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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 2/2. 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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Cheap round-trip flights

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American Airlines Logo
7:00 am - 10:28 amORD-JAX
2h 28mnonstop
American Airlines Logo
6:00 am - 12:28 pmJAX-ORD
7h 28m1 stop
$281American Airlines
Find Deal
Mon, Nov 24 - Tue, Dec 2
Multiple Airlines Logo
7:23 pm - 5:40 pmMDW-JAX
21h 17m1 stop
Multiple Airlines Logo
9:48 am - 1:21 pmJAX-MDW
28h 33m2 stops
$282Multiple Airlines
Find Deal
Thu, Dec 11 - Sun, Jan 4
Delta Logo
8:55 am - 5:27 pmORD-JAX
7h 32m1 stop
Delta Logo
2:00 pm - 6:52 pmJAX-ORD
5h 52m1 stop
$285Delta
Find Deal
Mon, Nov 24 - Thu, Nov 27
Delta Logo
6:00 am - 12:02 pmMDW-JAX
5h 02m1 stop
Delta Logo
6:38 pm - 11:40 pmJAX-MDW
6h 02m1 stop
$285Delta
Find Deal
Mon, Nov 24 - Mon, Nov 24
Southwest Logo
1:45 pm - 5:00 pmMDW-JAX
2h 15mnonstop
Southwest Logo
5:35 am - 7:00 amJAX-MDW
2h 25mnonstop
$286Southwest
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Thu, Dec 11 - Sat, Dec 13
United Airlines Logo
1:05 pm - 8:10 pmORD-JAX
6h 05m1 stop
United Airlines Logo
4:37 pm - 6:30 pmJAX-ORD
2h 53mnonstop
$287United Airlines
Find Deal
Thu, Dec 11 - Tue, Dec 16
Frontier Logo
5:30 am - 8:48 pmMDW-JAX
14h 18m1 stop
Frontier Logo
10:59 am - 10:43 pmJAX-MDW
12h 44m1 stop
$289Frontier
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Sun, Nov 23 - Mon, Nov 24
Southwest Logo
1:35 pm - 4:50 pmMDW-JAX
2h 15mnonstop
Southwest Logo
7:35 am - 1:55 pmJAX-MDW
7h 20m2 stops
$292Southwest
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Wed, Jan 28 - Tue, Feb 3
Frontier Logo
12:32 pm - 4:34 pmORD-JAX
27h 02m1 stop
Frontier Logo
7:23 pm - 9:27 pmJAX-ORD
27h 04m1 stop
$292Frontier
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Tue, Dec 23 - Mon, Dec 29
United Airlines Logo
6:00 pm - 9:32 pmORD-JAX
2h 32mnonstop
United Airlines Logo
4:37 pm - 6:30 pmJAX-ORD
2h 53mnonstop
$302United Airlines
Find Deal
Wed, Dec 3 - Sun, Dec 7

American Airlines flights from Chicago to Jacksonville

Our best American Airlines deals on Chicago to Jacksonville flight tickets
American Airlines
Nov 24
ORD7:00 amChicago O'Hare Intl
2h 28m
JAX10:28 amJacksonville
Dec 2
JAX6:00 amJacksonville
7h 28m
1 stop
ORD12:28 pmChicago O'Hare Intl
$281
Find similar
American Airlines
Dec 6
ORD1:53 pmChicago O'Hare Intl
2h 30m
JAX5:23 pmJacksonville
Dec 8
JAX6:49 amJacksonville
2h 52m
ORD8:41 amChicago O'Hare Intl
$286
Find similar
American Airlines
Dec 25
ORD8:25 amChicago O'Hare Intl
6h 39m
1 stop
JAX4:04 pmJacksonville
Jan 1
JAX9:33 amJacksonville
7h 32m
1 stop
ORD4:05 pmChicago O'Hare Intl
$290
Find similar

Frontier flights from Chicago to Jacksonville

Our best Frontier deals on Chicago to Jacksonville flight tickets
Frontier
Nov 2
ORD5:11 amChicago O'Hare Intl
10h 02m
1 stop
JAX4:13 pmJacksonville
Nov 10
JAX7:03 pmJacksonville
6h 56m
1 stop
ORD12:59 amChicago O'Hare Intl
$286
Find similar
Frontier
Nov 23
MDW5:30 amChicago Midway
14h 18m
1 stop
JAX8:48 pmJacksonville
Nov 24
JAX10:59 amJacksonville
12h 44m
1 stop
MDW10:43 pmChicago Midway
$289
Find similar
Frontier
Oct 31
ORD8:26 amChicago O'Hare Intl
12h 27m
1 stop
JAX9:53 pmJacksonville
Nov 3
JAX7:03 pmJacksonville
6h 56m
1 stop
ORD12:59 amChicago O'Hare Intl
$291
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 October 30, 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

