FlightsFrom 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 24 days ago

486,190 searches this week

171 airlines compared

80%+ AI score for best value

Fares are subject to change and may not be available for all dates. (Data last updated May 29, 2026.)

Today’s best flight deals from Chicago to Jacksonville

Explore current cheapest deals departing from Chicago to Jacksonville

September 15 - September 30

Cheapest
Earliest

MDW - Jacksonville

$247

$172

Round trip

September 29 - September 30

Cheapest
Best

MDW - Jacksonville

$296

$172

Round trip

September 22 - September 30

Cheapest

MDW - Jacksonville

$275

$172

Round trip

September 21 - September 30

MDW - Jacksonville

$273

$173

Round trip

September 22 - October 4

MDW - Jacksonville

$258

$180

Round trip

September 22 - October 11

MDW - Jacksonville

$250

$181

Round trip

September 15 - October 12

Earliest

MDW - Jacksonville

$243

$181

Round trip

September 29 - October 12

MDW - Jacksonville

$264

$181

Round trip

September 15 - October 11

Earliest

MDW - Jacksonville

$243

$181

Round trip

September 15 - September 21

Earliest

MDW - Jacksonville

$279

$182

Round trip

Unlock all 500+ flight deals to Jacksonville and get alerts when great deals appear

Route Intelligence — 486,190 Searches this Week

Insights for flights from Chicago to Jacksonville

A typical journey from Chicago to Jacksonville takes about 10h 35m, including connections. This duration reflects the fact that most itineraries for this route involve at least one stopover. Given the travel distance, planning for a full day of travel is advisable to account for layovers.
For those seeking cheap flights from Chicago to Jacksonville, fares typically range from $210–$449, with a median of $277. Right now, current fares are above the typical level for this route. Approximately 24% of recent fares were classified as a good price, indicating that competitive deals are available if you monitor prices.
The cheapest time to fly from Chicago to Jacksonville is often 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. These months tend to offer more budget-friendly options compared to other times of the year.
When flying from Chicago to Jacksonville, most itineraries connect at least once. Only 32.9% of recent fares were for direct flights from Chicago to Jacksonville. For those itineraries that do involve connections, the typical number of stopovers is 2, which contributes to the overall journey time.
The flight distance between Chicago and Jacksonville is approximately 1392 kilometers. This distance classifies the route as a short-haul journey, meaning it is a relatively shorter flight in terms of overall travel distance.

How much is a round trip from Chicago to Jacksonville

Regular price: $205 - $351

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

The regular price range for this route is typically between $205 and $351. The current lowest deal is $172 with Frontier Airlines, for travel from September 15 to September 30.

now $172

Low $205

High $351

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 $426. Prices are generally lower from January to December.

January

Cheapest

Flights from $211

March

Most Expensive

Flights from $426

Jan
Feb
Mar
Apr
May
Jun
Jul
Aug
Sep
Oct
Nov
Dec

Direct flights from Chicago to Jacksonville

Airline logo

American Airlines

Last-minute flights going from Chicago to Jacksonville

Thu, Jun 18

⌛ Last-Minute

ORD - Jacksonville

Deutsche Luft Hansa

Chicago (ORD) - Jacksonville (JAX)

Deutsche Luft Hansa

$509

$486

One-way

Fri, Jun 19

⌛ Last-Minute

ORD - Jacksonville

Frontier Airlines

Chicago (ORD) - Jacksonville (JAX)

Frontier Airlines

$499

$326

One-way

Wed, Jul 1

⌛ Last-Minute

MDW - Jacksonville

Frontier Airlines

Chicago (MDW) - Jacksonville (JAX)

Frontier Airlines

$374

$246

One-way

Thu, Jul 2

⌛ Last-Minute

RFD - Jacksonville

Allegiant Air

Chicago (RFD) - Jacksonville (JAX)

Allegiant Air

$329

$270

One-way

Thu, Jul 2

⌛ Last-Minute

RFD - Jacksonville

Allegiant Air

Chicago (RFD) - Jacksonville (JAX)

Allegiant Air

$361

$292

One-way

Fri, Jul 3

⌛ Last-Minute

MDW - Jacksonville

Southwest Airlines

Chicago (MDW) - Jacksonville (JAX)

Southwest Airlines

$384

$301

One-way

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

6 nights

Nov 24 - Nov 30

$602  →  $378

37%

3 nights

Nov 25 - Nov 28

$616  →  $398

35%

9 nights

Nov 21 - Nov 30

$596  →  $402

33%

10 nights

Nov 20 - Nov 30

$581  →  $402

31%

Popular Airports to fly from Chicago to Jacksonville

Chicago - Jacksonville route insights

💸 Price insights

Recent fares are above the typical level.

