Cheap Flight Tickets from Jacksonville (JAX) to Chicago (MDW), Starting at $279

Good to Know: Cheapest and Fastest JAX - MDW Flights

Useful information for finding best airline tickets from Jacksonville International to Chicago Midway International on your next trip.

Cheapest Round Trip Flight

$279

WN Southwest Airlines • 1 stop • 6h 40m

Nov 24 – Nov 30

The cheapest round trip flight from Jacksonville to Chicago (JAX-MDW-JAX) is currently $279

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Cheapest Direct Flight

$279

WN Southwest Airlines • nonstop • 3h 50m

Nov 24

The cheapest nonstop flight from Jacksonville to Chicago (JAX-MDW) is currently $279

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Fastest Flight

3h 45m

The fastest nonstop flight from Jacksonville to Chicago (JAX-MDW) takes 3h 45m

Top Airlines Flying from Jacksonville to Chicago

Southwest Airlines-WN

Southwest Airlines

Delta Airline, DL

Delta Airlines

Latest Flight Deals from Jacksonville (JAX) to Chicago (MDW)

Compare and book low fare round-trip air tickets from Jacksonville to Chicago. Ideal for travelers with confirmed return itineraries.

Nov 24 - Nov 30, Economy
WN
Jacksonville → Chicago
6h 40m
9:20 PM - 12:20 AM • 1 stop
WN
Jacksonville → Chicago
3h 35m
7:00 PM - 10:15 PM • nonstop
$279
Southwest Airlines
Nov 24 - Nov 30, Economy
WN
Jacksonville → Chicago
6h 40m
9:20 PM - 12:20 AM • 1 stop
WN
Jacksonville → Chicago
12h 35m
3:15 PM - 12:10 AM • 1 stop
$279
Southwest Airlines
Nov 24 - Nov 30, Economy
WN
Jacksonville → Chicago
10h 10m
11:00 AM - 4:10 PM • 2 stops
WN
Jacksonville → Chicago
8h 30m
12:50 PM - 7:00 PM • 2 stops
$279
Southwest Airlines
Nov 24 - Nov 30, Economy
WN
Jacksonville → Chicago
3h 45m
6:55 PM - 8:20 PM • nonstop
WN
Jacksonville → Chicago
8h 30m
12:50 PM - 7:00 PM • 2 stops
$279
Southwest Airlines
Nov 24 - Nov 30, Economy
DL
Jacksonville → Chicago
8h 20m
6:54 PM - 10:54 PM • 1 stop
DL
Jacksonville → Chicago
5h 49m
1:05 PM - 5:54 PM • 1 stop
$287
Delta Airlines
Nov 24 - Nov 30, Economy
DL
Jacksonville → Chicago
7h 9m
8:30 AM - 11:59 AM • 1 stop
DL
Jacksonville → Chicago
6h 44m
9:51 AM - 2:55 PM • 1 stop
$287
Delta Airlines

Fly from Jacksonville to Chicago with the Best Airfare Deals on FareLeaders

Looking for a cheap last-minute deal or the best round-trip flight from Jacksonville to Chicago? Find the biggest savings on one-way and round-trip tickets right here.

FAQs on Jacksonville to Chicago Flights

What are the airports in Jacksonville?
JAX
What’s the most popular airline flying from JAX to MDW?
The most popular airline flying from Jacksonville to Chicago are
Can I fly from JAX to MDW non-stop?
Yes, you can fly JAX to MDW non-stop on
Which airlines fly nonstop between Jacksonville and Chicago?
The non-stop flights between Jacksonville and Chicago are .
What’s the earliest departure time from JAX to MDW Airport?
The earliest flight leaves JAX at 7:05 am and lands in MDW - Chicago Midway International
What are the airports in Chicago?
ORD,MDW
Can I make changes to my Jacksonville to Chicago flight tickets or cancel them on FareLeaders.com?
No. We are an airfare comparison site. All the tickets are booked by the travel agent offering the flight deal and any changes or cancellations to be made are directly done directly by them or the airlines.
Can I cancel my flight tickets from JAX to MDW?
Read the fare rules of the Jacksonville to Chicago air tickets booked. Some airlines allow you to cancel the tickets within a stipulated time period with a cancellation fee.
Which airline alliances offer flights from Jacksonville and Chicago?
operate flights between Jacksonville and Chicago
How long does a flight from Jacksonville to Chicago take?
It takes approximately 2 hour to fly non-stop from JAX to MDW, which is 848.64 miles by air.
Which airlines provide the cheapest flights from Jacksonville (JAX) to Chicago (MDW) ?
In the past couple of days, the cheapest tickets to MDW from JAX were found on WN : USD 279
Do I need a passport to fly between JAX and MDW?
No
What’s the latest departure time from JAX to MDW ?
The last flight leaves JAX at 9:20 pm

Jacksonville (JAX) to Chicago (MDW): Airport Information

Origin Airport Jacksonville International , Jacksonville, US
Destination Airport Chicago Midway International , Chicago, US
Distance 849 miles

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