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 flights that include connections, travelers typically experience a median of 2 stopovers. This means that while direct options exist, a significant portion of flights will involve at least one stop.

How long is the flight from Jacksonville to Chicago?

A direct flight from Jacksonville to Chicago typically takes 2 hours and 53 minutes, covering a distance of 1368 kilometers. Flights with one stop, however, have a significantly longer median duration, 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 tend to drop frequently. This indicates that travelers may have regular opportunities to find deals. The route is classified as having frequent price drops, suggesting that monitoring prices can be beneficial for securing a good fare.

Flights From Jacksonville

To Chicago

Cheap Flights from Jacksonville to Chicago

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Deals from

Jacksonville

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

Prices updated 2 days ago

444 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 9, 2026.)

Today’s best flight deals from Jacksonville to Chicago

Explore current cheapest deals departing from Jacksonville to Chicago

2026-08-31 – 2026-09-02
JAX - Chicago
77% AI deal score
$425
$180
Round trip
2026-08-31 – 2026-09-23
JAX - Chicago
78% AI deal score
$315
$180
Round trip
2026-08-31 – 2026-09-22
JAX - Chicago
78% AI deal score
$315
$180
Round trip
2026-09-11 – 2026-09-14
JAX - Chicago
78% AI deal score
$306
$181
Round trip
2026-08-31 – 2026-09-21
JAX - Chicago
76% AI deal score
$315
$182
Round trip
2026-09-07 – 2026-10-06
JAX - Chicago
74% AI deal score
$242
$182
Round trip
2026-10-15 – 2026-10-18
JAX - Chicago
76% AI deal score
$290
$185
Round trip
2026-09-08 – 2026-09-10
JAX - Chicago
78% AI deal score
$310
$186
Round trip
2026-09-08 – 2026-09-13
JAX - Chicago
77% AI deal score
$301
$187
Round trip
2026-10-15 – 2026-10-19
JAX - Chicago
75% AI deal score
$290
$187
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: $241 - $424

Prices are currently below the regular range.

The regular price range for flights from Jacksonville to Chicago is $241-$424. The current lowest deal is $177 with Frontier Airlines for travel from Aug 31-Sep 29.

now $177

Low $241

High $424

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

Sat, Aug 8

⌛ Last-Minute

JAX - Chicago

Jacksonville (JAX) - Chicago (ORD)

Breeze Airways

$790

$398

One-way

Sun, Aug 9

⌛ Last-Minute

JAX - Chicago

Jacksonville (JAX) - Chicago (ORD)

Breeze Airways

$785

$401

One-way

Sun, Aug 9

⌛ Last-Minute

JAX - Chicago

Jacksonville (JAX) - Chicago (MDW)

Frontier Airlines

$602

$410

One-way

Mon, Aug 10

⌛ Last-Minute

JAX - Chicago

Jacksonville (JAX) - Chicago (MDW)

Frontier Airlines

$679

$350

One-way

Mon, Aug 10

⌛ Last-Minute

JAX - Chicago

Jacksonville (JAX) - Chicago (MDW)

Frontier Airlines

$683

$351

One-way

Tue, Aug 11

⌛ Last-Minute

JAX - Chicago

Jacksonville (JAX) - Chicago (ORD)

JetBlue Airways

$671

$392

One-way

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

3 nights

Aug 8 - Aug 11

$790 → $398

50%

4 nights

Aug 9 - Aug 13

$785 → $401

49%

3 nights

Aug 10 - Aug 13

$683 → $351

49%

4 nights

Aug 10 - Aug 14

$679 → $350

48%

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 at $177.

📅 Best time to fly

Fly in January for the best prices

Historically, January offers the lowest median prices at $171 for Jacksonville to Chicago.

⏱️ Flight duration

Direct flights take 2h 53m

The typical direct flight from Jacksonville to Chicago takes 2 hours and 53 minutes.

✈️ Airlines & availability

Connecting flights are dominant

Connecting flights make up 68% of recent deals, typically with 2 stopovers.

🏆 Airline highlight

United Airlines offers direct flights

United Airlines has offered direct flights on the Jacksonville to Chicago route historically.

🎯 Booking tip

Deals are frequent on this route

Deals for flights from Jacksonville to Chicago are frequent, appearing often over 30 days.

