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Cheap flights from Chicago to Jacksonville from $219

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 9/25. 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
1 adult, Economy, 0 bags

Find the cheapest flights from Chicago to Jacksonville

Cheap round-trip flights

Enter your travel dates to find the best prices.
Delta Logo
6:05 am - 1:41 pm
MDW
-
OAJ
6h 36m
1 stop
Delta Logo
4:15 pm - 10:44 pm
OAJ
-
MDW
7h 29m
1 stop
$389Delta
Tue, Sep 15 - Sat, Sep 19
Delta Logo
6:05 am - 11:15 am
MDW
-
OAJ
4h 10m
1 stop
Delta Logo
6:00 am - 11:54 am
OAJ
-
MDW
6h 54m
1 stop
$389Delta
Tue, Sep 8 - Tue, Sep 15
American Airlines Logo
11:50 am - 6:50 pm
ORD
-
OAJ
6h 00m
1 stop
American Airlines Logo
7:20 pm - 12:01 am
OAJ
-
ORD
5h 41m
1 stop
$389American Airlines
Wed, Sep 9 - Sat, Sep 12
American Airlines Logo
5:20 am - 1:27 pm
ORD
-
OAJ
7h 07m
1 stop
American Airlines Logo
7:20 pm - 10:31 pm
OAJ
-
ORD
4h 11m
1 stop
$389American Airlines
Thu, Sep 10 - Sat, Sep 12
American Airlines Logo
11:50 am - 6:50 pm
ORD
-
OAJ
6h 00m
1 stop
American Airlines Logo
7:20 pm - 12:01 am
OAJ
-
ORD
5h 41m
1 stop
$389American Airlines
Tue, Sep 15 - Sat, Sep 19
Delta Logo
8:05 am - 3:20 pm
ORD
-
OAJ
6h 15m
1 stop
Delta Logo
4:15 pm - 8:56 pm
OAJ
-
ORD
5h 41m
1 stop
$389Delta
Sat, Sep 5 - Sat, Sep 12
Delta Logo
5:30 am - 11:15 am
ORD
-
OAJ
4h 45m
1 stop
Delta Logo
6:50 pm - 11:59 pm
OAJ
-
ORD
6h 09m
1 stop
$389Delta
Tue, Sep 8 - Tue, Sep 15
Delta Logo
8:05 am - 3:20 pm
ORD
-
OAJ
6h 15m
1 stop
Delta Logo
4:15 pm - 8:56 pm
OAJ
-
ORD
5h 41m
1 stop
$389Delta
Sat, Sep 5 - Sat, Sep 12
Delta Logo
5:11 pm - 10:22 pm
MDW
-
OAJ
4h 11m
1 stop
Delta Logo
6:00 am - 12:39 pm
OAJ
-
MDW
7h 39m
2 stops
$394Delta
Tue, Sep 15 - Sat, Sep 19
Delta Logo
6:05 am - 11:15 am
MDW
-
OAJ
4h 10m
1 stop
Delta Logo
6:00 am - 12:39 pm
OAJ
-
MDW
7h 39m
2 stops
$394Delta
Tue, Sep 8 - Tue, Sep 15

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Delta flights from Chicago to Jacksonville, North Carolina

Our best Delta deals on Chicago to Jacksonville, North Carolina flight tickets
Delta
Sep 8
MDW6:05 amChicago Midway
4h 10m
1 stop
OAJ11:15 amJacksonville Albert J Ellis
Sep 15
OAJ6:00 amJacksonville Albert J Ellis
6h 54m
1 stop
MDW11:54 amChicago Midway
$389
Delta
Sep 8
MDW6:05 amChicago Midway
4h 10m
1 stop
OAJ11:15 amJacksonville Albert J Ellis
Sep 15
OAJ6:00 amJacksonville Albert J Ellis
7h 39m
2 stops
MDW12:39 pmChicago Midway
$394
Delta
Sep 5
ORD6:00 amChicago O'Hare Intl
8h 20m
2 stops
OAJ3:20 pmJacksonville Albert J Ellis
Sep 12
OAJ6:00 amJacksonville Albert J Ellis
12h 03m
2 stops
ORD5:03 pmChicago O'Hare Intl
$399

