How many flights from Chicago to Jacksonville are non-stop?

In the trailing 90 days, approximately 34% of flights from Chicago to Jacksonville were non-stop. For travelers who prefer connecting flights, the median number of stopovers historically observed is 2. This indicates that while direct options are available, a significant portion of flights on this route involve at least one stop.

What's the flight time from Chicago to Jacksonville?

The median direct flight time from Chicago to Jacksonville is typically 2 hours and 36 minutes, covering a distance of 1392 kilometers. For flights with one stop, the median duration is considerably longer, averaging 10 hours and 30 minutes. Travelers should consider these differences when planning their journey to Jacksonville.

How often do cheap flights from Chicago to Jacksonville come up?

Historically, cheap flights from Chicago to Jacksonville come up frequently. This route is classified as one where deals appear often. Travelers looking for budget-friendly options can typically find them with regularity.

Flights From Chicago

To Jacksonville

Cheap Flights from Chicago to Jacksonville

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Deals from

Chicago

RatePunk searches hundreds of travel sites at once for deals on flights to Jacksonville

Prices updated 2 days ago

405 airlines compared

80%+ AI score for best value

Fares are subject to change and may not be available for all dates. (Data last updated Jul 26, 2026.)

Today’s best flight deals from Chicago to Jacksonville

Explore current cheapest deals departing from Chicago to Jacksonville

2026-10-01 – 2026-10-04
CHI - Jacksonville
79% AI deal score
$278
$143
Round trip
2026-10-02 – 2026-10-04
CHI - Jacksonville
79% AI deal score
$278
$143
Round trip
2026-09-13 – 2026-10-04
CHI - Jacksonville
77% AI deal score
$238
$143
Round trip
2026-10-02 – 2026-10-26
CHI - Jacksonville
75% AI deal score
$231
$154
Round trip
2026-10-01 – 2026-10-26
CHI - Jacksonville
75% AI deal score
$231
$155
Round trip
2026-10-15 – 2026-10-26
CHI - Jacksonville
76% AI deal score
$246
$155
Round trip
2026-10-02 – 2026-10-21
CHI - Jacksonville
74% AI deal score
$233
$161
Round trip
2026-10-01 – 2026-10-21
CHI - Jacksonville
74% AI deal score
$232
$161
Round trip
2026-08-10 – 2026-08-12
CHI - Jacksonville
79% AI deal score
$319
$165
Round trip
2026-09-24 – 2026-09-26
CHI - Jacksonville
77% AI deal score
$281
$166
Round trip

Chicago to Jacksonville: Overview

Insights for flights from Chicago to Jacksonville

A typical journey from Chicago to Jacksonville, including connecting itineraries, has a median duration of 2h 36m. Given that most itineraries for this route involve at least one connection, this duration reflects the overall travel time you can expect. For flights with connections, the median journey time extends to 18h 33m, while non-stop flights have a median duration of 2h 36m.

When looking for cheap flights from Chicago to Jacksonville, fares right now are above the typical level. Over the past 90 days, prices for this route typically ranged from $262–$606, with a median of $362. Currently, 11% of recent fares are classified as a good price, indicating that finding a lower fare may require some flexibility.

The cheapest time to fly from Chicago to Jacksonville is typically in January, with a median fare of $211. Other cost-effective months include July, where the median fare is $217, and May, with a median fare of $244. Planning your trip during these months could help you secure a more favorable price.

Most itineraries for flights from Chicago to Jacksonville connect at least once, with only 34% of recent fares being non-stop. For those itineraries that do involve connections, the typical number of stopovers is 2. This means you should generally expect your journey to include at least one stop.

The route from Chicago to Jacksonville covers a distance of 1392 kilometers, classifying it as a short-haul flight. This distance typically translates to a relatively quick travel experience, especially for direct flights.

How much is a round trip from Chicago to Jacksonville

Regular price: $223 - $299

Prices for flights from Chicago to Jacksonville are currently below the regular range.

