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Cheap flights from Cleveland to Chicago from $93

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 6/12. 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

Enter your travel dates to find the best prices.
Frontier Logo
3:46 pm - 10:11 pm
CLE
-
MDW
7h 25m
1 stop
Frontier Logo
12:04 pm - 6:29 pm
MDW
-
CLE
5h 25m
1 stop
$158Frontier
Tue, Jun 9 - Wed, Jun 10
Frontier Logo
3:46 pm - 10:11 pm
CLE
-
MDW
7h 25m
1 stop
Frontier Logo
6:00 am - 6:29 pm
MDW
-
CLE
11h 29m
1 stop
$160Frontier
Tue, Jun 9 - Sat, Jun 13
Southwest Logo
6:40 am - 1:35 pm
CLE
-
MDW
7h 55m
2 stops
Southwest Logo
5:10 pm - 9:45 pm
MDW
-
CLE
3h 35m
1 stop
$162Southwest
Tue, Jun 16 - Tue, Jun 16
Frontier Logo
3:46 pm - 10:11 pm
CLE
-
MDW
7h 25m
1 stop
Frontier Logo
6:00 am - 6:29 pm
MDW
-
CLE
11h 29m
1 stop
$163Frontier
Wed, Jun 10 - Sat, Jun 13
Frontier Logo
6:01 pm - 11:09 am
CLE
-
MDW
18h 08m
1 stop
Frontier Logo
6:00 am - 6:29 pm
MDW
-
CLE
11h 29m
1 stop
$166Frontier
Sun, Jun 7 - Wed, Jun 10
Southwest Logo
6:40 am - 1:35 pm
CLE
-
MDW
7h 55m
2 stops
Southwest Logo
12:45 pm - 9:00 pm
MDW
-
CLE
7h 15m
2 stops
$167Southwest
Wed, Jul 29 - Tue, Aug 4
Frontier Logo
3:46 pm - 10:11 pm
CLE
-
MDW
7h 25m
1 stop
Frontier Logo
6:00 am - 8:55 pm
MDW
-
CLE
13h 55m
1 stop
$169Frontier
Tue, Jun 23 - Wed, Jul 1
Frontier Logo
3:46 pm - 11:04 am
CLE
-
MDW
20h 18m
1 stop
Frontier Logo
12:04 pm - 6:29 pm
MDW
-
CLE
5h 25m
1 stop
$171Frontier
Fri, Aug 28 - Mon, Aug 31
Frontier Logo
5:51 pm - 11:09 am
CLE
-
MDW
18h 18m
1 stop
Frontier Logo
6:00 am - 6:29 pm
MDW
-
CLE
11h 29m
1 stop
$173Frontier
Sun, Jun 28 - Sat, Jul 4
Frontier Logo
6:37 am - 10:11 pm
CLE
-
MDW
16h 34m
1 stop
Frontier Logo
12:04 pm - 8:55 pm
MDW
-
CLE
7h 51m
1 stop
$181Frontier
Tue, Jun 23 - Fri, Jul 3

Delta flights from Cleveland to Chicago Midway Airport

Our best Delta deals on Cleveland to Chicago Midway Airport flight tickets
Delta
Jun 17
CLE8:18 amCleveland Hopkins Intl
5h 28m
1 stop
MDW12:46 pmChicago Midway
Jun 17
MDW6:58 pmChicago Midway
4h 01m
1 stop
CLE11:59 pmCleveland Hopkins Intl
$208
Delta
Aug 15
CLE10:24 amCleveland Hopkins Intl
3h 15m
1 stop
MDW12:39 pmChicago Midway
Aug 17
MDW6:42 pmChicago Midway
4h 14m
1 stop
CLE11:56 pmCleveland Hopkins Intl
$211
Delta
Jul 19
CLE6:40 amCleveland Hopkins Intl
3h 28m
1 stop
MDW9:08 amChicago Midway
Jul 21
MDW6:58 pmChicago Midway
3h 58m
1 stop
CLE11:56 pmCleveland Hopkins Intl
$227

Frontier flights from Cleveland to Chicago Midway Airport

Our best Frontier deals on Cleveland to Chicago Midway Airport flight tickets
Frontier
Jun 9
CLE3:46 pmCleveland Hopkins Intl
7h 25m
1 stop
MDW10:11 pmChicago Midway
Jun 10
MDW12:04 pmChicago Midway
5h 25m
1 stop
CLE6:29 pmCleveland Hopkins Intl
$158
Frontier
Jun 9
CLE3:46 pmCleveland Hopkins Intl
7h 25m
1 stop
MDW10:11 pmChicago Midway
Jun 13
MDW6:00 amChicago Midway
11h 29m
1 stop
CLE6:29 pmCleveland Hopkins Intl
$160
Frontier
Jun 10
CLE3:46 pmCleveland Hopkins Intl
7h 25m
1 stop
MDW10:11 pmChicago Midway
Jun 13
MDW6:00 amChicago Midway
11h 29m
1 stop
CLE6:29 pmCleveland Hopkins Intl
$163

