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Cheap flights from Chicago to Jacksonville from $64

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Chicago to Jacksonville departing on 1/28. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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0 bags

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Find the cheapest flights from Chicago to Jacksonville

Cheap round-trip flights

Enter your travel dates to find the best prices.
Multiple Airlines Logo
5:40 am - 6:23 pm
ORD
-
JAX
11h 43m1 stop
Multiple Airlines Logo
9:42 pm - 10:42 pm
JAX
-
ORD
26h 00m2 stops
$266Multiple Airlines
Fri, Jan 23 - Sun, Jan 25
Multiple Airlines Logo
12:00 pm - 8:52 pm
ORD
-
JAX
31h 52m2 stops
Multiple Airlines Logo
5:28 pm - 10:44 pm
JAX
-
ORD
6h 16m1 stop
$267Multiple Airlines
Sat, Jan 24 - Sat, Jan 31
Multiple Airlines Logo
7:23 pm - 7:01 pm
ORD
-
JAX
22h 38m2 stops
Multiple Airlines Logo
10:56 am - 5:55 pm
JAX
-
ORD
7h 59m1 stop
$268Multiple Airlines
Tue, Mar 3 - Fri, Mar 6
Delta Logo
2:30 pm - 10:27 am
ORD
-
JAX
18h 57m1 stop
Delta Logo
5:39 pm - 11:59 pm
JAX
-
ORD
7h 20m1 stop
$269Delta
Sat, Jan 17 - Sun, Jan 18
Multiple Airlines Logo
6:20 am - 6:23 pm
MDW
-
JAX
11h 03m1 stop
Multiple Airlines Logo
5:51 pm - 11:45 am
JAX
-
MDW
18h 54m2 stops
$269Multiple Airlines
Fri, Jan 23 - Sun, Jan 25
Frontier Logo
5:05 am - 6:41 pm
ORD
-
JAX
12h 36m1 stop
Frontier Logo
7:53 pm - 4:57 pm
JAX
-
ORD
22h 04m1 stop
$270Frontier
Sat, Feb 14 - Mon, Feb 16
Frontier Logo
5:05 am - 6:41 pm
ORD
-
JAX
12h 36m1 stop
Frontier Logo
7:53 pm - 4:57 pm
JAX
-
ORD
22h 04m1 stop
$271Frontier
Sat, Feb 14 - Mon, Feb 16
Delta Logo
6:45 am - 2:18 pm
MDW
-
JAX
6h 33m1 stop
Delta Logo
6:30 am - 10:27 am
JAX
-
MDW
4h 57m1 stop
$275Delta
Sat, Jan 17 - Sun, Jan 18
Southwest Logo
1:25 pm - 9:15 pm
MDW
-
JAX
6h 50m2 stops
Southwest Logo
10:30 am - 4:35 pm
JAX
-
MDW
7h 05m2 stops
$277Southwest
Wed, Feb 18 - Wed, Feb 25
Southwest Logo
6:40 am - 11:45 am
MDW
-
JAX
4h 05m1 stop
Southwest Logo
7:35 am - 1:55 pm
JAX
-
MDW
7h 20m2 stops
$280Southwest
Sat, Jan 17 - Sun, Jan 18

American Airlines flights from Chicago to Jacksonville

Our best American Airlines deals on Chicago to Jacksonville flight tickets
American Airlines
Mar 10
ORD2:53 pmChicago O'Hare Intl
2h 31m
JAX6:24 pmJacksonville
Mar 17
JAX12:05 pmJacksonville
2h 57m
ORD2:02 pmChicago O'Hare Intl
$287
Find similar
American Airlines
Mar 6
ORD2:53 pmChicago O'Hare Intl
2h 31m
JAX6:24 pmJacksonville
Mar 10
JAX6:50 amJacksonville
2h 53m
ORD8:43 amChicago O'Hare Intl
$298
Find similar
American Airlines
Mar 7
ORD8:00 amChicago O'Hare Intl
2h 33m
JAX11:33 amJacksonville
Mar 13
JAX6:50 amJacksonville
2h 53m
ORD8:43 amChicago O'Hare Intl
$311
Find similar

Southwest flights from Chicago to Jacksonville

Our best Southwest deals on Chicago to Jacksonville flight tickets
Southwest
Feb 18
MDW1:25 pmChicago Midway
6h 50m
2 stops
JAX9:15 pmJacksonville
Feb 25
JAX10:30 amJacksonville
7h 05m
2 stops
MDW4:35 pmChicago Midway
$277
Find similar
Southwest
Jan 17
MDW6:40 amChicago Midway
4h 05m
1 stop
JAX11:45 amJacksonville
Jan 18
JAX7:35 amJacksonville
7h 20m
2 stops
MDW1:55 pmChicago Midway
$280
Find similar
Southwest
Jan 28
ORD1:45 pmChicago O'Hare Intl
6h 30m
1 stop
JAX9:15 pmJacksonville
Feb 4
JAX6:50 amJacksonville
8h 55m
2 stops
ORD2:45 pmChicago O'Hare Intl
$281
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from Chicago to Jacksonville that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, momondo users made 832,500 searches. Data last updated January 2, 2026.
Use the filters below to find and compare flights from Chicago to Jacksonville that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

