$55 Cheap Flights from Cleveland (CLE) to Chicago (MDW)

View $55 flight on Sat, Dec 6, 2025Opens in a new window

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

Cheap Flights from Cleveland to Chicago (CLE-MDW)

Prices were available within the past 7 days and start at $55 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, Dec 6 - Thu, Dec 11
CLE
Cleveland
MDW
Chicago
$120 Roundtrip, found 1 day ago
$120
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Sat, Dec 6 from Cleveland to Chicago, returning Thu, Dec 11, priced at $120 found 1 day ago
Frontier Airlines
Thu, Dec 11 - Mon, Dec 15
CLE
Cleveland
MDW
Chicago
$140 Roundtrip, found 1 day ago
$140
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Thu, Dec 11 from Cleveland to Chicago, returning Mon, Dec 15, priced at $140 found 1 day ago
Frontier Airlines
Mon, Nov 10 - Thu, Nov 13
CLE
Cleveland
MDW
Chicago
$160 Roundtrip, found 2 hours ago
$160
Roundtrip
found 2 hours ago
Select Frontier Airlines flight, departing Mon, Nov 10 from Cleveland to Chicago, returning Thu, Nov 13, priced at $160 found 2 hours ago
Frontier Airlines
Sat, Dec 6 - Mon, Dec 8
CLE
Cleveland
MDW
Chicago
$164 Roundtrip, found 1 day ago
$164
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Sat, Dec 6 from Cleveland to Chicago, returning Mon, Dec 8, priced at $164 found 1 day ago
Frontier Airlines
Mon, Nov 3 - Fri, Nov 7
CLE
Cleveland
MDW
Chicago
$176 Roundtrip, found 4 days ago
$176
Roundtrip
found 4 days ago
Select Frontier Airlines flight, departing Mon, Nov 3 from Cleveland to Chicago, returning Fri, Nov 7, priced at $176 found 4 days ago
Delta
Thu, Dec 4 - Mon, Dec 8
CLE
Cleveland
MDW
Chicago
$179 Roundtrip, found 3 days ago
$179
Roundtrip
found 3 days ago
Select Delta flight, departing Thu, Dec 4 from Cleveland to Chicago, returning Mon, Dec 8, priced at $179 found 3 days ago
Frontier Airlines
Mon, Nov 10 - Thu, Nov 13
CLE
Cleveland
MDW
Chicago
$180 Roundtrip, found 2 hours ago
$180
Roundtrip
found 2 hours ago
Select Frontier Airlines flight, departing Mon, Nov 10 from Cleveland to Chicago, returning Thu, Nov 13, priced at $180 found 2 hours ago
Southwest Airlines
Sat, Dec 13 - Mon, Dec 15
CLE
Cleveland
MDW
Chicago
$185 Roundtrip, found 6 hours ago
$185
Roundtrip
found 6 hours ago
Select Southwest Airlines flight, departing Sat, Dec 13 from Cleveland to Chicago, returning Mon, Dec 15, priced at $185 found 6 hours ago
Frontier Airlines
Mon, Nov 3 - Thu, Nov 13
CLE
Cleveland
MDW
Chicago
$190 Roundtrip, found 1 hour ago
$190
Roundtrip
found 1 hour ago
Select Frontier Airlines flight, departing Mon, Nov 3 from Cleveland to Chicago, returning Thu, Nov 13, priced at $190 found 1 hour ago
Southwest Airlines
Sat, Dec 13 - Mon, Dec 15
CLE
Cleveland
MDW
Chicago
$194 Roundtrip, found 6 hours ago
$194
Roundtrip
found 6 hours ago
Select Southwest Airlines flight, departing Sat, Dec 13 from Cleveland to Chicago, returning Mon, Dec 15, priced at $194 found 6 hours ago

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

September is typically the cheapest month to fly

From $88 - $367 per traveler.

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. Average driving time to city center is 23 minutes. Flights from $356
ORD
O'Hare Intl.
Average driving time to city center23 min
Flights from $356

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 $55 or cheap return flight from $120 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 December, 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.

Travel information

0
Origin airport
Hopkins Intl.
Destination airport
Midway Intl.
Airlines serving
Delta, Frontier Airlines, Southwest Airlines
Roundtrip price
$120
Distance
306 mi

Book with confidence

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 December. 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 $55 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.

 

Cleveland to Chicago Flights

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*Available to One Key members.