Latest deals
Insights
When to book
FAQs
Reviews
Price Alerts

Cheap flights from Chicago to Jacksonville from $55

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 1/24. 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

Discover deals from 900+ travel sites with momondo.

Save money when you book flights with momondo

Big names and deals

Big names and deals

Search 100s of travel sites to compare prices.

Filter for what you want

Filter for what you want

Free Wi-Fi? Stopover? Instantly customize your results.

Trusted and free

Trusted and free

We’re completely free to use - no hidden charges or fees.

Price Alerts

Price Alerts

Not ready to book? to track prices.
Search flight deals

Find the cheapest flights from Chicago to Jacksonville

Cheap round-trip flights

Enter your travel dates to find the best prices.
Frontier Logo
5:15 am - 9:20 pmORD-JAX
15h 05m1 stop
Frontier Logo
6:27 pm - 10:39 pmJAX-ORD
5h 12m1 stop
$283Frontier
Find Deal
vie., dic. 19 - lun., ene. 12
Southwest Logo
1:35 pm - 9:15 pmMDW-JAX
6h 40m2 stops
Southwest Logo
6:00 pm - 7:30 pmJAX-MDW
2h 30mnonstop
$284Southwest
Find Deal
mar., feb. 17 - lun., feb. 23
Frontier Logo
6:11 am - 5:40 pmORD-JAX
10h 29m1 stop
Frontier Logo
10:00 pm - 11:57 pmJAX-ORD
26h 57m2 stops
$285Frontier
Find Deal
vie., dic. 12 - dom., dic. 14
United Airlines Logo
6:04 pm - 9:42 pmORD-JAX
2h 38mnonstop
United Airlines Logo
1:45 pm - 6:37 pmJAX-ORD
5h 52m1 stop
$286United Airlines
Find Deal
lun., dic. 22 - mié., ene. 7
American Airlines Logo
8:20 am - 11:55 amORD-JAX
2h 35mnonstop
American Airlines Logo
6:49 am - 8:41 amJAX-ORD
2h 52mnonstop
$287American Airlines
Find Deal
mar., dic. 9 - mié., dic. 10
Southwest Logo
1:45 pm - 5:00 pmMDW-JAX
2h 15mnonstop
Southwest Logo
5:05 pm - 6:30 pmJAX-MDW
2h 25mnonstop
$287Southwest
Find Deal
mar., dic. 16 - jue., dic. 25
Delta Logo
1:16 pm - 8:40 pmORD-JAX
6h 24m1 stop
Delta Logo
8:20 am - 12:03 pmJAX-ORD
4h 43m1 stop
$288Delta
Find Deal
sáb., dic. 13 - mié., dic. 17
Delta Logo
6:45 am - 12:19 pmORD-JAX
4h 34m1 stop
Delta Logo
7:03 pm - 11:49 pmJAX-ORD
5h 46m1 stop
$289Delta
Find Deal
mar., feb. 17 - lun., feb. 23
United Airlines Logo
8:45 am - 2:58 pmORD-JAX
5h 13m1 stop
United Airlines Logo
11:40 am - 1:36 pmJAX-ORD
2h 56mnonstop
$290United Airlines
Find Deal
mar., dic. 9 - vie., dic. 19
Multiple Airlines Logo
6:12 am - 7:41 pmMDW-JAX
36h 29m2 stops
Multiple Airlines Logo
5:23 pm - 10:12 pmJAX-MDW
5h 49m1 stop
$294Multiple Airlines
Find Deal
jue., ene. 1 - lun., ene. 5

United Airlines flights from Chicago to Jacksonville

Our best United Airlines deals on Chicago to Jacksonville flight tickets
United Airlines
Dec 22
ORD6:04 pmChicago O'Hare Intl
2h 38m
JAX9:42 pmJacksonville
Jan 7
JAX1:45 pmJacksonville
5h 52m
1 stop
ORD6:37 pmChicago O'Hare Intl
$286
Find similar
United Airlines
Dec 9
ORD8:45 amChicago O'Hare Intl
5h 13m
1 stop
JAX2:58 pmJacksonville
Dec 19
JAX11:40 amJacksonville
2h 56m
ORD1:36 pmChicago O'Hare Intl
$290
Find similar
United Airlines
Dec 16
ORD1:05 pmChicago O'Hare Intl
6h 05m
1 stop
JAX8:10 pmJacksonville
Dec 25
JAX11:40 amJacksonville
2h 46m
ORD1:26 pmChicago O'Hare Intl
$297
Find similar

