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Cheap flights from Chicago to Jacksonville from $63

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.
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.
United Airlines Logo
10:35 am - 2:09 pm
ORD
-
JAX
2h 34mnonstop
United Airlines Logo
8:00 am - 9:46 am
JAX
-
ORD
2h 46mnonstop
$280United Airlines
Wed, Jan 7 - Fri, Jan 9
Delta Logo
8:00 am - 2:18 pm
ORD
-
JAX
5h 18m1 stop
Delta Logo
5:55 pm - 7:58 am
JAX
-
ORD
15h 03m1 stop
$282Delta
Sat, Jan 10 - Fri, Jan 16
Southwest Logo
1:35 pm - 4:50 pm
MDW
-
JAX
2h 15mnonstop
Southwest Logo
1:35 pm - 7:35 pm
JAX
-
MDW
7h 00m2 stops
$284Southwest
Tue, Jan 13 - Thu, Jan 15
Multiple Airlines Logo
7:57 pm - 6:01 pm
ORD
-
JAX
21h 04m1 stop
Multiple Airlines Logo
5:28 pm - 10:44 pm
JAX
-
ORD
6h 16m1 stop
$284Multiple Airlines
Thu, Dec 25 - Sat, Jan 31
Frontier Logo
5:25 am - 9:20 pm
ORD
-
JAX
14h 55m2 stops
Frontier Logo
8:54 am - 6:25 pm
JAX
-
ORD
10h 31m1 stop
$285Frontier
Thu, Jan 1 - Thu, Jan 15
Multiple Airlines Logo
6:00 am - 6:30 pm
MDW
-
JAX
11h 30m1 stop
Multiple Airlines Logo
9:49 am - 11:25 pm
JAX
-
MDW
14h 36m2 stops
$286Multiple Airlines
Fri, Feb 27 - Mon, Mar 2
Multiple Airlines Logo
5:25 am - 9:20 pm
ORD
-
JAX
14h 55m2 stops
Multiple Airlines Logo
7:23 pm - 4:00 pm
JAX
-
ORD
21h 37m1 stop
$286Multiple Airlines
Thu, Jan 1 - Mon, Jan 5
Southwest Logo
2:40 pm - 10:15 pm
MDW
-
JAX
6h 35m1 stop
Southwest Logo
5:30 pm - 6:55 pm
JAX
-
MDW
2h 25mnonstop
$287Southwest
Thu, Jan 15 - Sun, Jan 18
United Airlines Logo
1:00 pm - 8:10 pm
ORD
-
JAX
6h 10m1 stop
United Airlines Logo
4:38 pm - 6:25 pm
JAX
-
ORD
2h 47mnonstop
$287United Airlines
Thu, Jan 15 - Sun, Jan 18
Frontier Logo
2:15 pm - 9:20 pm
ORD
-
JAX
6h 05m1 stop
Frontier Logo
5:28 pm - 10:44 pm
JAX
-
ORD
6h 16m1 stop
$292Frontier
Mon, Dec 22 - Sat, Jan 31

United Airlines flights from Chicago to Jacksonville

Our best United Airlines deals on Chicago to Jacksonville flight tickets
United Airlines
Jan 7
ORD10:35 amChicago O'Hare Intl
2h 34m
JAX2:09 pmJacksonville
Jan 9
JAX8:00 amJacksonville
2h 46m
ORD9:46 amChicago O'Hare Intl
$280
Find similar
United Airlines
Jan 15
ORD1:00 pmChicago O'Hare Intl
6h 10m
1 stop
JAX8:10 pmJacksonville
Jan 18
JAX4:38 pmJacksonville
2h 47m
ORD6:25 pmChicago O'Hare Intl
$287
Find similar
United Airlines
Jan 7
ORD10:35 amChicago O'Hare Intl
2h 34m
JAX2:09 pmJacksonville
Jan 9
JAX1:45 pmJacksonville
5h 52m
1 stop
ORD6:37 pmChicago O'Hare Intl
$290
Find similar

Southwest flights from Chicago to Jacksonville

Our best Southwest deals on Chicago to Jacksonville flight tickets
Southwest
Jan 13
MDW1:35 pmChicago Midway
2h 15m
JAX4:50 pmJacksonville
Jan 15
JAX1:35 pmJacksonville
7h 00m
2 stops
MDW7:35 pmChicago Midway
$284
Find similar
Southwest
Jan 15
MDW2:40 pmChicago Midway
6h 35m
1 stop
JAX10:15 pmJacksonville
Jan 18
JAX5:30 pmJacksonville
2h 25m
MDW6:55 pmChicago Midway
$287
Find similar
Southwest
Jan 16
MDW1:35 pmChicago Midway
2h 15m
JAX4:50 pmJacksonville
Jan 18
JAX5:30 pmJacksonville
2h 25m
MDW6:55 pmChicago Midway
$288
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 December 10, 2025.
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

