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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 2/4. 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.
Frontier Logo
4:46 pm - 2:34 pm
MDW
-
JAX
20h 48m2 stops
Frontier Logo
5:58 pm - 10:19 pm
JAX
-
MDW
5h 21m1 stop
$266Frontier
Sat, Mar 7 - Fri, Mar 20
Multiple Airlines Logo
5:05 am - 6:41 pm
ORD
-
JAX
12h 36m1 stop
Multiple Airlines Logo
5:51 pm - 8:12 pm
JAX
-
ORD
27h 21m2 stops
$266Multiple Airlines
Sat, Feb 14 - Thu, Feb 19
Frontier Logo
1:20 pm - 8:01 pm
MDW
-
JAX
29h 41m2 stops
Frontier Logo
7:18 pm - 12:05 pm
JAX
-
MDW
17h 47m1 stop
$267Frontier
Wed, Jan 21 - Mon, Jan 26
United Airlines Logo
5:57 pm - 9:24 pm
ORD
-
JAX
2h 27mnonstop
United Airlines Logo
7:45 am - 9:35 am
JAX
-
ORD
2h 50mnonstop
$268United Airlines
Sat, Feb 21 - Mon, Feb 23
American Airlines Logo
7:34 pm - 10:58 pm
ORD
-
JAX
2h 24mnonstop
American Airlines Logo
7:00 am - 8:53 am
JAX
-
ORD
2h 53mnonstop
$269American Airlines
Thu, Feb 12 - Tue, Feb 17
Southwest Logo
6:50 pm - 10:05 pm
MDW
-
JAX
2h 15mnonstop
Southwest Logo
8:50 pm - 12:05 am
JAX
-
MDW
4h 15m1 stop
$270Southwest
Thu, Mar 12 - Mon, Mar 16
Frontier Logo
5:01 am - 5:13 pm
ORD
-
JAX
11h 12m1 stop
Frontier Logo
4:29 pm - 10:39 pm
JAX
-
ORD
7h 10m1 stop
$270Frontier
Fri, Mar 13 - Thu, Mar 19
Southwest Logo
1:55 pm - 9:05 pm
ORD
-
JAX
6h 10m1 stop
Southwest Logo
6:10 am - 3:30 pm
JAX
-
ORD
10h 20m1 stop
$271Southwest
Sat, Apr 25 - Sat, May 2
American Airlines Logo
4:48 pm - 11:51 pm
ORD
-
JAX
6h 03m1 stop
American Airlines Logo
7:00 am - 8:53 am
JAX
-
ORD
2h 53mnonstop
$272American Airlines
Sat, Feb 14 - Mon, Feb 16
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
$273United Airlines
Thu, Feb 5 - Sat, Feb 7

Frontier flights from Chicago to Jacksonville

Our best Frontier deals on Chicago to Jacksonville flight tickets
Frontier
Mar 7
MDW4:46 pmChicago Midway
20h 48m
2 stops
JAX2:34 pmJacksonville
Mar 20
JAX5:58 pmJacksonville
5h 21m
1 stop
MDW10:19 pmChicago Midway
$266
Frontier
Jan 16
ORD6:20 amChicago O'Hare Intl
12h 02m
1 stop
JAX7:22 pmJacksonville
Jan 23
JAX7:18 pmJacksonville
25h 26m
2 stops
ORD7:44 pmChicago O'Hare Intl
$267
Frontier
Mar 13
ORD5:01 amChicago O'Hare Intl
11h 12m
1 stop
JAX5:13 pmJacksonville
Mar 19
JAX4:29 pmJacksonville
7h 10m
1 stop
ORD10:39 pmChicago O'Hare Intl
$270

United Airlines flights from Chicago to Jacksonville

Our best United Airlines deals on Chicago to Jacksonville flight tickets
United Airlines
Feb 21
ORD5:57 pmChicago O'Hare Intl
2h 27m
JAX9:24 pmJacksonville
Feb 23
JAX7:45 amJacksonville
2h 50m
ORD9:35 amChicago O'Hare Intl
$268
United Airlines
Feb 21
ORD1:02 pmChicago O'Hare Intl
6h 12m
1 stop
JAX8:14 pmJacksonville
Feb 23
JAX7:45 amJacksonville
2h 50m
ORD9:35 amChicago O'Hare Intl
$278
United Airlines
Mar 5
ORD1:06 pmChicago O'Hare Intl
7h 15m
1 stop
JAX9:21 pmJacksonville
Mar 9
JAX6:00 amJacksonville
2h 51m
ORD7:51 amChicago O'Hare Intl
$305

