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Cheap flights from Jacksonville, North Carolina to Chicago from $324

This is the cheapest one-way 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 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

Discover deals from 900+ travel sites with momondo.

Find the cheapest flights from Jacksonville, North Carolina to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
Delta Logo
6:50 pm - 10:44 pmOAJ  Jacksonville Albert J Ellis-MDW Chicago Midway
4h 54m1 stop Atlanta Hartsfield-Jackson
Delta Logo
6:04 am - 11:10 amMDW  Chicago Midway-OAJ Jacksonville Albert J Ellis
4h 06m1 stop Atlanta Hartsfield-Jackson
$389Delta
Wed, Sep 30 - Sat, Oct 10
Delta Logo
12:00 pm - 6:33 pmOAJ  Jacksonville Albert J Ellis-MDW Chicago Midway
7h 33m2 stops Atlanta Hartsfield-Jackson Detroit Metropolitan Wayne County
Delta Logo
6:04 am - 11:10 amMDW  Chicago Midway-OAJ Jacksonville Albert J Ellis
4h 06m1 stop Atlanta Hartsfield-Jackson
$394Delta
Wed, Sep 30 - Sat, Oct 10
Delta Logo
12:00 pm - 6:33 pmOAJ  Jacksonville Albert J Ellis-MDW Chicago Midway
7h 33m2 stops Atlanta Hartsfield-Jackson Detroit Metropolitan Wayne County
Delta Logo
1:27 pm - 10:22 pmMDW  Chicago Midway-OAJ Jacksonville Albert J Ellis
7h 55m2 stops Detroit Metropolitan Wayne County Atlanta Hartsfield-Jackson
$399Delta
Wed, Sep 30 - Sat, Oct 10
Delta Logo
4:06 pm - 10:33 pmOAJ  Jacksonville Albert J Ellis-MDW Chicago Midway
7h 27m1 stop Atlanta Hartsfield-Jackson
Delta Logo
6:04 am - 1:51 pmMDW  Chicago Midway-OAJ Jacksonville Albert J Ellis
6h 47m1 stop Atlanta Hartsfield-Jackson
$423Delta
Sat, Oct 10 - Sun, Oct 11
Delta Logo
6:34 pm - 10:45 pmOAJ  Jacksonville Albert J Ellis-MDW Chicago Midway
5h 11m1 stop Atlanta Hartsfield-Jackson
Delta Logo
4:30 pm - 10:22 pmMDW  Chicago Midway-OAJ Jacksonville Albert J Ellis
4h 52m1 stop Atlanta Hartsfield-Jackson
$423Delta
Thu, Sep 17 - Sat, Sep 19
Delta Logo
4:15 pm - 10:36 pmOAJ  Jacksonville Albert J Ellis-MDW Chicago Midway
7h 21m1 stop Atlanta Hartsfield-Jackson
Delta Logo
6:05 am - 11:15 amMDW  Chicago Midway-OAJ Jacksonville Albert J Ellis
4h 10m1 stop Atlanta Hartsfield-Jackson
$423Delta
Sat, Sep 5 - Fri, Sep 11
Delta Logo
4:15 pm - 10:44 pmOAJ  Jacksonville Albert J Ellis-MDW Chicago Midway
7h 29m1 stop Atlanta Hartsfield-Jackson
Delta Logo
6:05 am - 1:41 pmMDW  Chicago Midway-OAJ Jacksonville Albert J Ellis
6h 36m1 stop Atlanta Hartsfield-Jackson
$423Delta
Sat, Sep 12 - Mon, Sep 21
Delta Logo
11:58 am - 6:32 pmOAJ  Jacksonville Albert J Ellis-ORD Chicago O'Hare Intl
7h 34m1 stop Atlanta Hartsfield-Jackson
Delta Logo
3:00 pm - 10:15 pmORD  Chicago O'Hare Intl-OAJ Jacksonville Albert J Ellis
6h 15m1 stop Atlanta Hartsfield-Jackson
$423Delta
Sat, Jan 16 - Fri, Jan 22
American Airlines Logo
6:12 pm - 11:00 pmOAJ  Jacksonville Albert J Ellis-ORD Chicago O'Hare Intl
5h 48m1 stop Charlotte Douglas
American Airlines Logo
6:29 am - 12:17 pmORD  Chicago O'Hare Intl-OAJ Jacksonville Albert J Ellis
4h 48m1 stop Charlotte Douglas
$477American Airlines
Mon, Oct 12 - Sun, Oct 18
American Airlines Logo
8:19 pm - 12:08 amOAJ  Jacksonville Albert J Ellis-ORD Chicago O'Hare Intl
4h 49m1 stop Charlotte Douglas
American Airlines Logo
5:00 am - 12:17 pmORD  Chicago O'Hare Intl-OAJ Jacksonville Albert J Ellis
6h 17m1 stop Charlotte Douglas
$477American Airlines
Mon, Oct 12 - Mon, Oct 19

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American Airlines flights from Jacksonville, North Carolina to Chicago

Our best American Airlines deals on Jacksonville, North Carolina to Chicago flight tickets
American Airlines
Oct 12
OAJ6:12 pmJacksonville Albert J Ellis
5h 48m
1 stop
ORD11:00 pmChicago O'Hare Intl
Oct 18
ORD6:29 amChicago O'Hare Intl
4h 48m
1 stop
OAJ12:17 pmJacksonville Albert J Ellis
$477
American Airlines
Oct 8
OAJ4:56 pmJacksonville Albert J Ellis
7h 04m
1 stop
ORD11:00 pmChicago O'Hare Intl
Oct 10
ORD9:02 amChicago O'Hare Intl
6h 29m
1 stop
OAJ4:31 pmJacksonville Albert J Ellis
$513
American Airlines
Oct 8
OAJ6:12 pmJacksonville Albert J Ellis
6h 56m
1 stop
ORD12:08 amChicago O'Hare Intl
Oct 11
ORD5:00 amChicago O'Hare Intl
6h 17m
1 stop
OAJ12:17 pmJacksonville Albert J Ellis
$557