American Airlines flights from Chicago to Jacksonville, North Carolina

Our best American Airlines deals on Chicago to Jacksonville, North Carolina flight tickets
American Airlines
Aug 28
ORD7:30 amChicago O'Hare Intl
4h 55m
1 stop
OAJ1:25 pmJacksonville Albert J Ellis
Aug 29
OAJ8:02 amJacksonville Albert J Ellis
7h 20m
1 stop
ORD2:22 pmChicago O'Hare Intl
$413
American Airlines
Aug 24
ORD6:49 amChicago O'Hare Intl
5h 36m
1 stop
OAJ1:25 pmJacksonville Albert J Ellis
Aug 28
OAJ7:09 pmJacksonville Albert J Ellis
5h 43m
1 stop
ORD11:52 pmChicago O'Hare Intl
$437
American Airlines
Aug 21
ORD11:53 amChicago O'Hare Intl
5h 45m
1 stop
OAJ6:38 pmJacksonville Albert J Ellis
Aug 25
OAJ7:09 pmJacksonville Albert J Ellis
5h 43m
1 stop
ORD11:52 pmChicago O'Hare Intl
$477

momondo Fare Finder

 
Customize your flight search to find flights from Chicago to Jacksonville, North Carolina 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 July 30, 2026.
Use the filters below to find and compare flights from Chicago to Jacksonville, North Carolina that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

