Southwest Airlines flights from Jacksonville (JAX) to Chicago (MDW)
Find comprehensive Southwest Airlines flight information, schedules, and booking details for direct flights from Jacksonville (JAX), US to Chicago (MDW), US. Southwest Airlines operates 0-2 flights daily flights on this route.• Flight Duration: 2h 20m - 2h 30m (average flight time)• Distance: 854 miles (1374 km) (air miles between airports)• Daily Flights: 0-2 flights (scheduled departures per day)
Jacksonville (JAX)
US
Chicago (MDW)
US
FLIGHT TIME
2h 20m - 2h 30m
FLIGHT DISTANCE
854 miles (1374 km)
2h 30m - 2h 30m
19:50
19:50
854 miles (1374 km)
January
1 (Show)
8
Southwest Airlines Flight Schedule from Jacksonville (JAX) to Chicago (MDW)
| Flight | Airline | Departure | Arrival | Aircraft |
|---|---|---|---|---|
WN4881 |  Southwest Airlines | 19:50 | 21:20:00 | Boeing 737MAX 8 Passenger |
Southwest Airlines Monthly Flight Calendar
December 2025
Route Insights
Pricing patterns: January typically offers lower prices due to reduced demand outside peak travel seasons.
Best departure times: Peak departure times are 19:00, offering more flight options and potentially better connections.
Jacksonville - Chicago flight price statistics
$363
ApproximateThe numbers are average prices found based on user searches for direct flights between the airports. It's calculated from the cheapest prices found per month for a round-trip with 1 adult and can vary depending on the amount of data we have for this particular route.
$239
Jan$398
Feb$419
Mar$399
Apr$341
May$538
Jun$345
Jul$336
Aug$326
Sep$283
Oct$388
Nov$338
DecSouthwest Airlines Terminal Information
Arrival Terminal at Chicago (MDW):
• Terminal : Southwest Airlines operates from this terminal
Frequently Asked Questions about Southwest Airlines Flights
How many Southwest Airlines flights operate from Jacksonville (JAX) to Chicago (MDW)?
Southwest Airlines operates 1 flight from Jacksonville (JAX) to Chicago (MDW).
What city does Chicago (MDW) airport serve?
Chicago (MDW) airport serves Chicago, US.
How long is the Southwest Airlines flight from Jacksonville (JAX) to Chicago (MDW)?
The flight duration is approximately 2h 20m - 2h 30m.
What is the distance from Jacksonville (JAX) to Chicago (MDW)?
The distance is 854 miles (1374 km).
What aircraft does Southwest Airlines use on this route?
Southwest Airlines uses Boeing 737MAX 8 Passenger on this route.
What is the cheapest month to fly Southwest Airlines from Jacksonville (JAX) to Chicago (MDW)?
January is typically the cheapest month to fly Southwest Airlines on this route.
What is the average price for a Southwest Airlines flight from Jacksonville (JAX) to Chicago (MDW)?
The average price for a round-trip Southwest Airlines flight on this route is approximately $363. Prices can vary based on booking time and demand.
How many Southwest Airlines flights operate per week on this route?
Southwest Airlines operates approximately 8 flights per week from Jacksonville (JAX) to Chicago (MDW).