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CA $110 Cheap Flights from Cleveland (CLE) to Chicago (MDW)

View CA $110 flight on Sun, Sep 6, 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 $110 for one-way flights and CA $191 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Southwest Airlines
Sat, Sep 5 - Sun, Sep 6
CLE
Cleveland
MDW
Chicago
CA $191 Roundtrip, found 3 days ago
CA $191
Roundtrip
found 3 days ago
Select Southwest Airlines flight, departing Sat, Sep 5 from Cleveland to Chicago, returning Sun, Sep 6, priced at CA $191 found 3 days ago
Delta
Sat, Sep 5 - Sat, Sep 12
CLE
Cleveland
MDW
Chicago
CA $229 Roundtrip, found 15 hours ago
CA $229
Roundtrip
found 15 hours ago
Select Delta flight, departing Sat, Sep 5 from Cleveland to Chicago, returning Sat, Sep 12, priced at CA $229 found 15 hours ago
Delta
Sat, Sep 5 - Sat, Sep 12
CLE
Cleveland
MDW
Chicago
CA $230 Roundtrip, found 15 hours ago
CA $230
Roundtrip
found 15 hours ago
Select Delta flight, departing Sat, Sep 5 from Cleveland to Chicago, returning Sat, Sep 12, priced at CA $230 found 15 hours ago
Delta
Sat, Sep 5 - Sat, Sep 12
CLE
Cleveland
MDW
Chicago
CA $279 Roundtrip, found 15 hours ago
CA $279
Roundtrip
found 15 hours ago
Select Delta flight, departing Sat, Sep 5 from Cleveland to Chicago, returning Sat, Sep 12, priced at CA $279 found 15 hours ago
Delta
Sat, Sep 5 - Sat, Sep 12
CLE
Cleveland
MDW
Chicago
CA $286 Roundtrip, found 15 hours ago
CA $286
Roundtrip
found 15 hours ago
Select Delta flight, departing Sat, Sep 5 from Cleveland to Chicago, returning Sat, Sep 12, priced at CA $286 found 15 hours ago
Delta
Sat, Sep 5 - Sat, Sep 12
CLE
Cleveland
MDW
Chicago
CA $287 Roundtrip, found 15 hours ago
CA $287
Roundtrip
found 15 hours ago
Select Delta flight, departing Sat, Sep 5 from Cleveland to Chicago, returning Sat, Sep 12, priced at CA $287 found 15 hours ago
Southwest Airlines
Sat, Sep 5 - Sun, Sep 6
CLE
Cleveland
MDW
Chicago
CA $310 Roundtrip, found 3 days ago
CA $310
Roundtrip
found 3 days ago
Select Southwest Airlines flight, departing Sat, Sep 5 from Cleveland to Chicago, returning Sun, Sep 6, priced at CA $310 found 3 days ago
Delta
Sat, Sep 5 - Sat, Sep 12
CLE
Cleveland
MDW
Chicago
CA $328 Roundtrip, found 15 hours ago
CA $328
Roundtrip
found 15 hours ago
Select Delta flight, departing Sat, Sep 5 from Cleveland to Chicago, returning Sat, Sep 12, priced at CA $328 found 15 hours ago
Delta
Sat, Sep 5 - Sat, Sep 12
CLE
Cleveland
MDW
Chicago
CA $335 Roundtrip, found 15 hours ago
CA $335
Roundtrip
found 15 hours ago
Select Delta flight, departing Sat, Sep 5 from Cleveland to Chicago, returning Sat, Sep 12, priced at CA $335 found 15 hours ago
Delta
Sat, Sep 5 - Sat, Sep 12
CLE
Cleveland
MDW
Chicago
CA $337 Roundtrip, found 15 hours ago
CA $337
Roundtrip
found 15 hours ago
Select Delta flight, departing Sat, Sep 5 from Cleveland to Chicago, returning Sat, Sep 12, priced at CA $337 found 15 hours ago

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

October is typically the cheapest month to fly

From CA $136 - CA $331 per traveller.

