$59 Cheap Flights from Jacksonville (JAX) to Chicago (MDW)

View $59 flight on Thu, Nov 13, 2025Opens in a new window

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

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Cheap Flights from Jacksonville to Chicago (JAX-MDW)

Prices were available within the past 7 days and start at $59 for one-way flights and $118 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Frontier Airlines
Thu, Nov 13 - Mon, Nov 17
JAX
Jacksonville
MDW
Chicago
$118 Roundtrip, found 9 hours ago
$118
Roundtrip
found 9 hours ago
Select Frontier Airlines flight, departing Thu, Nov 13 from Jacksonville to Chicago, returning Mon, Nov 17, priced at $118 found 9 hours ago
Frontier Airlines
Thu, Nov 13 - Sun, Nov 16
JAX
Jacksonville
MDW
Chicago
$139 Roundtrip, just found
$139
Roundtrip
just found
Select Frontier Airlines flight, departing Thu, Nov 13 from Jacksonville to Chicago, returning Sun, Nov 16, priced at $139 just found
Frontier Airlines
Sat, Nov 1 - Mon, Nov 3
JAX
Jacksonville
MDW
Chicago
$147 Roundtrip, found 3 hours ago
$147
Roundtrip
found 3 hours ago
Select Frontier Airlines flight, departing Sat, Nov 1 from Jacksonville to Chicago, returning Mon, Nov 3, priced at $147 found 3 hours ago
Frontier Airlines
Thu, Nov 13 - Sun, Nov 16
JAX
Jacksonville
MDW
Chicago
$162 Roundtrip, just found
$162
Roundtrip
just found
Select Frontier Airlines flight, departing Thu, Nov 13 from Jacksonville to Chicago, returning Sun, Nov 16, priced at $162 just found
Frontier Airlines
Sat, Nov 8 - Fri, Nov 14
JAX
Jacksonville
MDW
Chicago
$168 Roundtrip, just found
$168
Roundtrip
just found
Select Frontier Airlines flight, departing Sat, Nov 8 from Jacksonville to Chicago, returning Fri, Nov 14, priced at $168 just found
Frontier Airlines
Thu, Oct 23 - Sun, Oct 26
JAX
Jacksonville
MDW
Chicago
$176 Roundtrip, just found
$176
Roundtrip
just found
Select Frontier Airlines flight, departing Thu, Oct 23 from Jacksonville to Chicago, returning Sun, Oct 26, priced at $176 just found
Frontier Airlines
Fri, Nov 14 - Sun, Nov 16
JAX
Jacksonville
MDW
Chicago
$183 Roundtrip, just found
$183
Roundtrip
just found
Select Frontier Airlines flight, departing Fri, Nov 14 from Jacksonville to Chicago, returning Sun, Nov 16, priced at $183 just found
Frontier Airlines
Sat, Nov 8 - Fri, Nov 14
JAX
Jacksonville
MDW
Chicago
$191 Roundtrip, just found
$191
Roundtrip
just found
Select Frontier Airlines flight, departing Sat, Nov 8 from Jacksonville to Chicago, returning Fri, Nov 14, priced at $191 just found
Southwest Airlines
Sat, Nov 15 - Mon, Nov 17
JAX
Jacksonville
MDW
Chicago
$204 Roundtrip, found 11 hours ago
$204
Roundtrip
found 11 hours ago
Select Southwest Airlines flight, departing Sat, Nov 15 from Jacksonville to Chicago, returning Mon, Nov 17, priced at $204 found 11 hours ago
Delta
Sat, Nov 15 - Mon, Nov 17
JAX
Jacksonville
MDW
Chicago
$213 Roundtrip, found 11 hours ago
$213
Roundtrip
found 11 hours ago
Select Delta flight, departing Sat, Nov 15 from Jacksonville to Chicago, returning Mon, Nov 17, priced at $213 found 11 hours ago

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

February is typically the cheapest month to fly

From $141 - $787 per traveler.

Alternative airports near Chicago

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

Select flight to O'Hare Intl. ORD. Cheapest option available. Average driving time to city center is 23 minutes. Flights from $323
ORD
O'Hare Intl.
Cheapest
Average driving time to city center23 min
Flights from $323