JetBlue flights from Chicago to Jacksonville

Our best JetBlue deals on Chicago to Jacksonville flight tickets
JetBlue
Dec 8
ORD8:38 pmChicago O'Hare Intl
12h 29m
1 stop
JAX10:07 amJacksonville
Dec 15
JAX10:40 amJacksonville
12h 12m
1 stop
ORD9:52 pmChicago O'Hare Intl
$294
Find similar
JetBlue
Dec 5
ORD8:38 pmChicago O'Hare Intl
12h 49m
1 stop
JAX10:27 amJacksonville
Dec 7
JAX10:52 amJacksonville
24h 43m
1 stop
ORD10:35 amChicago O'Hare Intl
$296
Find similar
JetBlue
Dec 3
ORD7:00 amChicago O'Hare Intl
13h 51m
1 stop
JAX9:51 pmJacksonville
Dec 8
JAX6:38 pmJacksonville
28h 14m
1 stop
ORD9:52 pmChicago O'Hare Intl
$302
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 noviembre 19, 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

vie. 12/19

5:15 am-9:20 pm

1 stop15h 05m

Jacksonville

lun. 1/12

6:27 pm-10:39 pm

1 stop5h 12m

$283

ChicagoJacksonville

MDW - JAX

MDWJAX

Chicago Midway

mar. 2/17

1:35 pm-9:15 pm

2 stops6h 40m

Jacksonville

lun. 2/23

6:00 pm-7:30 pm

Nonstop2h 30m

$284

ChicagoJacksonville

ORD - JAX

ORDJAX

Chicago O'Hare Intl

vie. 12/12

6:11 am-5:40 pm

1 stop10h 29m

Jacksonville

dom. 12/14

10:00 pm-11:57 pm

2 stops26h 57m

$285

ChicagoJacksonville

ORD - JAX

ORDJAX

Chicago O'Hare Intl

lun. 12/22

6:04 pm-9:42 pm

Nonstop2h 38m

Jacksonville

mié. 1/7

1:45 pm-6:37 pm

1 stop5h 52m

$286

ChicagoJacksonville

ORD - JAX

ORDJAX

Chicago O'Hare Intl

mar. 12/9

8:20 am-11:55 am

Nonstop2h 35m

Jacksonville

mié. 12/10

6:49 am-8:41 am

Nonstop2h 52m

$287

ChicagoJacksonville

MDW - JAX

MDWJAX

Chicago Midway

mar. 12/16

1:45 pm-5:00 pm

Nonstop2h 15m

Jacksonville

jue. 12/25

5:05 pm-6:30 pm

Nonstop2h 25m

$287

ChicagoJacksonville

ORD - JAX

ORDJAX

Chicago O'Hare Intl

sáb. 12/13

1:16 pm-8:40 pm

1 stop6h 24m

Jacksonville

mié. 12/17

8:20 am-12:03 pm

1 stop4h 43m

$288

ChicagoJacksonville

ORD - JAX

ORDJAX

Chicago O'Hare Intl

mar. 2/17

6:45 am-12:19 pm

1 stop4h 34m

Jacksonville

lun. 2/23

7:03 pm-11:49 pm

1 stop5h 46m

$289

ChicagoJacksonville

ORD - JAX

ORDJAX

Chicago O'Hare Intl

mar. 12/9

8:45 am-2:58 pm

1 stop5h 13m

Jacksonville

vie. 12/19

11:40 am-1:36 pm

Nonstop2h 56m

$290

ChicagoJacksonville

MDW - JAX

MDWJAX

Chicago Midway

jue. 1/1

6:12 am-7:41 pm

2 stops36h 29m

Jacksonville

lun. 1/5

5:23 pm-10:12 pm

1 stop5h 49m

$294

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
1
2

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 $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 $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 $423.

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 $323 when looking at flights departing at noon. Flights to Jacksonville are more costly in the evening, with an average ticket price of $429. 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 $376 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 $328 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 17% 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 November 2025, prices for Chicago to Jacksonville flights are approximately 65% 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

$157

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 $157. The best round-trip flight deal from Chicago to Jacksonville found on momondo in the last 72 hours is $312.
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
3,105 reviews
Search Frontier flights
DeltaPriceFrom $144Free CancellationRating
7.9
8,002 reviews
Search Delta flights
American AirlinesPriceFrom $176Free CancellationRating
7.2
11,045 reviews
Search American Airlines flights
SouthwestPriceFrom $198Free CancellationRating
8.0
4,248 reviews
Search Southwest flights
United AirlinesPriceFrom $255Free CancellationRating
7.4
9,019 reviews
Search United Airlines flights
JetBluePriceFrom $265Free CancellationRating
7.2
2,902 reviews
Search JetBlue flights

  • Southwest Flights From Chicago to Jacksonville

    Southwest flies from Chicago to Jacksonville around 4 times per week, with 4,248 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 $414 round-trip. United Airlines operates 17 flights out of Chicago into Jacksonville in an average week, so prices vary by time and availability. 9,020 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.
Start using Trips
Find my bookings

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.
1 adult
vie. 12/19
vie. 12/26
By creating a price alert you accept our terms of use and privacy policy.

Find better results for your trip to the United States