Trade the Windy City for a beachside stay in Cozumel. When you choose to fly with Southwest Airlines® you’ll find cheap flights from Chicago Midway International Airport to Cozumel International Airport that will leave you with more than enough left over for a margarita upon arrival. Select your preferred flight to Cozumel and book with confidence today. Are your Cozumel trip dates flexible? Then explore all of the lowest fares we have available with the help of our Low Fare Calendar. To discover package deals on flights, hotels, rental cars, and more, explore Southwest Vacations® today.
Find flights from Chicago (Midway) to Cozumel and book today!
Departing from: Chicago Midway International Airport (MDW)
Arriving at: Cozumel International Airport (CZM)
Head down to the Caribbean island of Cozumel, which is located just a short boat ride from the coast of the Yucatán Peninsula, and discover a destination that’s both rich in history and filled with a thriving contemporary culture, thanks to its population of over 100,000 Cozumeleños. Whether you’re looking to stretch out in the sand at one of Cozumel’s many beachside resorts or explore the inland jungle once inhabited by the Mayans, there’s something for everyone in this sensational seaside locale.
With its pristine coastline, transparent waters, and plentiful coral reefs, Cozumel is an ideal location for those travelers in search of a taste of the tropical. If you’re interested in kicking off your sandals and catching some rays, you’ll find no shortage of places to do so. And while you’re relaxing, you’ll of course find a number of local flavors that perfectly complement your comfortable stay. Beyond the tequila and mescal made nearby in the Yucatán, you can sample from the comforting foods of the Yucatecan cuisine, which combines age-old Mayan influences with the more recent influx of Mexican, Spanish, and French touches to create an outstanding mixture.
Should you decide to break away from the beach and the coastal cuisine—though who could blame you if you don’t—you’ll have an array of excursions to choose from. The Mayan ruins at San Gervasio offer visitors a chance to see the remnants of a holy site, parts of which are dated at well over 1,000 years old. And if you’re up for a day trip, you can hop off the island and head to the magnificent Chichen Itza. The former location of one of the largest cities of the Mayan civilization, Chichen Itza comprises a range of incredibly well-maintained ruins that surround the site’s centerpiece, El Castillo, a stunning step pyramid.
Elsewhere on the eastern side of the Yucatán Peninsula, visitors can enjoy stopovers in the city of Cancún, known for its nightlife, or the towns of Playa del Carmen and Tulum, each of which offers similarly striking beaches to those of Cozumel. No matter where your trip to Cozumel takes you, you’re sure to find exciting experiences around every corner.
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.
At Southwest®, we know that what makes your trip from Chicago (Midway) to Cozumel memorable is more than just a cheap flight from Chicago Midway International Airport to Cozumel International Airport. So we offer a range of services and perks that span from booking to boarding to help ensure that your travel is as smooth as can be. See what goes into the Southwest Experience before you book your flight from Chicago (Midway) to Cozumel.
Wherever your globetrotting takes you next, you’ll find that it’s simple and fun to fly with Southwest. Find your next flight to Cozumel knowing that you won’t ever be surprised by hidden fees. Choose from low fares and, as always, your bags will fly free1. That’s our Transfarency® promise. Sign up for our Click 'N Save® emails today and keep up with all of our newest deals on flights. Meanwhile, you can find all of the latest info on tours, activities, and other hidden gems when you check out Southwest Airlines Experiences and earn Rapid Rewards points when you fly.
1First and second checked bags. Weight and size limits apply.
2Fare difference may apply.