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Cheap flights from Chicago to Jacksonville from $82

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 3/25. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
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.
Southwest Logo
12:05 pm - 9:05 pm
MDW
-
JAX
8h 00m
2 stops
Southwest Logo
7:20 am - 8:50 am
JAX
-
MDW
2h 30mnonstop
$275Southwest
Sat, Apr 25 - Wed, Apr 29
Frontier Logo
5:01 am - 5:08 pm
ORD
-
JAX
11h 07m
1 stop
Frontier Logo
12:31 pm - 10:52 am
JAX
-
ORD
23h 21m
1 stop
$275Frontier
Fri, Mar 20 - Sun, Mar 22
Multiple Airlines Logo
8:16 pm - 7:01 pm
ORD
-
JAX
21h 45m
2 stops
Multiple Airlines Logo
10:51 pm - 8:47 am
JAX
-
ORD
10h 56m
1 stop
$276Multiple Airlines
Tue, Feb 24 - Thu, Feb 26
United Airlines Logo
7:10 am - 10:49 am
ORD
-
JAX
2h 39mnonstop
United Airlines Logo
6:50 pm - 11:44 pm
JAX
-
ORD
5h 54m
1 stop
$277United Airlines
Wed, Mar 4 - Mon, Mar 9
American Airlines Logo
3:04 pm - 6:40 pm
ORD
-
JAX
2h 36mnonstop
American Airlines Logo
5:45 am - 7:49 am
JAX
-
ORD
3h 04mnonstop
$279American Airlines
Wed, Apr 15 - Mon, Apr 20
Delta Logo
6:40 pm - 12:01 am
MDW
-
JAX
4h 21m
1 stop
Delta Logo
7:04 pm - 10:31 pm
JAX
-
MDW
4h 27m
1 stop
$280Delta
Wed, Mar 4 - Sat, Mar 7
Delta Logo
9:50 am - 2:52 pm
ORD
-
JAX
4h 02m
1 stop
Delta Logo
7:59 pm - 11:59 pm
JAX
-
ORD
5h 00m
1 stop
$280Delta
Wed, Apr 15 - Mon, Apr 20
Multiple Airlines Logo
9:28 am - 7:33 pm
ORD
-
JAX
9h 05m
1 stop
Multiple Airlines Logo
9:03 pm - 5:10 pm
JAX
-
ORD
45h 07m
2 stops
$281Multiple Airlines
Wed, Mar 18 - Thu, Sep 3
United Airlines Logo
7:00 am - 10:36 am
ORD
-
JAX
2h 36mnonstop
United Airlines Logo
8:00 am - 9:50 am
JAX
-
ORD
2h 50mnonstop
$283United Airlines
Sat, Apr 4 - Sat, Apr 11
American Airlines Logo
7:53 pm - 11:31 pm
ORD
-
JAX
2h 38mnonstop
American Airlines Logo
5:45 am - 7:49 am
JAX
-
ORD
3h 04mnonstop
$285American Airlines
Sun, Apr 12 - Sat, Apr 18

American Airlines flights from Chicago to Jacksonville

Our best American Airlines deals on Chicago to Jacksonville flight tickets
American Airlines
Mar 7
ORD2:58 pmChicago O'Hare Intl
7h 30m
1 stop
JAX11:28 pmJacksonville
Mar 12
JAX8:07 pmJacksonville
5h 09m
1 stop
ORD12:16 amChicago O'Hare Intl
$277
American Airlines
Apr 15
ORD3:04 pmChicago O'Hare Intl
2h 36m
JAX6:40 pmJacksonville
Apr 20
JAX5:45 amJacksonville
3h 04m
ORD7:49 amChicago O'Hare Intl
$279
American Airlines
Apr 15
ORD7:15 amChicago O'Hare Intl
4h 24m
1 stop
JAX12:39 pmJacksonville
Apr 20
JAX8:19 pmJacksonville
4h 35m
1 stop
ORD11:54 pmChicago O'Hare Intl
$280

Delta flights from Chicago to Jacksonville

Our best Delta deals on Chicago to Jacksonville flight tickets
Delta
Mar 4
MDW6:40 pmChicago Midway
4h 21m
1 stop
JAX12:01 amJacksonville
Mar 7
JAX7:04 pmJacksonville
4h 27m
1 stop
MDW10:31 pmChicago Midway
$280
Delta
Mar 16
MDW6:07 pmChicago Midway
3h 54m
1 stop
JAX11:01 pmJacksonville
Mar 21
JAX5:28 pmJacksonville
6h 03m
1 stop
MDW10:31 pmChicago Midway
$310
Delta
Jun 13
ORD12:10 pmChicago O'Hare Intl
5h 45m
1 stop
JAX6:55 pmJacksonville
Jun 20
JAX2:30 pmJacksonville
6h 18m
1 stop
ORD7:48 pmChicago O'Hare Intl
$317

