$90 Cheap Flights from Chicago (MDW) to Jacksonville (JAX)

View $90 flight on Sat, Aug 30, 2025Opens in a new window

Popular airlines from Chicago Midway Airport (MDW) to Jacksonville International Airport (JAX)

Cheap Flights from Chicago to Jacksonville (MDW-JAX)

Prices were available within the past 7 days and start at $90 for one-way flights and $180 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Southwest Airlines
Thu, Aug 28 - Sat, Aug 30
MDW
Chicago
JAX
Jacksonville
$180 Roundtrip, found 1 day ago
$180
Roundtrip
found 1 day ago
Select Southwest Airlines flight, departing Thu, Aug 28 from Chicago to Jacksonville, returning Sat, Aug 30, priced at $180 found 1 day ago
Southwest Airlines
Sat, Aug 23 - Mon, Aug 25
MDW
Chicago
JAX
Jacksonville
$181 Roundtrip, just found
$181
Roundtrip
just found
Select Southwest Airlines flight, departing Sat, Aug 23 from Chicago to Jacksonville, returning Mon, Aug 25, priced at $181 just found
Frontier Airlines
Thu, Sep 18 - Mon, Sep 22
MDW
Chicago
JAX
Jacksonville
$184 Roundtrip, found 2 days ago
$184
Roundtrip
found 2 days ago
Select Frontier Airlines flight, departing Thu, Sep 18 from Chicago to Jacksonville, returning Mon, Sep 22, priced at $184 found 2 days ago
Frontier Airlines
Thu, Aug 28 - Sat, Sep 6
MDW
Chicago
JAX
Jacksonville
$185 Roundtrip, found 2 days ago
$185
Roundtrip
found 2 days ago
Select Frontier Airlines flight, departing Thu, Aug 28 from Chicago to Jacksonville, returning Sat, Sep 6, priced at $185 found 2 days ago
Frontier Airlines
Thu, Sep 18 - Thu, Sep 25
MDW
Chicago
JAX
Jacksonville
$186 Roundtrip, found 3 days ago
$186
Roundtrip
found 3 days ago
Select Frontier Airlines flight, departing Thu, Sep 18 from Chicago to Jacksonville, returning Thu, Sep 25, priced at $186 found 3 days ago
Frontier Airlines
Thu, Oct 16 - Mon, Oct 20
MDW
Chicago
JAX
Jacksonville
$189 Roundtrip, found 3 days ago
$189
Roundtrip
found 3 days ago
Select Frontier Airlines flight, departing Thu, Oct 16 from Chicago to Jacksonville, returning Mon, Oct 20, priced at $189 found 3 days ago
Southwest Airlines
Thu, Aug 28 - Sun, Aug 31
MDW
Chicago
JAX
Jacksonville
$190 Roundtrip, found 1 day ago
$190
Roundtrip
found 1 day ago
Select Southwest Airlines flight, departing Thu, Aug 28 from Chicago to Jacksonville, returning Sun, Aug 31, priced at $190 found 1 day ago
Southwest Airlines
Sat, Aug 23 - Mon, Aug 25
MDW
Chicago
JAX
Jacksonville
$191 Roundtrip, just found
$191
Roundtrip
just found
Select Southwest Airlines flight, departing Sat, Aug 23 from Chicago to Jacksonville, returning Mon, Aug 25, priced at $191 just found
Delta
Sat, Aug 23 - Mon, Aug 25
MDW
Chicago
JAX
Jacksonville
$192 Roundtrip, just found
$192
Roundtrip
just found
Select Delta flight, departing Sat, Aug 23 from Chicago to Jacksonville, returning Mon, Aug 25, priced at $192 just found
Southwest Airlines
Mon, Aug 18 - Thu, Aug 21
MDW
Chicago
JAX
Jacksonville
$194 Roundtrip, found 3 days ago
$194
Roundtrip
found 3 days ago
Select Southwest Airlines flight, departing Mon, Aug 18 from Chicago to Jacksonville, returning Thu, Aug 21, priced at $194 found 3 days ago

Find the cheapest month to fly from Chicago (MDW) to Jacksonville (JAX)

December is typically the cheapest month to fly

From $118 - $718 per traveler.

Graph displaying average flight prices per month

Flights from Chicago (MDW) to Jacksonville (JAX)
Origin airport
Midway Intl.
Destination airport
Jacksonville Intl.
Airlines serving
Delta, Frontier Airlines, Southwest Airlines
Roundtrip price
$180
Distance
849 mi
Average flight time
3 hours 15 mins

Chicago to Jacksonville Flights

The cheapest times to fly from Chicago to Jacksonville

On average, Thursday can be the cheapest time to fly, according to data from the Airlines Reporting Corporation (ARC), one of the world's biggest databases for global airline sales. The data reveals that you could save up to 16% by flying on a Thursday—the cheapest day to travel on average—instead of a Sunday—the most expensive. Some of the most affordable flights from Chicago to Jacksonville are during the month of August. You can find some of the cheapest flights from Chicago to Jacksonville with Expedia's search tool and vast selection of airlines.

 

The best time to book a flight from Chicago to Jacksonville

Sunday is one of the best days to book for cheap flights from Chicago to Jacksonville: Tickets reserved on a Sunday cost between 6% and 13% less than those reserved on a Friday, according to ARC data. The data also suggests booking early can also lead to cheaper airfares. You could save 24% by buying your tickets for domestic flights at least a month in advance and 10% by booking international flights 2 months in advance.