Frequently asked questions

How much does a flight from Cleveland, OH (CLE-Hopkins Intl.) to Chicago, IL (MDW-Midway Intl.) cost?
You can find one-way and return flights from CLE to MDW with Expedia. Flight prices vary based on the month and day of the week you want to travel, as well as the airline and how far in advance you book your ticket. Filter your search on Expedia by "Price (lowest to highest)" to see our cheapest fares first, and use the Price Tracking tool to receive alerts when CLE to MDW ticket fares go up or down.
What is the cheapest month to fly from Cleveland, OH (CLE-Hopkins Intl.) to Chicago, IL (MDW-Midway Intl.)?
The cheapest months to fly from CLE to MDW are typically during off-peak season when demand is low. Traveling in off-peak or shoulder months is usually a good way to secure cheap tickets, just remember to avoid flying during holidays if you are able to. Use the calendar view in your search to see which months have low fares on this route.
Which airlines fly direct from Cleveland, OH (CLE-Hopkins Intl.) to Chicago, IL (MDW-Midway Intl.)?
Only one airline offers direct flights from Cleveland, OH (CLE-Hopkins Intl.) to Chicago, IL (MDW-Midway Intl.). Southwest Airlines operates 25 direct flights from Cleveland, OH (CLE-Hopkins Intl.) to Chicago, IL (MDW-Midway Intl.) every week.
What is the cheapest airline that flies from Cleveland, OH (CLE-Hopkins Intl.) to Chicago, IL (MDW-Midway Intl.)?
Thurgood Marshall (BWI), starting from around CA$177. Southwest Airlines is one of the cheapest airlines offering nonstop return flights from Cleveland, OH (CLE-Hopkins Intl.) to Chicago, IL (MDW-Midway Intl.), with tickets starting from around CA$185 for flights that can be booked for departure within the next year. Southwest Airlines also offers one of the cheapest connecting return flights on this route, with a layover in Baltimore Washington Intl. These prices are for economy/coach class per adult. Use Expedia's search tool to compare the prices and schedules of airlines that fly this route to find the best option for your plans and budget.
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.) to Chicago, IL (MDW-Midway Intl.) will differ from traveler to traveler. If you like to fly early, Southwest Airlines offers early morning flights. If price is the most important factor, Southwest Airlines typically offers the lowest fares. Southwest Airlines offers the most daily flights from Cleveland, OH (CLE-Hopkins Intl.) to Chicago, IL (MDW-Midway Intl.), 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.)?
You'll find around 4 nonstop flights per day from Cleveland Hopkins International (CLE) to Chicago Midway International (MDW). For even more choices, look at flights that include layovers, as there are approximately 40 connecting flights per day. Some common connection points include Baltimore Washington International Thurgood Marshall (BWI), Nashville International (BNA), and Hartsfield-Jackson Atlanta International (ATL).
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 around 5:00 AM local time. This service is operated by Southwest Airlines. This is a seasonal service, active only in November. An early departure like this can help you make the most of 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.)?
You'll typically find the most flights from Cleveland, OH (CLE-Hopkins Intl.) to Chicago, IL (MDW-Midway Intl.) on a Sunday, with around 24 flights available. This gives you a good selection of options for your travel plans. Major airlines on this route include Southwest Airlines, Delta, and Frontier Airlines. Sunday offers notably more flight options compared to other days of the week, making it a convenient day to fly.
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.) to Chicago, IL (MDW-Midway Intl.) are in the morning, from 6am to 9am. Many major carriers, including Southwest Airlines, Delta and Frontier Airlines, offer flights during this window. Many travellers prefer this time because it allows for an early start to their day in Chicago.
How long does it take to fly from Cleveland, OH (CLE-Hopkins Intl.) to Chicago, IL (MDW-Midway Intl.)?
A nonstop flight from Cleveland, OH (CLE-Hopkins Intl.) to Chicago, IL (MDW-Midway Intl.) typically takes around 1 hour 18 minutes. This route covers a distance of approximately 492 kilometres. If you opt for a one-stop flight, your travel time will be longer, usually around 3 hours 30 minutes. Flights with two or more stops will take even longer, averaging about 9 hours 18 minutes. Keep in mind that actual flight times can vary due to factors like wind patterns and air traffic, so it's always a good idea to allow for some extra time when planning your trip.
Can you fly business or first class from Cleveland, OH (CLE-Hopkins Intl.) to Chicago, IL (MDW-Midway Intl.)?
Yes, you can fly business class or first class between Cleveland, OH (CLE-Hopkins Intl.) and Chicago, IL (MDW-Midway Intl.).You can fly business class with Frontier Airlines and Delta.First class cabins are available on Delta.
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, IL (MDW) from Cleveland, OH (CLE)?
From Hopkins Intl. (CLE), you can fly directly into Midway Intl. (MDW) in Chicago. Some flights may connect through major hubs like Baltimore Washington Intl. Thurgood Marshall (BWI), Nashville Intl. (BNA), or Lambert-St. Louis Intl. (STL) 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.
Airlines serving
Delta
Roundtrip price
CA $190
Distance
489 km

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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 $191 rising to CA $407.  

Here are more money-saving tips: 

  • Fly in September 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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*Available to Expedia members.