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Cheap flights from Jacksonville, North Carolina to Chicago from $169

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 6/23. 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
6:44 pm - 10:15 pm
OAJ
-
MDW
4h 31m
1 stop
Delta Logo
6:00 am - 11:19 am
MDW
-
OAJ
4h 19m
1 stop
$337Delta
Wed, Jul 15 - Wed, Jul 22
Delta Logo
4:35 pm - 10:15 pm
OAJ
-
MDW
6h 40m
1 stop
Delta Logo
1:18 pm - 10:29 pm
MDW
-
OAJ
8h 11m
2 stops
$382Delta
Wed, Jul 15 - Wed, Jul 22
Delta Logo
6:40 pm - 10:17 pm
OAJ
-
MDW
4h 37m
1 stop
Delta Logo
6:00 am - 11:21 am
MDW
-
OAJ
4h 21m
1 stop
$417Delta
Thu, Jul 2 - Mon, Jul 6
Delta Logo
6:40 pm - 10:17 pm
OAJ
-
MDW
4h 37m
1 stop
Delta Logo
4:25 pm - 10:30 pm
MDW
-
OAJ
5h 05m
1 stop
$418Delta
Thu, Jul 2 - Sat, Jul 4
Delta Logo
6:40 pm - 10:17 pm
OAJ
-
MDW
4h 37m
1 stop
Delta Logo
9:54 am - 10:30 pm
MDW
-
OAJ
11h 36m
2 stops
$423Delta
Thu, Jul 2 - Sat, Jul 4
Delta Logo
6:44 pm - 10:15 pm
OAJ
-
MDW
4h 31m
1 stop
Delta Logo
1:18 pm - 10:29 pm
MDW
-
OAJ
8h 11m
2 stops
$433Delta
Wed, Jul 15 - Wed, Jul 22
Delta Logo
6:40 pm - 10:17 pm
OAJ
-
MDW
4h 37m
1 stop
Delta Logo
6:00 am - 11:21 am
MDW
-
OAJ
4h 21m
1 stop
$499Delta
Thu, Jul 2 - Sun, Jul 5
Delta Logo
6:40 pm - 1:09 pm
OAJ
-
MDW
19h 29m
2 stops
Delta Logo
9:54 am - 10:30 pm
MDW
-
OAJ
11h 36m
2 stops
$552Delta
Thu, Jul 2 - Sat, Jul 4
Delta Logo
6:40 pm - 10:17 pm
OAJ
-
MDW
4h 37m
1 stop
Delta Logo
9:17 am - 10:30 pm
MDW
-
OAJ
12h 13m
2 stops
$564Delta
Thu, Jul 2 - Sun, Jul 5
Delta Logo
4:45 pm - 10:17 pm
OAJ
-
MDW
6h 32m
1 stop
Delta Logo
6:00 am - 11:21 am
MDW
-
OAJ
4h 21m
1 stop
$587Delta
Fri, Jun 12 - Sun, Jun 14

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
Jul 15
OAJ6:44 pmJacksonville Albert J Ellis
4h 31m
1 stop
MDW10:15 pmChicago Midway
Jul 22
MDW6:00 amChicago Midway
4h 19m
1 stop
OAJ11:19 amJacksonville Albert J Ellis
$337
Delta
Jul 15
OAJ4:35 pmJacksonville Albert J Ellis
6h 40m
1 stop
MDW10:15 pmChicago Midway
Jul 22
MDW1:18 pmChicago Midway
8h 11m
2 stops
OAJ10:29 pmJacksonville Albert J Ellis
$382
Delta
Jul 2
OAJ6:40 pmJacksonville Albert J Ellis
4h 37m
1 stop
MDW10:17 pmChicago Midway
Jul 6
MDW6:00 amChicago Midway
4h 21m
1 stop
OAJ11:21 amJacksonville Albert J Ellis
$417

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 May 22, 2026.
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

Cheapest round-trip
Quickest round-trip

JacksonvilleChicago

OAJ - MDW

OAJMDW

Jacksonville Albert J Ellis

Wed 7/15

6:44 pm-10:15 pm

1 stop4h 31m

Chicago Midway

Wed 7/22

6:00 am-11:19 am

1 stop4h 19m

$337

JacksonvilleChicago

OAJ - MDW

OAJMDW

Jacksonville Albert J Ellis

Wed 7/15

4:35 pm-10:15 pm

1 stop6h 40m

Chicago Midway

Wed 7/22

1:18 pm-10:29 pm

2 stops8h 11m

$382

JacksonvilleChicago

OAJ - MDW

OAJMDW

Jacksonville Albert J Ellis

Thu 7/2

6:40 pm-10:17 pm

1 stop4h 37m

Chicago Midway

Mon 7/6

6:00 am-11:21 am

1 stop4h 21m

$417

JacksonvilleChicago

OAJ - MDW

OAJMDW

Jacksonville Albert J Ellis

Thu 7/2

6:40 pm-10:17 pm

1 stop4h 37m

Chicago Midway

Sat 7/4

4:25 pm-10:30 pm

1 stop5h 05m

$418

JacksonvilleChicago

OAJ - MDW

OAJMDW

Jacksonville Albert J Ellis

Thu 7/2

6:40 pm-10:17 pm

1 stop4h 37m

Chicago Midway

Sat 7/4

9:54 am-10:30 pm

2 stops11h 36m

$423

JacksonvilleChicago

OAJ - MDW

OAJMDW

Jacksonville Albert J Ellis

Wed 7/15

6:44 pm-10:15 pm

1 stop4h 31m

Chicago Midway

Wed 7/22

1:18 pm-10:29 pm

2 stops8h 11m

$433

JacksonvilleChicago

OAJ - MDW

OAJMDW

Jacksonville Albert J Ellis

Thu 7/2

6:40 pm-10:17 pm

1 stop4h 37m

Chicago Midway

Sun 7/5

6:00 am-11:21 am

1 stop4h 21m

$499

JacksonvilleChicago

OAJ - MDW

OAJMDW

Jacksonville Albert J Ellis

Thu 7/2

6:40 pm-1:09 pm

2 stops19h 29m

Chicago Midway

Sat 7/4

9:54 am-10:30 pm

2 stops11h 36m

$552

JacksonvilleChicago

OAJ - MDW

OAJMDW

Jacksonville Albert J Ellis

Thu 7/2

6:40 pm-10:17 pm

1 stop4h 37m

Chicago Midway

Sun 7/5

9:17 am-10:30 pm

2 stops12h 13m

$564

JacksonvilleChicago

OAJ - MDW

OAJMDW

Jacksonville Albert J Ellis

Fri 6/12

4:45 pm-10:17 pm

1 stop6h 32m

Chicago Midway

Sun 6/14

6:00 am-11:21 am

1 stop4h 21m

$587

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 13 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 Midway Airport

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 Midway?

Delta is the most popular carrier operating from Jacksonville Albert J Ellis to Chicago Midway

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

Fastest flight time

4h 31m

Direct flights

None
The fastest flight from Jacksonville, North Carolina to Chicago Midway Airport takes 4h 31m
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.
Search flight deals

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

  • 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 31m.

  • 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.

Traveling to a place near Chicago?

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