$60 Cheap Flights from Chicago (MDW) to Cleveland (CLE)

View $60 flight on Mon, Nov 17, 2025Opens in a new window

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

Cheap Flights from Chicago to Cleveland (MDW-CLE)

Prices were available within the past 7 days and start at $60 for one-way flights and $120 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Frontier Airlines
Sat, Nov 15 - Mon, Nov 17
MDW
Chicago
CLE
Cleveland
$120 Roundtrip, found 2 hours ago
$120
Roundtrip
found 2 hours ago
Select Frontier Airlines flight, departing Sat, Nov 15 from Chicago to Cleveland, returning Mon, Nov 17, priced at $120 found 2 hours ago
Southwest Airlines
Tue, Dec 9 - Wed, Dec 10
MDW
Chicago
CLE
Cleveland
$151 Roundtrip, found 5 days ago
$151
Roundtrip
found 5 days ago
Select Southwest Airlines flight, departing Tue, Dec 9 from Chicago to Cleveland, returning Wed, Dec 10, priced at $151 found 5 days ago
Frontier Airlines
Fri, Nov 14 - Mon, Nov 17
MDW
Chicago
CLE
Cleveland
$153 Roundtrip, found 1 hour ago
$153
Roundtrip
found 1 hour ago
Select Frontier Airlines flight, departing Fri, Nov 14 from Chicago to Cleveland, returning Mon, Nov 17, priced at $153 found 1 hour ago
Delta
Tue, Dec 9 - Wed, Dec 10
MDW
Chicago
CLE
Cleveland
$157 Roundtrip, found 5 days ago
$157
Roundtrip
found 5 days ago
Select Delta flight, departing Tue, Dec 9 from Chicago to Cleveland, returning Wed, Dec 10, priced at $157 found 5 days ago
Frontier Airlines
Mon, Nov 10 - Mon, Nov 17
MDW
Chicago
CLE
Cleveland
$160 Roundtrip, found 2 hours ago
$160
Roundtrip
found 2 hours ago
Select Frontier Airlines flight, departing Mon, Nov 10 from Chicago to Cleveland, returning Mon, Nov 17, priced at $160 found 2 hours ago
Southwest Airlines
Tue, Dec 9 - Wed, Dec 10
MDW
Chicago
CLE
Cleveland
$161 Roundtrip, found 5 days ago
$161
Roundtrip
found 5 days ago
Select Southwest Airlines flight, departing Tue, Dec 9 from Chicago to Cleveland, returning Wed, Dec 10, priced at $161 found 5 days ago
Delta
Tue, Dec 9 - Wed, Dec 10
MDW
Chicago
CLE
Cleveland
$165 Roundtrip, found 5 days ago
$165
Roundtrip
found 5 days ago
Select Delta flight, departing Tue, Dec 9 from Chicago to Cleveland, returning Wed, Dec 10, priced at $165 found 5 days ago
Southwest Airlines
Tue, Dec 9 - Wed, Dec 10
MDW
Chicago
CLE
Cleveland
$166 Roundtrip, found 5 days ago
$166
Roundtrip
found 5 days ago
Select Southwest Airlines flight, departing Tue, Dec 9 from Chicago to Cleveland, returning Wed, Dec 10, priced at $166 found 5 days ago
Southwest Airlines
Sat, Jan 10 - Mon, Jan 12
MDW
Chicago
CLE
Cleveland
$170 Roundtrip, found 6 days ago
$170
Roundtrip
found 6 days ago
Select Southwest Airlines flight, departing Sat, Jan 10 from Chicago to Cleveland, returning Mon, Jan 12, priced at $170 found 6 days ago
Frontier Airlines
Thu, Nov 13 - Sun, Nov 16
MDW
Chicago
CLE
Cleveland
$173 Roundtrip, found 6 hours ago
$173
Roundtrip
found 6 hours ago
Select Frontier Airlines flight, departing Thu, Nov 13 from Chicago to Cleveland, returning Sun, Nov 16, priced at $173 found 6 hours ago

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

August is typically the cheapest month to fly

From $100 - $561 per traveler.

Alternative airports near Cleveland

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

Select flight to Hopkins Intl. CLE. Cheapest option available. Average driving time to city center is 15 minutes. Flights from $419
CLE
Hopkins Intl.
Cheapest
Average driving time to city center15 min
Flights from $419

