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Cheap flights from Jacksonville, North Carolina to Chicago from $290

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 12/22. 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

Enter your travel dates to find the best prices.
Delta Logo
11:44 am - 3:23 pmOAJ-MDW
4h 39m1 stop
Delta Logo
6:17 pm - 6:00 pmMDW-OAJ
22h 43m2 stops
$356Delta
Find Deal
Sat, Feb 14 - Wed, Feb 18
Delta Logo
11:44 am - 3:23 pmOAJ-MDW
4h 39m1 stop
Delta Logo
12:46 pm - 1:35 pmMDW-OAJ
23h 49m1 stop
$381Delta
Find Deal
Sat, Feb 14 - Wed, Feb 18
Delta Logo
11:44 am - 3:23 pmOAJ-MDW
4h 39m1 stop
Delta Logo
6:17 pm - 6:00 pmMDW-OAJ
22h 43m2 stops
$385Delta
Find Deal
Sat, Feb 14 - Wed, Feb 18
Delta Logo
5:40 am - 4:16 pmOAJ-MDW
11h 36m2 stops
Delta Logo
9:34 am - 10:37 pmMDW-OAJ
12h 03m2 stops
$421Delta
Find Deal
Sat, Feb 14 - Wed, Feb 18
Delta Logo
5:30 am - 9:54 amOAJ-MDW
5h 24m1 stop
Delta Logo
6:00 am - 11:13 amMDW-OAJ
4h 13m1 stop
$435Delta
Find Deal
Sat, Dec 6 - Wed, Dec 10
Delta Logo
5:30 am - 9:54 amOAJ-MDW
5h 24m1 stop
Delta Logo
6:00 am - 11:13 amMDW-OAJ
4h 13m1 stop
$549Delta
Find Deal
Sun, Dec 7 - Thu, Dec 11
Delta Logo
5:40 am - 4:16 pmOAJ-MDW
11h 36m2 stops
Delta Logo
7:17 pm - 1:35 pmMDW-OAJ
17h 18m2 stops
$631Delta
Find Deal
Sat, Feb 14 - Wed, Feb 18
Delta Logo
11:53 am - 4:31 pmOAJ-MDW
5h 38m1 stop
Delta Logo
9:50 am - 6:02 pmMDW-OAJ
7h 12m1 stop
$638Delta
Find Deal
Fri, Dec 19 - Mon, Dec 29
Delta Logo
5:30 am - 12:34 pmOAJ-MDW
8h 04m2 stops
Delta Logo
6:00 am - 11:13 amMDW-OAJ
4h 13m1 stop
$950Delta
Find Deal
Sat, Dec 6 - Wed, Dec 10
Delta Logo
5:30 am - 12:34 pmOAJ-MDW
8h 04m2 stops
Delta Logo
6:00 am - 1:44 pmMDW-OAJ
6h 44m1 stop
$1,017Delta
Find Deal
Sun, Dec 7 - Thu, Dec 11

Delta flights from Jacksonville, North Carolina to Chicago Midway Airport

Our best Delta deals on Jacksonville, North Carolina to Chicago Midway Airport flight tickets
Delta
Feb 14
OAJ11:44 amJacksonville Albert J Ellis
4h 39m
1 stop
MDW3:23 pmChicago Midway
Feb 18
MDW6:17 pmChicago Midway
22h 43m
2 stops
OAJ6:00 pmJacksonville Albert J Ellis
$356
Find similar
Delta
Feb 14
OAJ11:44 amJacksonville Albert J Ellis
4h 39m
1 stop
MDW3:23 pmChicago Midway
Feb 18
MDW12:46 pmChicago Midway
23h 49m
1 stop
OAJ1:35 pmJacksonville Albert J Ellis
$381
Find similar
Delta
Feb 14
OAJ11:44 amJacksonville Albert J Ellis
4h 39m
1 stop
MDW3:23 pmChicago Midway
Feb 18
MDW6:17 pmChicago Midway
22h 43m
2 stops
OAJ6:00 pmJacksonville Albert J Ellis
$385
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from Jacksonville, North Carolina to Chicago Midway Airport 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 November 22, 2025.
Use the filters below to find and compare flights from Jacksonville, North Carolina to Chicago Midway Airport that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