ChicagoJacksonville

ORD - JAX

ORDJAX

Chicago O'Hare Intl

Fri 1/23

5:40 am-6:23 pm

1 stop11h 43m

Jacksonville

Sun 1/25

9:42 pm-10:42 pm

2 stops26h 00m

$266

ChicagoJacksonville

ORD - JAX

ORDJAX

Chicago O'Hare Intl

Sat 1/24

12:00 pm-8:52 pm

2 stops31h 52m

Jacksonville

Sat 1/31

5:28 pm-10:44 pm

1 stop6h 16m

$267

ChicagoJacksonville

ORD - JAX

ORDJAX

Chicago O'Hare Intl

Tue 3/3

7:23 pm-7:01 pm

2 stops22h 38m

Jacksonville

Fri 3/6

10:56 am-5:55 pm

1 stop7h 59m

$268

ChicagoJacksonville

ORD - JAX

ORDJAX

Chicago O'Hare Intl

Sat 1/17

2:30 pm-10:27 am

1 stop18h 57m

Jacksonville

Sun 1/18

5:39 pm-11:59 pm

1 stop7h 20m

$269

ChicagoJacksonville

MDW - JAX

MDWJAX

Chicago Midway

Fri 1/23

6:20 am-6:23 pm

1 stop11h 03m

Jacksonville

Sun 1/25

5:51 pm-11:45 am

2 stops18h 54m

$269

ChicagoJacksonville

ORD - JAX

ORDJAX

Chicago O'Hare Intl

Sat 2/14

5:05 am-6:41 pm

1 stop12h 36m

Jacksonville

Mon 2/16

7:53 pm-4:57 pm

1 stop22h 04m

$270

ChicagoJacksonville

ORD - JAX

ORDJAX

Chicago O'Hare Intl

Sat 2/14

5:05 am-6:41 pm

1 stop12h 36m

Jacksonville

Mon 2/16

7:53 pm-4:57 pm

1 stop22h 04m

$271

ChicagoJacksonville

MDW - JAX

MDWJAX

Chicago Midway

Sat 1/17

6:45 am-2:18 pm

1 stop6h 33m

Jacksonville

Sun 1/18

6:30 am-10:27 am

1 stop4h 57m

$275

ChicagoJacksonville

MDW - JAX

MDWJAX

Chicago Midway

Wed 2/18

1:25 pm-9:15 pm

2 stops6h 50m

Jacksonville

Wed 2/25

10:30 am-4:35 pm

2 stops7h 05m

$277

ChicagoJacksonville

MDW - JAX

MDWJAX

Chicago Midway

Sat 1/17

6:40 am-11:45 am

1 stop4h 05m

Jacksonville

Sun 1/18

7:35 am-1:55 pm

2 stops7h 20m

$280

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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See travel insights to Jacksonville from

How to get the cheapest flight ticket from Chicago to Jacksonville

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

What is the cheapest month to fly to Jacksonville?

If you are unable to visit Jacksonville during the month of August, then departing from Chicago during the month September is also very affordable. Most momondo users find prices during this month for around $314.

What is the cheapest day to depart on your flight to Jacksonville?

According to our data, Thursday is the cheapest day to fly to Jacksonville from Chicago. The lowest ticket price found for a Thursday departure recently was $368. Keep in mind that prices can always vary depending on your route and whether or not you are flying domestic or international. On the other hand, Sunday is the most expensive day to depart from Chicago because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $410.

What is the cheapest time of day to depart on your flight to Jacksonville?

Flying to Jacksonville from Chicago at noon is the least expensive time of day to depart. momondo users have found prices as low as $328 when looking at flights departing at noon. Flights to Jacksonville are more costly in the evening, with an average ticket price of $407. Departure times in the evening fall within the peak daily travel times, which is why tickets can be more expensive.

What is the cheapest Chicago to Jacksonville flight route?

Fly from Chicago O'Hare Intl to Jacksonville for the best Chicago - Jacksonville flight prices

How far in advance should I book a flight to Jacksonville?

You are more likely to see cheaper flights to Jacksonville from Chicago when booking weeks ahead of your departure date. In general, you can expect to find flights to Jacksonville for around $371 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Jacksonville from Chicago for as low as $315 on momondo.

What cabin class options are available on Chicago to Jacksonville flights?

There are 4 cabin classes available to choose from on Chicago to Jacksonville flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

How have Chicago to Jacksonville flight prices changed over time?

As of January 2026, prices for Chicago to Jacksonville flights are approximately 37% more expensive when compared to flights at the same time last year.

