$86 Cheap Flights from Chicago (MDW) to Jacksonville (JAX)

View $86 flight on Thu, Oct 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 $86 for one-way flights and $160 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Frontier Airlines
Thu, Oct 30 - Thu, Nov 6
MDW
Chicago
JAX
Jacksonville
$160 Roundtrip, found 3 hours ago
$160
Roundtrip
found 3 hours ago
Select Frontier Airlines flight, departing Thu, Oct 30 from Chicago to Jacksonville, returning Thu, Nov 6, priced at $160 found 3 hours ago
Frontier Airlines
Thu, Nov 6 - Sat, Nov 8
MDW
Chicago
JAX
Jacksonville
$168 Roundtrip, found 2 hours ago
$168
Roundtrip
found 2 hours ago
Select Frontier Airlines flight, departing Thu, Nov 6 from Chicago to Jacksonville, returning Sat, Nov 8, priced at $168 found 2 hours ago
Frontier Airlines
Thu, Nov 6 - Sat, Nov 8
MDW
Chicago
JAX
Jacksonville
$176 Roundtrip, found 2 hours ago
$176
Roundtrip
found 2 hours ago
Select Frontier Airlines flight, departing Thu, Nov 6 from Chicago to Jacksonville, returning Sat, Nov 8, priced at $176 found 2 hours ago
Frontier Airlines
Mon, Oct 20 - Fri, Oct 24
MDW
Chicago
JAX
Jacksonville
$183 Roundtrip, just found
$183
Roundtrip
just found
Select Frontier Airlines flight, departing Mon, Oct 20 from Chicago to Jacksonville, returning Fri, Oct 24, priced at $183 just found
Frontier Airlines
Fri, Nov 7 - Sun, Nov 16
MDW
Chicago
JAX
Jacksonville
$185 Roundtrip, found 2 days ago
$185
Roundtrip
found 2 days ago
Select Frontier Airlines flight, departing Fri, Nov 7 from Chicago to Jacksonville, returning Sun, Nov 16, priced at $185 found 2 days ago
Frontier Airlines
Thu, Oct 16 - Thu, Oct 23
MDW
Chicago
JAX
Jacksonville
$191 Roundtrip, found 1 hour ago
$191
Roundtrip
found 1 hour ago
Select Frontier Airlines flight, departing Thu, Oct 16 from Chicago to Jacksonville, returning Thu, Oct 23, priced at $191 found 1 hour ago
Frontier Airlines
Thu, Oct 23 - Sun, Nov 2
MDW
Chicago
JAX
Jacksonville
$197 Roundtrip, found 2 days ago
$197
Roundtrip
found 2 days ago
Select Frontier Airlines flight, departing Thu, Oct 23 from Chicago to Jacksonville, returning Sun, Nov 2, priced at $197 found 2 days ago
Frontier Airlines
Thu, Oct 16 - Fri, Oct 31
MDW
Chicago
JAX
Jacksonville
$201 Roundtrip, found 1 day ago
$201
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Thu, Oct 16 from Chicago to Jacksonville, returning Fri, Oct 31, priced at $201 found 1 day ago
Southwest Airlines
Tue, Nov 11 - Fri, Nov 14
MDW
Chicago
JAX
Jacksonville
$202 Roundtrip, found 4 days ago
$202
Roundtrip
found 4 days ago
Select Southwest Airlines flight, departing Tue, Nov 11 from Chicago to Jacksonville, returning Fri, Nov 14, priced at $202 found 4 days ago
Delta
Fri, Oct 31 - Sat, Nov 1
MDW
Chicago
JAX
Jacksonville
$213 Roundtrip, found 1 day ago
$213
Roundtrip
found 1 day ago
Select Delta flight, departing Fri, Oct 31 from Chicago to Jacksonville, returning Sat, Nov 1, priced at $213 found 1 day ago

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

September is typically the cheapest month to fly

From $136 - $484 per traveler.

Alternative airports near Jacksonville

Prices were available within the past 7 days. Prices and availability are subject to change.

Select flight to Jacksonville Intl. JAX. Cheapest option available. Average driving time to city center is 19 minutes. Flights from $242
JAX
Jacksonville Intl.
Cheapest
Average driving time to city center19 min
Flights from $242

Frequently asked questions

How much does a flight from Midway Intl. Airport (MDW) to Jacksonville Intl. Airport (JAX) cost?
Lock in a cheap one-way flight from $86 or cheap return flight from $160 from Midway Intl. Airport (MDW) to Jacksonville Intl. Airport (JAX) with Expedia. Enter your travel dates and sort by "Price (lowest to highest)" to find our cheapest flight deals on this route.
What is the cheapest month to fly from Midway Intl. Airport (MDW) to Jacksonville Intl. Airport (JAX)?
October is the most affordable month to fly from MDW to JAX. Planning your trip for the off-season is often the key to landing a great deal.
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 Midway Intl. Airport (MDW) to Jacksonville Intl. Airport (JAX)?
Use the filters on Expedia to compare airlines and find the cheapest carrier that'll take you from MDW to JAX. Then, sort your results by "Price (lowest to highest)" to snag a good deal.
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.

Travel information

Travel information

Origin airport
Midway Intl.
Destination airport
Jacksonville Intl.
Airlines serving
Delta, Frontier Airlines, Southwest Airlines
Roundtrip price
$160
Distance
849 mi
Average flight time
4 hours 17 mins

Book with confidence

Book with confidence

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 October. 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 $86 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.

 

Chicago to Jacksonville Flights

Explore a world of travel with Expedia

Explore a world of travel with Expedia

*Available to One Key members.