Latest deals
Insights
When to book
FAQs
Price Alerts

Cheap flights from Jacksonville, North Carolina to Chicago from $209

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 8/14. 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

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
12:10 pm - 3:38 pm
OAJ
-
MDW
4h 28m
1 stop
Delta Logo
6:11 am - 11:30 am
MDW
-
OAJ
4h 19m
1 stop
$379Delta
Sat, Aug 8 - Sat, Aug 15
Delta Logo
5:40 am - 11:56 am
OAJ
-
MDW
7h 16m
1 stop
Delta Logo
6:00 am - 11:12 am
MDW
-
OAJ
4h 12m
1 stop
$417Delta
Thu, Dec 24 - Sat, Dec 26
Delta Logo
12:10 pm - 3:38 pm
OAJ
-
MDW
4h 28m
1 stop
Delta Logo
1:25 pm - 10:29 pm
MDW
-
OAJ
8h 04m
2 stops
$418Delta
Sat, Aug 8 - Sat, Aug 15
Delta Logo
5:40 am - 4:22 pm
OAJ
-
MDW
11h 42m
2 stops
Delta Logo
6:00 am - 11:12 am
MDW
-
OAJ
4h 12m
1 stop
$422Delta
Thu, Dec 24 - Sat, Dec 26
Delta Logo
12:10 pm - 3:38 pm
OAJ
-
MDW
4h 28m
1 stop
Delta Logo
6:11 am - 11:30 am
MDW
-
OAJ
4h 19m
1 stop
$423Delta
Sat, Aug 8 - Sat, Aug 15
Delta Logo
12:10 pm - 6:33 pm
OAJ
-
MDW
7h 23m
2 stops
Delta Logo
6:11 am - 11:30 am
MDW
-
OAJ
4h 19m
1 stop
$428Delta
Sat, Aug 8 - Sat, Aug 15
Delta Logo
12:10 pm - 6:33 pm
OAJ
-
MDW
7h 23m
2 stops
Delta Logo
1:25 pm - 10:29 pm
MDW
-
OAJ
8h 04m
2 stops
$467Delta
Sat, Aug 8 - Sat, Aug 15
Delta Logo
6:44 pm - 10:15 pm
OAJ
-
MDW
4h 31m
1 stop
Delta Logo
12:46 pm - 6:07 pm
MDW
-
OAJ
4h 21m
1 stop
$526Delta
Thu, Jul 23 - Fri, Aug 7
Delta Logo
12:10 pm - 6:33 pm
OAJ
-
MDW
7h 23m
2 stops
Delta Logo
1:25 pm - 10:29 pm
MDW
-
OAJ
8h 04m
2 stops
$533Delta
Sat, Aug 8 - Sat, Aug 15
Delta Logo
6:00 am - 10:05 am
OAJ
-
MDW
5h 05m
1 stop
Delta Logo
12:46 pm - 6:07 pm
MDW
-
OAJ
4h 21m
1 stop
$557Delta
Fri, Jul 24 - Fri, Aug 7

Save money when you book flights with momondo

Big names and deals

Big names and deals

Search 100s of travel sites to compare prices.

Filter for what you want

Filter for what you want

Free Wi-Fi? Stopover? Instantly customize your results.

Trusted and free

Trusted and free

We’re completely free to use - no hidden charges or fees.

Price Alerts

Price Alerts

Not ready to book? to track prices.
Search flight deals

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
Aug 8
OAJ12:10 pmJacksonville Albert J Ellis
4h 28m
1 stop
MDW3:38 pmChicago Midway
Aug 15
MDW6:11 amChicago Midway
4h 19m
1 stop
OAJ11:30 amJacksonville Albert J Ellis
$379
Delta
Aug 8
OAJ12:10 pmJacksonville Albert J Ellis
4h 28m
1 stop
MDW3:38 pmChicago Midway
Aug 15
MDW1:25 pmChicago Midway
8h 04m
2 stops
OAJ10:29 pmJacksonville Albert J Ellis
$418
Delta
Aug 8
OAJ12:10 pmJacksonville Albert J Ellis
4h 28m
1 stop
MDW3:38 pmChicago Midway
Aug 15
MDW6:11 amChicago Midway
4h 19m
1 stop
OAJ11:30 amJacksonville Albert J Ellis
$423