Recent fares from Chicago to Jacksonville are above the typical level, with a median price of $277.

📅 Best time to fly

January is historically the cheapest month to fly.

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

⏱️ Flight duration

Flights are typically 10h 35m long.

Flights from Chicago to Jacksonville typically take 10 hours and 35 minutes, including layovers.

✈️ Airlines & availability

Connecting flights are more common.

About 33% of recent deals are for direct flights. Connecting flights typically have 2 stopovers.

🏆 Airline highlight

American Airlines offers direct flights.

American Airlines is one of the carriers that historically offers direct flights on this route.

🎯 Booking tip

Deals appear frequently for this route.

Historically, deals for flights from Chicago to Jacksonville appear frequently, about once per day.

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

Chicago Rockford International (RFD)

Chicago Rockford International is an alternative departure airport for your trip to Jacksonville.

📍 ~120 km from Chicago (reachable by car)

💸 Flights from ~$194

O Hare International (ORD)

O Hare International is a major departure option for flights from Chicago to Jacksonville.

📍 ~25 km from Chicago (reachable by car or train)

💸 Flights from ~$182

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 is a major international hub with significantly more direct flight options and competitive pricing.

📍 ~180 km from Jacksonville (reachable by car)

💸 Flights from ~$97

Orlando Sanford International (SFB)

Cheapest

Orlando Sanford International is a primary hub for low-cost carriers, often providing much cheaper point-to-point domestic flights.

📍 ~170 km from Jacksonville (reachable by car)

💸 Flights from ~$85

Savannah/Hilton Head International (SAV)

Savannah/Hilton Head International is a reliable regional alternative with good domestic connectivity through major US carriers.

📍 ~200 km from Jacksonville (reachable by car)

💸 Flights from ~$186

Daytona Beach International (DAB)

Daytona Beach International is a relatively close alternative for major carriers with very low stress and quick transit.

📍 ~140 km from Jacksonville (reachable by car)

💸 Flights from ~$316

Gainesville Regional (GNV)

Gainesville Regional is the closest alternative airport geographically, useful for regional connections.

📍 ~100 km from Jacksonville (reachable by car)

