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 flights that do include stopovers, the median number of stopovers observed was 2. This indicates that while direct options are available, a significant portion of routes involve at least one connection. Travelers should consider this when planning their journey and evaluating travel time.

What's the flight time from Chicago to Jacksonville?

The typical direct flight time from Chicago to Jacksonville is approximately 2 hours and 36 minutes, covering a distance of 1392 kilometers. For flights with one stop, the median travel time increases significantly to about 10 hours and 30 minutes. This difference highlights the convenience of direct routes compared to those involving a layover. Travelers should factor in these durations when planning their itinerary.

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 with frequent deal availability. Travelers looking for more affordable options can expect to see them appear regularly. This consistent availability makes it easier to find a good price for this specific route.

Flights From Chicago

To Jacksonville

Cheap Flights from Chicago to Jacksonville

Browse current best options from Chicago. Become a member to unlock all deals and get alerts when new deals appear.

Deals from

Chicago

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

Prices updated 1 day ago

461 airlines compared

80%+ AI score for best value

Fares are subject to change and may not be available for all dates. (Data last updated Sep 14, 2026.)

Today’s best flight deals from Chicago to Jacksonville

Explore current cheapest deals departing from Chicago to Jacksonville

2026-10-20 – 2026-10-26
CHI - Jacksonville
80% AI deal score
$263
$136
Round trip
2026-10-14 – 2026-10-21
CHI - Jacksonville
78% AI deal score
$268
$152
Round trip
2026-10-14 – 2026-10-16
CHI - Jacksonville
77% AI deal score
$279
$159
Round trip
2026-10-07 – 2026-10-11
CHI - Jacksonville
77% AI deal score
$283
$166
Round trip
2026-11-10 – 2026-11-14
CHI - Jacksonville
80% AI deal score
$528
$166
Round trip
2026-10-01 – 2026-10-12
CHI - Jacksonville
73% AI deal score
$236
$167
Round trip
2026-10-28 – 2026-11-02
CHI - Jacksonville
76% AI deal score
$276
$170
Round trip
2026-10-07 – 2026-10-13
CHI - Jacksonville
75% AI deal score
$263
$172
Round trip
2026-10-08 – 2026-10-15
CHI - Jacksonville
75% AI deal score
$268
$178
Round trip
2026-10-24 – 2026-10-27
CHI - Jacksonville
74% AI deal score
$278
$180
Round trip

Chicago to Jacksonville: Overview

Insights for flights from Chicago to Jacksonville

A typical journey from Chicago to Jacksonville, including connections, takes about 2h 36m. This is considered a short-haul route, covering a distance of 1392 kilometers. While the direct flight time is also 2h 36m, most itineraries on this route involve at least one stop.

Right now, if you are looking for cheap flights from Chicago to Jacksonville, fares are typically $262–$606, with a median of $362. Current fares are above the typical level for this route. Only 11% of recent fares were classified as a good price, indicating that finding a low fare might require some flexibility.

When is the cheapest time to fly from Chicago to Jacksonville? The data indicates that January is typically the most affordable month, with a median fare of $211. July also offers competitive pricing, with a median fare of $217, followed by May at $244. These months present the best opportunities for finding lower prices.

Most itineraries for flights from Chicago to Jacksonville connect at least once, with only 34% of recent fares being direct. For connecting itineraries, the typical number of connections is 2. This means that while direct flights are available, you are more likely to find options that include one or more stops on your journey.

How much is a round trip from Chicago to Jacksonville

Regular price: $212 - $316

Prices are currently below the regular range.

The regular price range for flights from Chicago to Jacksonville is $212 to $316. The current lowest deal is $135 with Frontier Airlines, for travel from Oct 20-Oct 26.

now $135

Low $212

High $316

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. Generally, prices are 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

United Airlines

Last-minute flights going from Chicago to Jacksonville

Thu, Oct 1

⌛ Last-Minute

ORD - Jacksonville

Chicago (ORD) - Jacksonville (JAX)

Frontier Airlines

$235

$166

One-way

Thu, Oct 1

⌛ Last-Minute

ORD - Jacksonville

Chicago (ORD) - Jacksonville (JAX)

Frontier Airlines

$291

$194

One-way

Thu, Oct 1

⌛ Last-Minute

ORD - Jacksonville

Chicago (ORD) - Jacksonville (JAX)

Frontier Airlines

$291

$194

One-way

Mon, Oct 5

⌛ Last-Minute

ORD - Jacksonville

Chicago (ORD) - Jacksonville (JAX)

Frontier Airlines

$248

$186

One-way

Mon, Oct 5

⌛ Last-Minute

ORD - Jacksonville

Chicago (ORD) - Jacksonville (JAX)

Frontier Airlines

$251

$186

One-way

Tue, Oct 6

⌛ Last-Minute

ORD - Jacksonville

Chicago (ORD) - Jacksonville (JAX)

Frontier Airlines

$251

$187

One-way

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

4 nights

Nov 10 - Nov 14

$528 → $166

69%

3 nights

Nov 10 - Nov 13

$529 → $184

65%

3 nights

Nov 13 - Nov 16

$529 → $212

60%

3 nights

Nov 5 - Nov 8

$528 → $218

59%

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 11% considered good deals.

