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$395+ Cheap flights from Jacksonville, NC (OAJ) to Midway (MDW)

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 8/20. Fares are subject to change and may not be available on all flights or dates of travel.
OAJ — MDW
ago. 25 — sep. 11
lun. 8/25
lun. 9/1
1 adult, Economy
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Cheap flight deals from Jacksonville to Midway

Discover tips and strategies to find the most affordable flight options for your journey from Jacksonville (OAJ) to Midway (MDW). 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 agosto 20, 2025.

Round-trip from

$447
(Delta)
From Jacksonville Albert J Ellis to Chicago Midway
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Cheapest flights from Jacksonville to Midway
Explore the most affordable flight options available from Jacksonville to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on agosto 20, 2025.

This Delta deal was found by Cheapflights users on 8/18. 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.
mar. 8/194:30 pmOAJ - MDW
1 stop6h 14mDelta
sáb. 8/234:25 pmMDW - OAJ
1 stop4h 24mDelta
Deal found 8/18$395
This Delta deal was found by Cheapflights users on 8/18. 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.
mar. 8/194:30 pmOAJ - MDW
1 stop6h 14mDelta
dom. 8/246:04 amMDW - OAJ
1 stop4h 06mDelta
Deal found 8/18$440
This Delta deal was found by Cheapflights users on 8/20. 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.
jue. 9/45:55 amOAJ - MDW
1 stop4h 41mDelta
lun. 9/86:00 amMDW - OAJ
1 stop4h 10mDelta
Deal found 8/20$447
This Delta deal was found by Cheapflights users on 8/18. 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.
jue. 9/115:52 amOAJ - MDW
1 stop4h 48mDelta
jue. 9/186:00 amMDW - OAJ
1 stop4h 08mDelta
Deal found 8/18$488
This Delta deal was found by Cheapflights users on 8/18. 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.
mar. 9/25:55 amOAJ - MDW
1 stop4h 41mDelta
sáb. 9/66:00 amMDW - OAJ
1 stop4h 10mDelta
Deal found 8/18$496
This Delta deal was found by Cheapflights users on 8/19. 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.
vie. 11/216:25 pmOAJ - MDW
1 stop4h 19mDelta
sáb. 11/296:00 amMDW - OAJ
1 stop6h 40mDelta
Deal found 8/19$568
This Delta deal was found by Cheapflights users on 8/18. 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.
mié. 8/2011:51 amOAJ - MDW
2 stops21h 44mDelta
sáb. 8/236:04 amMDW - OAJ
1 stop4h 06mDelta
Deal found 8/18$672
This Delta deal was found by Cheapflights users on 8/18. 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.
sáb. 8/234:30 pmOAJ - MDW
1 stop5h 42mDelta
mié. 8/2710:31 amMDW - OAJ
1 stop4h 16mDelta
Deal found 8/18$705
This Delta deal was found by Cheapflights users on 8/18. 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.
jue. 8/215:55 amOAJ - MDW
1 stop4h 41mDelta
mié. 8/2710:31 amMDW - OAJ
1 stop4h 16mDelta
Deal found 8/18$750

Cheapflights Fare Finder

 
Customize your flight search to find flights from Jacksonville to Midway 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 agosto 20, 2025.
Use the filters below to find and compare flights from Jacksonville to Chicago Midway Airport that are best for you.

Fly from

Jacksonville

Fly to

Midway

Route

Depart

Return

Price

JacksonvilleChicago

OAJ - MDW

OAJMDW

Jacksonville Albert J Ellis

jue. 9/4

5:55 am-9:36 am

1 stop4h 41m

Chicago Midway

lun. 9/8

6:00 am-11:10 am

1 stop4h 10m

$447

JacksonvilleChicago

OAJ - MDW

OAJMDW

Jacksonville Albert J Ellis

jue. 9/11

5:52 am-9:40 am

1 stop4h 48m

Chicago Midway

jue. 9/18

6:00 am-11:08 am

1 stop4h 08m

$488

JacksonvilleChicago

OAJ - MDW

OAJMDW

Jacksonville Albert J Ellis

mar. 9/2

5:55 am-9:36 am

1 stop4h 41m

Chicago Midway

sáb. 9/6

6:00 am-11:10 am

1 stop4h 10m

$496

JacksonvilleChicago

OAJ - MDW

OAJMDW

Jacksonville Albert J Ellis

vie. 11/21

6:25 pm-9:44 pm

1 stop4h 19m

Chicago Midway

sáb. 11/29

6:00 am-1:40 pm

1 stop6h 40m

$568

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/20

Best time to book a flight from Jacksonville to Midway

Have a flexible travel schedule? Discover the best time to fly to Midway from Jacksonville 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 Jacksonville to Midway. 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 from for flights from Jacksonville to Chicago Midway?

    Located just 11.3 mi from the city center, Jacksonville Albert J Ellis is the airport most travelers will use when flying to Chicago Midway from Jacksonville. Booking flights from Albert J Ellis (OAJ) to Chicago Midway should be relatively easy as there are 0 daily outbound flights to Chicago Midway from 0 different airlines.

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

    Departing from Jacksonville, North Carolina to Chicago Midway Airport will take you 4h 41m. The distance between Jacksonville, North Carolina and Chicago Midway Airport is about 729 mi.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Jacksonville to Midway 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 Jacksonville, North Carolina to Chicago Midway Airport?

    Currently, April is the cheapest month in which you can book a flight from Jacksonville, North Carolina to Chicago Midway Airport (average of $160). Flying from Jacksonville, North Carolina to Chicago Midway Airport in November is currently the most expensive (average of $249). 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

Traveling to a place near Chicago Midway Airport?

Book flights to Chicago Midway Airport if you plan to visit one of these locations
Merrillville
Lansing
Hammond
Benton Harbor
Porter
Chesterton

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