💸 Flights from ~$398

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

Aug 01

Jacksonville, United States

82% AI deal score

$1,050

$569

Save $481

From ORD

Elite

Aug 11

Jacksonville, United States

80% AI deal score

$774

$497

Save $277

From ORD

Elite

Aug 19

Jacksonville, United States

80% AI deal score

$790

$497

Save $293

From ORD

Elite

Jul 22

Jacksonville, United States

80% AI deal score

$760

$497

Save $263

From ORD

Elite

Aug 04

Jacksonville, United States

80% AI deal score

$875

$545

Save $330

From ORD

Elite

Aug 13

Jacksonville, United States

80% AI deal score

$930

$548

Save $382

From ORD

Elite

Jul 07

Jacksonville, United States

79% AI deal score

$736

$497

Save $239

From ORD

Elite

Jul 15

Jacksonville, United States

79% AI deal score

$711

$497

Save $214

From ORD

Elite

Aug 11

Jacksonville, United States

79% AI deal score

$844

$546

Save $298

From ORD

Elite

Jul 22

Jacksonville, United States

79% AI deal score

$906

$569

Save $337

From ORD

Elite

Jul 29

Jacksonville, United States

79% AI deal score

$883

$569

Save $314

From ORD

Elite

Jul 20

Jacksonville, United States

79% AI deal score

$918

$569

Save $349

From ORD

Elite

Aug 07

Jacksonville, United States

79% AI deal score

$1,010

$618

Save $392

From ORD

Elite

Jul 31

Jacksonville, United States

78% AI deal score

$848

$569

Save $279

From ORD

Elite

Jul 15

Jacksonville, United States

78% AI deal score

$830

$569

Save $261

From ORD

Elite

Aug 13

Jacksonville, United States

77% AI deal score

$832

$595

Save $237

From ORD

Elite

Jul 11

Jacksonville, United States

77% AI deal score

$899

$606

Save $293

From ORD

Elite

Jul 13

Jacksonville, United States

77% AI deal score

$917

$617

Save $300

From ORD

Elite

Jul 10

Jacksonville, United States

77% AI deal score

$903

$617

Save $286

From ORD

Elite

Jul 07

Jacksonville, United States

77% AI deal score

$929

$617

Save $312

From ORD

Elite

Aug 03

Jacksonville, United States

77% AI deal score

$869

$618

Save $251

From ORD

Elite

Aug 01

Jacksonville, United States

77% AI deal score

$868

$618

Save $250

From ORD

Elite

Jul 28

Jacksonville, United States

76% AI deal score

$738

$569

Save $169

From ORD

Elite

Oct 24

Jacksonville, United States

76% AI deal score

$811

$595

Save $216

From ORD

Elite

Jul 29

Jacksonville, United States

76% AI deal score

$858

$607

Save $251

From ORD

Elite

Sep 21

Jacksonville, United States

75% AI deal score

$766

$595

Save $171

From ORD

Elite

Jul 15

Jacksonville, United States

75% AI deal score

$653

$525

Save $128

From ORD

Elite

Jul 10

Jacksonville, United States

70% AI deal score

$747

$617

Save $130

From ORD

Elite

Sep 07

Jacksonville, United States

70% AI deal score

$752

$618

Save $134

From ORD

Elite

Jul 30

Jacksonville, United States

70% AI deal score

$739

$618

Save $121

From ORD

Elite

Jul 08

Jacksonville, United States

70% AI deal score

$641

$525

Save $116

From ORD

Elite

Oct 21

Jacksonville, United States

70% AI deal score

$792

$574

Save $218

From ORD

Elite

Sep 28

Jacksonville, United States

70% AI deal score

$864

$623

Save $241

From ORD

Elite

Dec 05

Jacksonville, United States

69% AI deal score

$663

$574

Save $89

From ORD

Elite

Nov 05

Jacksonville, United States

69% AI deal score

$793

$646

Save $147

From ORD

Elite

Aug 12

Jacksonville, United States

68% AI deal score

$780

$635

Save $145

From ORD

Elite

Aug 10

Jacksonville, United States

68% AI deal score

$781

$646

Save $135

From ORD

Elite

Aug 02

Jacksonville, United States

67% AI deal score

$776

$684

Save $92

From ORD

Elite

Oct 22

Jacksonville, United States

67% AI deal score

$798

$684

Save $114

From ORD

Elite

Nov 19

Jacksonville, United States

67% AI deal score

$793

$707

Save $86

From ORD

Elite

Jun 23

Jacksonville, United States

67% AI deal score

$796

$729

Save $67

From ORD

Elite

Jul 31

Jacksonville, United States

66% AI deal score

$645

$597

Save $48

From ORD

Elite

Jul 15

Jacksonville, United States

66% AI deal score

$640

$597

Save $43

From ORD

Elite

Aug 01

Jacksonville, United States

66% AI deal score

$782

$692

Save $90

From ORD

Elite

Nov 21

Jacksonville, United States

66% AI deal score

$777

$706

Save $71

From ORD

Elite

Jul 15

Jacksonville, United States

65% AI deal score

$638

$615

Save $23

From ORD

Elite

Nov 26

Jacksonville, United States

50% AI deal score

$829

$809

Save $20

From ORD

Elite

Nov 01

Jacksonville, United States

50% AI deal score

$833

$809

Save $24

From ORD

Elite

Jul 07

Jacksonville, United States

49% AI deal score

$639

$634

Save $5

From ORD

Elite

Jul 20

Jacksonville, United States

49% AI deal score

$647

$635

Save $12

From ORD

Elite

Jul 13

Jacksonville, United States

49% AI deal score

$652

$645

Save $7

From ORD

Elite

Jul 17

Jacksonville, United States