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

Aug 29

Chicago, United States

81% AI deal score

$995

$587

Save $408

United Airlines

Business Class

From JAX

Elite

Aug 28

Chicago, United States

81% AI deal score

$1,024

$587

Save $437

United Airlines

Business Class

From JAX

Elite

Sep 02

Chicago, United States

80% AI deal score

$862

$542

Save $320

United Airlines

Business Class

From JAX

Elite

Sep 03

Chicago, United States

80% AI deal score

$872

$542

Save $330

United Airlines

Business Class

From JAX

Elite

Aug 31

Chicago, United States

80% AI deal score

$1,652

$553

Save $1,099

From JAX

Chicago, United States

78% AI deal score

$882

$497

Save $385

From JAX

Elite

Sep 14

Chicago, United States

78% AI deal score

$863

$587

Save $276

United Airlines

Business Class

From JAX

Elite

Sep 25

Chicago, United States

78% AI deal score

$874

$587

Save $287

United Airlines

Business Class

From JAX

Elite

Sep 09

Chicago, United States

78% AI deal score

$872

$587

Save $285

United Airlines

Business Class

Frequently Asked Questions About Flights to Chicago

Historically, the optimal time to purchase 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. Even flights booked 60+ days in advance were slightly higher, with an average price of $298.

Across the trailing quarter, a good price for a flight from Jacksonville to Chicago is considered to be $277 or less. The median price for this route over the same period was $383. Prices can go significantly higher, with 75% of observed prices being $634 or less. Aiming for a price below $277 would represent a favorable deal.

Historically, the cheapest months to fly from Jacksonville to Chicago are February, with a median price of $191, and January, with a median price of $204. June also shows a relatively lower median price of $259. The annual median price for this route is $383, indicating that these months offer substantial savings compared to the yearly 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: $241 - $424

Prices are currently below the regular range.

The regular price range for flights from Jacksonville to Chicago is $241-$424. The current lowest deal is $177 with Frontier Airlines for travel from Aug 31-Sep 29.

now $177

Low $241

High $424

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

Sat, Aug 8

⌛ Last-Minute

JAX - Chicago

Jacksonville (JAX) - Chicago (ORD)

Breeze Airways

$790

$398

One-way

Sun, Aug 9

⌛ Last-Minute

JAX - Chicago

Jacksonville (JAX) - Chicago (ORD)

Breeze Airways

$785

$401

One-way

Sun, Aug 9

⌛ Last-Minute

JAX - Chicago

Jacksonville (JAX) - Chicago (MDW)

Frontier Airlines

$602

$410

One-way

Mon, Aug 10

⌛ Last-Minute

JAX - Chicago

Jacksonville (JAX) - Chicago (MDW)

Frontier Airlines

$679

$350

One-way

Mon, Aug 10

⌛ Last-Minute

JAX - Chicago

Jacksonville (JAX) - Chicago (MDW)

Frontier Airlines

$683

$351

One-way

Tue, Aug 11

⌛ Last-Minute

JAX - Chicago

Jacksonville (JAX) - Chicago (ORD)

JetBlue Airways

$671

$392

One-way

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

3 nights

Aug 8 - Aug 11

$790 → $398

50%

4 nights

Aug 9 - Aug 13

$785 → $401

49%

3 nights

Aug 10 - Aug 13

$683 → $351

49%

4 nights

Aug 10 - Aug 14

$679 → $350

48%

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 at $177.

📅 Best time to fly

Fly in January for the best prices

Historically, January offers the lowest median prices at $171 for Jacksonville to Chicago.

⏱️ Flight duration

Direct flights take 2h 53m

The typical direct flight from Jacksonville to Chicago takes 2 hours and 53 minutes.

✈️ Airlines & availability

Connecting flights are dominant

Connecting flights make up 68% of recent deals, typically with 2 stopovers.

🏆 Airline highlight

United Airlines offers direct flights

United Airlines has offered direct flights on the Jacksonville to Chicago route historically.

🎯 Booking tip

Deals are frequent on this route

Deals for flights from Jacksonville to Chicago are frequent, appearing often over 30 days.

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

$1,652

$553

Save $1,099

From JAX

Chicago, United States

78% AI deal score

$882

$497

Save $385

From JAX

Elite

Sep 14

Chicago, United States

78% AI deal score

$863

$587

Save $276

United Airlines

Business Class

From JAX

Elite

Sep 25

Chicago, United States

78% AI deal score

$874

$587

Save $287

United Airlines

Business Class

From JAX

Elite

Sep 09

Chicago, United States

78% AI deal score

$872

$587

Save $285

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

Fly in January for the best prices

Direct flights take 2h 53m

Connecting flights are dominant

United Airlines offers direct flights

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

Aug 29

Aug 28

Sep 02

Sep 03

Aug 31

Aug 25

Sep 05

Sep 05

Sep 05

Sep 14

Sep 25

Sep 09

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

Fly in January for the best prices

Direct flights take 2h 53m

Connecting flights are dominant

United Airlines offers direct flights

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

Aug 29

Aug 28

Sep 02

Sep 03

Aug 31

Aug 25

Sep 05

Sep 05

Sep 05

Sep 14

Sep 25

Sep 09

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?