Latest deals
Insights
When to book
FAQs
Reviews
Price Alerts

Cheap flights from Cleveland to Chicago from $59

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.
Southwest Logo
7:55 pm - 8:30 pmCLE  Cleveland Hopkins Intl-MDW Chicago Midway
1h 35mnonstop
Southwest Logo
3:50 pm - 8:50 pmMDW  Chicago Midway-CLE Cleveland Hopkins Intl
4h 00m1 stop Lambert-St Louis
$127Southwest
Thu, Nov 5 - Tue, Nov 10
Southwest Logo
8:20 pm - 8:35 pmCLE  Cleveland Hopkins Intl-MDW Chicago Midway
1h 15mnonstop
Southwest Logo
6:25 pm - 11:50 pmMDW  Chicago Midway-CLE Cleveland Hopkins Intl
4h 25m1 stop Baltimore/Washington
$127Southwest
Mon, Oct 19 - Mon, Oct 26
Southwest Logo
8:20 pm - 8:35 pmCLE  Cleveland Hopkins Intl-MDW Chicago Midway
1h 15mnonstop
Southwest Logo
5:50 pm - 10:30 pmMDW  Chicago Midway-CLE Cleveland Hopkins Intl
3h 40m1 stop Lambert-St Louis
$127Southwest
Mon, Oct 19 - Mon, Oct 26
Southwest Logo
1:55 pm - 2:25 pmCLE  Cleveland Hopkins Intl-MDW Chicago Midway
1h 30mnonstop
Southwest Logo
3:50 pm - 8:45 pmMDW  Chicago Midway-CLE Cleveland Hopkins Intl
3h 55m1 stop Lambert-St Louis
$127Southwest
Mon, Dec 7 - Thu, Dec 10
Southwest Logo
9:00 pm - 11:55 pmCLE  Cleveland Hopkins Intl-MDW Chicago Midway
3h 55m1 stop Nashville Intl
Southwest Logo
8:00 am - 10:15 amMDW  Chicago Midway-CLE Cleveland Hopkins Intl
1h 15mnonstop
$127Southwest
Mon, Oct 19 - Wed, Oct 21
Southwest Logo
8:35 am - 8:55 amCLE  Cleveland Hopkins Intl-MDW Chicago Midway
1h 20mnonstop
Southwest Logo
7:05 am - 1:00 pmMDW  Chicago Midway-CLE Cleveland Hopkins Intl
4h 55m1 stop Nashville Intl
$127Southwest
Wed, Oct 28 - Thu, Oct 29
Southwest Logo
7:10 pm - 7:35 pmCLE  Cleveland Hopkins Intl-MDW Chicago Midway
1h 25mnonstop
Southwest Logo
6:30 am - 12:45 pmMDW  Chicago Midway-CLE Cleveland Hopkins Intl
5h 15m1 stop Lambert-St Louis
$127Southwest
Thu, Dec 10 - Thu, Dec 17
Southwest Logo
2:20 pm - 2:35 pmCLE  Cleveland Hopkins Intl-MDW Chicago Midway
1h 15mnonstop
Southwest Logo
7:05 am - 1:00 pmMDW  Chicago Midway-CLE Cleveland Hopkins Intl
4h 55m1 stop Nashville Intl
$127Southwest
Tue, Oct 27 - Thu, Oct 29
Frontier Logo
7:00 am - 5:45 pmCLE  Cleveland Hopkins Intl-MDW Chicago Midway
11h 45m1 stop Atlanta Hartsfield-Jackson
Frontier Logo
1:12 pm - 8:26 pmMDW  Chicago Midway-CLE Cleveland Hopkins Intl
6h 14m1 stop Dallas/Fort Worth
$135Frontier
Thu, Oct 15 - Fri, Oct 16
Frontier Logo
3:46 pm - 11:47 pmCLE  Cleveland Hopkins Intl-MDW Chicago Midway
9h 01m1 stop Atlanta Hartsfield-Jackson
Frontier Logo
7:25 am - 1:34 pmMDW  Chicago Midway-CLE Cleveland Hopkins Intl
5h 09m1 stop Atlanta Hartsfield-Jackson
$135Frontier
Fri, Oct 30 - Sat, Oct 31

Save money when you book flights with momondo

Big names and deals

Big names and deals

Search 100s of travel sites to compare prices.

Filter for what you want

Filter for what you want

Free Wi-Fi? Stopover? Instantly customize your results.

Trusted and free

Trusted and free

We’re completely free to use - no hidden charges or fees.

Price Alerts

Price Alerts

Not ready to book? to track prices.
Search flight deals

Southwest flights from Cleveland to Chicago Midway Airport

Our best Southwest deals on Cleveland to Chicago Midway Airport flight tickets
Southwest
Oct 19
CLE8:20 pmCleveland Hopkins Intl
1h 15m
MDW8:35 pmChicago Midway
Oct 26
MDW5:50 pmChicago Midway
3h 40m
1 stop
CLE10:30 pmCleveland Hopkins Intl
$127
Southwest
Oct 12
CLE2:40 pmCleveland Hopkins Intl
1h 15m
MDW2:55 pmChicago Midway
Oct 14
MDW9:40 amChicago Midway
6h 05m
2 stops
CLE4:45 pmCleveland Hopkins Intl
$132
Southwest
Oct 19
CLE9:00 pmCleveland Hopkins Intl
3h 55m
1 stop
MDW11:55 pmChicago Midway
Oct 26
MDW5:50 pmChicago Midway
3h 40m
1 stop
CLE10:30 pmCleveland Hopkins Intl
$137

