Can I fly direct from Jacksonville to Chicago?

Yes, direct flights from Jacksonville to Chicago are available. Historically, approximately 32% of flights on this route have been direct. For journeys involving connections, flights typically include a median of 2 stopovers. Travelers prioritizing convenience may find direct options, while those with more flexible schedules might consider flights with connections.

How long is the flight from Jacksonville to Chicago?

The typical direct flight from Jacksonville to Chicago has a median duration of 2 hours and 53 minutes. This covers an approximate distance of 1368 kilometers. For flights with one stop, the median duration is significantly longer, averaging 13 hours and 32 minutes. Travelers should consider these differences when planning their journey.

How often do Jacksonville to Chicago flight prices drop?

Historically, flight prices for the Jacksonville to Chicago route have shown frequent drops. This indicates that travelers on this route often have opportunities to find deals. Over the trailing 30 days, this route has consistently been classified as one with frequent price fluctuations, suggesting regular chances for price reductions.

Flights From Jacksonville

To Chicago

Cheap Flights from Jacksonville to Chicago

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

Deals from

Jacksonville

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

Prices updated today

456 airlines compared

80%+ AI score for best value

Fares are subject to change and may not be available for all dates. (Data last updated Aug 31, 2026.)

Today’s best flight deals from Jacksonville to Chicago

Explore current cheapest deals departing from Jacksonville to Chicago

2026-10-10 – 2026-10-12
JAX - Chicago
77% AI deal score
$302
$176
Round trip
2026-10-15 – 2026-10-19
JAX - Chicago
77% AI deal score
$302
$176
Round trip
2026-10-08 – 2026-10-13
JAX - Chicago
77% AI deal score
$297
$176
Round trip
2026-09-17 – 2026-09-28
JAX - Chicago
76% AI deal score
$275
$177
Round trip
2026-11-04 – 2026-11-08
JAX - Chicago
74% AI deal score
$275
$189
Round trip
2026-10-02 – 2026-10-06
JAX - Chicago
76% AI deal score
$290
$194
Round trip
2026-11-04 – 2026-11-12
JAX - Chicago
77% AI deal score
$284
$194
Round trip
2026-10-14 – 2026-11-12
JAX - Chicago
75% AI deal score
$247
$194
Round trip
2026-10-20 – 2026-10-27
JAX - Chicago
48% AI deal score
$155
$195
Round trip
2026-10-13 – 2026-10-24
JAX - Chicago
47% AI deal score
$137
$195
Round trip

Jacksonville to Chicago: Overview

Insights for flights from Jacksonville to Chicago

A typical journey from Jacksonville to Chicago takes about 2h 53m, including connections. This is a short-haul route, covering a distance of 1368 kilometers.

When looking for cheap flights from Jacksonville to Chicago, you'll find that fares typically range from $277–$634, with a median of $383. Right now, current fares are above the typical level, and only 7% of recent fares were classified as a good price.

The cheapest time to fly from Jacksonville to Chicago is often in February, with a median fare of $191. January also offers lower prices, with a median of $204, followed by June at $259.

Most itineraries for flights from Jacksonville to Chicago connect at least once, with only 32% of recent fares being non-stop. For connecting flights, the typical number of stopovers is 2.

How much is a round trip from Jacksonville to Chicago

Regular price: $232 - $356

Prices are currently below the regular range.

The regular price range for flights from Jacksonville to Chicago is $232 to $356. The current lowest deal is $176 with Frontier Airlines, for travel from Sep 17-Sep 28.

now $176

Low $232

High $356

The cheapest time to fly from Jacksonville to Chicago

The cheapest month to fly from JAX to CHI is January, with a median price of $171. The most expensive month is April, with a median price of $470. Generally, prices are lower from January to December.