Wed 1/7

10:35 am-2:09 pm

Nonstop2h 34m

Jacksonville

Fri 1/9

8:00 am-9:46 am

Nonstop2h 46m

$280

ChicagoJacksonville

ORD - JAX

ORDJAX

Chicago O'Hare Intl

Sat 1/10

8:00 am-2:18 pm

1 stop5h 18m

Jacksonville

Fri 1/16

5:55 pm-7:58 am

1 stop15h 03m

$282

ChicagoJacksonville

MDW - JAX

MDWJAX

Chicago Midway

Tue 1/13

1:35 pm-4:50 pm

Nonstop2h 15m

Jacksonville

Thu 1/15

1:35 pm-7:35 pm

2 stops7h 00m

$284

ChicagoJacksonville

ORD - JAX

ORDJAX

Chicago O'Hare Intl

Thu 12/25

7:57 pm-6:01 pm

1 stop21h 04m

Jacksonville

Sat 1/31

5:28 pm-10:44 pm

1 stop6h 16m

$284

ChicagoJacksonville

ORD - JAX

ORDJAX

Chicago O'Hare Intl

Thu 1/1

5:25 am-9:20 pm

2 stops14h 55m

Jacksonville

Thu 1/15

8:54 am-6:25 pm

1 stop10h 31m

$285

ChicagoJacksonville

MDW - JAX

MDWJAX

Chicago Midway

Fri 2/27

6:00 am-6:30 pm

1 stop11h 30m

Jacksonville

Mon 3/2

9:49 am-11:25 pm

2 stops14h 36m

$286

ChicagoJacksonville

ORD - JAX

ORDJAX

Chicago O'Hare Intl

Thu 1/1

5:25 am-9:20 pm

2 stops14h 55m

Jacksonville

Mon 1/5

7:23 pm-4:00 pm

1 stop21h 37m

$286

ChicagoJacksonville

MDW - JAX

MDWJAX

Chicago Midway

Thu 1/15

2:40 pm-10:15 pm

1 stop6h 35m

Jacksonville

Sun 1/18

5:30 pm-6:55 pm

Nonstop2h 25m

$287

ChicagoJacksonville

ORD - JAX

ORDJAX

Chicago O'Hare Intl

Thu 1/15

1:00 pm-8:10 pm

1 stop6h 10m

Jacksonville

Sun 1/18

4:38 pm-6:25 pm

Nonstop2h 47m

$287

ChicagoJacksonville

ORD - JAX

ORDJAX

Chicago O'Hare Intl

Mon 12/22

2:15 pm-9:20 pm

1 stop6h 05m

Jacksonville

Sat 1/31

5:28 pm-10:44 pm

1 stop6h 16m

$292

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 $371. 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 $419.

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 $329 when looking at flights departing at noon. Flights to Jacksonville are more costly in the evening, with an average ticket price of $424. 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 Midway 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 $370 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 $319 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?

No. A direct flight is the cheapest option for a flight between Chicago to Jacksonville.

How have Chicago to Jacksonville flight prices changed over time?

As of December 2025, prices for Chicago to Jacksonville flights are approximately 35% 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

$173

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 $173. The best round-trip flight deal from Chicago to Jacksonville found on momondo in the last 72 hours is $328.
The fastest flight from Chicago to Jacksonville takes 2h 15m
Direct flights go from Chicago to Jacksonville every day.
There is 1 airport near Jacksonville: 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
5.8
3,085 reviews
Search Frontier flights
DeltaPriceFrom $144Free CancellationRating
7.9
8,007 reviews
Search Delta flights
American AirlinesPriceFrom $176Free CancellationRating
7.2
11,048 reviews
Search American Airlines flights
SouthwestPriceFrom $203Free CancellationRating
7.9
4,252 reviews
Search Southwest flights
United AirlinesPriceFrom $254Free CancellationRating
7.4
9,093 reviews
Search United Airlines flights
JetBluePriceFrom $265Free CancellationRating
7.2
2,899 reviews
Search JetBlue flights

  • Southwest Flights From Chicago to Jacksonville

    Southwest flies from Chicago to Jacksonville around 4 times per week, with 4,252 momondo users rating the airline 7.9/10. 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 $383 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 $254, round-trip. It should be noted that an average United Airlines flight deal for this route in this time was higher, at $399 round-trip. United Airlines operates 13 flights out of Chicago into Jacksonville in an average week, so prices vary by time and availability. 9,093 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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