CA $191 Cheap Flights from Cleveland (CLE) to Chicago (MDW)

View CA $191 flight on Thu, May 28, 2026Opens 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 (CLE) to Chicago (MDW)

Prices were available within the past 7 days and start at CA $191 for one-way flights and CA $252 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Delta
Sat, May 16 - Wed, May 20
CLE
Cleveland
MDW
Chicago
CA $252 Roundtrip, found 5 days ago
CA $252
Roundtrip
found 5 days ago
Select Delta flight, departing Sat, May 16 from Cleveland to Chicago, returning Wed, May 20, priced at CA $252 found 5 days ago
Delta
Sat, May 16 - Thu, May 21
CLE
Cleveland
MDW
Chicago
CA $289 Roundtrip, found 5 days ago
CA $289
Roundtrip
found 5 days ago
Select Delta flight, departing Sat, May 16 from Cleveland to Chicago, returning Thu, May 21, priced at CA $289 found 5 days ago
Delta
Sun, May 17 - Wed, May 20
CLE
Cleveland
MDW
Chicago
CA $367 Roundtrip, found 5 days ago
CA $367
Roundtrip
found 5 days ago
Select Delta flight, departing Sun, May 17 from Cleveland to Chicago, returning Wed, May 20, priced at CA $367 found 5 days ago
Delta
Sun, May 17 - Thu, May 21
CLE
Cleveland
MDW
Chicago
CA $404 Roundtrip, found 5 days ago
CA $404
Roundtrip
found 5 days ago
Select Delta flight, departing Sun, May 17 from Cleveland to Chicago, returning Thu, May 21, priced at CA $404 found 5 days ago
Delta
Mon, May 11 - Wed, May 20
CLE
Cleveland
MDW
Chicago
CA $421 Roundtrip, found 5 days ago
CA $421
Roundtrip
found 5 days ago
Select Delta flight, departing Mon, May 11 from Cleveland to Chicago, returning Wed, May 20, priced at CA $421 found 5 days ago
Delta
Tue, Jun 16 - Wed, Jun 17
CLE
Cleveland
MDW
Chicago
CA $433 Roundtrip, found 6 days ago
CA $433
Roundtrip
found 6 days ago
Select Delta flight, departing Tue, Jun 16 from Cleveland to Chicago, returning Wed, Jun 17, priced at CA $433 found 6 days ago
Delta
Thu, May 14 - Sat, May 16
CLE
Cleveland
MDW
Chicago
CA $458 Roundtrip, found 5 days ago
CA $458
Roundtrip
found 5 days ago
Select Delta flight, departing Thu, May 14 from Cleveland to Chicago, returning Sat, May 16, priced at CA $458 found 5 days ago
Delta
Tue, Jun 16 - Wed, Jun 17
CLE
Cleveland
MDW
Chicago
CA $462 Roundtrip, found 6 days ago
CA $462
Roundtrip
found 6 days ago
Select Delta flight, departing Tue, Jun 16 from Cleveland to Chicago, returning Wed, Jun 17, priced at CA $462 found 6 days ago
Delta
Mon, Jun 15 - Tue, Jun 16
CLE
Cleveland
MDW
Chicago
CA $487 Roundtrip, found 6 days ago
CA $487
Roundtrip
found 6 days ago
Select Delta flight, departing Mon, Jun 15 from Cleveland to Chicago, returning Tue, Jun 16, priced at CA $487 found 6 days ago
Delta
Mon, Jun 15 - Tue, Jun 16
CLE
Cleveland
MDW
Chicago
CA $488 Roundtrip, found 6 days ago
CA $488
Roundtrip
found 6 days ago
Select Delta flight, departing Mon, Jun 15 from Cleveland to Chicago, returning Tue, Jun 16, priced at CA $488 found 6 days ago

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 centre is 23 minutes. Flights from CA $421
ORD
O'Hare Intl.
Cheapest
Average driving time to city centre23 min
Flights from CA $421