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 February 8, 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

MDW - JAX

MDWJAX

Chicago Midway

Sat 4/25

12:05 pm-9:05 pm

2 stops8h 00m

Jacksonville

Wed 4/29

7:20 am-8:50 am

Nonstop2h 30m

$275

ChicagoJacksonville

ORD - JAX

ORDJAX

Chicago O'Hare Intl

Fri 3/20

5:01 am-5:08 pm

1 stop11h 07m

Jacksonville

Sun 3/22

12:31 pm-10:52 am

1 stop23h 21m

$275

ChicagoJacksonville

ORD - JAX

ORDJAX

Chicago O'Hare Intl

Tue 2/24

8:16 pm-7:01 pm

2 stops21h 45m

Jacksonville

Thu 2/26

10:51 pm-8:47 am

1 stop10h 56m

$276

ChicagoJacksonville

ORD - JAX

ORDJAX

Chicago O'Hare Intl

Wed 3/4

7:10 am-10:49 am

Nonstop2h 39m

Jacksonville

Mon 3/9

6:50 pm-11:44 pm

1 stop5h 54m

$277

ChicagoJacksonville

ORD - JAX

ORDJAX

Chicago O'Hare Intl

Wed 4/15

3:04 pm-6:40 pm

Nonstop2h 36m

Jacksonville

Mon 4/20

5:45 am-7:49 am

Nonstop3h 04m

$279

ChicagoJacksonville

MDW - JAX

MDWJAX

Chicago Midway

Wed 3/4

6:40 pm-12:01 am

1 stop4h 21m

Jacksonville

Sat 3/7

7:04 pm-10:31 pm

1 stop4h 27m

$280

ChicagoJacksonville

ORD - JAX

ORDJAX

Chicago O'Hare Intl

Wed 4/15

9:50 am-2:52 pm

1 stop4h 02m

Jacksonville

Mon 4/20

7:59 pm-11:59 pm

1 stop5h 00m

$280

ChicagoJacksonville

ORD - JAX

ORDJAX

Chicago O'Hare Intl

Wed 3/18

9:28 am-7:33 pm

1 stop9h 05m

Jacksonville

Thu 9/3

9:03 pm-5:10 pm

2 stops45h 07m

$281

ChicagoJacksonville

ORD - JAX

ORDJAX

Chicago O'Hare Intl

Sat 4/4

7:00 am-10:36 am

Nonstop2h 36m

Jacksonville

Sat 4/11

8:00 am-9:50 am

Nonstop2h 50m

$283

ChicagoJacksonville

ORD - JAX

ORDJAX

Chicago O'Hare Intl

Sun 4/12

7:53 pm-11:31 pm

Nonstop2h 38m

Jacksonville

Sat 4/18

5:45 am-7:49 am

Nonstop3h 04m

$285

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 typical price of a round-trip flight between Chicago and Jacksonville?

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 $305.

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

According to our data, Saturday is the cheapest day to fly to Jacksonville from Chicago. The lowest ticket price found for a Saturday departure recently was $334. 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 $399.

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 $341 when looking at flights departing at noon. Flights to Jacksonville are more costly in the afternoon, with an average ticket price of $375. Departure times in the afternoon 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 $363 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 $311 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.

Can stopping save me money on Chicago to Jacksonville flights?

You could potentially save up to 49% on your flight if you consider stops on a Chicago to Jacksonville flight.

How have Chicago to Jacksonville flight prices changed over time?

As of February 2026, prices for Chicago to Jacksonville flights are approximately 34% cheaper 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 15m

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 $308.
The fastest flight from Chicago to Jacksonville takes 2h 15m
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 15m.

  • 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
3,051 reviews
Search Frontier flights
American AirlinesPriceFrom $179Free CancellationRating
7.2
11,255 reviews
Search American Airlines flights
SouthwestPriceFrom $203Free CancellationRating
8.0
4,281 reviews
Search Southwest flights
United AirlinesPriceFrom $248Free CancellationRating
7.4
9,259 reviews
Search United Airlines flights
JetBluePriceFrom $254Free CancellationRating
7.2
2,895 reviews
Search JetBlue flights

  • Southwest Flights From Chicago to Jacksonville

    Southwest flies from Chicago to Jacksonville around 5 times per week, with 4,282 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 $379 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 $248, round-trip. It should be noted that an average United Airlines flight deal for this route in this time was higher, at $383 round-trip. United Airlines operates 8 flights out of Chicago into Jacksonville in an average week, so prices vary by time and availability. 9,259 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
Kingsland
Ponte Vedra Beach
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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