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 May 20, 2026.
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

Cheapest round-trip

ClevelandChicago

CLE - MDW

CLEMDW

Cleveland Hopkins Intl

Tue 6/9

3:46 pm-10:11 pm

1 stop7h 25m

Chicago Midway

Wed 6/10

12:04 pm-6:29 pm

1 stop5h 25m

$158

ClevelandChicago

CLE - MDW

CLEMDW

Cleveland Hopkins Intl

Tue 6/9

3:46 pm-10:11 pm

1 stop7h 25m

Chicago Midway

Sat 6/13

6:00 am-6:29 pm

1 stop11h 29m

$160
Quickest round-trip

ClevelandChicago

CLE - MDW

CLEMDW

Cleveland Hopkins Intl

Tue 6/16

6:40 am-1:35 pm

2 stops7h 55m

Chicago Midway

Tue 6/16

5:10 pm-9:45 pm

1 stop3h 35m

$162

ClevelandChicago

CLE - MDW

CLEMDW

Cleveland Hopkins Intl

Wed 6/10

3:46 pm-10:11 pm

1 stop7h 25m

Chicago Midway

Sat 6/13

6:00 am-6:29 pm

1 stop11h 29m

$163

ClevelandChicago

CLE - MDW

CLEMDW

Cleveland Hopkins Intl

Sun 6/7

6:01 pm-11:09 am

1 stop18h 08m

Chicago Midway

Wed 6/10

6:00 am-6:29 pm

1 stop11h 29m

$166

ClevelandChicago

CLE - MDW

CLEMDW

Cleveland Hopkins Intl

Wed 7/29

6:40 am-1:35 pm

2 stops7h 55m

Chicago Midway

Tue 8/4

12:45 pm-9:00 pm

2 stops7h 15m

$167

ClevelandChicago

CLE - MDW

CLEMDW

Cleveland Hopkins Intl

Tue 6/23

3:46 pm-10:11 pm

1 stop7h 25m

Chicago Midway

Wed 7/1

6:00 am-8:55 pm

1 stop13h 55m

$169

ClevelandChicago

CLE - MDW

CLEMDW

Cleveland Hopkins Intl

Fri 8/28

3:46 pm-11:04 am

1 stop20h 18m

Chicago Midway

Mon 8/31

12:04 pm-6:29 pm

1 stop5h 25m

$171

ClevelandChicago

CLE - MDW

CLEMDW

Cleveland Hopkins Intl

Sun 6/28

5:51 pm-11:09 am

1 stop18h 18m

Chicago Midway

Sat 7/4

6:00 am-6:29 pm

1 stop11h 29m

$173

ClevelandChicago

CLE - MDW

CLEMDW

Cleveland Hopkins Intl

Tue 6/23

6:37 am-10:11 pm

1 stop16h 34m

Chicago Midway

Fri 7/3

12:04 pm-8:55 pm

1 stop7h 51m

$181

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 typical price of a round-trip flight between Cleveland and Chicago Midway Airport?

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 $214. If you are unable to visit Chicago Midway Airport during the month of September, then departing from Cleveland during the month April is also very affordable. Most momondo users find prices during this month for around $234.

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 $368. 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, Monday 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 $407.

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 $311 when looking at flights departing in the afternoon. Try not to purchase tickets in the morning because they tend to be around $410. 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 to Chicago Midway Airport flights?

There is only 1 cabin class available to choose from on Cleveland to Chicago Midway Airport 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?

No. A direct flight is the cheapest option for a flight between Cleveland to Chicago Midway Airport.

How have Cleveland to Chicago Midway Airport flight prices changed over time?

As of May 2026, prices for Cleveland to Chicago Midway Airport flights are approximately 25% cheaper when compared to flights at the same time last year.

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

$223

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 $223. The best round-trip flight deal from Cleveland to Chicago Midway Airport found on momondo in the last 72 hours is $275.
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

Frequently asked questions about flying from Cleveland to Chicago Midway Airport

  • 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 $137Free CancellationRating
7.9
4,284 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 $137. Generally, Southwest has 15 flights on this route every week with an average price of $263. 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
Saint Joseph
Benton Harbor
Portage
Lansing
Valparaiso
Munster
Schererville
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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