Southwest® flights from Miami to Chicago (Midway) from $46
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Low fares from Miami to Chicago (Midway)
$
Miami (MIA)to
Chicago (Midway) (MDW)
Depart: 01/14/2026
One-way
Basic
From
$46
Seen: 2 hrs ago
Miami (MIA)to
Chicago (Midway) (MDW)
Depart: 02/25/2026
One-way
Basic
From
$46
Seen: 1 hour ago
Miami (MIA)to
Chicago (Midway) (MDW)
Depart: 01/27/2026
One-way
Basic
From
$46
Seen: 30 minutes ago
Miami (MIA)to
Chicago (Midway) (MDW)
Depart: 01/27/2026
One-way
Choice
From
$66
Seen: 30 minutes ago
Miami (MIA)to
Chicago (Midway) (MDW)
Depart: 01/14/2026
One-way
Choice
From
$66
Seen: 2 hrs ago
Miami (MIA)to
Chicago (Midway) (MDW)
Depart: 02/25/2026
One-way
Choice
From
$66
Seen: 1 hour ago
Explore flights from Miami to Chicago (Midway)
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Travel tips for your next Southwest flight
How to board the plane earlier on open seating flights departing on or before January 26, 2026:
Southwest seats are first come, first served based on check-in order. But there are ways to board the plane earlier!
- Purchase EarlyBird Check-In®1 for automatic check-in and a better boarding position.
- Purchase Upgraded Boarding2 to get an A1-A15 boarding position (depending on availability).
- Purchase a Business Select® fare or upgrade to Business Select to get a guaranteed A1-A15 boarding position.
Enjoy movies, sips, and snacks during your flight.
Take advantage of inflight entertainment with free movies4, free live TV5, free texting6, and $8 inflight Internet7.
We also offer free sodas, coffee, and snacks8—learn more about the inflight food and beverage experience.
Make the most of our Rapid Rewards® Program.
Rapid Rewards Members can redeem their points for flights, hotel stays, rental cars, gift cards, and more. And your points never expire!
Flight Details
Departing from:
Miami International Airport
Arriving at:
Chicago Midway International Airport
Average flight time:
3 hours 5 minutes
Distance:
1182 miles
Route Information
145† Weekly flights
- 1‡ Nonstop flight per day Monday through Friday
- 1‡ Nonstop flight on Saturday
- 1‡ Nonstop flight on Sunday
† Weekly flights based on DOT published scheduled average flights Monday through Sunday between 9/1/2025 and 9/30/2025. Note: route may not operate every day of the week.
‡ Nonstop flights based on DOT published scheduled average flights Monday through Sunday between 9/1/2025 and 9/30/2025.
Explore Chicago (Midway)
Chicago may be the City that Works, but it plays just as well. When you deplane at Chicago Midway International Airport, grab a rental car, hail a ride, or board the Orange Line and head into the heart of the city to find your favorite way to play. While the train will take you directly into the Loop—what they call their downtown business district—there’s no need to spend your stay in this tourist favorite. Chicago is a city of neighborhoods, built of vibrant immigrant communities—see what you’ll discover.
Whether you’re a first-time visitor or have found Chicago to be a long-time favorite destination, everyone can find something new to learn at the Chicago History Museum. Founded in 1856, the museum calls the Lincoln Park neighborhood on the north side home. After your visit, consider stopping by Lincoln Park Zoo—one of the last remaining free-admission zoos in the U.S. If after you explore the fauna you crave some knowledge of flora, Lincoln Park is also home to the Peggy Notebaert Nature Museum.
Questions we hear the most
The average flight time from Miami to Chicago (Midway) is 3 hours 5 minutes.
There are 145 weekly flights from Miami to Chicago (Midway) on Southwest Airlines.
Yes, Southwest flies nonstop from Miami to Chicago (Midway) once per day from Monday through Friday.
Yes, Southwest flies nonstop from Miami to Chicago (Midway) once per day on Saturdays and Sundays.
To find the lowest fares by day and time to fly Miami 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 Miami 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.
Check out the Southwest Airlines® Help Center for answers about everything Southwest.
Explore Flights from Other Popular Origins
Popular Flights from Miami
1EarlyBird Check-In® pricing starts at $15 one-way, and is subject to availability. Pricing may vary based on the popularity and length of each (one-way) flight. Please see optional travel charges for more details.
2Upgraded boarding prices and benefits are per eligible segment. Flights must be within 24 hours of departure to be eligible for upgraded boarding.
3Where available. Available only on WiFi-enabled aircraft. Limited-time offer.
4Due to licensing restrictions, on WiFi-enabled international flights, free live TV and iHeartRadio may not be available for the full duration of flight.
5Texting only allows access to iMessage and WhatsApp (which must be downloaded and activated before connecting to SouthwestWiFi).
6Internet 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.
7Flights traveling 175 miles or less will have only water available. Complimentary snacks are served on flights over 175 miles. If you’re flying between Hawaii and the continental U.S., you’ll have even more snacks to choose from.