January

Cheapest

Flights from $171

April

Most Expensive

Flights from $470

Jan

Feb

Mar

Apr

May

Jun

Jul

Aug

Sep

Oct

Nov

Dec

Direct flights from Jacksonville to Chicago

United Airlines

Last-minute flights going from Jacksonville to Chicago

Tue, Sep 1

⌛ Last-Minute

JAX - Chicago

Jacksonville (JAX) - Chicago (MDW)

Frontier Airlines

$455

$308

One-way

Tue, Sep 1

⌛ Last-Minute

JAX - Chicago

Jacksonville (JAX) - Chicago (MDW)

Frontier Airlines

$559

$315

One-way

Thu, Sep 3

⌛ Last-Minute

JAX - Chicago

Jacksonville (JAX) - Chicago (ORD)

Frontier Airlines

$518

$315

One-way

Thu, Sep 3

⌛ Last-Minute

JAX - Chicago

Jacksonville (JAX) - Chicago (MDW)

Frontier Airlines

$545

$320

One-way

Thu, Sep 3

⌛ Last-Minute

JAX - Chicago

Jacksonville (JAX) - Chicago (MDW)

Frontier Airlines

$547

$320

One-way

Thu, Sep 3

⌛ Last-Minute

JAX - Chicago

Jacksonville (JAX) - Chicago (ORD)

Frontier Airlines

$514

$330

One-way

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

3 nights

Sep 1 - Sep 4

$559 → $315

44%

4 nights

Sep 4 - Sep 8

$534 → $304

43%

1 night

Sep 3 - Sep 4

$547 → $320

42%

2 nights

Sep 3 - Sep 5

$545 → $320

41%

Popular Airports to fly from Jacksonville to Chicago

Jacksonville - Chicago route insights

💸 Price insights

Recent fares are above the typical level.

Recent fares from Jacksonville to Chicago are above the typical level, with a median of $383.

📅 Best time to fly

February is historically the cheapest month to fly.

Historically, February offers the lowest median price at $191 for flights from Jacksonville to Chicago.

⏱️ Flight duration

Direct flights average 2h 53m.

Direct flights from Jacksonville to Chicago typically take 2h 53m, while connecting flights average 17h 47m.

✈️ Airlines & availability

Connecting flights are dominant.

Connecting flights make up 68% of routes, with a median of 2 stopovers when connecting.

🏆 Airline highlight

Frontier Airlines has a deal for $176.

Frontier Airlines offers a deal for $176 from Jacksonville to Chicago (Sep 17-Sep 28).

🎯 Booking tip

Deals are frequent on this route.

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

Jacksonville main airports to depart from

Jacksonville International (JAX)

Cheapest

Jacksonville International is a convenient departure airport for flights from Jacksonville to Chicago.

📍 ~18 km from Jacksonville (reachable by car)

💸 Flights from ~$158

Chicago main airports to arrive at

O Hare International (ORD)

Cheapest

O Hare International Airport is a major hub, offering extensive connections for your trip to Chicago.

📍 ~25 km from Chicago (reachable by car, train, and bus)

💸 Flights from ~$158

Airports nearby Chicago used as alternative

General Mitchell International (MKE)

General Mitchell International is a major international airport with significant carrier presence and direct flight options.

📍 ~135 km from Chicago (reachable by car or train)