 

How to find cheap round-trip tickets from Chicago to Jacksonville

Being flexible with your dates and using Expedia's Price Drop Protection and Price Tracking features are some of the best ways of finding a cheap ticket from Chicago to Jacksonville in 2025. You can also book with separate airlines for your outbound and return journeys, from $90 one-way. Expedia also offers Price Drop Protection, so if the cost of your airfare goes down after booking, you'll receive a credit for the difference*. This is available for a small fee, and is free to One Key Gold and Platinum tier members.

 

Expedia's Price Tracking feature means you can stay on top of airfares without manually checking every day. It sends you automated price alerts for cheap Chicago to Jacksonville flights and uses historical data to indicate when the best time to book is. Download Expedia's free app to activate this handy tool in a few easy taps.

 

You could also save big by booking one of Expedia's vacation packages. Bundling together your Chicago to Jacksonville airfare with your accommodations and car rental is often cheaper than booking everything separately. There’s also One Key, Expedia's generous rewards program. Join for free and you could earn One Key cash on most bookings to save on future adventures.

 

*Terms apply.

 

Disclaimer: ARC The statistics are based on average round-trip ticket prices between January and August 2023. The percentages you see are averages.

 

Frequently asked questions

How much does a flight from Midway Intl. Airport (MDW) to Jacksonville Intl. Airport (JAX) cost?
You'll find cheap return tickets from Midway Intl. Airport (MDW) to Jacksonville Intl. Airport (JAX) starting from $181. Book a seat and start your adventure. This information is based on the cheapest price found on Expedia for this return journey departing within the next three months. This airfare is for a Southwest Airlines flight leaving MDW on July 22 2025 and touching down at JAX. The price was last updated on July 2 2025 and has not changed since.
What is the cheapest month to fly from MDW to JAX?
The cheapest flights from MDW to JAX are usually during off-peak season, when demand is lower. To save money, avoid flying during public holidays, school breaks and major local events.
Which airlines fly direct from Midway Intl. Airport (MDW) to Jacksonville Intl. Airport (JAX)?
When jetting out of Midway Intl. Airport (MDW), you can get on a direct flight to Jacksonville Intl. Airport (JAX) with Southwest Airlines.
What is the cheapest airline that flies from MDW to JAX?
At the moment, the cheapest airline offering one-way flights from MDW to JAX is Southwest Airlines. You can jet off on this route from $91. This fare is based on the lowest price found on Expedia departing within the next three months. The flight takes off from MDW on September 20 2025. Prices were last updated on July 2 2025 and have not changed since.
How many flights per day from Midway Intl. Airport (MDW) to Jacksonville Intl. Airport (JAX)?
On average, you can take your pick of 6 direct flights departing from Midway Intl. Airport (MDW) to Jacksonville Intl. Airport (JAX) every week. If you don't find one that fits your travel plans, consider hopping on a flight that includes a layover. Filter your search on Expedia to include one or more stops and select the next best alternative.
What are the most popular departure times for flights from Midway Intl. Airport (MDW) to Jacksonville Intl. Airport (JAX)?
Flights between MDW and JAX are their busiest at 12 PM. If you want a quieter trip and potentially cheaper tickets, choose a time outside the usual busy windows.
What day of the week has the most flights from MDW to JAX?
If you jet off on a Friday, you'll get the widest range of options for flights from Midway Intl. Airport (MDW) to Jacksonville Intl. Airport (JAX).
What is the earliest flight from Midway Intl. Airport (MDW) to Jacksonville Intl. Airport (JAX)?
Midway Intl. Airport (MDW)'s first flight to Jacksonville Intl. Airport (JAX) takes off at approximately 9:00AM UTC-6. With a total travel time of 2h 15m, you'll arrive at around 12:15PM UTC-5.
How long does it take to fly from Midway Intl. Airport (MDW) to Jacksonville Intl. Airport (JAX)?
The average flight duration from MDW to JAX is 2 hours and 15 minutes, covering a total distance of 850 mi.
What is the best time to fly from Midway Intl. Airport (MDW) to Jacksonville Intl. Airport (JAX)?
To reach Jacksonville Intl. Airport (JAX) on time, book a flight that leaves from Midway Intl. Airport (MDW) before 3 PM. The likelihood of cancellations is 22% higher, on average, for departures after this time.**Most reliable time of the day and month to travel recommendation is based on January through August 2024 flight status data sourced from OAG's global flight data platform.
What airports do you fly into for Jacksonville from Midway Intl. Airport (MDW)?
Explore your flight options from Midway Intl. Airport (MDW) to Jacksonville Intl. Airport (JAX). This is the only airport in Jacksonville you can jet into if you're taking a direct flight.
Is it cheaper to buy a plane ticket from Midway Intl. Airport (MDW) to Jacksonville Intl. Airport (JAX) last-minute?
Holding off until just before your departure to book a flight from MDW to JAX generally means paying more. While it's possible to find some last-minute discounts, they aren't always guaranteed. Allow some flexibility in your schedule to boost your chances of landing a bargain.
Is it cheaper to book a MDW to JAX flight and hotel package?
Compared with arranging hotels and flights separately, booking a MDW to JAX flight and hotel package with Expedia could result in significant savings. Better yet, having everything in one place will take the hassle out of planning your trip. Simply pick your flights and choose from our wide range of hotels, then personalize your trip with extras like tours and car rentals.
Can I cancel or change the date of my flight from Midway Intl. Airport (MDW) to Jacksonville Intl. Airport (JAX)?
Generally, it's possible to cancel or reschedule your MDW to JAX flight. However, if it's been more than 24 hours since booking, additional charges may apply. Refer to your airline's policies in your itinerary to see what changes are allowed and whether any costs are involved. You'll also find more information on our Customer Service portal.

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*Available to One Key members.