JacksonvilleChicago

OAJ - MDW

OAJMDW

Jacksonville Albert J Ellis

Sat 2/14

11:44 am-3:23 pm

1 stop4h 39m

Chicago Midway

Wed 2/18

6:17 pm-6:00 pm

2 stops22h 43m

$356

JacksonvilleChicago

OAJ - MDW

OAJMDW

Jacksonville Albert J Ellis

Sat 2/14

11:44 am-3:23 pm

1 stop4h 39m

Chicago Midway

Wed 2/18

12:46 pm-1:35 pm

1 stop23h 49m

$381

JacksonvilleChicago

OAJ - MDW

OAJMDW

Jacksonville Albert J Ellis

Sat 2/14

11:44 am-3:23 pm

1 stop4h 39m

Chicago Midway

Wed 2/18

6:17 pm-6:00 pm

2 stops22h 43m

$385

JacksonvilleChicago

OAJ - MDW

OAJMDW

Jacksonville Albert J Ellis

Sat 2/14

5:40 am-4:16 pm

2 stops11h 36m

Chicago Midway

Wed 2/18

9:34 am-10:37 pm

2 stops12h 03m

$421

JacksonvilleChicago

OAJ - MDW

OAJMDW

Jacksonville Albert J Ellis

Sat 12/6

5:30 am-9:54 am

1 stop5h 24m

Chicago Midway

Wed 12/10

6:00 am-11:13 am

1 stop4h 13m

$435

JacksonvilleChicago

OAJ - MDW

OAJMDW

Jacksonville Albert J Ellis

Sun 12/7

5:30 am-9:54 am

1 stop5h 24m

Chicago Midway

Thu 12/11

6:00 am-11:13 am

1 stop4h 13m

$549

JacksonvilleChicago

OAJ - MDW

OAJMDW

Jacksonville Albert J Ellis

Sat 2/14

5:40 am-4:16 pm

2 stops11h 36m

Chicago Midway

Wed 2/18

7:17 pm-1:35 pm

2 stops17h 18m

$631

JacksonvilleChicago

OAJ - MDW

OAJMDW

Jacksonville Albert J Ellis

Fri 12/19

11:53 am-4:31 pm

1 stop5h 38m

Chicago Midway

Mon 12/29

9:50 am-6:02 pm

1 stop7h 12m

$638

JacksonvilleChicago

OAJ - MDW

OAJMDW

Jacksonville Albert J Ellis

Sat 12/6

5:30 am-12:34 pm

2 stops8h 04m

Chicago Midway

Wed 12/10

6:00 am-11:13 am

1 stop4h 13m

$950

JacksonvilleChicago

OAJ - MDW

OAJMDW

Jacksonville Albert J Ellis

Sun 12/7

5:30 am-12:34 pm

2 stops8h 04m

Chicago Midway

Thu 12/11

6:00 am-1:44 pm

1 stop6h 44m

$1,017

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 12 resultsSorted by cheapest first
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When to book flights from Jacksonville, North Carolina to Chicago Midway Airport

Are you open to changing your travel dates? Check out the ideal times to fly from Jacksonville, North Carolina to Chicago Midway Airport 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 Midway Airport (OAJ to MDW) flight deals and tips

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

Direct flights

None
There are no direct flights from Jacksonville, North Carolina to Chicago Midway Airport. There are no popular flight routes from Jacksonville, North Carolina to Chicago Midway Airport.
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  • How far is Jacksonville Albert J Ellis to Chicago Midway by plane?

    A flight from Jacksonville Albert J Ellis to Chicago Midway will travel around 739.6 mi. By plane, this route typically takes 4h 39m.

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

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

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

    The minimum age a child must be to fly alone is five but airlines that offer an unaccompanied minor (UNMR) service will have their own age restrictions, including rules around flight length, timings, and stopovers. We always recommend checking with the individual airline you are booking with to travel from Jacksonville Albert J Ellis Airport to Chicago Midway Airport.

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

    The necessary travel and health documents for your Chicago Midway Airport 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.

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

    Price Alerts will notify you by email when the price for flights to Chicago Midway Airport from Jacksonville, North Carolina decreases. To activate this, select your desired travel dates and search for offers. While browsing through offers you’ll see the Price Alert widget toggle. Click it to turn on notifications.

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

    Plan your trips smart with the “Price Forecast” feature, which uses flight data to help you pick the best days to fly for the lowest fares. Our “Price Calendar” helps you get the most for your money by showing you when it’s most advantageous to fly. Curate your own travel experiences for less with “Explore”. Expert travel hacks to fuel your next adventure are a click away with “Discover” by momondo. Set up our “Price Alerts” to track fare changes and book when prices are at their lowest point.

  • How does momondo find its flight prices?

    We show prices from over 700+ competitors with a single click. With options from airlines and OTAs from across our 30 international markets, we are able to show you a diverse range of deals to create your adventure.

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
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Saint John

Why use momondo?

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

Finding the right flight to Chicago from Jacksonville 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 Chicago quick and easy, saving you time and money.

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

Yes. momondo allows you to filter the results for Jacksonville to Chicago flights to just show those with flexible booking policies.

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

momondo provides multiple filters to help you find the best flight to Chicago from Jacksonville. Filter by price, airline, airports, cabin, aircraft, payment method, number of stops and more.

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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