Cheap Flight Tickets from Chicago (MDW) to Jacksonville (JAX), Starting at $303

Good to Know: Cheapest and Fastest MDW - JAX Flights

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

Cheapest Round Trip Flight

$308

WN Southwest Airlines • 1 stop • 19h 5m

Aug 28 – Aug 31

The cheapest round trip flight from Chicago to Jacksonville (MDW-JAX-MDW) is currently $308

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Cheapest Direct Flight

$303

WN Southwest Airlines • nonstop • 3h 35m

Aug 28

The cheapest nonstop flight from Chicago to Jacksonville (MDW-JAX) is currently $303

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Fastest Flight

3h 35m

The fastest nonstop flight from Chicago to Jacksonville (MDW-JAX) takes 3h 35m

Top Airlines Flying from Chicago to Jacksonville

Southwest Airlines-WN

Southwest Airlines

Delta Airline, DL

Delta Airlines

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

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

Aug 28 - Aug 31, Economy
WN
Chicago → Jacksonville
19h 5m
7:30 AM - 8:15 PM • 1 stop
WN
Chicago → Jacksonville
3h 45m
7:00 AM - 8:25 AM • nonstop
$308
Southwest Airlines
Aug 28 - Aug 31, Economy
WN
Chicago → Jacksonville
10h 25m
5:55 AM - 1:20 PM • 1 stop
WN
Chicago → Jacksonville
3h 45m
7:00 AM - 8:25 AM • nonstop
$308
Southwest Airlines
Aug 28 - Aug 31, Economy
WN
Chicago → Jacksonville
15h 5m
10:10 AM - 8:15 PM • 2 stops
WN
Chicago → Jacksonville
3h 45m
7:00 AM - 8:25 AM • nonstop
$314
Southwest Airlines
Aug 28 - Aug 31, Economy
WN
Chicago → Jacksonville
15h 15m
10:00 AM - 8:15 PM • 2 stops
WN
Chicago → Jacksonville
3h 45m
7:00 AM - 8:25 AM • nonstop
$314
Southwest Airlines
Aug 28 - Aug 31, Economy
WN
Chicago → Jacksonville
10h 15m
1:00 PM - 8:15 PM • 1 stop
WN
Chicago → Jacksonville
9h 15m
2:00 PM - 6:55 PM • 1 stop
$314
Southwest Airlines
Aug 28 - Aug 31, Economy
WN
Chicago → Jacksonville
13h 25m
12:00 PM - 9:05 PM • 2 stops
WN
Chicago → Jacksonville
3h 45m
7:00 AM - 8:25 AM • nonstop
$314
Southwest Airlines

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

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

FAQs on Chicago to Jacksonville Flights

What are the airports in Chicago?
ORD,MDW
What’s the most popular airline flying from MDW to JAX?
The most popular airline flying from Chicago to Jacksonville are
Can I fly from MDW to JAX non-stop?
Yes, you can fly MDW to JAX non-stop on
Which airlines fly nonstop between Chicago and Jacksonville?
The non-stop flights between Chicago and Jacksonville are .
What’s the earliest departure time from MDW to JAX Airport?
The earliest flight leaves MDW at 5:55 am and lands in JAX - Jacksonville International
What are the airports in Jacksonville?
JAX
Can I make changes to my Chicago to Jacksonville 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 MDW to JAX?
Read the fare rules of the Chicago to Jacksonville 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 Chicago and Jacksonville?
operate flights between Chicago and Jacksonville
How long does a flight from Chicago to Jacksonville take?
It takes approximately 2 hour to fly non-stop from MDW to JAX, which is 848.64 miles by air.
Which airlines provide the cheapest flights from Chicago (MDW) to Jacksonville (JAX) ?
In the past couple of days, the cheapest tickets to JAX from MDW were found on WN : USD 308
Do I need a passport to fly between MDW and JAX?
No
What’s the latest departure time from MDW to JAX ?
The last flight leaves MDW at 6:45 pm

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

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

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