Visit the City that Works! Chicago (Midway) invites you to experience everything this Midwestern cultural hub has to offer.
Book flights from Cleveland to Chicago (Midway) with Southwest Airlines®. It’s easy to find the Cleveland Hopkins International Airport to Chicago Midway International Airport flight to make your booking and travel a breeze. Whether you’re traveling for business or pleasure, solo or with the whole family, you’ll enjoy flying Southwest®. Have flexible travel dates? Plug them into the Low Fare Calendar and see the lowest fares available within your travel window. You may also want to browse Southwest Vacations® to see special offers and package deals on flights, hotels, rental cars, and more.
Explore your options and book your Cleveland to Chicago (Midway) flight with Southwest today!
Best Airline in the U.S. and North America & Best Economy Class and Low Cost Airline in North America.
Cleveland, OH to Chicago (Midway), IL
*Restrictions and exclusions apply. Seats and dates are limited. Select markets. 27 travel days available.
During the ongoing COVID-19 pandemic, the availability, health and safety procedures, operations, and schedules for local attractions are changing constantly. Please contact attractions directly for hours of operation, potential temperature screenings, and other possible health and safety procedures and restrictions. Visit our COVID-19 Travel Information page for information about potential restrictions on air travel.
Departing from: Cleveland Hopkins International Airport (CLE)
Arriving at: Chicago Midway International Airport (MDW)
Other popular flights from Cleveland
View our interactive map
One child over 14 days and under two (2) years of age, not occupying a seat, may be carried free of charge when traveling with an adult (12 years of age or older). Learn more.
Customers flying with a pet are subject to a pet fare. To learn more about traveling with your furry friend, explore the Southwest® pet policy.
Minors under the age of 18 are not permitted to fly unaccompanied on international flights or any itinerary that includes an international flight. Learn more.
Start packing! Every ticketed Customer’s first two checked bags are free. Learn more.
Chicago Midway International Airport is a quick 30-minute 'L' ride from downtown Chicago. Get going—adventure awaits.
At Southwest, we know it takes more than great deals on Chicago (Midway) airfares and convenient scheduling options to make your trip memorable. So from booking to boarding, we offer services and features designed to make your travel from Cleveland to Chicago (Midway) the best it can be. Learn more about the Southwest® travel experience before you book your flight from Cleveland Hopkins International Airport to Chicago Midway International Airport.
Flying with Southwest is simple and fun, no matter which of our dozens of exciting destinations you choose. When you search for your next flight to Chicago (Midway), know that you won’t be surprised at checkout. Low fares and no hidden fees. That's Transfarency®. And as always, two bags fly free®1. Want the latest news, information, and promotional offers from Southwest? Sign up to receive email from us. Looking for tours, activities, and more hidden gems to add to your Chicago (Midway) adventure? Explore getaways with Southwest®. Book your flight today and know that you'll earn Rapid Rewards® points when you fly.
1First and second checked bags. Weight and size limits apply.
2Fare difference may apply.
To find the cheapest day and time to fly Cleveland to Chicago (Midway) with Southwest, check out our Low Fare Calendar.
You can rent a car at Chicago Midway International Airport—book yours with your flight.
Yes! Flights from Cleveland to Chicago (Midway)—or from here or there to anywhere—can be changed with no change fees. Fare difference may apply.
Check the status of your upcoming Southwest flight here.
Check out the Southwest Airlines® FAQs for answers about everything Southwest.
Discussion Forum and StoriesMobile Apps