Delta flights from Jacksonville, North Carolina to Chicago

Our best Delta deals on Jacksonville, North Carolina to Chicago flight tickets
Delta
Sep 30
OAJ6:50 pmJacksonville Albert J Ellis
4h 54m
1 stop
MDW10:44 pmChicago Midway
Oct 10
MDW6:04 amChicago Midway
4h 06m
1 stop
OAJ11:10 amJacksonville Albert J Ellis
$389
Delta
Sep 30
OAJ12:00 pmJacksonville Albert J Ellis
7h 33m
2 stops
MDW6:33 pmChicago Midway
Oct 10
MDW6:04 amChicago Midway
4h 06m
1 stop
OAJ11:10 amJacksonville Albert J Ellis
$394
Delta
Sep 30
OAJ12:00 pmJacksonville Albert J Ellis
7h 33m
2 stops
MDW6:33 pmChicago Midway
Oct 10
MDW1:27 pmChicago Midway
7h 55m
2 stops
OAJ10:22 pmJacksonville Albert J Ellis
$399

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 August 11, 2026.
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

Cheapest round-trip
Quickest round-trip

JacksonvilleChicago

OAJ Jacksonville Albert J Ellis - MDW Chicago Midway

OAJMDW

Jacksonville Albert J Ellis

Wed 9/30

6:50 pm-10:44 pm

1 stop4h 54m

Chicago Midway

Sat 10/10

6:04 am-11:10 am

1 stop4h 06m

$389

JacksonvilleChicago

OAJ Jacksonville Albert J Ellis - MDW Chicago Midway

OAJMDW

Jacksonville Albert J Ellis

Wed 9/30

12:00 pm-6:33 pm

2 stops7h 33m

Chicago Midway

Sat 10/10

6:04 am-11:10 am

1 stop4h 06m

$394

JacksonvilleChicago

OAJ Jacksonville Albert J Ellis - MDW Chicago Midway

OAJMDW

Jacksonville Albert J Ellis

Wed 9/30

12:00 pm-6:33 pm

2 stops7h 33m

Chicago Midway

Sat 10/10

1:27 pm-10:22 pm

2 stops7h 55m

$399

JacksonvilleChicago

OAJ Jacksonville Albert J Ellis - MDW Chicago Midway

OAJMDW

Jacksonville Albert J Ellis

Sat 10/10

4:06 pm-10:33 pm

1 stop7h 27m

Chicago Midway

Sun 10/11

6:04 am-1:51 pm

1 stop6h 47m

$423

JacksonvilleChicago

OAJ Jacksonville Albert J Ellis - MDW Chicago Midway

OAJMDW

Jacksonville Albert J Ellis

Thu 9/17

6:34 pm-10:45 pm

1 stop5h 11m

Chicago Midway

Sat 9/19

4:30 pm-10:22 pm

1 stop4h 52m

$423

JacksonvilleChicago

OAJ Jacksonville Albert J Ellis - MDW Chicago Midway

OAJMDW

Jacksonville Albert J Ellis

Sat 9/5

4:15 pm-10:36 pm

1 stop7h 21m

Chicago Midway

Fri 9/11

6:05 am-11:15 am

1 stop4h 10m

$423

JacksonvilleChicago

OAJ Jacksonville Albert J Ellis - MDW Chicago Midway

OAJMDW

Jacksonville Albert J Ellis

Sat 9/12

4:15 pm-10:44 pm

1 stop7h 29m

Chicago Midway

Mon 9/21

6:05 am-1:41 pm

1 stop6h 36m

$423

JacksonvilleChicago

OAJ Jacksonville Albert J Ellis - ORD Chicago O'Hare Intl

OAJORD

Jacksonville Albert J Ellis

Sat 1/16

11:58 am-6:32 pm

1 stop7h 34m

Chicago O'Hare Intl

Fri 1/22

3:00 pm-10:15 pm

1 stop6h 15m

$423

JacksonvilleChicago

OAJ Jacksonville Albert J Ellis - ORD Chicago O'Hare Intl

OAJORD

Jacksonville Albert J Ellis

Mon 10/12

6:12 pm-11:00 pm

1 stop5h 48m

Chicago O'Hare Intl

Sun 10/18

6:29 am-12:17 pm

1 stop4h 48m

$477

JacksonvilleChicago

OAJ Jacksonville Albert J Ellis - ORD Chicago O'Hare Intl

OAJORD

Jacksonville Albert J Ellis

Mon 10/12

8:19 pm-12:08 am

1 stop4h 49m

Chicago O'Hare Intl

Mon 10/19

5:00 am-12:17 pm

1 stop6h 17m

$477

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 Chicago from

How to get the cheapest flight ticket from Jacksonville, North Carolina to Chicago

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 airline that flies from Jacksonville Albert J Ellis to Chicago?

Delta and American Airlines are the most popular carriers operating from Jacksonville Albert J Ellis to Chicago

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

Fastest flight time

4h 48m

Direct flights

None
The fastest flight from Jacksonville, North Carolina to Chicago takes 4h 48m
There are no direct flights from Jacksonville, North Carolina to Chicago. There are no popular flight routes from Jacksonville, North Carolina to Chicago.
Search flight deals

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

  • 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 48m.

  • 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 $397Free CancellationRating
7.1
11,903 reviews
Search American Airlines flights

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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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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