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Flights from Midway with Southwest Airlines®.
Say goodbye to the City of the Big Shoulders and jet off for an adventure—see where Southwest® flies from Chicago Midway International Airport.
Southwest Airlines is proud to serve Chicago Midway International Airport.
Boarding a Southwest flight departing Midway is a snap—just hop on the “L” train! The Orange Line will take you directly to the airport, the first stop on your adventure beyond the Second City. Of course, long-term parking and calling a car are always options, too.
A world-class city like Chicago has something for everyone and pockets of cultures from around the globe, but it doesn’t have everything. Ocean views? Not one, though Lake Michigan is lovely. Mountain peaks? The only heights you’ll find among the flat terrain of this Midwestern hub are skyscrapers. Dry desert heat is of course unheard of—that lovely lake sure does make it plenty humid in the summertime. There’s so much world out there to explore beyond the Chicagoland area, and Southwest can take you there. And since Chicago Midway International Airport is a Southwest Airlines hub, many of those flights out of Chi-Town are direct!
It’s time for a change of scenery. Take a break from the hustle and bustle of big-city life (or trade Second City vibes for the buzz of another metropolis) with a flight on Southwest Airlines. Whether you choose an oceanside getaway, a desert retreat, or to disappear into another walk of life entirely, Southwest can take you there from Chicago Midway International Airport. Discover all your destination and flight options and rack up those Rapid Rewards® points when you fly. Know your booking process will be straightforward from flight selection to checkout to boarding. Learn more about what makes the Southwest® Experience different.
Experience otherworldly theme parks or enjoy the down to earth vibes in this Central Florida city that’s the perfect steppingstone for once in a lifetime day trips.
Points bookings do not include taxes, fees, and other government/airport charges of at least $5.60 per one-way flight.
Seats and days are limited. Fares may vary by destination, flight, and day of week and won't be available on some flights that operate during very busy travel times and holiday periods.
Fares may be combined with other Southwest Airlines® combinable fares. If combining with other fares, the most restrictive fare's rules apply.
Fares are nonrefundable but may be applied toward future travel on Southwest Airlines®, as long as reservations are canceled at least ten minutes prior to the scheduled departure. Failure to cancel prior to departure will result in forfeiture of remaining funds on the reservation.
Any change in itinerary may result in an increase in fare. Standby travel may require an upgrade to the Anytime fare depending on Rapid Rewards® tier status.
Fares are subject to change until ticketed.
Offer applies only to published, scheduled service.
Got flexible travel plans?
Use our Low Fare Calendar to find the lowest fares on flights from Midway available inside your travel window.
Cities with daily nonstop flights Monday through Friday from MDW
69†
Cities with daily nonstop flights Saturday through Sunday from MDW
70‡
*Weekly flights based on DOT published scheduled average flights Monday through Sunday between 6/1/2023 and 6/30/2023. Note: route may not operate every day of the week.
†Nonstop flights based on DOT published scheduled average flights Monday through Friday between 6/1/2023 and 6/30/2023.
‡Nonstop flights based on DOT published scheduled average flights Saturday through Sunday between 6/1/2023 and 6/30/2023.
Your trip comes with low fares and no hidden fees. That's Transfarency®.
We want to make your trip special, so we're taking everything you love about Southwest and bringing it all to your travels. Get everything Transfarency has to offer on your next trip, only with Southwest.
You can use your points to book any seat, on any flight, no exceptions. Any day, any time, any flight, your points are ready to take you to where you want to go.
Your points don’t expire.
You can earn points on flights and on everyday purchases with our partners, which makes getting to your destination easy. No matter when, or where, you earn them, your points won’t expire.
1First and second checked bags. Weight and size limits apply.
2Fare difference may apply.
3Failure to cancel a reservation at least 10 minutes prior to departure may result in forfeited Travel Funds.
4Flight credits unexpired on or created on or after July 28, 2022, do not expire and will show an expiration date until our systems are updated. See full details here.
5Where available. Available only on WiFi-enabled aircraft. Limited-time offer.
6Due to licensing restrictions, on WiFi-enabled international flights, free live TV and iHeartRadio may not be available for the full duration of flight.
7Internet access for $8 per device from takeoff to landing. Price is subject to change. May not be available for the full duration of flight. In order to provide a top-notch Internet experience, we prohibit access to certain high-bandwidth applications and websites. We also prohibit access to certain obscene or offensive content.