📅 Best time to fly

January offers the lowest median price

Historically, January, July, and May offer the lowest median prices for flights from Chicago to Jacksonville.

⏱️ 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 dominant

Connecting flights are dominant on this route, making up 66% of available options.

🏆 Airline highlight

Frontier Airlines offers a recent deal at $135

A recent deal on Frontier Airlines from Chicago to Jacksonville was found for $135.

🎯 Booking tip

Deals are frequent on this route

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

Chicago main airports to depart from

Chicago Midway International (MDW)

Cheapest

Chicago Midway International is a convenient option for flights from Chicago to Jacksonville, often offering competitive prices.

📍 ~14 km from Chicago city center (reachable by car or public transport).

💸 Flights from ~$185

Jacksonville main airports to arrive at

Jacksonville International (JAX)

Cheapest

Jacksonville International Airport is a convenient arrival option for travelers heading to Jacksonville.

📍 ~18 km from Jacksonville (reachable by car)

💸 Flights from ~$177

Airports nearby Jacksonville used as alternative

Orlando International (MCO)

Orlando International (MCO) is a major international hub with more direct flight options and often lower fares.

📍 ~225 km from Jacksonville (approximately a 2.5-hour drive)

💸 Flights from ~$137

Business & First Class Flight Deals to Jacksonville

Discover luxury on the budget with premium cabin class on flights from Chicago to Jacksonville.

Elite

Best Elite deals to Jacksonville

Exclusive daily First Class, Business Class, and Premium Economy flight deals, refreshed every 24 hours.

From ORD

Elite

Jan 16

Jacksonville, United States

84% AI deal score

$1,017

$553

Save $464

United Airlines

Business Class

From ORD

Elite

Sep 17

Jacksonville, United States

80% AI deal score

$1,518

$811

Save $707

United Airlines

Business Class

From ORD

Elite

Oct 27

Jacksonville, United States

79% AI deal score

$888

$543

Save $345

United Airlines

Business Class

From ORD

Elite

Oct 10

Jacksonville, United States

79% AI deal score

$851

$543

Save $308

United Airlines

Business Class

From ORD

Elite

Oct 20

Jacksonville, United States

79% AI deal score

$891

$545

Save $346

United Airlines

Business Class

From ORD

Elite

Oct 07

Jacksonville, United States

79% AI deal score

$868

$545

Save $323

United Airlines

Business Class

From ORD

Elite

Oct 20

Jacksonville, United States

79% AI deal score

$893

$563

Save $330

United Airlines

Business Class

From ORD

Elite

Oct 07

Jacksonville, United States

78% AI deal score

$882

$563

Save $319

United Airlines

Business Class

From ORD

Elite

Oct 31

Jacksonville, United States

78% AI deal score

$934

$586

Save $348

United Airlines

Business Class

From ORD

Elite

Oct 24

Jacksonville, United States

77% AI deal score

$762

$543

Save $219

United Airlines

Business Class

From ORD

Elite

Oct 17

Jacksonville, United States

77% AI deal score

$748

$543

Save $205

United Airlines

Business Class

From ORD

Elite

Nov 04

Jacksonville, United States

77% AI deal score

$732

$545

Save $187

United Airlines

Business Class

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. Booking closer to the departure date, such as 0-6 days out, sees the average price increase significantly to about $678. For those planning within a 28-59 day window, the average price is approximately $374, indicating that earlier booking generally leads to more favorable prices.

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 observed fares being $606 or less. Travelers aiming for a more economical trip should target prices at or below the $262 threshold.

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 pricing, with a median of $244. These months tend to be more affordable compared to the annual median price of $362 for this route. Planning your travel during these times could result in more cost-effective flights.

Related routes

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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: $212 - $316

Prices are currently below the regular range.

The regular price range for flights from Chicago to Jacksonville is $212 to $316. The current lowest deal is $135 with Frontier Airlines, for travel from Oct 20-Oct 26.

now $135

Low $212

High $316

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

United Airlines

Last-minute flights going from Chicago to Jacksonville

Thu, Oct 1

⌛ Last-Minute

ORD - Jacksonville

Chicago (ORD) - Jacksonville (JAX)

Frontier Airlines

$235

$166

One-way

Thu, Oct 1

⌛ Last-Minute

ORD - Jacksonville

Chicago (ORD) - Jacksonville (JAX)

Frontier Airlines

$291

$194

One-way

Thu, Oct 1

⌛ Last-Minute

ORD - Jacksonville

Chicago (ORD) - Jacksonville (JAX)