💸 Flights from ~$254

Business & First Class Flight Deals to Chicago

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

Elite

Best Elite deals to Chicago

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

From JAX

Elite

Sep 16

Chicago, United States

82% AI deal score

$873

$497

Save $376

United Airlines

Business Class

From JAX

Elite

Sep 19

Chicago, United States

82% AI deal score

$883

$497

Save $386

United Airlines

Business Class

From JAX

Elite

Nov 07

Chicago, United States

81% AI deal score

$827

$497

Save $330

United Airlines

Business Class

From JAX

Elite

Sep 14

Chicago, United States

81% AI deal score

$825

$497

Save $328

United Airlines

Business Class

From JAX

Elite

Sep 16

Chicago, United States

81% AI deal score

$813

$497

Save $316

United Airlines

Business Class

From JAX

Elite

Sep 12

Chicago, United States

81% AI deal score

$833

$497

Save $336

United Airlines

Business Class

From JAX

Elite

Sep 15

Chicago, United States

81% AI deal score

$812

$497

Save $315

United Airlines

Business Class

From JAX

Elite

Oct 06

Chicago, United States

80% AI deal score

$807

$497

Save $310

United Airlines

Business Class

From JAX

Elite

Sep 21

Chicago, United States

80% AI deal score

$822

$497

Save $325

United Airlines

Business Class

From JAX

Elite

Oct 21

Chicago, United States

80% AI deal score

$829

$497

Save $332

United Airlines

Business Class

From JAX

Elite

Sep 19

Chicago, United States

80% AI deal score

$817

$497

Save $320

United Airlines

Business Class

From JAX

Elite

Sep 16

Chicago, United States

80% AI deal score

$818

$497

Save $321

United Airlines

Business Class

Frequently Asked Questions About Flights to Chicago

Historically, the optimal booking window for flights from Jacksonville to Chicago is typically between 28 and 59 days prior to departure. During this period, the average price observed was $249. Prices tend to increase significantly closer to the departure date, with flights booked 0-6 days out averaging around $533. For those booking 7-13 days in advance, the average price was approximately $406.

Across the trailing quarter, a good price for a flight from Jacksonville to Chicago was considered to be $277 or less. The median price for this route over the same period was $383. Prices can vary, with 75% of observed fares being $634 or less. Travelers aiming for a more economical trip should target prices at or below the $277 threshold.

Historically, the cheapest months to fly from Jacksonville to Chicago include February, with a median price of $191, and January, with a median price of $204. June also presented a relatively lower median price of $259. The annual median price for this route was $383, indicating that these months offer more budget-friendly options compared to the overall average.

Related routes

More routes from Jacksonville

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Flights to Chicago from other cities

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Jacksonville to Chicago: Overview

Insights for flights from Jacksonville to Chicago

A typical journey from Jacksonville to Chicago takes about 2h 53m, including connections. This is a short-haul route, covering a distance of 1368 kilometers.

Most itineraries for flights from Jacksonville to Chicago connect at least once, with only 32% of recent fares being non-stop. For connecting flights, the typical number of stopovers is 2.

How much is a round trip from Jacksonville to Chicago

Regular price: $232 - $356

Prices are currently below the regular range.

The regular price range for flights from Jacksonville to Chicago is $232 to $356. The current lowest deal is $176 with Frontier Airlines, for travel from Sep 17-Sep 28.

now $176

Low $232

High $356

The cheapest time to fly from Jacksonville to Chicago

January

Cheapest

Flights from $171

April

Most Expensive

Flights from $470

Jan

Feb

Mar

Apr

May

Jun

Jul

Aug

Sep

Oct

Nov

Dec

Direct flights from Jacksonville to Chicago

United Airlines

Last-minute flights going from Jacksonville to Chicago

Tue, Sep 1

⌛ Last-Minute

JAX - Chicago

Jacksonville (JAX) - Chicago (MDW)

Frontier Airlines

$455

$308

One-way

Tue, Sep 1

⌛ Last-Minute

JAX - Chicago

Jacksonville (JAX) - Chicago (MDW)

Frontier Airlines

$559

$315

One-way

Thu, Sep 3

⌛ Last-Minute

JAX - Chicago

Jacksonville (JAX) - Chicago (ORD)

Frontier Airlines

$518

$315

One-way

Thu, Sep 3

⌛ Last-Minute

JAX - Chicago

Jacksonville (JAX) - Chicago (MDW)

Frontier Airlines

$545

$320

One-way

Thu, Sep 3

⌛ Last-Minute

JAX - Chicago

Jacksonville (JAX) - Chicago (MDW)

Frontier Airlines

$547

$320

One-way

Thu, Sep 3

⌛ Last-Minute

JAX - Chicago

Jacksonville (JAX) - Chicago (ORD)

Frontier Airlines

$514

$330

One-way

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

3 nights

Sep 1 - Sep 4

$559 → $315

44%

4 nights

Sep 4 - Sep 8

$534 → $304

43%

1 night

Sep 3 - Sep 4

$547 → $320

42%

2 nights

Sep 3 - Sep 5

$545 → $320

41%

Popular Airports to fly from Jacksonville to Chicago

Jacksonville - Chicago route insights

💸 Price insights

Recent fares are above the typical level.

Recent fares from Jacksonville to Chicago are above the typical level, with a median of $383.