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 July 13, 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

Sat 8/8

12:10 pm-3:38 pm

1 stop4h 28m

Chicago Midway

Sat 8/15

6:11 am-11:30 am

1 stop4h 19m

$379

JacksonvilleChicago

OAJ - MDW

OAJMDW

Jacksonville Albert J Ellis

Thu 12/24

5:40 am-11:56 am

1 stop7h 16m

Chicago Midway

Sat 12/26

6:00 am-11:12 am

1 stop4h 12m

$417

JacksonvilleChicago

OAJ - MDW

OAJMDW

Jacksonville Albert J Ellis

Sat 8/8

12:10 pm-3:38 pm

1 stop4h 28m

Chicago Midway

Sat 8/15

1:25 pm-10:29 pm

2 stops8h 04m

$418

JacksonvilleChicago

OAJ - MDW

OAJMDW

Jacksonville Albert J Ellis

Thu 12/24

5:40 am-4:22 pm

2 stops11h 42m

Chicago Midway

Sat 12/26

6:00 am-11:12 am

1 stop4h 12m

$422

JacksonvilleChicago

OAJ - MDW

OAJMDW

Jacksonville Albert J Ellis

Sat 8/8

12:10 pm-3:38 pm

1 stop4h 28m

Chicago Midway

Sat 8/15

6:11 am-11:30 am

1 stop4h 19m

$423

JacksonvilleChicago

OAJ - MDW

OAJMDW

Jacksonville Albert J Ellis

Sat 8/8

12:10 pm-6:33 pm

2 stops7h 23m

Chicago Midway

Sat 8/15

6:11 am-11:30 am

1 stop4h 19m

$428

JacksonvilleChicago

OAJ - MDW

OAJMDW

Jacksonville Albert J Ellis

Sat 8/8

12:10 pm-6:33 pm

2 stops7h 23m

Chicago Midway

Sat 8/15

1:25 pm-10:29 pm

2 stops8h 04m

$467

JacksonvilleChicago

OAJ - MDW

OAJMDW

Jacksonville Albert J Ellis

Thu 7/23

6:44 pm-10:15 pm

1 stop4h 31m

Chicago Midway

Fri 8/7

12:46 pm-6:07 pm

1 stop4h 21m

$526

JacksonvilleChicago

OAJ - MDW

OAJMDW

Jacksonville Albert J Ellis

Sat 8/8

12:10 pm-6:33 pm

2 stops7h 23m

Chicago Midway

Sat 8/15

1:25 pm-10:29 pm

2 stops8h 04m

$533

JacksonvilleChicago

OAJ - MDW

OAJMDW

Jacksonville Albert J Ellis

Fri 7/24

6:00 am-10:05 am

1 stop5h 05m

Chicago Midway

Fri 8/7

12:46 pm-6:07 pm

1 stop4h 21m

$557

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 16 resultsSorted by cheapest first
1
2

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 28m

Direct flights

None
The fastest flight from Jacksonville, North Carolina to Chicago Midway Airport takes 4h 28m
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 28m.

  • 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
Merrillville
New Buffalo
Hammond
Portage
Benton Harbor
Saint Joseph
Lansing
Valparaiso
Schererville
Munster
Chesterton
Monticello
Crown Point
Porter
Griffith
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.

An easier way to manage your Chicago Midway Airport trip

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.
Start using Trips
Find my bookings

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.
1 adult
Wed 8/12
Wed 8/19
By creating a price alert you accept our terms of use and privacy policy.

Find better results for your trip to Chicago