When to book flights from Chicago to Jacksonville

Are you open to changing your travel dates? Check out the ideal times to fly from Chicago to Jacksonville according to our flight data. Find out which month and days have the cheapest flights.
Estimated round-trip price

Cheap Chicago to Jacksonville (CHI to JAX) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Chicago to Jacksonville

Best Price Found

$127

Fastest flight time

2h 10m

Direct flights

Every day

Airports in Jacksonville

1 airport
The best one-way flight to Jacksonville from Chicago in the past 72 hours is $127. The best round-trip flight deal from Chicago to Jacksonville found on momondo in the last 72 hours is $279.
The fastest flight from Chicago to Jacksonville takes 2h 10m
Direct flights go from Chicago to Jacksonville every day.
There is 1 airport in Jacksonville. From Chicago there are direct flights to Jacksonville (JAX).
Search flight deals

  • How far is Chicago to Jacksonville by plane?

    The straight-line distance from Chicago to Jacksonville is 863.3 mi. By plane, this route typically takes 2h 10m.

  • When did momondo last update prices for flights from Chicago to Jacksonville Airport?

    Prices for flights from Chicago to Jacksonville Airport are updated daily.

  • How many operators does momondo search for flights from Chicago to Jacksonville Airport?

  • How old do you have to be to fly from Chicago to Jacksonville Airport?

    The minimum age for a child to fly alone is five, but airlines offering an unaccompanied minor (UNMR) service may have their age restrictions, such as regulations concerning flight duration, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Chicago to Jacksonville Airport.

  • What documentation or ID do you need to fly to Jacksonville Airport?

    The travel and health documents you'll need for your trip to Jacksonville Airport may differ based on your itinerary and personal situation. Typically, you should have several documents on hand, such as a national ID card or driver's license and a passport that is valid for six months after your intended arrival at Jacksonville Airport. It is always advisable to seek advice from your airline or a trusted third party, such as IATA.

  • What is the most popular plane model from Chicago to Jacksonville?

  • What is the most popular airline from Chicago to Jacksonville?

Best airlines flying from Chicago to Jacksonville

Compare and see reviews for airlines that fly from Chicago to Jacksonville with momondo
Airline
Rating
Free Cancellation
Price
FrontierPriceFrom $112Free CancellationRating
5.7
3,069 reviews
Search Frontier flights
DeltaPriceFrom $144Free CancellationRating
7.9
8,021 reviews
Search Delta flights
American AirlinesPriceFrom $176Free CancellationRating
7.2
11,073 reviews
Search American Airlines flights
SouthwestPriceFrom $203Free CancellationRating
8.0
4,254 reviews
Search Southwest flights
United AirlinesPriceFrom $247Free CancellationRating
7.4
9,132 reviews
Search United Airlines flights
JetBluePriceFrom $286Free CancellationRating
7.2
2,906 reviews
Search JetBlue flights

  • Southwest Flights From Chicago to Jacksonville

    Southwest flies from Chicago to Jacksonville around 2 times per week, with 4,252 momondo users rating the airline 8.0/10. The cheapest Southwest deal from Chicago to Jacksonville in the last 72 hours was $203 (round-trip), much lower than the average airfare cost of $380 for Southwest flights on this route.

  • United Airlines Flights From Chicago to Jacksonville

    The best United Airlines deal for Chicago to Jacksonville flight tickets found on momondo in the last 72 hours was $247, round-trip. It should be noted that an average United Airlines flight deal for this route in this time was higher, at $395 round-trip. United Airlines operates 18 flights out of Chicago into Jacksonville in an average week, so prices vary by time and availability. 9,132 United Airlines reviews by users on momondo have scored the airline at 7.4/10.

Traveling to a place near Jacksonville?

Book flights to Jacksonville if you plan to visit one of these locations
Fernandina Beach
Jacksonville Beach
Orange Park
Ponte Vedra Beach
Kingsland
Waycross
Atlantic Beach
Neptune Beach
St Johns
Yulee
Cumberland Island

Why use momondo?

Why should I use momondo to find a flight deal from Chicago to Jacksonville?

momondo collates all your flight options in one place and lets you filter them to find the perfect flight from Chicago to Jacksonville. momondo saves you time and could save you money on your trip.

Can I find flights from Chicago to Jacksonville with flexible booking policies on momondo?

Yes. momondo enables you to select and highlight flights to Jacksonville from Chicago with this policy.

How can momondo help me find flights from Chicago to Jacksonville?

momondo helps you find the best flight between Chicago and Jacksonville by providing filters to narrow your choice of flights to those matching your criteria. You can select flights based on numerous factors such as price, departure and landing times, airport and airline.

I’m not ready to book a flight from Chicago to Jacksonville right now. Can momondo alert me if prices change?

Yes momondo offers price alerts on flights to Jacksonville from Chicago. After performing a search on this page you should be able to see the price alert set up feature. Simply provide a valid email address and momondo will instantly alert you when prices change.

An easier way to manage your Jacksonville trip

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.
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