Regularly, flights from Chicago to Jacksonville range from $223 to $299. The current lowest deal is $176 with Frontier Airlines for travel from Oct 22-Oct 26.

now $176

Low $223

High $299

The cheapest time to fly from Chicago to Jacksonville

The cheapest month to fly from Chicago to Jacksonville is January, with a median price of $211. The most expensive month is March, with a median price of $577. Prices are generally lower from January to December.

January

Cheapest

Flights from $211

March

Most Expensive

Flights from $577

Jan

Feb

Mar

Apr

May

Jun

Jul

Aug

Sep

Oct

Nov

Dec

Direct flights from Chicago to Jacksonville

Southwest Airlines

Last-minute flights going from Chicago to Jacksonville

Tue, Jul 28

⌛ Last-Minute

MDW - Jacksonville

Chicago (MDW) - Jacksonville (JAX)

Frontier Airlines

$529

$352

One-way

Sat, Aug 1

⌛ Last-Minute

MDW - Jacksonville

Chicago (MDW) - Jacksonville (JAX)

Frontier Airlines

$540

$353

One-way

Sun, Aug 2

⌛ Last-Minute

MDW - Jacksonville

Chicago (MDW) - Jacksonville (JAX)

Allegiant Air

$439

$319

One-way

Tue, Aug 4

⌛ Last-Minute

MDW - Jacksonville

Chicago (MDW) - Jacksonville (JAX)

Frontier Airlines

$424

$243

One-way

Tue, Aug 4

⌛ Last-Minute

MDW - Jacksonville

Chicago (MDW) - Jacksonville (JAX)

Frontier Airlines

$371

$255

One-way

Tue, Aug 4

⌛ Last-Minute

MDW - Jacksonville

Chicago (MDW) - Jacksonville (JAX)

Frontier Airlines

$372

$273

One-way

Biggest price drops on these dates for flights from Chicago to Jacksonville

5 nights

Nov 11 - Nov 16

$578 → $179

69%

2 nights

Nov 13 - Nov 15

$582 → $232

60%

12 nights

Nov 4 - Nov 16

$496 → $183

63%

7 nights

Dec 5 - Dec 12

$455 → $216

52%

Popular Airports to fly from Chicago to Jacksonville

Chicago - Jacksonville route insights

💸 Price insights

Recent fares are above the typical level

Recent fares for Chicago to Jacksonville are above the typical level, with a median price of $362.

📅 Best time to fly

January is historically the cheapest month to fly

Historically, the cheapest month to fly from Chicago to Jacksonville is January, with a median price of $211.

⏱️ Flight duration

Direct flights take 2h 36m

Direct flights from Chicago to Jacksonville typically take 2h 36m, while connecting flights average 18h 33m.

✈️ Airlines & availability

Connecting flights are more common

Connecting flights are more common on this route, making up 66% of recent bookings.

🏆 Airline highlight

Southwest Airlines offers direct flights

Southwest Airlines offers direct flights from Chicago to Jacksonville, providing a convenient travel option.

🎯 Booking tip

Deals are frequent on this route

Deals on flights from Chicago to Jacksonville are frequent, appearing often over a 30-day window.

Chicago main airports to depart from

Chicago Midway International (MDW)

Cheapest

Consider Chicago Midway International for flights from Chicago to Jacksonville, often offering competitive prices.

📍 ~15 km from Chicago (reachable by car)

💸 Flights from ~$172

Jacksonville main airports to arrive at

Jacksonville International (JAX)

Cheapest

Jacksonville International Airport is a convenient arrival option for flights from Chicago to Jacksonville.

📍 ~20 km from Jacksonville (reachable by car)

💸 Flights from ~$172

Airports nearby Jacksonville used as alternative

Orlando International (MCO)

Orlando International (MCO) is a major international hub that often provides lower fares due to high competition.

