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$339+ Cheap flights from Midway (MDW) to Jacksonville, NC (OAJ)

This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 1/21. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — OAJ
Oct 16 — Oct 231
Thu 10/16
Thu 10/23
1 adult, Economy
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Cheap 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 September 16, 2025.

Round-trip from

$339
(Delta)

Popular in

December

Cheapest in

October

Average price

$390
From Chicago Midway to Jacksonville Albert J Ellis
Search Deals
Highest demand for flights based on searches. 16% potential increase in price ($88 potential increase over avg. RT price).
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Cheapest flight prices on average. 5% potential price decrease ($25 potential savings vs. average RT price).
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Average for round-trip flights in September 2025
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Find 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 September 16, 2025.

This Delta deal was found by Cheapflights users on 9/15. 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 9/166:00 amMDW - OAJ
1 stop4h 08mDelta
Sat 9/205:05 pmOAJ - MDW
1 stop5h 05mDelta
Deal found 9/15$395
This Delta deal was found by Cheapflights users on 9/15. 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 11/276:00 amMDW - OAJ
1 stop5h 44mDelta
Tue 12/211:50 amOAJ - MDW
1 stop5h 46mDelta
Deal found 9/15$399
This Delta deal was found by Cheapflights users on 9/15. 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 10/411:00 amMDW - OAJ
1 stop4h 20mDelta
Mon 10/611:53 amOAJ - MDW
1 stop5h 16mDelta
Deal found 9/15$401
This Delta deal was found by Cheapflights users on 9/15. 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 9/1812:43 pmMDW - OAJ
1 stop4h 32mDelta
Tue 9/235:52 amOAJ - MDW
1 stop4h 48mDelta
Deal found 9/15$440
This Delta deal was found by Cheapflights users on 9/15. 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 10/26:00 amMDW - OAJ
1 stop4h 08mDelta
Sun 10/55:52 amOAJ - MDW
1 stop6h 56mDelta
Deal found 9/15$467
This Delta deal was found by Cheapflights users on 9/15. 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 9/1810:35 amMDW - OAJ
1 stop6h 40mDelta
Mon 9/2211:51 amOAJ - MDW
1 stop6h 44mDelta
Deal found 9/15$485
This Delta deal was found by Cheapflights users on 9/15. 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 10/156:00 amMDW - OAJ
1 stop4h 13mDelta
Sun 10/196:53 pmOAJ - MDW
1 stop4h 21mDelta
Deal found 9/15$522
This Delta deal was found by Cheapflights users on 9/14. 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.
Mon 9/296:00 amMDW - OAJ
1 stop4h 08mDelta
Fri 10/35:52 amOAJ - MDW
1 stop4h 48mDelta
Deal found 9/14$525
This Delta deal was found by Cheapflights users on 9/15. 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 9/1912:43 pmMDW - OAJ
1 stop4h 32mDelta
Sat 9/205:05 pmOAJ - MDW
1 stop5h 05mDelta
Deal found 9/15$552
This Delta deal was found by Cheapflights users on 9/14. 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 12/239:54 amMDW - OAJ
1 stop7h 09mDelta
Tue 12/305:40 amOAJ - MDW
1 stop4h 29mDelta
Deal found 9/14$574
This Delta deal was found by Cheapflights users on 9/15. 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 9/1912:43 pmMDW - OAJ
1 stop4h 32mDelta
Mon 9/2211:51 amOAJ - MDW
1 stop6h 44mDelta
Deal found 9/15$593
This Delta deal was found by Cheapflights users on 9/15. 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 9/1810:35 amMDW - OAJ
1 stop6h 40mDelta
Sun 9/2111:51 amOAJ - MDW
1 stop6h 44mDelta
Deal found 9/15$597

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 September 16, 2025.
Use the filters below to find and compare flights from Chicago Midway Airport to Jacksonville that are best for you.

Fly from

Midway

Fly to

Jacksonville

Route

Depart

Return

Price

ChicagoJacksonville

MDW - OAJ

MDWOAJ

Chicago Midway

Wed 1/21

6:00 am-11:10 am

1 stop4h 10m

Jacksonville Albert J Ellis

Tue 1/27

12:00 pm-4:25 pm

1 stop5h 25m

$339

ChicagoJacksonville

MDW - OAJ

MDWOAJ

Chicago Midway

Wed 1/21

6:00 am-11:10 am

1 stop4h 10m

Jacksonville Albert J Ellis

Mon 1/26

11:06 am-4:25 pm

1 stop6h 19m

$363

ChicagoJacksonville

MDW - OAJ

MDWOAJ

Chicago Midway

Thu 1/22

6:00 am-11:10 am

1 stop4h 10m

Jacksonville Albert J Ellis

Wed 1/28

5:40 am-9:23 am

1 stop4h 43m

$363

ChicagoJacksonville

MDW - OAJ

MDWOAJ

Chicago Midway

Thu 1/22

6:00 am-11:10 am

1 stop4h 10m

Jacksonville Albert J Ellis

Mon 1/26

6:25 pm-9:46 pm

1 stop4h 21m

$387

ChicagoJacksonville

MDW - OAJ

MDWOAJ

Chicago Midway

Thu 11/27

6:00 am-12:44 pm

1 stop5h 44m

Jacksonville Albert J Ellis

Tue 12/2

11:50 am-4:36 pm

1 stop5h 46m

$399

ChicagoJacksonville

MDW - OAJ

MDWOAJ

Chicago Midway

Sat 10/4

11:00 am-4:20 pm

1 stop4h 20m

Jacksonville Albert J Ellis

Mon 10/6

11:53 am-4:09 pm

1 stop5h 16m

$401

ChicagoJacksonville

MDW - OAJ

MDWOAJ

Chicago Midway

Thu 10/2

6:00 am-11:08 am

1 stop4h 08m

Jacksonville Albert J Ellis

Sun 10/5

5:52 am-11:48 am

1 stop6h 56m

$467

ChicagoJacksonville

MDW - OAJ

MDWOAJ

Chicago Midway

Wed 10/15

6:00 am-11:13 am

1 stop4h 13m

Jacksonville Albert J Ellis

Sun 10/19

6:53 pm-10:14 pm

1 stop4h 21m

$522

ChicagoJacksonville

MDW - OAJ

MDWOAJ

Chicago Midway

Mon 9/29

6:00 am-11:08 am

1 stop4h 08m

Jacksonville Albert J Ellis

Fri 10/3

5:52 am-9:40 am

1 stop4h 48m

$525

ChicagoJacksonville

MDW - OAJ

MDWOAJ

Chicago Midway

Tue 12/23

9:54 am-6:03 pm

1 stop7h 09m

Jacksonville Albert J Ellis

Tue 12/30

5:40 am-9:09 am

1 stop4h 29m

$574

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/15

Showing 1-10 of 11 results
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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 10m. 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.

  • What is the cheapest month to book a flight from Chicago Midway Airport to Jacksonville, North Carolina?

    Currently, August is the cheapest month in which you can book a flight from Chicago Midway Airport to Jacksonville, North Carolina (average of $366). Flying from Chicago Midway Airport to Jacksonville, North Carolina in December is currently the most expensive (average of $490). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

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