ChicagoJacksonville

MDW - OAJ

MDWOAJ

Chicago Midway

Tue 9/15

6:05 am-1:41 pm

1 stop6h 36m

Jacksonville Albert J Ellis

Sat 9/19

4:15 pm-10:44 pm

1 stop7h 29m

$389

ChicagoJacksonville

MDW - OAJ

MDWOAJ

Chicago Midway

Tue 9/8

6:05 am-11:15 am

1 stop4h 10m

Jacksonville Albert J Ellis

Tue 9/15

6:00 am-11:54 am

1 stop6h 54m

$389

ChicagoJacksonville

ORD - OAJ

ORDOAJ

Chicago O'Hare Intl

Wed 9/9

11:50 am-6:50 pm

1 stop6h 00m

Jacksonville Albert J Ellis

Sat 9/12

7:20 pm-12:01 am

1 stop5h 41m

$389

ChicagoJacksonville

ORD - OAJ

ORDOAJ

Chicago O'Hare Intl

Thu 9/10

5:20 am-1:27 pm

1 stop7h 07m

Jacksonville Albert J Ellis

Sat 9/12

7:20 pm-10:31 pm

1 stop4h 11m

$389

ChicagoJacksonville

ORD - OAJ

ORDOAJ

Chicago O'Hare Intl

Tue 9/15

11:50 am-6:50 pm

1 stop6h 00m

Jacksonville Albert J Ellis

Sat 9/19

7:20 pm-12:01 am

1 stop5h 41m

$389

ChicagoJacksonville

ORD - OAJ

ORDOAJ

Chicago O'Hare Intl

Sat 9/5

8:05 am-3:20 pm

1 stop6h 15m

Jacksonville Albert J Ellis

Sat 9/12

4:15 pm-8:56 pm

1 stop5h 41m

$389
Quickest round-trip

ChicagoJacksonville

ORD - OAJ

ORDOAJ

Chicago O'Hare Intl

Tue 9/8

5:30 am-11:15 am

1 stop4h 45m

Jacksonville Albert J Ellis

Tue 9/15

6:50 pm-11:59 pm

1 stop6h 09m

$389

ChicagoJacksonville

ORD - OAJ

ORDOAJ

Chicago O'Hare Intl

Sat 9/5

8:05 am-3:20 pm

1 stop6h 15m

Jacksonville Albert J Ellis

Sat 9/12

4:15 pm-8:56 pm

1 stop5h 41m

$389

ChicagoJacksonville

MDW - OAJ

MDWOAJ

Chicago Midway

Tue 9/15

5:11 pm-10:22 pm

1 stop4h 11m

Jacksonville Albert J Ellis

Sat 9/19

6:00 am-12:39 pm

2 stops7h 39m

$394

ChicagoJacksonville

MDW - OAJ

MDWOAJ

Chicago Midway

Tue 9/8

6:05 am-11:15 am

1 stop4h 10m

Jacksonville Albert J Ellis

Tue 9/15

6:00 am-12:39 pm

2 stops7h 39m

$394

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 14 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, North Carolina

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

Can stopping save me money on Chicago to Jacksonville, North Carolina flights?

You could potentially save up to 33% on your flight if you consider stops on a Chicago to Jacksonville, North Carolina flight.

When to book flights from Chicago to Jacksonville, North Carolina

Are you open to changing your travel dates? Check out the ideal times to fly from Chicago to Jacksonville, North Carolina according to our flight data. Find out which month and days have the cheapest flights.
Estimated round-trip price

Cheap Chicago to Jacksonville, North Carolina (CHI to OAJ) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Chicago to Jacksonville, North Carolina

Fastest flight time

4h 19m

Direct flights

None
The fastest flight from Chicago to Jacksonville, North Carolina takes 4h 19m
There are no direct flights from Chicago to Jacksonville, North Carolina. There are no popular flight routes from Chicago to Jacksonville, North Carolina.
Search flight deals

Frequently asked questions about flying from Chicago to Jacksonville, North Carolina

  • How far is Chicago to Jacksonville Albert J Ellis by plane?

    Chicago and Jacksonville Albert J Ellis are 738.6 mi apart from one another. Flights usually cover this in 4h 19m, depending on flying conditions and air traffic around both airports.

  • When did momondo last update prices for flights from Chicago to Jacksonville Albert J Ellis Airport?

    Prices for flights from Chicago to Jacksonville Albert J Ellis Airport are refreshed on a daily basis.

  • How old do you have to be to fly from Chicago to Jacksonville Albert J Ellis 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 Albert J Ellis Airport.

  • What documentation or ID do you need to fly to Jacksonville Albert J Ellis Airport?

    The travel and health documents required for your trip to Jacksonville Albert J Ellis Airport can vary based on your itinerary and personal situation. As a rule, consider having multiple documents such as a national ID card or driver’s license, and a passport valid for six-months after you plan to arrive at Jacksonville Albert J Ellis Airport. We always recommend checking with your airline or a trusted third party such as IATA to get advice.

Traveling to a place near Jacksonville?

Book flights to Jacksonville if you plan to visit one of these locations
North Topsail Beach

Why use momondo?

Why should I use momondo to find a flight deal from Chicago to Jacksonville?

Finding the right flight to Jacksonville from Chicago is quick and easy when you have a range of options in front of you, from reputable agents and recognisable airlines. Options that can then be filtered down to find the best fit. That is what momondo does. We make finding flights to Jacksonville quick and easy, saving you time and money.

Can I find flights from Chicago to Jacksonville with flexible booking policies on momondo?

Yes. All flights to Jacksonville from Chicago on momondo can be compared and filtered by various policies on offer, including flexible booking.

How can momondo help me find flights from Chicago to Jacksonville?

momondo offers useful filters to help you find the right flight. Choose specific flight times, airports or even what payment method you prefer. We have numerous options to help you book your ideal flight from Chicago to Jacksonville.

I’m not ready to book a flight from Chicago to Jacksonville right now. Can momondo alert me if prices change?

Yes. momondo can track prices for Chicago to Jacksonville flights and alert you when they change. Perform a search to set up the price alert. All that is required is a valid email address.

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