Frequently asked questions

Which airlines fly direct from Cleveland, OH (CLE-Hopkins Intl.) to Chicago, IL (MDW-Midway Intl.)?
Enter CLE to MDW and your travel dates, then apply the 'Nonstop' filter to see only direct flights.
How do I find cheap flights from Cleveland, OH (CLE-Hopkins Intl.) to Chicago, IL (MDW-Midway Intl.)?
To find a cheap flight from Cleveland, OH (CLE-Hopkins Intl.) to Chicago, IL (MDW-Midway Intl.), be flexible with your dates. Traveling outside of peak vacation months and booking a mid-week flight can help you save. Early morning and late night flights are often more affordable, too. Expedia allows you to compare flight times, airlines and routes all in one place to find low fares. You can also set up Price Tracking and receive alerts when fares go up or down.
What is the best airline to fly with from Cleveland, OH (CLE-Hopkins Intl.) to Chicago, IL (MDW-Midway Intl.)?
The best airline to fly with from Cleveland, OH (CLE-Hopkins Intl.) (CLE) to Chicago, IL (MDW-Midway Intl.) (MDW) will differ from traveler to traveler. If you like to fly early, WN offers early morning flights. If price is the most important factor, WN typically offers the lowest fares. WN offers the most daily flights from Cleveland, OH (CLE-Hopkins Intl.) (CLE) to Chicago, IL (MDW-Midway Intl.) (MDW), which is great if flexibility is what you value most. The best carrier for this journey could also be the one you have a loyalty membership with, as flying with that airline or another airline within the same alliance could help you collect points or enjoy lounge access.
What is the best time to fly from Cleveland, OH (CLE-Hopkins Intl.) to Chicago, IL (MDW-Midway Intl.)?
The best time to fly is usually mid-week (Tuesday or Wednesday) and during early morning hours as flights tend to be cheaper, less crowded, and generally more on-time. Avoid major holidays and peak vacation seasons for smoother travel. Combining off-peak days and hours often gives the best combination of cost, comfort, and convenience.
How many flights per day from Cleveland, OH (CLE-Hopkins Intl.) to Chicago, IL (MDW-Midway Intl.)?
There are approximately 3 nonstop flights per day from Cleveland, OH (CLE-Hopkins Intl.) (CLE) to Chicago, IL (MDW-Midway Intl.) (MDW). For even more choice, look at flights that include layovers. You'll find around 43 connecting flights per day. Some common connection points include Baltimore Washington Intl. Thurgood Marshall (BWI), Nashville Intl. (BNA), and Lambert-St. Louis Intl. (STL).
What is the earliest flight from Cleveland, OH (CLE-Hopkins Intl.) to Chicago, IL (MDW-Midway Intl.)?
The earliest flight from Cleveland, OH (CLE-Hopkins Intl.) to Chicago, IL (MDW-Midway Intl.) typically departs at approximately 5:00 AM local time. This service is operated by Southwest Airlines and is seasonal, active only in November. An early departure like this can help maximize your time at your destination. To compare early flights on Expedia, select the "Early Morning" and "Morning" filters in your search.
What day of the week has the most flights from Cleveland, OH (CLE-Hopkins Intl.) to Chicago, IL (MDW-Midway Intl.)?
If you're flying from Cleveland, OH (CLE-Hopkins Intl.) to Chicago, IL (MDW-Midway Intl.), you'll typically find the most flights on a Sunday, with around 24 flights available. This gives you plenty of options to choose from. Looking at the overall week, flight schedules are fairly consistent, with Sunday offering only slightly more flights than other days. Major airlines on this route include Southwest Airlines, Delta Air Lines, and Frontier Airlines.
What are the most popular departure times for flights from Cleveland, OH (CLE-Hopkins Intl.) to Chicago, IL (MDW-Midway Intl.)?
The most popular departure times for flights from Cleveland, OH (CLE-Hopkins Intl.) (CLE) to Chicago, IL (MDW-Midway Intl.) (MDW) are in the morning, from 6am to 9am. About 31% of passengers prefer this time window. Many major carriers, including Delta Air Lines and Southwest Airlines, offer flights during this window. This timing works well for travelers who want to arrive at their destination early in the day, giving them more time for business or leisure activities.