Frequently asked questions

How much does a flight from Midway Intl. Airport (MDW) to Hopkins Intl. Airport (CLE) cost?
Secure a cheap one-way flight from $60 or cheap return flight from $120 from Midway Intl. Airport (MDW) to Hopkins Intl. Airport (CLE) with Expedia. Enter your travel dates and sort by "Price (lowest to highest)" to see our cheapest flight deals on this route.
What is the cheapest month to fly from Midway Intl. Airport (MDW) to Hopkins Intl. Airport (CLE)?
The cheapest month to fly from MDW to CLE is November, when demand is low. Off-peak season is typically when airlines offer better prices between these airports.
Which airlines fly direct from Midway Intl. Airport (MDW) to Hopkins Intl. Airport (CLE)?
You can fly directly from Midway Intl. Airport (MDW) to Hopkins Intl. Airport (CLE) on a Southwest Airlines flight.
What is the cheapest airline that flies from Midway Intl. Airport (MDW) to Hopkins Intl. Airport (CLE)?
To find the cheapest airline that'll fly you from MDW to CLE, use Expedia's filter tool. Customize your search based on what's important to you, such as preferred carriers and flight duration. You can then sort your results by "Price (lowest to highest)" to see the cheapest fares upfront.
How many flights per day from Midway Intl. Airport (MDW) to Hopkins Intl. Airport (CLE)?
With, on average, 2 direct flights departing from Midway Intl. Airport (MDW) to Hopkins Intl. Airport (CLE) daily, you'll be jetting off in no time.
What are the most popular departure times for flights from Midway Intl. Airport (MDW) to Hopkins Intl. Airport (CLE)?
The 10 AM departures from MDW to CLE are typically the busiest. These flights can come with a higher price due to their popularity. If you're looking to save, choose a less crowded time to fly.
What day of the week has the most flights from MDW to CLE?
Friday has the most flights from Midway Intl. Airport (MDW) to Hopkins Intl. Airport (CLE). Consider traveling on this day and you'll have the best chance of finding a departure that fits your schedule.
What is the earliest flight from Midway Intl. Airport (MDW) to Hopkins Intl. Airport (CLE)?
Take the earliest flight at around 10:00AM UTC-6, departing from Midway Intl. Airport (MDW). You'll be flying for about 1h 15m, touching down at Hopkins Intl. Airport (CLE) at approximately 12:15PM UTC-5.
How long does it take to fly from Midway Intl. Airport (MDW) to Hopkins Intl. Airport (CLE)?
The average flight time from MDW to CLE is 1 hour and 14 minutes, covering a total distance of 310 mi.
What airline has the least delays from MDW to CLE?
Consider traveling with Southwest Airlines if you'd like to go straight from Midway Intl. Airport (MDW) to Hopkins Intl. Airport (CLE) without any delays. This carrier has the strongest track record for punctuality, with an on-time score of 89%. Want to be notified if anything changes? You can keep an eye on your flight status using the Expedia App.
What is the best time to fly from Midway Intl. Airport (MDW) to Hopkins Intl. Airport (CLE)?
Book a flight from Midway Intl. Airport (MDW) to Hopkins Intl. Airport (CLE) that leaves before 3 PM to reduce the risk of cancellations and delays. Later departures have a 22% higher chance of being canceled, on average.**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 Cleveland from Midway Intl. Airport (MDW)?
If you're boarding a direct flight from Midway Intl. Airport (MDW) to Cleveland, Hopkins Intl. Airport (CLE) is the only airport you can touch down at.
Is it cheaper to buy a plane ticket from Midway Intl. Airport (MDW) to Hopkins Intl. Airport (CLE) last-minute?
Holding off until just before your trip to book a ticket from MDW to CLE often results in higher prices. While you might find some last-minute offers, they're not always guaranteed. Be flexible with your travel plans for the best chance of landing a bargain.
Is it cheaper to book a MDW to CLE flight and hotel package?
Compared with arranging flights and hotels separately, booking a MDW to CLE flight and hotel package with Expedia could result in significant savings. Better still, managing everything in one place will take the stress out of planning your trip. Simply pick your flights and choose from our extensive range of stays, then tailor your trip with other add-ons like activities, tours and car rentals.
Can I cancel or change the date of my flight from Midway Intl. Airport (MDW) to Hopkins Intl. Airport (CLE)?
Typically, you can cancel or reschedule your MDW to CLE flight. However, additional charges may apply, especially if you made your booking over 24 hours ago. Double-check your itinerary for the airline's guidelines and fees on flight changes, or if you'd like more details, go to our Customer Service portal.

Travel information

Origin airport
Midway Intl.
Destination airport
Hopkins Intl.
Airlines serving
Delta, Frontier Airlines, Southwest Airlines
Roundtrip price
$120
Distance
306 mi
Average flight time
2 hours 12 mins

Book with confidence

Chicago to Cleveland Flights

The cheapest times to fly from Chicago to Cleveland

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 Chicago to Cleveland are during the month of November. You can find some of the cheapest flights from Chicago to Cleveland with Expedia's search tool and vast selection of airlines.

 

The best time to book a flight from Chicago to Cleveland

Sunday is one of the best days to book for cheap flights from Chicago to Cleveland: 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 Chicago to Cleveland

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 Chicago to Cleveland in 2025. You can also book with separate airlines for your outbound and return journeys, from $60 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 Chicago to Cleveland 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 Chicago to Cleveland 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.

 

Chicago to Cleveland Flights

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*Available to One Key members.