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$194+ Cheap flights from Jacksonville, NC (OAJ) to Midway (MDW)

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 11/18. Fares are subject to change and may not be available on all flights or dates of travel.
OAJ — MDW
Oct 17 — Oct 241
Fri 10/17
Fri 10/24
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 September 17, 2025.

Round-trip from

$363
(Delta)

One-way from

$194
(Delta)
From Jacksonville Albert J Ellis to Chicago Midway
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One-way flight from Jacksonville Albert J Ellis to Chicago Midway
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Find flight deals from Jacksonville to Midway

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 September 17, 2025.

This Delta deal was found by Cheapflights users on 9/16. 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.
Tue 11/1811:50 amOAJ - MDW
1 stop5h 48mDelta
Mon 11/246:00 amMDW - OAJ
1 stop4h 10mDelta
Deal found 9/16$363
This Delta deal was found by Cheapflights users on 9/16. 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.
Sat 11/1511:50 amOAJ - MDW
1 stop4h 53mDelta
Sun 11/236:00 amMDW - OAJ
1 stop6h 46mDelta
Deal found 9/16$373
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 9/305:52 amOAJ - MDW
1 stop4h 48mDelta
Sat 10/44:25 pmMDW - OAJ
1 stop4h 23mDelta
Deal found 9/15$395
This Delta deal was found by Cheapflights users on 9/16. 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.
Fri 11/146:44 pmOAJ - MDW
1 stop5h 48mDelta
Sun 11/236:00 amMDW - OAJ
1 stop6h 46mDelta
Deal found 9/16$405
This Delta deal was found by Cheapflights users on 9/16. 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 10/14:30 pmOAJ - MDW
1 stop6h 06mDelta
Sun 10/56:00 amMDW - OAJ
1 stop4h 08mDelta
Deal found 9/16$431
This Delta deal was found by Cheapflights users on 9/17. 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.
Thu 10/25:52 amOAJ - MDW
1 stop4h 48mDelta
Mon 10/610:35 amMDW - OAJ
1 stop6h 38mDelta
Deal found 9/17$467
This Delta deal was found by Cheapflights users on 9/16. 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.
Fri 9/1911:51 amOAJ - MDW
1 stop6h 44mDelta
Sun 9/216:00 amMDW - OAJ
1 stop4h 08mDelta
Deal found 9/16$715
This Delta deal was found by Cheapflights users on 9/17. 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.
Thu 10/96:53 pmOAJ - MDW
1 stop4h 21mDelta
Fri 10/246:00 amMDW - OAJ
1 stop7h 21mDelta
Deal found 9/17$719
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 10/105:48 amOAJ - MDW
1 stop4h 52mDelta
Tue 10/146:00 amMDW - OAJ
1 stop4h 13mDelta
Deal found 9/15$829
This Delta deal was found by Cheapflights users on 9/17. 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.
Fri 10/176:53 pmOAJ - MDW
1 stop4h 21mDelta
Fri 10/241:08 pmMDW - OAJ
2 stops8h 35mDelta
Deal found 9/17$874

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 September 17, 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

Tue 11/18

11:50 am-4:38 pm

1 stop5h 48m

Chicago Midway

Mon 11/24

6:00 am-11:10 am

1 stop4h 10m

$363

JacksonvilleChicago

OAJ - MDW

OAJMDW

Jacksonville Albert J Ellis

Sat 11/15

11:50 am-3:43 pm

1 stop4h 53m

Chicago Midway

Sun 11/23

6:00 am-1:46 pm

1 stop6h 46m

$373

JacksonvilleChicago

OAJ - MDW

OAJMDW

Jacksonville Albert J Ellis

Tue 11/18

5:30 am-9:52 am

1 stop5h 22m

Chicago Midway

Sun 11/23

6:00 am-11:10 am

1 stop4h 10m

$373

JacksonvilleChicago

OAJ - MDW

OAJMDW

Jacksonville Albert J Ellis

Tue 9/30

5:52 am-9:40 am

1 stop4h 48m

Chicago Midway

Sat 10/4

4:25 pm-9:48 pm

1 stop4h 23m

$395

JacksonvilleChicago

OAJ - MDW

OAJMDW

Jacksonville Albert J Ellis

Fri 11/14

5:30 am-9:52 am

1 stop5h 22m

Chicago Midway

Sun 11/16

6:00 am-1:46 pm

1 stop6h 46m

$405

JacksonvilleChicago

OAJ - MDW

OAJMDW

Jacksonville Albert J Ellis

Fri 10/17

6:53 pm-10:14 pm

1 stop4h 21m

Chicago Midway

Fri 10/24

5:04 pm-10:43 pm

1 stop4h 39m

$431

JacksonvilleChicago

OAJ - MDW

OAJMDW

Jacksonville Albert J Ellis

Wed 10/1

4:30 pm-9:36 pm

1 stop6h 06m

Chicago Midway

Sun 10/5

6:00 am-11:08 am

1 stop4h 08m

$431

JacksonvilleChicago

OAJ - MDW

OAJMDW

Jacksonville Albert J Ellis

Thu 10/2

5:52 am-9:40 am

1 stop4h 48m

Chicago Midway

Mon 10/6

10:35 am-6:13 pm

1 stop6h 38m

$467

JacksonvilleChicago

OAJ - MDW

OAJMDW

Jacksonville Albert J Ellis

Thu 10/9

6:53 pm-10:14 pm

1 stop4h 21m

Chicago Midway

Fri 10/24

6:00 am-2:21 pm

1 stop7h 21m

$719

JacksonvilleChicago

OAJ - MDW

OAJMDW

Jacksonville Albert J Ellis

Tue 11/18

5:30 am-11:52 am

1 stop7h 22m

$194

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/16

Showing 1-10 of 11 results
1
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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 5h 48m. 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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