$110 Cheap Flights from Jacksonville (JAX) to Chicago (MDW)

View $110 flight on Mon, Jun 9, 2025Opens in a new window

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

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Find available prices by choosing your travel dates.

Cheap Flights from Jacksonville to Chicago (JAX-MDW)

Prices were available within the past 7 days and start at $110 for one-way flights and $248 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Frontier Airlines
Mon, Jun 2 - Fri, Jun 6
JAX
Jacksonville
MDW
Chicago
$248 Roundtrip, found 15 hours ago
$248
Roundtrip
found 15 hours ago
Select Frontier Airlines flight, departing Mon, Jun 2 from Jacksonville to Chicago, returning Fri, Jun 6, priced at $248 found 15 hours ago
Frontier Airlines
Mon, May 19 - Mon, May 26
JAX
Jacksonville
MDW
Chicago
$260 Roundtrip, found 21 hours ago
$260
Roundtrip
found 21 hours ago
Select Frontier Airlines flight, departing Mon, May 19 from Jacksonville to Chicago, returning Mon, May 26, priced at $260 found 21 hours ago
Frontier Airlines
Fri, Jun 6 - Fri, Jun 13
JAX
Jacksonville
MDW
Chicago
$261 Roundtrip, found 2 days ago
$261
Roundtrip
found 2 days ago
Select Frontier Airlines flight, departing Fri, Jun 6 from Jacksonville to Chicago, returning Fri, Jun 13, priced at $261 found 2 days ago
Southwest Airlines
Fri, May 30 - Mon, Jun 2
JAX
Jacksonville
MDW
Chicago
$269 Roundtrip, found 1 day ago
$269
Roundtrip
found 1 day ago
Select Southwest Airlines flight, departing Fri, May 30 from Jacksonville to Chicago, returning Mon, Jun 2, priced at $269 found 1 day ago
Frontier Airlines
Mon, May 19 - Fri, May 23
JAX
Jacksonville
MDW
Chicago
$270 Roundtrip, found 3 days ago
$270
Roundtrip
found 3 days ago
Select Frontier Airlines flight, departing Mon, May 19 from Jacksonville to Chicago, returning Fri, May 23, priced at $270 found 3 days ago
Southwest Airlines
Tue, Jun 3 - Mon, Jun 9
JAX
Jacksonville
MDW
Chicago
$274 Roundtrip, just found
$274
Roundtrip
just found
Select Southwest Airlines flight, departing Tue, Jun 3 from Jacksonville to Chicago, returning Mon, Jun 9, priced at $274 just found
Delta
Fri, May 30 - Mon, Jun 2
JAX
Jacksonville
MDW
Chicago
$278 Roundtrip, found 1 day ago
$278
Roundtrip
found 1 day ago
Select Delta flight, departing Fri, May 30 from Jacksonville to Chicago, returning Mon, Jun 2, priced at $278 found 1 day ago
Frontier Airlines
Fri, Jun 6 - Fri, Jun 13
JAX
Jacksonville
MDW
Chicago
$279 Roundtrip, found 5 days ago
$279
Roundtrip
found 5 days ago
Select Frontier Airlines flight, departing Fri, Jun 6 from Jacksonville to Chicago, returning Fri, Jun 13, priced at $279 found 5 days ago
Frontier Airlines
Mon, Jun 2 - Fri, Jun 13
JAX
Jacksonville
MDW
Chicago
$281 Roundtrip, found 1 day ago
$281
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Mon, Jun 2 from Jacksonville to Chicago, returning Fri, Jun 13, priced at $281 found 1 day ago
Delta
Tue, Jun 3 - Mon, Jun 9
JAX
Jacksonville
MDW
Chicago
$283 Roundtrip, just found
$283
Roundtrip
just found
Select Delta flight, departing Tue, Jun 3 from Jacksonville to Chicago, returning Mon, Jun 9, priced at $283 just found

Frequently asked questions

How much does a flight from Jacksonville Intl. Airport (JAX) to Midway Intl. Airport (MDW) cost?
You’ll find cheap return tickets from Jacksonville Intl. Airport (JAX) to Midway Intl. Airport (MDW) starting from $282. Grab a seat and set off on your next 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 and United flight leaving JAX on May 17 2025 and touching down at MDW. The price was last updated on April 23 2025 and has not changed since.
What is the cheapest month to fly from JAX to MDW?
The cheapest flights from JAX to MDW 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 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 JAX to MDW?
With prices as low as $139 for a one-way flight from JAX to MDW, Southwest Airlines is currently the cheapest airline operating this route. This fare is based on the lowest price found on Expedia departing within the next three months. The flight takes off from JAX on July 4 2025. Prices were last updated on April 23 2025 and have not changed since.
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.
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