How long does it take to fly from Cleveland, OH (CLE-Hopkins Intl.) to Chicago, IL (MDW-Midway Intl.)?
A nonstop flight from CLE to MDW typically takes around 1 hour 20 minutes, covering approximately 306 miles. Connecting flights on this route usually add 2 hours 10 minutes to your travel time. Keep in mind that actual flight times can vary due to wind patterns, weather, and air traffic.
Can you fly business or first class from Cleveland, OH (CLE-Hopkins Intl.) to Chicago, IL (MDW-Midway Intl.)?
Select the "Business class" and "First class" filters when looking for CLE to MDW flights on Expedia. This is the easiest way to compare prices, routes and flight times for your trip.
How do I earn miles on a Cleveland, OH (CLE-Hopkins Intl.) to Chicago, IL (MDW-Midway Intl.) flight with Expedia?
It's easy to earn miles on a Cleveland, OH (CLE-Hopkins Intl.) to Chicago, IL (MDW-Midway Intl.) flight when you book with Expedia. Before you confirm your booking, simply select your frequent flyer program and enter your program number. As a member of One Key™, you can also earn OneKeyCash™* on top of your airline miles when you book with Expedia. *Excludes taxes and fees. OneKeyCash is not redeemable for cash and can only be used on Expedia and other participating brands.
What airports do you fly into for Chicago from Hopkins Intl. (CLE)?
When traveling from Hopkins Intl. (CLE) to Chicago, you can fly into O'Hare Intl. (ORD) and Midway Intl. (MDW). Some flights may connect through major hubs like Charlotte-Douglas Intl. (CLT), Ronald Reagan Washington National (DCA), Baltimore Washington Intl. Thurgood Marshall (BWI) before reaching Chicago. Compare routes and airports on Expedia to find the best flight options for your travel plans.
Is it cheaper to buy a plane ticket from Cleveland, OH (CLE-Hopkins Intl.) to Chicago, IL (MDW-Midway Intl.) at the last minute?
Typically, booking a last minute flight from Cleveland, OH (CLE-Hopkins Intl.) to Chicago, IL (MDW-Midway Intl.) will be more expensive than booking in advance. As the departure date approaches, there are usually fewer seats available which can drive up the cost. However, if there's some wiggle room with your travel dates and times, you could bag a cheap last-minute fare.
Is it cheaper to book a Cleveland, OH (CLE-Hopkins Intl.) to Chicago, IL (MDW-Midway Intl.) flight and hotel package?
Securing a Cleveland, OH (CLE-Hopkins Intl.) to Chicago, IL (MDW-Midway Intl.) flight and hotel package is usually cheaper than booking separately. With Expedia, you can enjoy the ease of organizing your travels all in one place. Select from our extensive range of stays and then add flights, activities and car rentals to your booking. Bundle everything together, and you could save hundreds of dollars.
Can I cancel or change the date of my flight from Cleveland, OH (CLE-Hopkins Intl.) to Chicago, IL (MDW-Midway Intl.)?
If you booked your Cleveland, OH (CLE-Hopkins Intl.) to Chicago, IL (MDW-Midway Intl.) flight within the last 24 hours, you may be able to modify or cancel it without any fees. Depending on the airline and the type of ticket you have, additional charges may apply for changes beyond this timeframe. Airline policies and contact information can be found in your itinerary or confirmation email. Or, head to our Customer Service portal if you'd like more information.

Travel information

0
Origin airport
Hopkins Intl.
Destination airport
Midway Intl.
Roundtrip price
CA $251
Distance
489 km

Book with confidence

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 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 $252 rising to CA $488.  

Here are more money-saving tips: 

  • Fly in May 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.

Cleveland to Chicago Flights

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