49% AI deal score

$669

From ORD

Elite

Jul 17

Jacksonville, United States

49% AI deal score

$669

From ORD

Elite

Jul 18

Jacksonville, United States

49% AI deal score

$669

From ORD

Elite

Jul 22

Jacksonville, United States

49% AI deal score

$692

From ORD

Elite

Jul 23

Jacksonville, United States

49% AI deal score

$707

From ORD

Elite

Jul 06

Jacksonville, United States

49% AI deal score

$717

From ORD

Elite

Jul 13

Jacksonville, United States

49% AI deal score

$717

From ORD

Elite

Jul 19

Jacksonville, United States

49% AI deal score

$730

From ORD

Elite

Nov 19

Jacksonville, United States

49% AI deal score

$847

From ORD

Elite

Oct 29

Jacksonville, United States

41% AI deal score

$1,114

From ORD

Elite

Nov 17

Jacksonville, United States

41% AI deal score

$1,114

From ORD

Elite

Dec 01

Jacksonville, United States

41% AI deal score

$1,114

From ORD

Elite

Dec 05

Jacksonville, United States

41% AI deal score

$1,114

From ORD

Elite

Nov 20

Jacksonville, United States

40% AI deal score

$1,154

From ORD

Elite

Dec 02

Jacksonville, United States

38% AI deal score

$1,419

From ORD

Elite

Nov 08

Jacksonville, United States

38% AI deal score

$1,419

From ORD

Elite

Nov 04

Jacksonville, United States

38% AI deal score

$1,419

From ORD

Elite

Jul 10

Jacksonville, United States

37% AI deal score

$3,665

From ORD

Elite

Jul 10

Jacksonville, United States

37% AI deal score

$3,679

From ORD

Elite

Aug 28

Jacksonville, United States

37% AI deal score

$3,707

From ORD

Elite

Aug 28

Jacksonville, United States

37% AI deal score

$3,720

From ORD

Elite

Jul 10

Jacksonville, United States

37% AI deal score

$3,738

From ORD

Elite

Jul 10

Jacksonville, United States

37% AI deal score

$3,745

From ORD

Elite

Jul 10

Jacksonville, United States

37% AI deal score

$3,745

From ORD

Elite

Jul 24

Jacksonville, United States

37% AI deal score

$3,789

From ORD

Elite

Jul 20

Jacksonville, United States

37% AI deal score

$3,808

From ORD

Elite

Jul 24

Jacksonville, United States

37% AI deal score

$3,812

From ORD

Elite

Jul 24

Jacksonville, United States

37% AI deal score

$3,814

From ORD

Elite

Jul 31

Jacksonville, United States

37% AI deal score

$3,817

From ORD

Elite

Jul 31

Jacksonville, United States

37% AI deal score

$3,819

From ORD

Elite

Jul 24

Jacksonville, United States

37% AI deal score

$3,826

From ORD

Elite

Jul 31

Jacksonville, United States

37% AI deal score

$3,832

From ORD

Elite

Jul 24

Jacksonville, United States

37% AI deal score

$3,834

From ORD

Elite

Jul 31

Jacksonville, United States

37% AI deal score

$3,840

From ORD

Elite

Jul 24

Jacksonville, United States

37% AI deal score

$3,842

From ORD

Elite

Jul 31

Jacksonville, United States

37% AI deal score

$3,843

From ORD

Elite

Jul 30

Jacksonville, United States

37% AI deal score

$3,843

From ORD

Elite

Jul 30

Jacksonville, United States

37% AI deal score

$3,845

From ORD

Elite

Jul 10

Jacksonville, United States

37% AI deal score

$3,848

From ORD

Elite

Jul 10

Jacksonville, United States

37% AI deal score

$3,853

From ORD

Elite

Jul 30

Jacksonville, United States

37% AI deal score

$3,857

From ORD

Elite

Jul 24

Jacksonville, United States

37% AI deal score

$3,862

From ORD

Elite

Jul 30

Jacksonville, United States

37% AI deal score

$3,866

From ORD

Elite

Jul 31

Jacksonville, United States

37% AI deal score

$3,867

From ORD

Elite

Jul 30

Jacksonville, United States

37% AI deal score

$3,868

From ORD

Elite

Jul 10

Jacksonville, United States

37% AI deal score

$3,871

From ORD

Elite

Aug 14

Jacksonville, United States

37% AI deal score

$3,875

From ORD

Elite

Jul 10

Jacksonville, United States

37% AI deal score

$3,879

From ORD

Elite

Jul 24

Jacksonville, United States

37% AI deal score

$3,881

Frequently Asked Questions About Flights to Jacksonville

Historically, booking flights from Chicago to Jacksonville 60+ days in advance typically yields the lowest average prices, around $303. Prices tend to increase as the departure date approaches. For example, flights booked 28-59 days out have an average price of $374, while those booked within 0-6 days of departure average $678. Planning ahead can result in significant savings on this route.

Across the trailing quarter, a good price for a flight from Chicago to Jacksonville is considered to be $210 or less. The median price for this route was $277. Prices can vary, with 75% of observed prices being $449 or less. Travelers aiming for the lower end of the price spectrum should target fares around the $210 mark.

Historically, January has been the cheapest month to fly from Chicago to Jacksonville, with a median price of $211. July also offers relatively low prices, with a median of $217. The annual median price for this route is $277, indicating that prices in January and July are notably below the yearly average.