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$285+ Cheap flights from Midway (MDW) to Jacksonville, NC (OAJ)

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 6/1. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — OAJ
Jun 22 — Jun 291
Mon 6/22
Mon 6/29
1 adult, Economy
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Cheap flight deals from Midway to Jacksonville

Cheapest flights from Midway to Jacksonville
Explore the most affordable flight options available from Midway to Jacksonville. Find the lowest fares from popular airlines and budget airlines, with prices last updated on May 23, 2026.

This Delta deal was found by Cheapflights users on 5/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/146:00 am
MDW
-
OAJ
1 stop4h 19m
Delta
Sat 7/1812:11 pm
OAJ
-
MDW
1 stop4h 26m
Delta
Deal found 5/21$358
This Delta deal was found by Cheapflights users on 5/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/1811:05 am
MDW
-
OAJ
1 stop5h 55m
Delta
Wed 6/246:40 pm
OAJ
-
MDW
1 stop4h 37m
Delta
Deal found 5/19$377
This Delta deal was found by Cheapflights users on 5/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/54:30 pm
MDW
-
OAJ
1 stop4h 48m
Delta
Mon 9/75:40 am
OAJ
-
MDW
1 stop5h 10m
Delta
Deal found 5/18$392
This Delta deal was found by Cheapflights users on 5/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/36:00 am
MDW
-
OAJ
1 stop4h 15m
Delta
Sun 9/611:06 am
OAJ
-
MDW
1 stop5h 21m
Delta
Deal found 5/18$417
This Delta deal was found by Cheapflights users on 5/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/46:00 am
MDW
-
OAJ
1 stop6h 42m
Delta
Mon 9/711:06 am
OAJ
-
MDW
2 stops8h 25m
Delta
Deal found 5/18$422
This Delta deal was found by Cheapflights users on 5/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/96:00 am
MDW
-
OAJ
1 stop4h 21m
Delta
Sat 6/134:45 pm
OAJ
-
MDW
1 stop6h 32m
Delta
Deal found 5/18$483
This Delta deal was found by Cheapflights users on 5/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/512:53 pm
MDW
-
OAJ
1 stop4h 12m
Delta
Tue 6/96:40 pm
OAJ
-
MDW
1 stop4h 37m
Delta
Deal found 5/21$501
This Delta deal was found by Cheapflights users on 5/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/106:00 am
MDW
-
OAJ
1 stop11h 00m
Delta
Sat 6/134:45 pm
OAJ
-
MDW
1 stop6h 32m
Delta
Deal found 5/18$506
This Delta deal was found by Cheapflights users on 5/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/96:00 am
MDW
-
OAJ
1 stop4h 21m
Delta
Thu 6/116:40 pm
OAJ
-
MDW
1 stop4h 37m
Delta
Deal found 5/18$511

Find flight deals from Midway to Jacksonville

Discover tips and strategies to find the most affordable flight options for your journey from Midway (MDW) to Jacksonville (OAJ). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated May 23, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$358
(Delta)

One-way from

$285
(Delta)
Provider with most accurate pricing for Chicago Midway-Jacksonville Albert J Ellis flight deals.
Search Deals
Provider most trusted by Cheapflights users for Chicago Midway-Jacksonville Albert J Ellis flights.
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From Chicago Midway to Jacksonville Albert J Ellis
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One-way flight from Chicago Midway to Jacksonville Albert J Ellis
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Cheapflights Fare Finder

 
Customize your flight search to find flights from Midway to Jacksonville 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, Cheapflights users made 2,558,603 searches. Data last updated May 23, 2026.
Use the filters below to find and compare flights from Chicago Midway Airport to Jacksonville that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip
Quickest round-trip

