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$209+ 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 8/31. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — OAJ
Aug 23 — Aug 301
Sat 8/23
Sat 8/30
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 August 18, 2025.

Round-trip from

$362
(Delta)

One-way from

$209
(Delta)

Popular in

December

Cheapest in

January
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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Highest demand for flights based on searches. 12% potential increase in price ($64 potential increase over avg. RT price).
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Cheapest flight prices on average. 5% potential price decrease ($24 potential savings vs. average RT price).
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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 August 18, 2025.

This Delta deal was found by Cheapflights users on 8/16. 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 9/246:00 amMDW - OAJ
1 stop4h 08mDelta
Fri 9/2611:51 amOAJ - MDW
1 stop7h 00mDelta
Deal found 8/16$362
This Delta deal was found by Cheapflights users on 8/17. 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.
Sun 9/146:00 amMDW - OAJ
1 stop4h 08mDelta
Sat 9/205:52 amOAJ - MDW
1 stop4h 55mDelta
Deal found 8/17$433
This Delta deal was found by Cheapflights users on 8/16. 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.
Sun 12/76:00 amMDW - OAJ
1 stop4h 14mDelta
Sat 12/134:30 pmOAJ - MDW
1 stop6h 14mDelta
Deal found 8/16$488
This Delta deal was found by Cheapflights users on 8/15. 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.
Sun 8/316:00 amMDW - OAJ
1 stop4h 10mDelta
Thu 9/44:30 pmOAJ - MDW
1 stop5h 56mDelta
Deal found 8/15$505
This Delta deal was found by Cheapflights users on 8/17. 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 9/16:00 amMDW - OAJ
1 stop4h 10mDelta
Fri 9/54:30 pmOAJ - MDW
1 stop5h 56mDelta
Deal found 8/17$718
This Delta deal was found by Cheapflights users on 8/16. 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.
Sun 12/146:00 amMDW - OAJ
1 stop6h 40mDelta
Sat 12/206:43 pmOAJ - MDW
1 stop4h 22mDelta
Deal found 8/16$737
This Delta deal was found by Cheapflights users on 8/17. 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 11/256:00 amMDW - OAJ
1 stop6h 40mDelta
Sun 11/306:25 pmOAJ - MDW
1 stop4h 19mDelta
Deal found 8/17$834

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 August 18, 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 9/24

6:00 am-11:08 am

1 stop4h 08m

Jacksonville Albert J Ellis

Fri 9/26

11:51 am-5:51 pm

1 stop7h 00m

$362

ChicagoJacksonville

MDW - OAJ

MDWOAJ

Chicago Midway

Sun 9/14

6:00 am-11:08 am

1 stop4h 08m

Jacksonville Albert J Ellis

Sat 9/20

5:52 am-9:47 am

1 stop4h 55m

$433

ChicagoJacksonville

MDW - OAJ

MDWOAJ

Chicago Midway

Sun 12/7

6:00 am-11:14 am

1 stop4h 14m

Jacksonville Albert J Ellis

Sat 12/13

4:30 pm-9:44 pm

1 stop6h 14m

$488

ChicagoJacksonville

MDW - OAJ

MDWOAJ

Chicago Midway

Sun 8/31

6:00 am-11:10 am

1 stop4h 10m

Jacksonville Albert J Ellis

Thu 9/4

4:30 pm-9:26 pm

1 stop5h 56m

$505

ChicagoJacksonville

MDW - OAJ

MDWOAJ

Chicago Midway

Mon 9/1

6:00 am-11:10 am

1 stop4h 10m

Jacksonville Albert J Ellis

Fri 9/5

4:30 pm-9:26 pm

1 stop5h 56m

$718

ChicagoJacksonville

MDW - OAJ

MDWOAJ

Chicago Midway

Sun 12/14

6:00 am-1:40 pm

1 stop6h 40m

Jacksonville Albert J Ellis

Sat 12/20

6:43 pm-10:05 pm

1 stop4h 22m

$737

ChicagoJacksonville

MDW - OAJ

MDWOAJ

Chicago Midway

Wed 11/26

6:00 am-1:40 pm

1 stop6h 40m

Jacksonville Albert J Ellis

Sun 11/30

6:25 pm-9:44 pm

1 stop4h 19m

$834

ChicagoJacksonville

MDW - OAJ

MDWOAJ

Chicago Midway

Tue 11/25

6:00 am-1:40 pm

1 stop6h 40m

Jacksonville Albert J Ellis

Sun 11/30

6:25 pm-9:44 pm

1 stop4h 19m

$834

ChicagoJacksonville

MDW - OAJ

MDWOAJ

Chicago Midway

Sun 8/31

6:00 am-11:10 am

1 stop4h 10m

$209

ChicagoJacksonville

MDW - OAJ

MDWOAJ

Chicago Midway

Sat 8/30

7:17 pm-11:10 am

2 stops14h 53m

$244

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/18

Showing 1-10 of 15 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 08m. 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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