📍 ~180 km from Jacksonville (reachable by car)

💸 Flights from ~$93

Business & First Class Flight Deals to Jacksonville

79% AI deal score

$918

$569

Save $349

Frequently Asked Questions About Flights to Jacksonville

Historically, the best time to book flights from Chicago to Jacksonville is typically 60+ days before departure. During this period, the average price for a flight is around $303. Prices tend to increase as the departure date approaches, with flights booked 0-6 days out averaging $678. For those booking 28-59 days in advance, the average price is approximately $374, indicating a significant saving by planning ahead.

Across the trailing quarter, a good price for a flight from Chicago to Jacksonville is considered to be $262 or less. The median price for this route over the same period was $362. Prices can vary, with 75% of flights historically costing $606 or less. Aiming for prices at or below the $262 threshold can help secure a more economical fare.

Historically, the cheapest months to fly from Chicago to Jacksonville include January, with a median price of $211, and July, with a median price of $217. May also offers competitive prices, with a median of $244. The annual median price for this route is $362, so flying in these months can offer significant savings compared to the yearly average.

Related routes

More routes from Chicago

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Flights to Jacksonville from other cities

Flights from Charlotte to Jacksonville Flights from Dallas to Jacksonville Flights from Denver to Jacksonville Flights from Houston to Jacksonville Flights from Madrid to Jacksonville Flights from Memphis to Jacksonville Flights from Miami to Jacksonville Flights from New York to Jacksonville Flights from Philadelphia to Jacksonville Flights from Phoenix to Jacksonville Flights from Pittsburgh to Jacksonville Flights from Reykjavik to Jacksonville

Chicago to Jacksonville: Overview

Insights for flights from Chicago to Jacksonville

How much is a round trip from Chicago to Jacksonville

Regular price: $223 - $299

Prices for flights from Chicago to Jacksonville are currently below the regular range.

Regularly, flights from Chicago to Jacksonville range from $223 to $299. The current lowest deal is $176 with Frontier Airlines for travel from Oct 22-Oct 26.

now $176

Low $223

High $299

The cheapest time to fly from Chicago to Jacksonville

January

Cheapest

Flights from $211

March

Most Expensive

Flights from $577

Jan

Feb

Mar

Apr

May

Jun

Jul

Aug

Sep

Oct

Nov

Dec

Direct flights from Chicago to Jacksonville

Southwest Airlines

Last-minute flights going from Chicago to Jacksonville

Tue, Jul 28

⌛ Last-Minute

MDW - Jacksonville

Chicago (MDW) - Jacksonville (JAX)

Frontier Airlines

$529

$352

One-way

Sat, Aug 1

⌛ Last-Minute

MDW - Jacksonville

Chicago (MDW) - Jacksonville (JAX)

Frontier Airlines

$540

$353

One-way

Sun, Aug 2

⌛ Last-Minute

MDW - Jacksonville

Chicago (MDW) - Jacksonville (JAX)

Allegiant Air

$439

$319

One-way

Tue, Aug 4

⌛ Last-Minute

MDW - Jacksonville

Chicago (MDW) - Jacksonville (JAX)

Frontier Airlines

$424

$243

One-way

Tue, Aug 4

⌛ Last-Minute

MDW - Jacksonville

Chicago (MDW) - Jacksonville (JAX)

Frontier Airlines

$371

$255

One-way

Tue, Aug 4

⌛ Last-Minute

MDW - Jacksonville

Chicago (MDW) - Jacksonville (JAX)

Frontier Airlines

$372

$273

One-way

Biggest price drops on these dates for flights from Chicago to Jacksonville

5 nights

Nov 11 - Nov 16

$578 → $179

69%

2 nights

Nov 13 - Nov 15

$582 → $232

60%

12 nights

Nov 4 - Nov 16

$496 → $183

63%

7 nights

Dec 5 - Dec 12

$455 → $216

52%

Popular Airports to fly from Chicago to Jacksonville