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Find low faresSouthwest® flights from Jacksonville to Chicago (Midway) from $108
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Low fares from Jacksonville to Chicago (Midway)
$
Jacksonville (JAX)to
Chicago (Midway) (MDW)
Depart: 02/21/2026
One-way
Basic
From
$108
Seen: 20 hrs ago
Jacksonville (JAX)to
Chicago (Midway) (MDW)
Depart: 02/28/2026
One-way
Basic
From
$108
Seen: 17 hrs ago
Jacksonville (JAX)to
Chicago (Midway) (MDW)
Depart: 05/09/2026
One-way
Basic
From
$117
Seen: 10 hrs ago
Jacksonville (JAX)to
Chicago (Midway) (MDW)
Depart: 04/25/2026
One-way
Basic
From
$117
Seen: 5 hrs ago
Jacksonville (JAX)to
Chicago (Midway) (MDW)
Depart: 03/03/2026
One-way
Basic
From
$119
Seen: 5 hrs ago
Jacksonville (JAX)to
Chicago (Midway) (MDW)
Depart: 02/24/2026
One-way
Basic
From
$119
Seen: 17 hrs ago
Explore flights from Jacksonville to Chicago (Midway)
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Flight Details
Departing from:
Jacksonville International Airport
Arriving at:
Chicago Midway International Airport
Average flight time:
2 hours 23 minutes
Distance:
849 miles
Route Information
150† 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.
Questions we hear the most
The average flight time from Jacksonville to Chicago (Midway) is 2 hours 23 minutes.
There are 150 weekly flights from Jacksonville to Chicago (Midway) on Southwest Airlines.
Yes, Southwest flies nonstop from Jacksonville to Chicago (Midway) once per day from Monday through Friday.
Yes, Southwest flies nonstop from Jacksonville to Chicago (Midway) once per day on Saturdays and Sundays.
To find the lowest fares by day and time to fly Jacksonville 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 Jacksonville 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.