ChicagoJacksonville

MDW - OAJ

MDWOAJ

Chicago Midway

Sun 8/2

6:00 am-11:19 am

1 stop4h 19m

Jacksonville Albert J Ellis

Sat 8/8

12:07 pm-3:38 pm

1 stop4h 31m

$417

ChicagoJacksonville

MDW - OAJ

MDWOAJ

Chicago Midway

Tue 6/9

6:00 am-11:21 am

1 stop4h 21m

Jacksonville Albert J Ellis

Thu 6/11

6:40 pm-10:17 pm

1 stop4h 37m

$511

ChicagoJacksonville

MDW - OAJ

MDWOAJ

Chicago Midway

Thu 6/18

9:17 am-10:30 pm

2 stops12h 13m

Jacksonville Albert J Ellis

Wed 6/24

6:40 pm-10:17 pm

1 stop4h 37m

$537

ChicagoJacksonville

MDW - OAJ

MDWOAJ

Chicago Midway

Mon 6/8

11:05 am-6:00 pm

1 stop5h 55m

Jacksonville Albert J Ellis

Sat 6/13

4:45 pm-10:17 pm

1 stop6h 32m

$587

ChicagoJacksonville

MDW - OAJ

MDWOAJ

Chicago Midway

Sat 6/6

10:45 am-10:04 pm

1 stop10h 19m

Jacksonville Albert J Ellis

Fri 6/12

6:40 pm-10:17 pm

1 stop4h 37m

$658

ChicagoJacksonville

MDW - OAJ

MDWOAJ

Chicago Midway

Sun 6/7

7:16 pm-11:21 am

2 stops15h 05m

Jacksonville Albert J Ellis

Sat 6/13

4:45 pm-10:17 pm

1 stop6h 32m

$704

ChicagoJacksonville

MDW - OAJ

MDWOAJ

Chicago Midway

Mon 6/8

11:05 am-6:00 pm

1 stop5h 55m

Jacksonville Albert J Ellis

Tue 6/9

6:40 pm-10:17 pm

1 stop4h 37m

$712

ChicagoJacksonville

MDW - OAJ

MDWOAJ

Chicago Midway

Wed 6/10

9:17 am-10:30 pm

2 stops12h 13m

Jacksonville Albert J Ellis

Fri 6/12

12:06 pm-6:11 pm

2 stops31h 05m

$797

ChicagoJacksonville

MDW - OAJ

MDWOAJ

Chicago Midway

Fri 6/5

9:22 am-10:04 pm

2 stops11h 42m

Jacksonville Albert J Ellis

Tue 6/9

6:00 am-12:46 pm

2 stops7h 46m

$1,299
Cheapest one-way
Quickest one-way

ChicagoJacksonville

MDW - OAJ

MDWOAJ

Chicago Midway

Mon 6/1

10:59 am-6:05 pm

1 stop6h 06m

$285

Flights are sorted by cheapest round-trip flights first.

Deals found on 5/18

Sorted by cheapest first
  • Most accurate provider: When it comes to deals on Chicago Midway Airport-Jacksonville, North Carolina flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Chicago Midway Airport-Jacksonville, North Carolina flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Chicago Midway Airport-Jacksonville, North Carolina flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Chicago Midway Airport-Jacksonville, North Carolina flights, Cheapflights users trust FlightHub the most. FlightHub has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Chicago Midway Airport-Jacksonville, North Carolina flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

Best time to book a flight from Midway to Jacksonville

Have a flexible travel schedule? Discover the best time to fly to Jacksonville from Midway with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Related info for your journey

Find useful and relevant information for your journey from Midway to Jacksonville. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly into for flights to Jacksonville from Chicago Midway?

    Jacksonville Albert J Ellis (OAJ) is the airport you will fly into if you book a flight from Chicago Midway to Jacksonville. You should not have trouble finding flights to Albert J Ellis from Chicago Midway; the airport handles an average of 0 inbound flights from Chicago Midway per day. You should also have plenty of airline options to choose from since 0 airlines have flights to the Jacksonville airport from Chicago Midway. It is only a 11.3 mi journey from Albert J Ellis (OAJ) to Jacksonville’s city center.

  • How long is the flight from Chicago Midway Airport to Jacksonville, North Carolina?

    There are many flights that can get you from Chicago Midway Airport to Jacksonville, North Carolina in 4h 19m. Fly via Delta to get the fastest option. The distance from Chicago Midway Airport to Jacksonville, North Carolina is about 729 mi.

  • Can I find deals for flights from Midway to Jacksonville that include hotel bookings?

    Yes. In addition to deals on Midway to Jacksonville flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Midway to Jacksonville?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Midway to Jacksonville.

  • Can I find deals for business class flights from Midway to Jacksonville?

    Yes. Cheapflights offers flight deals from Midway to Jacksonville by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

See more FAQs

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