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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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Cheap round-trip flights

Enter your travel dates to find the best prices.
Delta Logo
6:00 am - 12:48 pm
CLE
-
MDW
7h 48m2 stops
Delta Logo
11:21 am - 5:51 pm
MDW
-
CLE
5h 30m1 stop
$202Delta
Sat, Jan 17 - Sun, Jan 18
Southwest Logo
6:50 pm - 10:05 pm
CLE
-
MDW
4h 15m1 stop
Southwest Logo
9:55 am - 12:10 pm
MDW
-
CLE
1h 15mnonstop
$203Southwest
Mon, Jan 12 - Sat, Jan 17
Frontier Logo
9:00 pm - 9:58 pm
CLE
-
MDW
25h 58m1 stop
Frontier Logo
12:33 pm - 12:21 am
MDW
-
CLE
10h 48m1 stop
$204Frontier
Wed, Apr 8 - Sat, Apr 11
Frontier Logo
11:53 am - 7:52 pm
CLE
-
MDW
8h 59m1 stop
Frontier Logo
5:01 pm - 1:44 pm
MDW
-
CLE
19h 43m2 stops
$205Frontier
Fri, Jan 23 - Mon, Jan 26
Frontier Logo
6:24 pm - 10:34 am
CLE
-
MDW
17h 10m2 stops
Frontier Logo
8:22 am - 11:37 pm
MDW
-
CLE
14h 15m1 stop
$207Frontier
Mon, Jan 12 - Sat, Jan 17
Multiple Airlines Logo
7:10 am - 10:19 pm
CLE
-
MDW
16h 09m1 stop
Multiple Airlines Logo
7:20 pm - 10:42 pm
MDW
-
CLE
26h 22m2 stops
$210Multiple Airlines
Thu, Jan 15 - Mon, Jan 19
Southwest Logo
6:15 am - 6:55 am
CLE
-
MDW
1h 40mnonstop
Southwest Logo
7:55 pm - 10:10 pm
MDW
-
CLE
1h 15mnonstop
$211Southwest
Tue, Feb 3 - Tue, Feb 10
Frontier Logo
8:25 pm - 10:17 pm
CLE
-
MDW
26h 52m2 stops
Frontier Logo
6:10 am - 11:13 pm
MDW
-
CLE
16h 03m1 stop
$212Frontier
Tue, Jan 6 - Sat, Jan 10
Frontier Logo
11:26 am - 10:12 pm
CLE
-
MDW
11h 46m1 stop
Frontier Logo
12:41 pm - 11:13 pm
MDW
-
CLE
9h 32m1 stop
$213Frontier
Mon, Jan 5 - Thu, Jan 8
Frontier Logo
5:45 am - 11:41 pm
CLE
-
MDW
18h 56m1 stop
Frontier Logo
3:29 pm - 6:07 am
MDW
-
CLE
13h 38m2 stops
$216Frontier
Thu, Feb 19 - Mon, Mar 2

Delta flights from Cleveland to Chicago Midway Airport

Our best Delta deals on Cleveland to Chicago Midway Airport flight tickets
Delta
Jan 17
CLE6:00 amCleveland Hopkins Intl
7h 48m
2 stops
MDW12:48 pmChicago Midway
Jan 18
MDW11:21 amChicago Midway
5h 30m
1 stop
CLE5:51 pmCleveland Hopkins Intl
$202
Find similar
Delta
Jan 14
CLE6:30 amCleveland Hopkins Intl
7h 39m
1 stop
MDW1:09 pmChicago Midway
Jan 14
MDW5:31 pmChicago Midway
6h 08m
1 stop
CLE12:39 amCleveland Hopkins Intl
$231
Find similar
Delta
Jan 18
CLE6:00 amCleveland Hopkins Intl
7h 48m
2 stops
MDW12:48 pmChicago Midway
Jan 25
MDW6:35 pmChicago Midway
4h 21m
1 stop
CLE11:56 pmCleveland Hopkins Intl
$242
Find similar

