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Find low faresSouthwest® flights from Chicago (Midway) to Jacksonville from $119
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1 Passenger
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Low fares from Chicago (Midway) to Jacksonville
$
Chicago (Midway) (MDW)to
Jacksonville (JAX)
Depart: 03/04/2026
One-way
Basic
From
$119
Seen: 7 hrs ago
Chicago (Midway) (MDW)to
Jacksonville (JAX)
Depart: 03/07/2026
One-way
Basic
From
$122
Seen: 10 hrs ago
Chicago (Midway) (MDW)to
Jacksonville (JAX)
Depart: 02/25/2026
One-way
Basic
From
$129
Seen: 7 hrs ago
Chicago (Midway) (MDW)to
Jacksonville (JAX)
Depart: 02/28/2026
One-way
Basic
From
$136
Seen: 7 hrs ago
Chicago (Midway) (MDW)to
Jacksonville (JAX)
Depart: 05/11/2026
One-way
Basic
From
$142
Seen: 22 hrs ago
Chicago (Midway) (MDW)to
Jacksonville (JAX)
Depart: 04/27/2026
One-way
Basic
From
$142
Seen: 11 hrs ago
Explore flights from Chicago (Midway) to Jacksonville
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Flight Details
Departing from:
Chicago Midway International Airport
Arriving at:
Jacksonville International Airport
Average flight time:
2 hours 10 minutes
Distance:
849 miles
Route Information
142† 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 Chicago (Midway) to Jacksonville is 2 hours 10 minutes.
There are 142 weekly flights from Chicago (Midway) to Jacksonville on Southwest Airlines.
Yes, Southwest flies nonstop from Chicago (Midway) to Jacksonville once per day from Monday through Friday.
Yes, Southwest flies nonstop from Chicago (Midway) to Jacksonville once per day on Saturdays and Sundays.
To find the lowest fares by day and time to fly Chicago (Midway) to Jacksonville with Southwest, check out our Low Fare Calendar.
You can rent a car at Jacksonville International Airport book yours with your flight.
Yes! Flights from Chicago (Midway) to Jacksonville—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.