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 11, 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 3/7

4:46 pm-2:34 pm

2 stops20h 48m

Jacksonville

Fri 3/20

5:58 pm-10:19 pm

1 stop5h 21m

$266

ChicagoJacksonville

ORD - JAX

ORDJAX

Chicago O'Hare Intl

Sat 2/14

5:05 am-6:41 pm

1 stop12h 36m

Jacksonville

Thu 2/19

5:51 pm-8:12 pm

2 stops27h 21m

$266

ChicagoJacksonville

MDW - JAX

MDWJAX

Chicago Midway

Wed 1/21

1:20 pm-8:01 pm

2 stops29h 41m

Jacksonville

Mon 1/26

7:18 pm-12:05 pm

1 stop17h 47m

$267

ChicagoJacksonville

ORD - JAX

ORDJAX

Chicago O'Hare Intl

Sat 2/21

5:57 pm-9:24 pm

Nonstop2h 27m

Jacksonville

Mon 2/23

7:45 am-9:35 am

Nonstop2h 50m

$268

ChicagoJacksonville

ORD - JAX

ORDJAX

Chicago O'Hare Intl

Thu 2/12

7:34 pm-10:58 pm

Nonstop2h 24m

Jacksonville

Tue 2/17

7:00 am-8:53 am

Nonstop2h 53m

$269

ChicagoJacksonville

MDW - JAX

MDWJAX

Chicago Midway

Thu 3/12

6:50 pm-10:05 pm

Nonstop2h 15m

Jacksonville

Mon 3/16

8:50 pm-12:05 am

1 stop4h 15m

$270

ChicagoJacksonville

ORD - JAX

ORDJAX

Chicago O'Hare Intl

Fri 3/13

5:01 am-5:13 pm

1 stop11h 12m

Jacksonville

Thu 3/19

4:29 pm-10:39 pm

1 stop7h 10m

$270

ChicagoJacksonville

ORD - JAX

ORDJAX

Chicago O'Hare Intl

Sat 4/25

1:55 pm-9:05 pm

1 stop6h 10m

Jacksonville

Sat 5/2

6:10 am-3:30 pm

1 stop10h 20m

$271

ChicagoJacksonville

ORD - JAX

ORDJAX

Chicago O'Hare Intl

Sat 2/14

4:48 pm-11:51 pm

1 stop6h 03m

Jacksonville

Mon 2/16

7:00 am-8:53 am

Nonstop2h 53m

$272

ChicagoJacksonville

ORD - JAX

ORDJAX

Chicago O'Hare Intl

Thu 2/5

10:35 am-2:09 pm

Nonstop2h 34m

Jacksonville

Sat 2/7

8:00 am-9:46 am

Nonstop2h 46m

$273

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, Friday is the cheapest day to fly to Jacksonville from Chicago. The lowest ticket price found for a Friday departure recently was $367. 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 $408.

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 $335 when looking at flights departing at noon. Flights to Jacksonville are more costly in the evening, with an average ticket price of $387. 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 $366 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 $299 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 January 2026, 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 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 $162. 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
3,058 reviews
Search Frontier flights
DeltaPriceFrom $144Free CancellationRating
7.9
8,038 reviews
Search Delta flights
American AirlinesPriceFrom $176Free CancellationRating
7.2
11,102 reviews
Search American Airlines flights
SouthwestPriceFrom $203Free CancellationRating
8.0
4,252 reviews
Search Southwest flights
United AirlinesPriceFrom $244Free CancellationRating
7.4
9,145 reviews
Search United Airlines flights
JetBluePriceFrom $288Free CancellationRating
7.2
2,889 reviews
Search JetBlue flights

  • Southwest Flights From Chicago to Jacksonville

    Southwest flies from Chicago to Jacksonville around 4 times per week, with 4,254 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 $244, 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 16 flights out of Chicago into Jacksonville in an average week, so prices vary by time and availability. 9,145 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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