CA $123 Cheap Flights from Cleveland (CLE) to Chicago (MDW)

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

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Cheap flights from Cleveland (CLE) to Chicago (MDW)

Prices were available within the past 7 days and start at CA $123 for one-way flights and CA $245 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

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

September is typically the cheapest month to fly

From CA $132 - CA $410 per traveller.

Graph displaying average flight prices per month

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Flight from Cleveland to Chicago (CLE - MDW) route information
Origin airport
Hopkins Intl.
Destination airport
Midway Intl.
Roundtrip price
CA $244
Distance
489 km

Cleveland to Chicago Flights

The easy way to book your flights from Cleveland to Chicago 

With Expedia, it’s simple to find and book flights to Chicago from Cleveland whether you’re traveling for business or pleasure. Enter your travel dates, hit search, and choose your flight from 20 airlines that cover this route. There are Southwest Airlines nonstop flights to Midway Intl., too.  

Choose your preferred carrier and cabin class with the advanced search tool and select your ideal departure time. Then, if you want, you can see just nonstop or refundable flights. And if you’re traveling last minute, just enter the date to check out flights from Cleveland to Chicago today, tomorrow, or this week.  

 

Save dollars with cheap flights from Hopkins Intl., CLE to Midway Intl., MDW 

Sort your search results by price to find great deals on your flight from Cleveland to Chicago—you get all your cheapest options first. Grab yourself a bargain now—the lowest price on flights to Chicago from Cleveland currently is just CA $245 rising to CA $605.  

Here are more money-saving tips: 

  • Fly in October when flight prices are normally at their lowest 
  • Book about a month to 6 weeks before you travel for the best prices to Chicago  
  • Avoid peak season and weekends when flights can cost more
  • Early morning and late-night flights are sometimes cheaper, so try varying your travel times 
  • One surefire way to save money on your flight is to book your flight and hotel together with Expedia. Sometimes, the savings are so large that the flight is basically free! 

 

Reasons to choose Expedia for your flight to Chicago from Cleveland 

Whatever your destination, budget, or reason to travel, in just one quick search, you can choose from loads of flights, airlines, and cabin classes. The filters make it quick and easy to find your ideal flights, and if you choose one of the flexible options, you won’t be charged to change your flight. So book your flight to Chicago with Expedia today.

Frequently asked questions

How much is a flight from Hopkins Intl. Airport (CLE) to MDW?
Based on fares listed within the last 7 days on Expedia for flights departing within the next year, round-trip journeys between Cleveland Hopkins Intl. Airport and Midway Intl. Airport (MDW) start from CA $245. Book today to secure the best price for your trip. Prices and availability are subject to change. Additional terms apply.
Do I need to pay a cancellation fee if I cancel my flight from Cleveland Hopkins Intl. Airport to MDW?
Each air carrier has its own terms and conditions. If you do decide to cancel, follow the simple instructions on our Customer Service Portal.
How do I find cheap flights from CLE to Midway Intl. Airport (MDW) that have flexible change policies?
Plenty of airlines will allow you to reschedule your flight without a change fee. All you pay is the cost difference between the two flights. When searching for CLE to Chicago Airport flights, you'll see a "No change fees" box for you to pick.
How many hours is the flight from Hopkins Intl. Airport (CLE) to Midway Intl. Airport (MDW)?
Get comfy in your seat, select a movie and 5 hours and 14 minutes will fly by in a jiffy. That's how long it takes to travel to Midway Intl. Airport (MDW) from Cleveland Hopkins Intl. Airport.
How far is the flight from CLE to Midway Airport?
A flight distance of just 490 kilometres separates Cleveland and Chicago. Once you're up in the air, you won't have time to do much more than read the magazine in your seat pocket.
Which airlines fly direct from Cleveland Hopkins Intl. Airport to Chicago Airport?
Flying directly from Hopkins Intl. Airport (CLE) to Midway Intl. Airport (MDW) is a cinch with Southwest Airlines (WN). This top carrier offers 73 flights every month.
Are Hopkins Intl. Airport (CLE) to Midway Airport flight tickets cheaper when they're purchased at the last minute?
It is possible to find great last-minute deals from Cleveland Hopkins Intl. Airport to Midway Intl. Airport (MDW), but there's no guarantee. As many airlines publish prices up to 12 months in advance, it's worthwhile keeping an eye on fares early and being ready to book when you see a bargain. Expedia compares air carrier prices and updates flight deals all the time, so you can feel confident knowing you're always seeing the latest offers.

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