Frontier Airlines

$291

$194

One-way

Mon, Oct 5

⌛ Last-Minute

ORD - Jacksonville

Chicago (ORD) - Jacksonville (JAX)

Frontier Airlines

$248

$186

One-way

Mon, Oct 5

⌛ Last-Minute

ORD - Jacksonville

Chicago (ORD) - Jacksonville (JAX)

Frontier Airlines

$251

$186

One-way

Tue, Oct 6

⌛ Last-Minute

ORD - Jacksonville

Chicago (ORD) - Jacksonville (JAX)

Frontier Airlines

$251

$187

One-way

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

4 nights

Nov 10 - Nov 14

$528 → $166

69%

3 nights

Nov 10 - Nov 13

$529 → $184

65%

3 nights

Nov 13 - Nov 16

$529 → $212

60%

3 nights

Nov 5 - Nov 8

$528 → $218

59%

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 11% considered good deals.

📅 Best time to fly

January offers the lowest median price

Historically, January, July, and May offer the lowest median prices for flights from Chicago to Jacksonville.

⏱️ 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 dominant

Connecting flights are dominant on this route, making up 66% of available options.

🏆 Airline highlight

Frontier Airlines offers a recent deal at $135

A recent deal on Frontier Airlines from Chicago to Jacksonville was found for $135.

🎯 Booking tip

Deals are frequent on this route

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

Chicago main airports to depart from

Chicago Midway International (MDW)

Cheapest

Chicago Midway International is a convenient option for flights from Chicago to Jacksonville, often offering competitive prices.

📍 ~14 km from Chicago city center (reachable by car or public transport).

💸 Flights from ~$185

Jacksonville main airports to arrive at

Jacksonville International (JAX)

Cheapest

Jacksonville International Airport is a convenient arrival option for travelers heading to Jacksonville.

📍 ~18 km from Jacksonville (reachable by car)

💸 Flights from ~$177

Airports nearby Jacksonville used as alternative

Orlando International (MCO)

Orlando International (MCO) is a major international hub with more direct flight options and often lower fares.

Jacksonville, United States

77% AI deal score

$732

$545

Save $187

United Airlines

Business Class

Frequently Asked Questions About Flights to Jacksonville

Cheap Flights from Chicago to Jacksonville

Today’s best flight deals from Chicago to Jacksonville

Chicago to Jacksonville: Overview

Insights for flights from Chicago to Jacksonville

How much is a round trip from Chicago to Jacksonville

The cheapest time to fly from Chicago to Jacksonville

Direct flights from Chicago to Jacksonville

Last-minute flights going from Chicago to Jacksonville

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

Popular Airports to fly from Chicago to Jacksonville

Chicago - Jacksonville route insights

Recent fares are above the typical level

January offers the lowest median price

Direct flights take 2h 36m

Connecting flights are dominant

Frontier Airlines offers a recent deal at $135

Deals are frequent on this route

Chicago main airports to depart from

Jacksonville main airports to arrive at

Airports nearby Jacksonville used as alternative

Business & First Class Flight Deals to Jacksonville

Best Elite deals to Jacksonville

Jan 16

Sep 17

Oct 27

Oct 10

Oct 20

Oct 07

Oct 20

Oct 07

Oct 31

Oct 24

Oct 17

Nov 04

Frequently Asked Questions About Flights to Jacksonville

When is the best time to book flights from Chicago to Jacksonville?

What is a good price for a flight from Chicago to Jacksonville?

When is the cheapest time of year to fly from Chicago to Jacksonville?

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

What's the flight time from Chicago to Jacksonville?

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

Related routes

More routes from Chicago

Flights to Jacksonville from other cities

Chicago to Jacksonville: Overview

Insights for flights from Chicago to Jacksonville

How much is a round trip from Chicago to Jacksonville

The cheapest time to fly from Chicago to Jacksonville

Direct flights from Chicago to Jacksonville

Last-minute flights going from Chicago to Jacksonville

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

Popular Airports to fly from Chicago to Jacksonville

Chicago - Jacksonville route insights

Recent fares are above the typical level

January offers the lowest median price

Direct flights take 2h 36m

Connecting flights are dominant

Frontier Airlines offers a recent deal at $135

Deals are frequent on this route

Chicago main airports to depart from

Jacksonville main airports to arrive at

Airports nearby Jacksonville used as alternative

Business & First Class Flight Deals to Jacksonville

Best Elite deals to Jacksonville

Jan 16

Sep 17

Oct 27

Oct 10

Oct 20

Oct 07

Oct 20

Oct 07

Oct 31

Oct 24

Oct 17

Nov 04

Frequently Asked Questions About Flights to Jacksonville

When is the best time to book flights from Chicago to Jacksonville?

What is a good price for a flight from Chicago to Jacksonville?

When is the cheapest time of year to fly from Chicago to Jacksonville?