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Cheap flights from Jacksonville, North Carolina to Chicago from $297

This is the cheapest round-trip flight price found by a momondo user in the last 72 hours by searching for a flight from Jacksonville, North Carolina to Chicago departing on 8/27. 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 Jacksonville, North Carolina to Chicago

Cheap round-trip flights

American Airlines Logo
7:17 pm - 10:59 pmOAJ-ORD
4h 42m1 stop
American Airlines Logo
8:35 am - 2:16 pmORD-OAJ
4h 41m1 stop
$297American Airlines
Find Deal
Wed, Aug 27 - Sat, Aug 30
Delta Logo
6:25 pm - 11:53 pmOAJ-ORD
6h 28m1 stop
Delta Logo
7:10 am - 1:40 pmORD-OAJ
5h 30m1 stop
$331Delta
Find Deal
Thu, Dec 4 - Mon, Dec 8
Delta Logo
6:43 pm - 11:58 pmOAJ-ORD
6h 15m1 stop
Delta Logo
5:50 am - 11:10 amORD-OAJ
4h 20m1 stop
$342Delta
Find Deal
Fri, Jan 2 - Tue, Jan 6
American Airlines Logo
6:10 am - 9:49 amOAJ-ORD
4h 39m1 stop
American Airlines Logo
6:25 pm - 11:48 pmORD-OAJ
4h 23m1 stop
$343American Airlines
Find Deal
Wed, Aug 27 - Fri, Aug 29
Delta Logo
6:53 pm - 10:14 pmOAJ-MDW
4h 21m1 stop
Delta Logo
6:00 am - 11:13 amMDW-OAJ
4h 13m1 stop
$356Delta
Find Deal
Sun, Oct 19 - Wed, Oct 22
Delta Logo
5:40 am - 10:03 amOAJ-ORD
5h 23m1 stop
Delta Logo
7:10 am - 1:40 pmORD-OAJ
5h 30m1 stop
$359Delta
Find Deal
Thu, Dec 4 - Sun, Dec 7
Delta Logo
6:53 pm - 10:14 pmOAJ-MDW
4h 21m1 stop
Delta Logo
6:00 am - 11:13 amMDW-OAJ
4h 13m1 stop
$365Delta
Find Deal
Mon, Oct 13 - Thu, Oct 16
American Airlines Logo
8:01 am - 2:10 pmOAJ-ORD
7h 09m1 stop
American Airlines Logo
8:09 am - 5:35 pmORD-OAJ
8h 26m2 stops
$377American Airlines
Find Deal
Wed, Aug 27 - Sat, Aug 30
American Airlines Logo
8:03 pm - 11:53 pmOAJ-ORD
4h 50m1 stop
American Airlines Logo
7:10 am - 1:16 pmORD-OAJ
5h 06m1 stop
$387American Airlines
Find Deal
Fri, Oct 10 - Sun, Oct 12
Delta Logo
6:53 pm - 11:57 pmOAJ-ORD
6h 04m1 stop
Delta Logo
5:20 am - 11:13 amORD-OAJ
4h 53m1 stop
$395Delta
Find Deal
Sun, Oct 19 - Wed, Oct 22

American Airlines flights from Jacksonville, North Carolina to Chicago

Our best American Airlines deals on Jacksonville, North Carolina to Chicago flight tickets
American Airlines
Aug 27
OAJ7:17 pmJacksonville Albert J Ellis
4h 42m
1 stop
ORD10:59 pmChicago O'Hare Intl
Aug 30
ORD8:35 amChicago O'Hare Intl
4h 41m
1 stop
OAJ2:16 pmJacksonville Albert J Ellis
$297
Find similar
American Airlines
Aug 27
OAJ6:10 amJacksonville Albert J Ellis
4h 39m
1 stop
ORD9:49 amChicago O'Hare Intl
Aug 29
ORD6:25 pmChicago O'Hare Intl
4h 23m
1 stop
OAJ11:48 pmJacksonville Albert J Ellis
$343
Find similar
American Airlines
Aug 27
OAJ8:01 amJacksonville Albert J Ellis
7h 09m
1 stop
ORD2:10 pmChicago O'Hare Intl
Aug 30
ORD8:09 amChicago O'Hare Intl
8h 26m
2 stops
OAJ5:35 pmJacksonville Albert J Ellis
$377
Find similar

