Cheap Flight Tickets from Jacksonville (JAX) to Chicago (MDW), Starting at $136

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

$143

WN Southwest Airlines • 1 stop • 9h 10m

Oct 21 – Oct 22

The cheapest round trip flight from Jacksonville to Chicago (JAX-MDW-JAX) is currently $143

🔍 Search Flights

Cheapest One way Flight

$376

DL Delta Airlines • 1 stop • 10h 11m

Aug 22

The cheapest one way flight from Jacksonville to Chicago (JAX-MDW) is currently $376

🔍 Search Flights

Cheapest Direct Flight

$136

WN Southwest Airlines • nonstop • 3h 40m

Oct 21

The cheapest nonstop flight from Jacksonville to Chicago (JAX-MDW) is currently $136

🔍 Search Flights

Fastest Flight

3h 40m

The fastest nonstop flight from Jacksonville to Chicago (JAX-MDW) takes 3h 40m

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.

Oct 21 - Oct 22, Economy
WN
Jacksonville → Chicago
9h 10m
6:55 PM - 11:45 PM • 1 stop
WN
Jacksonville → Chicago
3h 35m
3:00 PM - 6:15 PM • nonstop
$143
Southwest Airlines
Oct 21 - Oct 22, Economy
WN
Jacksonville → Chicago
10h 15m
4:05 PM - 9:20 PM • 1 stop
WN
Jacksonville → Chicago
3h 35m
3:00 PM - 6:15 PM • nonstop
$143
Southwest Airlines
Oct 21 - Oct 22, Economy
WN
Jacksonville → Chicago
12h 35m
10:00 AM - 4:55 PM • 1 stop
WN
Jacksonville → Chicago
3h 35m
3:00 PM - 6:15 PM • nonstop
$143
Southwest Airlines
Oct 21 - Oct 22, Economy
WN
Jacksonville → Chicago
3h 40m
12:45 PM - 2:05 PM • nonstop
WN
Jacksonville → Chicago
10h 15m
2:50 PM - 10:05 PM • 2 stops
$146
Southwest Airlines
Oct 21 - Oct 22, Economy
WN
Jacksonville → Chicago
7h 5m
10:00 AM - 1:25 PM • 1 stop
WN
Jacksonville → Chicago
7h 30m
7:05 AM - 12:55 PM • 1 stop
$149
Southwest Airlines
Oct 21 - Oct 22, Economy
WN
Jacksonville → Chicago
6h 40m
7:10 PM - 10:10 PM • 1 stop
WN
Jacksonville → Chicago
5h 40m
11:50 AM - 4:30 PM • 1 stop
$149
Southwest 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 6:00 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 DL : USD 971
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 7:10 pm

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

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

More Flight Options for Jacksonville (JAX) and Chicago (MDW)

Why Fareleaders for JAX to MDW Plane Tickets

Lowest Prices
Lowest Prices
Uncover the best deals on Jacksonville to Chicago flights by comparing fares from hundreds of airlines and agencies.
New Deals
New Deals Everyday
Get the best prices on JAX to MDW flights—we update our fares daily so you never miss a saving.
Best Travel Options
No Service Fees
Compare hundreds of Jacksonville to Chicago flights and secure the best deals—we never add any service fees.
Get Fare Drop Alert
Be the first to know when fares drop for the Jacksonville (JAX) to Chicago (MDW)
Terms and Conditions*