Mon 11/24

7:00 am-10:28 am

Nonstop2h 28m

Jacksonville

Tue 12/2

6:00 am-12:28 pm

1 stop7h 28m

$281

ChicagoJacksonville

MDW - JAX

MDWJAX

Chicago Midway

Thu 12/11

7:23 pm-5:40 pm

1 stop21h 17m

Jacksonville

Sun 1/4

9:48 am-1:21 pm

2 stops28h 33m

$282

ChicagoJacksonville

ORD - JAX

ORDJAX

Chicago O'Hare Intl

Mon 11/24

8:55 am-5:27 pm

1 stop7h 32m

Jacksonville

Thu 11/27

2:00 pm-6:52 pm

1 stop5h 52m

$285

ChicagoJacksonville

MDW - JAX

MDWJAX

Chicago Midway

Mon 11/24

6:00 am-12:02 pm

1 stop5h 02m

Jacksonville

Mon 11/24

6:38 pm-11:40 pm

1 stop6h 02m

$285

ChicagoJacksonville

MDW - JAX

MDWJAX

Chicago Midway

Thu 12/11

1:45 pm-5:00 pm

Nonstop2h 15m

Jacksonville

Sat 12/13

5:35 am-7:00 am

Nonstop2h 25m

$286

ChicagoJacksonville

ORD - JAX

ORDJAX

Chicago O'Hare Intl

Thu 12/11

1:05 pm-8:10 pm

1 stop6h 05m

Jacksonville

Tue 12/16

4:37 pm-6:30 pm

Nonstop2h 53m

$287

ChicagoJacksonville

MDW - JAX

MDWJAX

Chicago Midway

Sun 11/23

5:30 am-8:48 pm

1 stop14h 18m

Jacksonville

Mon 11/24

10:59 am-10:43 pm

1 stop12h 44m

$289

ChicagoJacksonville

MDW - JAX

MDWJAX

Chicago Midway

Wed 1/28

1:35 pm-4:50 pm

Nonstop2h 15m

Jacksonville

Tue 2/3

7:35 am-1:55 pm

2 stops7h 20m

$292

ChicagoJacksonville

ORD - JAX

ORDJAX

Chicago O'Hare Intl

Tue 12/23

12:32 pm-4:34 pm

1 stop27h 02m

Jacksonville

Mon 12/29

7:23 pm-9:27 pm

1 stop27h 04m

$292

ChicagoJacksonville

ORD - JAX

ORDJAX

Chicago O'Hare Intl

Wed 12/3

6:00 pm-9:32 pm

Nonstop2h 32m

Jacksonville

Sun 12/7

4:37 pm-6:30 pm

Nonstop2h 53m

$302

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, Wednesday is the cheapest day to fly to Jacksonville from Chicago. The lowest ticket price found for a Wednesday departure recently was $376. 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 $424.

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 $325 when looking at flights departing at noon. Flights to Jacksonville are more costly in the evening, with an average ticket price of $426. 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 $374 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 $324 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 34% 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 October 2025, prices for Chicago to Jacksonville flights are approximately 9% 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

$162

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 $162. The best round-trip flight deal from Chicago to Jacksonville found on momondo in the last 72 hours is $303.
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
3,123 reviews
Search Frontier flights
DeltaPriceFrom $144Free CancellationRating
7.9
7,993 reviews
Search Delta flights
American AirlinesPriceFrom $176Free CancellationRating
7.2
11,030 reviews
Search American Airlines flights
SouthwestPriceFrom $198Free CancellationRating
8.0
4,242 reviews
Search Southwest flights
United AirlinesPriceFrom $255Free CancellationRating
7.4
8,998 reviews
Search United Airlines flights
JetBluePriceFrom $265Free 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 4,242 momondo users rating the airline 8.0/10. The cheapest Southwest deal from Chicago to Jacksonville in the last 72 hours was $198 (round-trip), much lower than the average airfare cost of $390 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 $255, round-trip. It should be noted that an average United Airlines flight deal for this route in this time was higher, at $413 round-trip. United Airlines operates 9 flights out of Chicago into Jacksonville in an average week, so prices vary by time and availability. 8,998 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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