$64 Cheap Flights from Cleveland (CLE) to Chicago (MDW)

View $64 flight on Wed, Aug 27, 2025Opens in a new window

Popular airlines from Cleveland Hopkins International Airport (CLE) to Chicago Midway Airport (MDW)

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Cheap Flights from Cleveland to Chicago (CLE-MDW)

Prices were available within the past 7 days and start at $64 for one-way flights and $127 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Southwest Airlines
Sat, Sep 6 - Tue, Sep 9
CLE
Cleveland
MDW
Chicago
$127 Roundtrip, just found
$127
Roundtrip
just found
Select Southwest Airlines flight, departing Sat, Sep 6 from Cleveland to Chicago, returning Tue, Sep 9, priced at $127 just found
Southwest Airlines
Wed, Aug 27 - Fri, Aug 29
CLE
Cleveland
MDW
Chicago
$139 Roundtrip, just found
$139
Roundtrip
just found
Select Southwest Airlines flight, departing Wed, Aug 27 from Cleveland to Chicago, returning Fri, Aug 29, priced at $139 just found
Southwest Airlines
Tue, Aug 26 - Wed, Aug 27
CLE
Cleveland
MDW
Chicago
$142 Roundtrip, found 4 days ago
$142
Roundtrip
found 4 days ago
Select Southwest Airlines flight, departing Tue, Aug 26 from Cleveland to Chicago, returning Wed, Aug 27, priced at $142 found 4 days ago
Southwest Airlines
Thu, Aug 21 - Sun, Aug 24
CLE
Cleveland
MDW
Chicago
$151 Roundtrip, just found
$151
Roundtrip
just found
Select Southwest Airlines flight, departing Thu, Aug 21 from Cleveland to Chicago, returning Sun, Aug 24, priced at $151 just found
Delta
Sat, Sep 6 - Tue, Sep 9
CLE
Cleveland
MDW
Chicago
$152 Roundtrip, just found
$152
Roundtrip
just found
Select Delta flight, departing Sat, Sep 6 from Cleveland to Chicago, returning Tue, Sep 9, priced at $152 just found
Frontier Airlines
Sat, Sep 6 - Tue, Sep 9
CLE
Cleveland
MDW
Chicago
$158 Roundtrip, just found
$158
Roundtrip
just found
Select Frontier Airlines flight, departing Sat, Sep 6 from Cleveland to Chicago, returning Tue, Sep 9, priced at $158 just found
Southwest Airlines
Thu, Nov 13 - Mon, Nov 17
CLE
Cleveland
MDW
Chicago
$161 Roundtrip, found 11 hours ago
$161
Roundtrip
found 11 hours ago
Select Southwest Airlines flight, departing Thu, Nov 13 from Cleveland to Chicago, returning Mon, Nov 17, priced at $161 found 11 hours ago
Southwest Airlines
Sat, Sep 6 - Tue, Sep 9
CLE
Cleveland
MDW
Chicago
$162 Roundtrip, just found
$162
Roundtrip
just found
Select Southwest Airlines flight, departing Sat, Sep 6 from Cleveland to Chicago, returning Tue, Sep 9, priced at $162 just found
Delta
Sun, Aug 31 - Thu, Sep 4
CLE
Cleveland
MDW
Chicago
$164 Roundtrip, just found
$164
Roundtrip
just found
Select Delta flight, departing Sun, Aug 31 from Cleveland to Chicago, returning Thu, Sep 4, priced at $164 just found
Southwest Airlines
Mon, Aug 25 - Wed, Aug 27
CLE
Cleveland
MDW
Chicago
$167 Roundtrip, found 5 days ago
$167
Roundtrip
found 5 days ago
Select Southwest Airlines flight, departing Mon, Aug 25 from Cleveland to Chicago, returning Wed, Aug 27, priced at $167 found 5 days ago

Find the cheapest month to fly from Cleveland (CLE) to Chicago (MDW)

August is typically the cheapest month to fly

From $97 - $378 per traveler.

Graph displaying average flight prices per month

Alternative airports near Chicago

Prices were available within the past 7 days. Prices and availability are subject to change.

Select flight to O'Hare Intl. ORD. Cheapest option available. Average driving time to city center is 23 minutes. Flights from $244
ORD
O'Hare Intl.
Cheapest
Average driving time to city center23 min
Flights from $244
0
Flights from Cleveland (CLE) to Chicago (MDW)
Origin airport
Hopkins Intl.
Destination airport
Midway Intl.
Airlines serving
Delta, Frontier Airlines, Southwest Airlines
Roundtrip price
$127
Distance
306 mi

Cleveland to Chicago Flights

The cheapest times to fly from Cleveland to Chicago

On average, Thursday can be the cheapest time to fly, according to data from the Airlines Reporting Corporation (ARC), one of the world's biggest databases for global airline sales. The data reveals that you could save up to 16% by flying on a Thursday—the cheapest day to travel on average—instead of a Sunday—the most expensive. Some of the most affordable flights from Cleveland to Chicago are during the month of September. You can find some of the cheapest flights from Cleveland to Chicago with Expedia's search tool and vast selection of airlines.

 

The best time to book a flight from Cleveland to Chicago

Sunday is one of the best days to book for cheap flights from Cleveland to Chicago: Tickets reserved on a Sunday cost between 6% and 13% less than those reserved on a Friday, according to ARC data. The data also suggests booking early can also lead to cheaper airfares. You could save 24% by buying your tickets for domestic flights at least a month in advance and 10% by booking international flights 2 months in advance.

