$67 Cheap Flights from Cleveland (CLE) to Chicago (MDW)

View $67 flight on Mon, Nov 17, 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 $67 for one-way flights and $108 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Southwest Airlines
Wed, Oct 8 - Fri, Oct 10
CLE
Cleveland
MDW
Chicago
$108 Roundtrip, found 2 days ago
$108
Roundtrip
found 2 days ago
Select Southwest Airlines flight, departing Wed, Oct 8 from Cleveland to Chicago, returning Fri, Oct 10, priced at $108 found 2 days ago
Southwest Airlines
Thu, Oct 30 - Sun, Nov 2
CLE
Cleveland
MDW
Chicago
$115 Roundtrip, found 2 days ago
$115
Roundtrip
found 2 days ago
Select Southwest Airlines flight, departing Thu, Oct 30 from Cleveland to Chicago, returning Sun, Nov 2, priced at $115 found 2 days ago
Southwest Airlines
Wed, Aug 27 - Sun, Aug 31
CLE
Cleveland
MDW
Chicago
$128 Roundtrip, found 2 days ago
$128
Roundtrip
found 2 days ago
Select Southwest Airlines flight, departing Wed, Aug 27 from Cleveland to Chicago, returning Sun, Aug 31, priced at $128 found 2 days ago
Southwest Airlines
Wed, Sep 24 - Thu, Sep 25
CLE
Cleveland
MDW
Chicago
$131 Roundtrip, found 2 days ago
$131
Roundtrip
found 2 days ago
Select Southwest Airlines flight, departing Wed, Sep 24 from Cleveland to Chicago, returning Thu, Sep 25, priced at $131 found 2 days ago
Southwest Airlines
Thu, Sep 11 - Sat, Sep 13
CLE
Cleveland
MDW
Chicago
$137 Roundtrip, found 2 days ago
$137
Roundtrip
found 2 days ago
Select Southwest Airlines flight, departing Thu, Sep 11 from Cleveland to Chicago, returning Sat, Sep 13, priced at $137 found 2 days ago
Southwest Airlines
Fri, Sep 26 - Sat, Sep 27
CLE
Cleveland
MDW
Chicago
$139 Roundtrip, found 1 day ago
$139
Roundtrip
found 1 day ago
Select Southwest Airlines flight, departing Fri, Sep 26 from Cleveland to Chicago, returning Sat, Sep 27, priced at $139 found 1 day ago
Southwest Airlines
Wed, Oct 8 - Sun, Oct 12
CLE
Cleveland
MDW
Chicago
$142 Roundtrip, found 6 days ago
$142
Roundtrip
found 6 days ago
Select Southwest Airlines flight, departing Wed, Oct 8 from Cleveland to Chicago, returning Sun, Oct 12, priced at $142 found 6 days ago
Southwest Airlines
Mon, Aug 25 - Sun, Aug 31
CLE
Cleveland
MDW
Chicago
$146 Roundtrip, found 4 days ago
$146
Roundtrip
found 4 days ago
Select Southwest Airlines flight, departing Mon, Aug 25 from Cleveland to Chicago, returning Sun, Aug 31, priced at $146 found 4 days ago
Delta
Wed, Oct 8 - Fri, Oct 10
CLE
Cleveland
MDW
Chicago
$152 Roundtrip, found 2 days ago
$152
Roundtrip
found 2 days ago
Select Delta flight, departing Wed, Oct 8 from Cleveland to Chicago, returning Fri, Oct 10, priced at $152 found 2 days ago
Frontier Airlines
Sat, Sep 13 - Tue, Sep 16
CLE
Cleveland
MDW
Chicago
$161 Roundtrip, found 1 day ago
$161
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Sat, Sep 13 from Cleveland to Chicago, returning Tue, Sep 16, priced at $161 found 1 day ago

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

September is typically the cheapest month to fly

From $96 - $298 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 $280
ORD
O'Hare Intl.
Cheapest
Average driving time to city center23 min
Flights from $280
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
$108
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 October. 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 $67 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?
Snag a cheap one-way flight from $67 or cheap return flight from $108 from Hopkins Intl. Airport (CLE) to Midway Intl. Airport (MDW) with Expedia. Enter your travel dates and sort by "Price (lowest to highest)" to find our cheapest flight offers on this route.
What is the cheapest month to fly from Hopkins Intl. Airport (CLE) to Midway Intl. Airport (MDW)?
The cheapest month to fly from CLE to MDW is October, when there's less demand. Off-peak season is often when better flight deals are available between these airports.
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 Hopkins Intl. Airport (CLE) to Midway Intl. Airport (MDW)?
Expedia's filter tool lets you easily compare different airlines, departure times and fares all in one place. Customize the search to your preferences, then sort by "Price (lowest to highest)" to find the carrier with the cheapest CLE to MDW flight.
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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*Available to One Key members.