Frontier flights from Cleveland to Chicago Midway Airport

Our best Frontier deals on Cleveland to Chicago Midway Airport flight tickets
Frontier
Oct 30
CLE3:46 pmCleveland Hopkins Intl
9h 01m
1 stop
MDW11:47 pmChicago Midway
Nov 14
MDW7:25 amChicago Midway
5h 09m
1 stop
CLE1:34 pmCleveland Hopkins Intl
$135
Frontier
Oct 31
CLE8:30 amCleveland Hopkins Intl
10h 17m
1 stop
MDW5:47 pmChicago Midway
Nov 14
MDW7:25 amChicago Midway
5h 09m
1 stop
CLE1:34 pmCleveland Hopkins Intl
$188
Frontier
Oct 17
CLE3:46 pmCleveland Hopkins Intl
8h 57m
1 stop
MDW11:43 pmChicago Midway
Oct 19
MDW1:12 pmChicago Midway
6h 14m
1 stop
CLE8:26 pmCleveland Hopkins Intl
$190

momondo Fare Finder

 
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 Cleveland Hopkins Intl - MDW Chicago Midway

CLEMDW

Cleveland Hopkins Intl

Thu 11/5

7:55 pm-8:30 pm

Nonstop1h 35m

Chicago Midway

Tue 11/10

3:50 pm-8:50 pm

1 stop4h 00m

$127

ClevelandChicago

CLE Cleveland Hopkins Intl - MDW Chicago Midway

CLEMDW

Cleveland Hopkins Intl

Mon 10/19

8:20 pm-8:35 pm

Nonstop1h 15m

Chicago Midway

Mon 10/26

6:25 pm-11:50 pm

1 stop4h 25m

$127
Quickest round-trip

ClevelandChicago

CLE Cleveland Hopkins Intl - MDW Chicago Midway

CLEMDW

Cleveland Hopkins Intl

Mon 10/19

8:20 pm-8:35 pm

Nonstop1h 15m

Chicago Midway

Mon 10/26

5:50 pm-10:30 pm

1 stop3h 40m

$127

ClevelandChicago

CLE Cleveland Hopkins Intl - MDW Chicago Midway

CLEMDW

Cleveland Hopkins Intl

Mon 12/7

1:55 pm-2:25 pm

Nonstop1h 30m

Chicago Midway

Thu 12/10

3:50 pm-8:45 pm

1 stop3h 55m

$127

ClevelandChicago

CLE Cleveland Hopkins Intl - MDW Chicago Midway

CLEMDW

Cleveland Hopkins Intl

Mon 10/19

9:00 pm-11:55 pm

1 stop3h 55m

Chicago Midway

Wed 10/21

8:00 am-10:15 am

Nonstop1h 15m

$127

ClevelandChicago

CLE Cleveland Hopkins Intl - MDW Chicago Midway

CLEMDW

Cleveland Hopkins Intl

Wed 10/28

8:35 am-8:55 am

Nonstop1h 20m

Chicago Midway

Thu 10/29

7:05 am-1:00 pm

1 stop4h 55m

$127

ClevelandChicago

CLE Cleveland Hopkins Intl - MDW Chicago Midway

CLEMDW

Cleveland Hopkins Intl

Thu 12/10

7:10 pm-7:35 pm

Nonstop1h 25m

Chicago Midway

Thu 12/17

6:30 am-12:45 pm

1 stop5h 15m

$127

ClevelandChicago

CLE Cleveland Hopkins Intl - MDW Chicago Midway

CLEMDW

Cleveland Hopkins Intl

Tue 10/27

2:20 pm-2:35 pm

Nonstop1h 15m

Chicago Midway

Thu 10/29

7:05 am-1:00 pm

1 stop4h 55m

$127

ClevelandChicago

CLE Cleveland Hopkins Intl - MDW Chicago Midway

CLEMDW

Cleveland Hopkins Intl

Thu 10/15

7:00 am-5:45 pm

1 stop11h 45m

Chicago Midway

Fri 10/16

1:12 pm-8:26 pm

1 stop6h 14m

$135

ClevelandChicago

CLE Cleveland Hopkins Intl - MDW Chicago Midway

CLEMDW

Cleveland Hopkins Intl

Fri 10/30

3:46 pm-11:47 pm

1 stop9h 01m

Chicago Midway

Sat 10/31

7:25 am-1:34 pm

1 stop5h 09m

$135

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
1
2

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?

Prices are currently low for flights on this route.

Typical prices usually range from $234 to $431.
The lowest price recently found on this route was $127.

What is the cheapest month to fly to Chicago Midway Airport?

The month of August is, on average, the cheapest month to fly to Chicago Midway Airport from Cleveland, with most prices found around $234. If you are unable to visit Chicago Midway Airport during the month of August, 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 $389. 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 $443.

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 $339 when looking at flights departing in the afternoon. Try not to purchase tickets in the morning because they tend to be around $437. 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 September 2026, prices for Cleveland to Chicago Midway Airport flights are approximately 6% 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

$59

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 $59. The best round-trip flight deal from Cleveland to Chicago Midway Airport found on momondo in the last 72 hours is $127.
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 $134Free CancellationRating
8.0
4,196 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 $134. Generally, Southwest has 15 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
Lansing
Saint Joseph
Valparaiso
Schererville
Munster
Chesterton
Monticello
Porter
Crown Point
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

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.
Start using Trips
Find my bookings

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.
1 adult
Tue 10/20
Tue 10/27
By creating a price alert you accept our terms of use and privacy policy.

Find better results for your trip to Chicago