Delta flights from Jacksonville, North Carolina to Chicago

Our best Delta deals on Jacksonville, North Carolina to Chicago flight tickets
Delta
Dec 4
OAJ6:25 pmJacksonville Albert J Ellis
6h 28m
1 stop
ORD11:53 pmChicago O'Hare Intl
Dec 8
ORD7:10 amChicago O'Hare Intl
5h 30m
1 stop
OAJ1:40 pmJacksonville Albert J Ellis
$331
Find similar
Delta
Jan 2
OAJ6:43 pmJacksonville Albert J Ellis
6h 15m
1 stop
ORD11:58 pmChicago O'Hare Intl
Jan 6
ORD5:50 amChicago O'Hare Intl
4h 20m
1 stop
OAJ11:10 amJacksonville Albert J Ellis
$342
Find similar
Delta
Oct 19
OAJ6:53 pmJacksonville Albert J Ellis
4h 21m
1 stop
MDW10:14 pmChicago Midway
Oct 22
MDW6:00 amChicago Midway
4h 13m
1 stop
OAJ11:13 amJacksonville Albert J Ellis
$356
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from Jacksonville, North Carolina to Chicago 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 31, 2025.
Use the filters below to find and compare flights from Jacksonville, North Carolina to Chicago that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

JacksonvilleChicago

OAJ - ORD

OAJORD

Jacksonville Albert J Ellis

Wed 8/27

7:17 pm-10:59 pm

1 stop4h 42m

Chicago O'Hare Intl

Sat 8/30

8:35 am-2:16 pm

1 stop4h 41m

$297

JacksonvilleChicago

OAJ - ORD

OAJORD

Jacksonville Albert J Ellis

Thu 12/4

6:25 pm-11:53 pm

1 stop6h 28m

Chicago O'Hare Intl

Mon 12/8

7:10 am-1:40 pm

1 stop5h 30m

$331

JacksonvilleChicago

OAJ - ORD

OAJORD

Jacksonville Albert J Ellis

Fri 1/2

6:43 pm-11:58 pm

1 stop6h 15m

Chicago O'Hare Intl

Tue 1/6

5:50 am-11:10 am

1 stop4h 20m

$342

JacksonvilleChicago

OAJ - ORD

OAJORD

Jacksonville Albert J Ellis

Wed 8/27

6:10 am-9:49 am

1 stop4h 39m

Chicago O'Hare Intl

Fri 8/29

6:25 pm-11:48 pm

1 stop4h 23m

$343

JacksonvilleChicago

OAJ - MDW

OAJMDW

Jacksonville Albert J Ellis

Sun 10/19

6:53 pm-10:14 pm

1 stop4h 21m

Chicago Midway

Wed 10/22

6:00 am-11:13 am

1 stop4h 13m

$356

JacksonvilleChicago

OAJ - ORD

OAJORD

Jacksonville Albert J Ellis

Thu 12/4

5:40 am-10:03 am

1 stop5h 23m

Chicago O'Hare Intl

Sun 12/7

7:10 am-1:40 pm

1 stop5h 30m

$359

JacksonvilleChicago

OAJ - MDW

OAJMDW

Jacksonville Albert J Ellis

Mon 10/13

6:53 pm-10:14 pm

1 stop4h 21m

Chicago Midway

Thu 10/16

6:00 am-11:13 am

1 stop4h 13m

$365

JacksonvilleChicago

OAJ - ORD

OAJORD

Jacksonville Albert J Ellis

Wed 8/27

8:01 am-2:10 pm

1 stop7h 09m

Chicago O'Hare Intl

Sat 8/30

8:09 am-5:35 pm

2 stops8h 26m

$377

JacksonvilleChicago

OAJ - ORD

OAJORD

Jacksonville Albert J Ellis

Fri 10/10

8:03 pm-11:53 pm

1 stop4h 50m

Chicago O'Hare Intl

Sun 10/12

7:10 am-1:16 pm

1 stop5h 06m

$387

JacksonvilleChicago

OAJ - ORD

OAJORD

Jacksonville Albert J Ellis

Sun 10/19

6:53 pm-11:57 pm

1 stop6h 04m

Chicago O'Hare Intl

Wed 10/22

5:20 am-11:13 am

1 stop4h 53m

$395

Flights are sorted by cheapest round-trip flights first.