Frequently asked questions

How much does a flight from Jacksonville Intl. Airport (JAX) to Midway Intl. Airport (MDW) cost?
Get a cheap one-way flight from $59 or cheap return flight from $118 from Jacksonville Intl. Airport (JAX) to Midway Intl. Airport (MDW) 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 Jacksonville Intl. Airport (JAX) to Midway Intl. Airport (MDW)?
Planning your trip for November is a great way to save, as it's the cheapest month for flights between JAX and MDW. You'll typically find the lowest prices during off-peak months.
Which airlines fly direct from Jacksonville Intl. Airport (JAX) to Midway Intl. Airport (MDW)?
Catch a nonstop flight with Southwest Airlines and head straight from Jacksonville Intl. Airport (JAX) to Midway Intl. Airport (MDW).
What is the cheapest airline that flies from Jacksonville Intl. Airport (JAX) to Midway Intl. Airport (MDW)?
Use the filters on Expedia to compare different airlines and find the most affordable carrier that'll take you from JAX to MDW. Then, sort your results by "Price (lowest to highest)" to snag a great deal.
How many flights per day from Jacksonville Intl. Airport (JAX) to Midway Intl. Airport (MDW)?
On average, you can pick from 6 direct flights every week from Jacksonville Intl. Airport (JAX) to Midway Intl. Airport (MDW). To broaden your travel options, consider taking a flight with a layover. Enter your details on Expedia and then set the filter tool to include one stop or more.
What are the most popular departure times for flights from Jacksonville Intl. Airport (JAX) to Midway Intl. Airport (MDW)?
More travelers fly between JAX and MDW at 4 PM than at any other time. Prefer a quieter experience? Travel outside of rush hours and it's possible you'll save on your fare as well.
What day of the week has the most flights from JAX to MDW?
Friday offers the most flights from Jacksonville Intl. Airport (JAX) to Midway Intl. Airport (MDW). Consider jetting off on this day and you'll have a greater chance of finding a departure that works with your plans.
What is the earliest flight from Jacksonville Intl. Airport (JAX) to Midway Intl. Airport (MDW)?
The first flight of the day leaving from Jacksonville Intl. Airport (JAX) is at around 4:20PM UTC-5. Board this plane and you'll reach Midway Intl. Airport (MDW) at approximately 6:00PM UTC-6. The overall travel time is 2h 40m.
How long does it take to fly from Jacksonville Intl. Airport (JAX) to Midway Intl. Airport (MDW)?
The average flight duration from JAX to MDW is 2 hours and 40 minutes, covering a total distance of 850 mi.
What airline has the least delays from JAX to MDW?
Southwest Airlines has the best track record for on-time direct flights from Jacksonville Intl. Airport (JAX) to Midway Intl. Airport (MDW), with an on-time score of 80%. Use the Expedia App to see your flight schedule before you go and get real-time alerts about any trip changes.
What is the best time to fly from Jacksonville Intl. Airport (JAX) to Midway Intl. Airport (MDW)?
To avoid possible delays on the Jacksonville Intl. Airport (JAX) to Midway Intl. Airport (MDW) route, aim to travel before 3 PM. Later flights have a 22% higher chance of cancellation.**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 Chicago from Jacksonville Intl. Airport (JAX)?
You can arrive at O'Hare Intl. Airport (ORD) or Midway Intl. Airport (MDW) when you travel to Chicago on a direct flight from Jacksonville Intl. Airport (JAX).
Is it cheaper to buy a plane ticket from Jacksonville Intl. Airport (JAX) to Midway Intl. Airport (MDW) last-minute?
Booking your ticket from JAX to MDW just before your journey is usually more expensive. But if you're flexible with your itinerary, you could bag a cheap last-minute fare.
Is it cheaper to book a JAX to MDW flight and hotel package?
Securing a JAX to MDW flight and hotel package tends to be cheaper than booking separately. With Expedia, you can enjoy the ease of organizing your travels all in one place. Pick from our extensive range of stays and then add car rentals, activities and flights to your booking. Bundle everything together, and you could save hundreds of dollars.
Can I cancel or change the date of my flight from Jacksonville Intl. Airport (JAX) to Midway Intl. Airport (MDW)?
If you reserved your JAX to MDW flight in the last 24 hours, you may be able to cancel or modify it without fees. Depending on the airline and the type of fare you purchased, additional charges may apply for changes beyond that time. Airline policies and contact information can be found in your itinerary or confirmation email. Or, head to our Customer Service portal if you'd like more information.

Book with confidence

Jacksonville to Chicago Flights

The cheapest times to fly from Jacksonville to Chicago

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 Jacksonville to Chicago are during the month of November. You can find some of the cheapest flights from Jacksonville to Chicago with Expedia's search tool and vast selection of airlines.

 

The best time to book a flight from Jacksonville to Chicago

Sunday is one of the best days to book for cheap flights from Jacksonville to Chicago: 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 Jacksonville to Chicago

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 Jacksonville to Chicago in 2025. You can also book with separate airlines for your outbound and return journeys, from $59 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 Jacksonville to Chicago 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 Jacksonville to Chicago 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.

 

Jacksonville to Chicago Flights

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*Available to One Key members.