📅 Best time to fly

February is historically the cheapest month to fly.

Historically, February offers the lowest median price at $191 for flights from Jacksonville to Chicago.

⏱️ Flight duration

Direct flights average 2h 53m.

Direct flights from Jacksonville to Chicago typically take 2h 53m, while connecting flights average 17h 47m.

✈️ Airlines & availability

Connecting flights are dominant.

Connecting flights make up 68% of routes, with a median of 2 stopovers when connecting.

🏆 Airline highlight

Frontier Airlines has a deal for $176.

Frontier Airlines offers a deal for $176 from Jacksonville to Chicago (Sep 17-Sep 28).

🎯 Booking tip

Deals are frequent on this route.

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

Jacksonville main airports to depart from

Jacksonville International (JAX)

Cheapest

Jacksonville International is a convenient departure airport for flights from Jacksonville to Chicago.

📍 ~18 km from Jacksonville (reachable by car)

💸 Flights from ~$158

Chicago main airports to arrive at

O Hare International (ORD)

Cheapest

O Hare International Airport is a major hub, offering extensive connections for your trip to Chicago.

📍 ~25 km from Chicago (reachable by car, train, and bus)

💸 Flights from ~$158

Airports nearby Chicago used as alternative

General Mitchell International (MKE)

General Mitchell International is a major international airport with significant carrier presence and direct flight options.

Chicago, United States

80% AI deal score

$818

$497

Save $321

United Airlines

Business Class

Frequently Asked Questions About Flights to Chicago

Cheap Flights from Jacksonville to Chicago

Today’s best flight deals from Jacksonville to Chicago

Jacksonville to Chicago: Overview

Insights for flights from Jacksonville to Chicago

How much is a round trip from Jacksonville to Chicago

The cheapest time to fly from Jacksonville to Chicago

Direct flights from Jacksonville to Chicago

Last-minute flights going from Jacksonville to Chicago

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

Popular Airports to fly from Jacksonville to Chicago

Jacksonville - Chicago route insights

Recent fares are above the typical level.

February is historically the cheapest month to fly.

Direct flights average 2h 53m.

Connecting flights are dominant.

Frontier Airlines has a deal for $176.

Deals are frequent on this route.

Jacksonville main airports to depart from

Chicago main airports to arrive at

Airports nearby Chicago used as alternative

Business & First Class Flight Deals to Chicago

Best Elite deals to Chicago

Sep 16

Sep 19

Nov 07

Sep 14

Sep 16

Sep 12

Sep 15

Oct 06

Sep 21

Oct 21

Sep 19

Sep 16

Frequently Asked Questions About Flights to Chicago

When should I buy Jacksonville to Chicago tickets?

How much should a flight from Jacksonville to Chicago cost?

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

Can I fly direct from Jacksonville to Chicago?

How long is the flight from Jacksonville to Chicago?

How often do Jacksonville to Chicago flight prices drop?

Related routes

More routes from Jacksonville

Flights to Chicago from other cities

Jacksonville to Chicago: Overview

Insights for flights from Jacksonville to Chicago

How much is a round trip from Jacksonville to Chicago

The cheapest time to fly from Jacksonville to Chicago

Direct flights from Jacksonville to Chicago

Last-minute flights going from Jacksonville to Chicago

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

Popular Airports to fly from Jacksonville to Chicago

Jacksonville - Chicago route insights

Recent fares are above the typical level.

February is historically the cheapest month to fly.

Direct flights average 2h 53m.

Connecting flights are dominant.

Frontier Airlines has a deal for $176.

Deals are frequent on this route.

Jacksonville main airports to depart from

Chicago main airports to arrive at

Airports nearby Chicago used as alternative

Business & First Class Flight Deals to Chicago

Best Elite deals to Chicago

Sep 16

Sep 19

Nov 07

Sep 14

Sep 16

Sep 12

Sep 15

Oct 06

Sep 21

Oct 21

Sep 19

Sep 16

Frequently Asked Questions About Flights to Chicago

When should I buy Jacksonville to Chicago tickets?

How much should a flight from Jacksonville to Chicago cost?

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