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Cheap flights from Cleveland to Chicago from $69

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 10/15. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
1 adult, Economy, 0 bags

Find the cheapest flights from Cleveland to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
Delta Logo
10:34 am - 12:48 pm
CLE
-
MDW
3h 14m
1 stop
Delta Logo
9:29 am - 3:12 pm
MDW
-
CLE
4h 43m
1 stop
$157Delta
Wed, Oct 21 - Tue, Nov 3
Southwest Logo
3:15 pm - 8:30 pm
CLE
-
MDW
6h 15m
1 stop
Southwest Logo
4:25 pm - 6:40 pm
MDW
-
CLE
1h 15mnonstop
$163Southwest
Sat, Aug 8 - Thu, Aug 13
Southwest Logo
8:50 am - 9:00 am
CLE
-
MDW
1h 10mnonstop
Southwest Logo
6:35 am - 1:15 pm
MDW
-
CLE
5h 40m
1 stop
$166Southwest
Thu, Sep 3 - Sat, Sep 5
Delta Logo
6:43 am - 9:17 am
CLE
-
MDW
3h 34m
1 stop
Delta Logo
9:24 am - 1:40 pm
MDW
-
CLE
3h 16m
1 stop
$167Delta
Wed, Aug 26 - Sat, Aug 29
Southwest Logo
8:35 am - 8:55 am
CLE
-
MDW
1h 20mnonstop
Southwest Logo
4:20 pm - 11:45 pm
MDW
-
CLE
6h 25m
2 stops
$171Southwest
Wed, Oct 28 - Fri, Oct 30
Southwest Logo
6:05 pm - 10:20 pm
CLE
-
MDW
5h 15m
1 stop
Southwest Logo
6:35 am - 1:15 pm
MDW
-
CLE
5h 40m
1 stop
$176Southwest
Thu, Sep 3 - Sat, Sep 5
Delta Logo
10:24 am - 12:39 pm
CLE
-
MDW
3h 15m
1 stop
Delta Logo
9:24 am - 3:28 pm
MDW
-
CLE
5h 04m
1 stop
$178Delta
Thu, Aug 27 - Sat, Aug 29
Southwest Logo
7:20 pm - 9:55 pm
CLE
-
MDW
3h 35m
1 stop
Southwest Logo
12:45 pm - 9:00 pm
MDW
-
CLE
7h 15m
2 stops
$181Southwest
Mon, Aug 10 - Tue, Aug 11
Delta Logo
6:00 am - 9:18 am
CLE
-
MDW
4h 18m
1 stop
Delta Logo
9:30 am - 1:35 pm
MDW
-
CLE
3h 05m
1 stop
$186Delta
Fri, Oct 30 - Sat, Nov 14
Delta Logo
3:49 pm - 6:33 pm
CLE
-
MDW
3h 44m
1 stop
Delta Logo
9:24 am - 1:40 pm
MDW
-
CLE
3h 16m
1 stop
$188Delta
Mon, Aug 24 - Thu, Aug 27

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Southwest flights from Cleveland to Chicago Midway Airport

Our best Southwest deals on Cleveland to Chicago Midway Airport flight tickets
Southwest
Aug 8
CLE3:15 pmCleveland Hopkins Intl
6h 15m
1 stop
MDW8:30 pmChicago Midway
Aug 13
MDW4:25 pmChicago Midway
1h 15m
CLE6:40 pmCleveland Hopkins Intl
$163
Southwest
Sep 3
CLE8:50 amCleveland Hopkins Intl
1h 10m
MDW9:00 amChicago Midway
Sep 5
MDW6:35 amChicago Midway
5h 40m
1 stop
CLE1:15 pmCleveland Hopkins Intl
$166
Southwest
Oct 28
CLE8:35 amCleveland Hopkins Intl
1h 20m
MDW8:55 amChicago Midway
Oct 30
MDW4:20 pmChicago Midway
6h 25m
2 stops
CLE11:45 pmCleveland Hopkins Intl
$171

Delta flights from Cleveland to Chicago Midway Airport

Our best Delta deals on Cleveland to Chicago Midway Airport flight tickets
Delta
Aug 26
CLE6:43 amCleveland Hopkins Intl
3h 34m
1 stop
MDW9:17 amChicago Midway
Aug 29
MDW9:24 amChicago Midway
3h 16m
1 stop
CLE1:40 pmCleveland Hopkins Intl
$167
Delta
Aug 27
CLE10:24 amCleveland Hopkins Intl
3h 15m
1 stop
MDW12:39 pmChicago Midway
Aug 29
MDW9:24 amChicago Midway
5h 04m
1 stop
CLE3:28 pmCleveland Hopkins Intl
$178
Delta
Oct 30
CLE6:00 amCleveland Hopkins Intl
4h 18m
1 stop
MDW9:18 amChicago Midway
Nov 14
MDW9:30 amChicago Midway
3h 05m
1 stop
CLE1:35 pmCleveland Hopkins Intl
$186

