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Cheap flights from Jacksonville, North Carolina to Chicago from $367

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 3/24. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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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
5:40 am - 9:56 amOAJ-MDW
5h 16m1 stop
Delta Logo
6:00 am - 11:10 amMDW-OAJ
4h 10m1 stop
$367Delta
Find Deal
mar., mar. 24 - sáb., mar. 28
Delta Logo
11:06 am - 4:25 pmOAJ-MDW
6h 19m1 stop
Delta Logo
6:00 am - 1:39 pmMDW-OAJ
6h 39m1 stop
$399Delta
Find Deal
mar., mar. 24 - sáb., mar. 28
Delta Logo
5:48 am - 9:40 amOAJ-MDW
4h 52m1 stop
Delta Logo
6:00 am - 2:21 pmMDW-OAJ
7h 21m1 stop
$467Delta
Find Deal
jue., oct. 16 - lun., oct. 20
Delta Logo
2:25 pm - 12:35 pmOAJ-MDW
23h 10m2 stops
Delta Logo
6:00 am - 1:39 pmMDW-OAJ
6h 39m1 stop
$489Delta
Find Deal
mar., mar. 24 - sáb., mar. 28
Delta Logo
5:40 am - 6:34 pmOAJ-MDW
13h 54m2 stops
Delta Logo
6:00 am - 1:39 pmMDW-OAJ
6h 39m1 stop
$498Delta
Find Deal
mar., mar. 24 - sáb., mar. 28
Delta Logo
5:40 am - 6:34 pmOAJ-MDW
13h 54m2 stops
Delta Logo
6:00 am - 11:10 amMDW-OAJ
4h 10m1 stop
$516Delta
Find Deal
mar., mar. 24 - sáb., mar. 28
Delta Logo
5:30 am - 9:54 amOAJ-MDW
5h 24m1 stop
Delta Logo
3:29 pm - 9:36 pmMDW-OAJ
5h 07m1 stop
$528Delta
Find Deal
dom., dic. 14 - mié., dic. 31
Delta Logo
4:30 pm - 10:14 pmOAJ-MDW
6h 44m1 stop
Delta Logo
6:00 am - 2:21 pmMDW-OAJ
7h 21m1 stop
$652Delta
Find Deal
mié., oct. 15 - dom., oct. 19
Delta Logo
6:53 pm - 10:14 pmOAJ-MDW
4h 21m1 stop
Delta Logo
1:08 pm - 10:43 pmMDW-OAJ
8h 35m2 stops
$945Delta
Find Deal
jue., oct. 16 - lun., oct. 20
Delta Logo
5:30 am - 9:52 amOAJ-MDW
5h 22m1 stop
Delta Logo
6:00 am - 1:46 pmMDW-OAJ
6h 46m1 stop
$959Delta
Find Deal
jue., nov. 27 - dom., nov. 30

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
Mar 24
OAJ5:40 amJacksonville Albert J Ellis
5h 16m
1 stop
MDW9:56 amChicago Midway
Mar 28
MDW6:00 amChicago Midway
4h 10m
1 stop
OAJ11:10 amJacksonville Albert J Ellis
$367
Find similar
Delta
Mar 24
OAJ11:06 amJacksonville Albert J Ellis
6h 19m
1 stop
MDW4:25 pmChicago Midway
Mar 28
MDW6:00 amChicago Midway
6h 39m
1 stop
OAJ1:39 pmJacksonville Albert J Ellis
$399
Find similar
Delta
Oct 16
OAJ5:48 amJacksonville Albert J Ellis
4h 52m
1 stop
MDW9:40 amChicago Midway
Oct 20
MDW6:00 amChicago Midway
7h 21m
1 stop
OAJ2:21 pmJacksonville Albert J Ellis
$467
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 octubre 2, 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

mar. 3/24

5:40 am-9:56 am

1 stop5h 16m

Chicago Midway

sáb. 3/28

6:00 am-11:10 am

1 stop4h 10m

$367

JacksonvilleChicago

OAJ - MDW

OAJMDW

Jacksonville Albert J Ellis

mar. 3/24

11:06 am-4:25 pm

1 stop6h 19m

Chicago Midway

sáb. 3/28

6:00 am-1:39 pm

1 stop6h 39m

$399

JacksonvilleChicago

OAJ - MDW

OAJMDW

Jacksonville Albert J Ellis

jue. 10/16

5:48 am-9:40 am

1 stop4h 52m

Chicago Midway

lun. 10/20

6:00 am-2:21 pm

1 stop7h 21m

$467

JacksonvilleChicago

OAJ - MDW

OAJMDW

Jacksonville Albert J Ellis

mar. 3/24

2:25 pm-12:35 pm

2 stops23h 10m

Chicago Midway

sáb. 3/28

6:00 am-1:39 pm

1 stop6h 39m

$489

JacksonvilleChicago

OAJ - MDW

OAJMDW

Jacksonville Albert J Ellis

mar. 3/24

5:40 am-6:34 pm

2 stops13h 54m

Chicago Midway

sáb. 3/28

6:00 am-1:39 pm

1 stop6h 39m

$498

JacksonvilleChicago

OAJ - MDW

OAJMDW

Jacksonville Albert J Ellis

mar. 3/24

5:40 am-6:34 pm

2 stops13h 54m

Chicago Midway

sáb. 3/28

6:00 am-11:10 am

1 stop4h 10m

$516

JacksonvilleChicago

OAJ - MDW

OAJMDW

Jacksonville Albert J Ellis

dom. 12/14

5:30 am-9:54 am

1 stop5h 24m

Chicago Midway

mié. 12/31

3:29 pm-9:36 pm

1 stop5h 07m

$528

JacksonvilleChicago

OAJ - MDW

OAJMDW

Jacksonville Albert J Ellis

mié. 10/15

4:30 pm-10:14 pm

1 stop6h 44m

Chicago Midway

dom. 10/19

6:00 am-2:21 pm

1 stop7h 21m

$652

JacksonvilleChicago

OAJ - MDW

OAJMDW

Jacksonville Albert J Ellis

jue. 10/16

6:53 pm-10:14 pm

1 stop4h 21m

Chicago Midway

lun. 10/20

1:08 pm-10:43 pm

2 stops8h 35m

$945

JacksonvilleChicago

OAJ - MDW

OAJMDW

Jacksonville Albert J Ellis

jue. 11/27

5:30 am-9:52 am

1 stop5h 22m

Chicago Midway

dom. 11/30

6:00 am-1:46 pm

1 stop6h 46m

$959

Flights are sorted by cheapest round-trip flights first.

Sorted by cheapest first

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 21m.

  • 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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Portage
Schererville
Valparaiso
Crown Point
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Porter
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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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