Frontier flights from Cleveland to Chicago Midway Airport

Our best Frontier deals on Cleveland to Chicago Midway Airport flight tickets
Frontier
Apr 8
CLE9:00 pmCleveland Hopkins Intl
25h 58m
1 stop
MDW9:58 pmChicago Midway
Apr 11
MDW12:33 pmChicago Midway
10h 48m
1 stop
CLE12:21 amCleveland Hopkins Intl
$204
Find similar
Frontier
Jan 23
CLE11:53 amCleveland Hopkins Intl
8h 59m
1 stop
MDW7:52 pmChicago Midway
Jan 26
MDW5:01 pmChicago Midway
19h 43m
2 stops
CLE1:44 pmCleveland Hopkins Intl
$205
Find similar
Frontier
Jan 19
CLE8:00 amCleveland Hopkins Intl
53h 05m
2 stops
MDW12:05 pmChicago Midway
Jan 26
MDW5:01 pmChicago Midway
13h 33m
1 stop
CLE7:34 amCleveland Hopkins Intl
$207
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 23, 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 1/17

6:00 am-12:48 pm

2 stops7h 48m

Chicago Midway

Sun 1/18

11:21 am-5:51 pm

1 stop5h 30m

$202

ClevelandChicago

CLE - MDW

CLEMDW

Cleveland Hopkins Intl

Mon 1/12

6:50 pm-10:05 pm

1 stop4h 15m

Chicago Midway

Sat 1/17

9:55 am-12:10 pm

Nonstop1h 15m

$203

ClevelandChicago

CLE - MDW

CLEMDW

Cleveland Hopkins Intl

Wed 4/8

9:00 pm-9:58 pm

1 stop25h 58m

Chicago Midway

Sat 4/11

12:33 pm-12:21 am

1 stop10h 48m

$204

ClevelandChicago

CLE - MDW

CLEMDW

Cleveland Hopkins Intl

Fri 1/23

11:53 am-7:52 pm

1 stop8h 59m

Chicago Midway

Mon 1/26

5:01 pm-1:44 pm

2 stops19h 43m

$205

ClevelandChicago

CLE - MDW

CLEMDW

Cleveland Hopkins Intl

Mon 1/12

6:24 pm-10:34 am

2 stops17h 10m

Chicago Midway

Sat 1/17

8:22 am-11:37 pm

1 stop14h 15m

$207

ClevelandChicago

CLE - MDW

CLEMDW

Cleveland Hopkins Intl

Thu 1/15

7:10 am-10:19 pm

1 stop16h 09m

Chicago Midway

Mon 1/19

7:20 pm-10:42 pm

2 stops26h 22m

$210

ClevelandChicago

CLE - MDW

CLEMDW

Cleveland Hopkins Intl

Tue 2/3

6:15 am-6:55 am

Nonstop1h 40m

Chicago Midway

Tue 2/10

7:55 pm-10:10 pm

Nonstop1h 15m

$211

ClevelandChicago

CLE - MDW

CLEMDW

Cleveland Hopkins Intl

Tue 1/6

8:25 pm-10:17 pm

2 stops26h 52m

Chicago Midway

Sat 1/10

6:10 am-11:13 pm

1 stop16h 03m

$212

ClevelandChicago

CLE - MDW

CLEMDW

Cleveland Hopkins Intl

Mon 1/5

11:26 am-10:12 pm

1 stop11h 46m

Chicago Midway

Thu 1/8

12:41 pm-11:13 pm

1 stop9h 32m

$213

ClevelandChicago

CLE - MDW

CLEMDW

Cleveland Hopkins Intl

Thu 2/19

5:45 am-11:41 pm

1 stop18h 56m

Chicago Midway

Mon 3/2

3:29 pm-6:07 am

2 stops13h 38m

$216

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 $371. 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 $412.

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 $336 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 35% 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

$170

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 $170. The best round-trip flight deal from Cleveland to Chicago Midway Airport found on momondo in the last 72 hours is $341.
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 $140Free CancellationRating
8.0
4,253 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 14 flights on this route every week with an average price of $271. 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
Valparaiso
Schererville
Munster
Crown Point
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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