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 July 19, 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

Wed 10/21

10:34 am-12:48 pm

1 stop3h 14m

Chicago Midway

Tue 11/3

9:29 am-3:12 pm

1 stop4h 43m

$157

ClevelandChicago

CLE - MDW

CLEMDW

Cleveland Hopkins Intl

Sat 8/8

3:15 pm-8:30 pm

1 stop6h 15m

Chicago Midway

Thu 8/13

4:25 pm-6:40 pm

Nonstop1h 15m

$163
Quickest round-trip

ClevelandChicago

CLE - MDW

CLEMDW

Cleveland Hopkins Intl

Thu 9/3

8:50 am-9:00 am

Nonstop1h 10m

Chicago Midway

Sat 9/5

6:35 am-1:15 pm

1 stop5h 40m

$166

ClevelandChicago

CLE - MDW

CLEMDW

Cleveland Hopkins Intl

Wed 8/26

6:43 am-9:17 am

1 stop3h 34m

Chicago Midway

Sat 8/29

9:24 am-1:40 pm

1 stop3h 16m

$167

ClevelandChicago

CLE - MDW

CLEMDW

Cleveland Hopkins Intl

Wed 10/28

8:35 am-8:55 am

Nonstop1h 20m

Chicago Midway

Fri 10/30

4:20 pm-11:45 pm

2 stops6h 25m

$171

ClevelandChicago

CLE - MDW

CLEMDW

Cleveland Hopkins Intl

Thu 9/3

6:05 pm-10:20 pm

1 stop5h 15m

Chicago Midway

Sat 9/5

6:35 am-1:15 pm

1 stop5h 40m

$176

ClevelandChicago

CLE - MDW

CLEMDW

Cleveland Hopkins Intl

Thu 8/27

10:24 am-12:39 pm

1 stop3h 15m

Chicago Midway

Sat 8/29

9:24 am-3:28 pm

1 stop5h 04m

$178

ClevelandChicago

CLE - MDW

CLEMDW

Cleveland Hopkins Intl

Mon 8/10

7:20 pm-9:55 pm

1 stop3h 35m

Chicago Midway

Tue 8/11

12:45 pm-9:00 pm

2 stops7h 15m

$181

ClevelandChicago

CLE - MDW

CLEMDW

Cleveland Hopkins Intl

Fri 10/30

6:00 am-9:18 am

1 stop4h 18m

Chicago Midway

Sat 11/14

9:30 am-1:35 pm

1 stop3h 05m

$186

ClevelandChicago

CLE - MDW

CLEMDW

Cleveland Hopkins Intl

Mon 8/24

3:49 pm-6:33 pm

1 stop3h 44m

Chicago Midway

Thu 8/27

9:24 am-1:40 pm

1 stop3h 16m

$188

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 $205. 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, Saturday is the cheapest day to fly to Chicago Midway Airport from Cleveland. The lowest ticket price found for a Saturday departure recently was $378. 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 $421.

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 $330 when looking at flights departing in the afternoon. Try not to purchase tickets in the morning because they tend to be around $421. 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 July 2026, prices for Cleveland to Chicago Midway Airport flights are approximately 45% more expensive 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

$200

Fastest flight time

1h 10m

Direct flights

Mon, Wed, Thu, Fri, Sat and Sun
The best one-way flight to Chicago Midway Airport from Cleveland in the past 72 hours is $200. The best round-trip flight deal from Cleveland to Chicago Midway Airport found on momondo in the last 72 hours is $256.
The fastest flight from Cleveland to Chicago Midway Airport takes 1h 10m
Direct flights go from Cleveland to Chicago Midway Airport on Monday, Wednesday, Thursday, Friday, Saturday and Sunday. The only airline offering direct flights is Southwest.
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 10m, 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
8.0
4,242 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 18 flights on this route every week with an average price of $259. 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
Portage
Benton Harbor
Saint Joseph
Lansing
Valparaiso
Schererville
Munster
Chesterton
Monticello
Crown Point
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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