 

How to find cheap round-trip tickets from Cleveland to Chicago

Being flexible with your dates and using Expedia's Price Drop Protection and Price Tracking features are some of the best ways of finding a cheap ticket from Cleveland to Chicago in 2025. You can also book with separate airlines for your outbound and return journeys, from $64 one-way. Expedia also offers Price Drop Protection, so if the cost of your airfare goes down after booking, you'll receive a credit for the difference*. This is available for a small fee, and is free to One Key Gold and Platinum tier members.

 

Expedia's Price Tracking feature means you can stay on top of airfares without manually checking every day. It sends you automated price alerts for cheap Cleveland to Chicago flights and uses historical data to indicate when the best time to book is. Download Expedia's free app to activate this handy tool in a few easy taps.

 

You could also save big by booking one of Expedia's vacation packages. Bundling together your Cleveland to Chicago airfare with your accommodations and car rental is often cheaper than booking everything separately. There’s also One Key, Expedia's generous rewards program. Join for free and you could earn One Key cash on most bookings to save on future adventures.

 

*Terms apply.

 

Disclaimer: ARC The statistics are based on average round-trip ticket prices between January and August 2023. The percentages you see are averages.

 

Frequently asked questions

How much does a flight from Hopkins Intl. Airport (CLE) to Midway Intl. Airport (MDW) cost?
You can pick up cheap return fares starting at $127 from Hopkins Intl. Airport (CLE) to Midway Intl. Airport (MDW). This information is based on the cheapest price found on Expedia for this return journey departing within the next three months. This airfare is for a Southwest Airlines flight leaving CLE on August 16 2025 and touching down at MDW. The price was last updated on July 23 2025 and has not changed since.
What is the cheapest month to fly from CLE to MDW?
The cheapest flights from CLE to MDW are usually during off-peak season, when demand is lower. To save money, avoid flying during public holidays, school breaks and major local events.
Which airlines fly direct from Hopkins Intl. Airport (CLE) to Midway Intl. Airport (MDW)?
Catch a nonstop flight with Southwest Airlines and journey straight from Hopkins Intl. Airport (CLE) to Midway Intl. Airport (MDW).
What is the cheapest airline that flies from CLE to MDW?
Currently, the cheapest airline offering one-way flights from CLE to MDW is Southwest Airlines. You can jet off on this route from $64. This fare is based on the lowest price found on Expedia departing within the next three months. The flight takes off from CLE on October 16 2025. Prices were last updated on July 23 2025 and have not changed since.
How many flights per day from Hopkins Intl. Airport (CLE) to Midway Intl. Airport (MDW)?
With an average of 2 direct flights that operate from Hopkins Intl. Airport (CLE) to Midway Intl. Airport (MDW) daily, you'll be on your way in no time.
What are the most popular departure times for flights from Hopkins Intl. Airport (CLE) to Midway Intl. Airport (MDW)?
The 7 AM departures from CLE to MDW are the top choice for many travelers. These flights can come with a higher price due to their popularity. If you're looking to save, book during off-peak hours.
What day of the week has the most flights from CLE to MDW?
If you jet off on a Friday, you'll get the widest range of options for flights from Hopkins Intl. Airport (CLE) to Midway Intl. Airport (MDW).
What is the earliest flight from Hopkins Intl. Airport (CLE) to Midway Intl. Airport (MDW)?
Hopkins Intl. Airport (CLE)'s earliest flight to Midway Intl. Airport (MDW) takes off at approximately 6:55AM UTC-5. With a travel time of 1h 30m, you'll arrive at around 7:25AM UTC-6.
How long does it take to fly from Hopkins Intl. Airport (CLE) to Midway Intl. Airport (MDW)?
The average flight duration from CLE to MDW is 1 hour and 25 minutes, covering a total distance of 310 mi.
What is the best time to fly from Hopkins Intl. Airport (CLE) to Midway Intl. Airport (MDW)?
Opt for a flight from Hopkins Intl. Airport (CLE) to Midway Intl. Airport (MDW) that takes off before 3 PM to reduce the likelihood of delays. Departures after this time are on average 22% more likely to be canceled.**Most reliable time of the day and month to travel recommendation is based on January through August 2024 flight status data sourced from OAG's global flight data platform.
What airports do you fly into for Chicago from Hopkins Intl. Airport (CLE)?
Take a direct flight from Hopkins Intl. Airport (CLE) to Chicago and arrive at O'Hare Intl. Airport (ORD). Another gateway to the city is Midway Intl. Airport (MDW).
Is it cheaper to buy a plane ticket from Hopkins Intl. Airport (CLE) to Midway Intl. Airport (MDW) last-minute?
Booking your plane ticket from CLE to MDW right before your getaway is typically more expensive. But if you're flexible with your departure times and dates, you could snag a cheap last-minute fare.
Is it cheaper to book a CLE to MDW flight and hotel package?
Compared with arranging hotels and flights separately, booking a CLE to MDW flight and hotel package with Expedia could result in significant savings. What's more, having everything in one convenient place will take the stress out of planning your trip. Simply secure your flights and choose from our wide range of hotels, then tailor your trip with other add-ons like activities and car rentals.
Can I cancel or change the date of my flight from Hopkins Intl. Airport (CLE) to Midway Intl. Airport (MDW)?
Generally, it's possible to cancel or reschedule your CLE to MDW flight. However, for bookings made more than 24 hours ago, additional fees may apply. Check your airline's policies in your itinerary to see what changes are allowed and whether any costs are involved. You'll also find more information on our Customer Service portal.

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Chicago nearby Airports

Chicago

Cleveland to O'Hare Intl.
$126.96
*Available to One Key members.