCleveland Hopkins Intl
$143
Find similar
Frontier
Oct 26
CLE6:33 pmCleveland Hopkins Intl
7h 03m
1 stop
MDW12:36 amChicago Midway
Oct 27
MDW12:11 pmChicago Midway
12h 48m
1 stop
CLE1:59 amCleveland Hopkins Intl
$144
Find similar

Southwest flights from Cleveland to Chicago Midway Airport

Our best Southwest deals on Cleveland to Chicago Midway Airport flight tickets
Southwest
Nov 3
CLE4:35 pmCleveland Hopkins Intl
1h 20m
MDW4:55 pmChicago Midway
Nov 5
MDW5:35 amChicago Midway
5h 50m
1 stop
CLE12:25 pmCleveland Hopkins Intl
$142
Find similar
Southwest
Nov 1
CLE12:55 pmCleveland Hopkins Intl
1h 15m
MDW1:10 pmChicago Midway
Nov 4
MDW5:35 amChicago Midway
5h 50m
1 stop
CLE12:25 pmCleveland Hopkins Intl
$151
Find similar
Southwest
Oct 28
CLE7:20 pmCleveland Hopkins Intl
3h 45m
1 stop
MDW10:05 pmChicago Midway
Oct 29
MDW8:35 pmChicago Midway
1h 10m
CLE10:45 pmCleveland Hopkins Intl
$156
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 September 11, 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

Mon 11/3

6:48 pm-12:30 am

1 stop6h 42m

Chicago Midway

Wed 11/5

2:06 pm-12:22 pm

1 stop21h 16m

$139

ClevelandChicago

CLE - MDW

CLEMDW

Cleveland Hopkins Intl

Mon 11/3

4:35 pm-4:55 pm

Nonstop1h 20m

Chicago Midway

Wed 11/5

5:35 am-12:25 pm

1 stop5h 50m

$142

ClevelandChicago

CLE - MDW

CLEMDW

Cleveland Hopkins Intl

Fri 9/26

11:27 am-8:52 pm

1 stop10h 25m

Chicago Midway

Fri 10/3

5:15 pm-12:43 am

1 stop6h 28m

$143

ClevelandChicago

CLE - MDW

CLEMDW

Cleveland Hopkins Intl

Sun 10/26

6:33 pm-12:36 am

1 stop7h 03m

Chicago Midway

Mon 10/27

12:11 pm-1:59 am

1 stop12h 48m

$144

ClevelandChicago

CLE - MDW

CLEMDW

Cleveland Hopkins Intl

Sat 11/1

12:55 pm-1:10 pm

Nonstop1h 15m

Chicago Midway

Tue 11/4

5:35 am-12:25 pm

1 stop5h 50m

$151

ClevelandChicago

CLE - MDW

CLEMDW

Cleveland Hopkins Intl

Fri 9/26

5:30 am-4:00 pm

1 stop11h 30m

Chicago Midway

Fri 10/3

5:15 pm-12:43 am

1 stop6h 28m

$153

ClevelandChicago

CLE - MDW

CLEMDW

Cleveland Hopkins Intl

Fri 9/26

11:27 am-8:52 pm

1 stop10h 25m

Chicago Midway

Sun 9/28

6:21 am-8:17 pm

1 stop12h 56m

$154

ClevelandChicago

CLE - MDW

CLEMDW

Cleveland Hopkins Intl

Sat 10/4

7:19 pm-11:41 pm

1 stop5h 22m

Chicago Midway

Sun 10/5

6:21 am-12:35 am

1 stop17h 14m

$155

ClevelandChicago

CLE - MDW

CLEMDW

Cleveland Hopkins Intl

Tue 9/30

8:12 am-11:48 am

1 stop4h 36m

Chicago Midway

Wed 10/1

10:35 am-5:03 pm

1 stop5h 28m

$177

ClevelandChicago

CLE - MDW

CLEMDW

Cleveland Hopkins Intl

Fri 10/24

6:24 pm-10:14 pm

1 stop4h 50m

Chicago Midway

Mon 10/27

1:08 pm-11:21 pm

2 stops9h 13m

$182

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 $237.

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 $375. 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 $419.

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 $356 when looking at flights departing in the evening. Try not to purchase tickets in the morning because they tend to be around $401. 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

$163

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 $163. The best round-trip flight deal from Cleveland to Chicago Midway Airport found on momondo in the last 72 hours is $236.
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 $141Free CancellationRating
8.0
4,248 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 $141. Generally, Southwest has 20 flights on this route every week with an average price of $277. 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
Lansing
Portage
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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