Sorted by cheapest first

When to book flights from Jacksonville, North Carolina to Chicago

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

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

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

Best Price Found

$297

Fastest flight time

4h 05m

Direct flights

None

Airports in Chicago

2 airports
The best flight deal from Jacksonville, North Carolina to Chicago found on momondo in the last 72 hours is $297
The fastest flight from Jacksonville, North Carolina to Chicago takes 4h 05m
There are no direct flights from Jacksonville, North Carolina to Chicago. Popular non-direct routes for this connection are Jacksonville Albert J Ellis Airport - Chicago O'Hare Intl Airport and Jacksonville Albert J Ellis Airport - Chicago Midway Airport.
There are 2 airports near Chicago: Chicago O'Hare Intl (ORD), Chicago Midway (MDW)
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  • How far is Jacksonville Albert J Ellis to Chicago by plane?

    The distance between Jacksonville Albert J Ellis and Chicago is about 738.6 mi. A reasonable flight in good conditions will take 4h 05m.

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

    Prices for flights from Jacksonville Albert J Ellis Airport to Chicago are updated daily.

  • How many operators does momondo search for flights from Jacksonville Albert J Ellis Airport to Chicago?

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

    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 Jacksonville Albert J Ellis Airport to Chicago.

  • What documentation or ID do you need to fly to Chicago?

    The necessary travel and health documents for your Chicago trip may vary depending on your travel plans and individual circumstances. Generally, you should have various documents, such as a national ID card or driver's license and a passport that is valid for six months beyond your scheduled arrival date. We recommend seeking advice from your airline or a trusted third party, such as IATA.

Best airlines flying from Jacksonville, North Carolina to Chicago

Compare and see reviews for airlines that fly from Jacksonville, North Carolina to Chicago with momondo
Airline
Rating
Free Cancellation
Price
American AirlinesPriceFrom $336Free CancellationRating
7.2
10,000 reviews
Search American Airlines flights

  • How do I get Price Alerts for flights from Jacksonville, North Carolina to Chicago?

    You can take advantage of momondo’s Price Alerts by first searching for your flights to Jacksonville, North Carolina from Chicago. Flight offers will be shown to you in real-time. From there you can create a Price Alert by using our on-site widget.

  • How can I save money on flights from Jacksonville, North Carolina to Chicago with momondo?

    With “Price Forecast”, learn how soon you should book your flight in advance. Down to the day of week and time of day, our information can inform you on the ideal time to book to save on your travel. Our “Price Calendar” shows you at a quick glance when to book your travel for lower rates. By setting “Price Alerts” you can monitor changes in price and target the ideal time to book. Search for your trip destination by budget amount via our “Explore” feature. Whether you’re looking for ideas for your next travel adventure or cost-cutting tips, our “Discover” content is a great place to start.

  • How does momondo find its flight prices?

    momondo shows deals across 700+ competitors all at once. momondo is active in 30 international markets, so you can have access to a wide range of options from airlines and OTAs alike.

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
New Buffalo
Hammond
Benton Harbor
Saint Joseph
Portage
Lansing
Schererville
Valparaiso
Crown Point
Munster
Chesterton
Monticello
Porter
Griffith
Saint John

Why use momondo?

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

It is quick and easy to find Jacksonville to Chicago flights on momondo. We search and return numerous flight options from various airlines and agents. You can then use our filters to narrow your search until you have found the most convenient flight to Chicago that suits you.

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

Flights from Jacksonville to Chicago with flexible booking policies can be found by using the search form above and then selecting our dedicated flexible booking filter, which will highlight only the flights where this policy is applied.

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

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 Jacksonville to Chicago.

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

If you are not ready to book a flight from Jacksonville to Chicago now, use our insights above to find helpful tips or alternatively set up a price alert, where momondo will track prices on flights to Chicago and let you know when they change.

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Find better results for your trip to the United States

Fly into one of these airports located in Chicago

Airports listed have a maximum distance of 78.5 mi from Chicago
Chicago Midway Airport
Chicago O'Hare Intl Airport
Chicago Greater Rockford Airport