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$377+ 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 5/22. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — OAJ
Jan 10 — Jan 171
Sat 1/10
Sat 1/17
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 December 11, 2025.

This Delta deal was found by Cheapflights users on 12/9. 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 12/239:50 amMDW - OAJ
1 stop7h 12mDelta
Sun 12/285:35 amOAJ - MDW
1 stop4h 30mDelta
Deal found 12/9$803
This Delta deal was found by Cheapflights users on 12/9. 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 12/299:50 amMDW - OAJ
1 stop7h 12mDelta
Tue 12/305:35 amOAJ - MDW
1 stop4h 30mDelta
Deal found 12/9$826
This Delta deal was found by Cheapflights users on 12/9. 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 12/279:50 amMDW - OAJ
1 stop7h 12mDelta
Sat 1/35:35 amOAJ - MDW
1 stop4h 30mDelta
Deal found 12/9$1,259
This Delta deal was found by Cheapflights users on 12/9. 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 12/249:29 amMDW - OAJ
2 stops10h 07mDelta
Sun 12/285:35 amOAJ - MDW
1 stop4h 30mDelta
Deal found 12/9$1,381

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 December 11, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$377
(Delta)

Popular in

December

Cheapest in

January

Average price

$708
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.
Search Deals
From Chicago Midway to Jacksonville Albert J Ellis
Search Deals
Highest demand for flights based on searches. 7% potential increase in price ($35 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 6% potential price decrease ($29 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 2025
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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 December 11, 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

Fri 5/22

6:00 am-1:40 pm

1 stop6h 40m

Jacksonville Albert J Ellis

Mon 5/25

6:25 pm-9:45 pm

1 stop4h 20m

$377

ChicagoJacksonville

MDW - OAJ

MDWOAJ

Chicago Midway

Thu 3/26

6:30 am-1:40 pm

1 stop6h 10m

Jacksonville Albert J Ellis

Thu 4/2

11:50 am-4:53 pm

1 stop6h 03m

$462

ChicagoJacksonville

MDW - OAJ

MDWOAJ

Chicago Midway

Thu 2/12

12:46 pm-5:59 pm

1 stop4h 13m

Jacksonville Albert J Ellis

Mon 2/16

6:40 pm-10:42 pm

1 stop5h 02m

$533

ChicagoJacksonville

MDW - OAJ

MDWOAJ

Chicago Midway

Tue 12/23

9:50 am-6:02 pm

1 stop7h 12m

Jacksonville Albert J Ellis

Sun 12/28

5:35 am-9:05 am

1 stop4h 30m

$803

ChicagoJacksonville

MDW - OAJ

MDWOAJ

Chicago Midway

Wed 12/24

6:00 am-12:55 pm

1 stop5h 55m

Jacksonville Albert J Ellis

Sun 12/28

6:42 pm-10:22 pm

1 stop4h 40m

$803

ChicagoJacksonville

MDW - OAJ

MDWOAJ

Chicago Midway

Mon 12/29

9:50 am-6:02 pm

1 stop7h 12m

Jacksonville Albert J Ellis

Tue 12/30

5:35 am-9:05 am

1 stop4h 30m

$826

ChicagoJacksonville

MDW - OAJ

MDWOAJ

Chicago Midway

Sat 12/27

9:50 am-6:02 pm

1 stop7h 12m

Jacksonville Albert J Ellis

Sat 1/3

5:35 am-9:05 am

1 stop4h 30m

$1,259

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/10

Compare providers for flights from Midway to Jacksonville

Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Midway to Jacksonville in December.
ProviderPrice AccuracyTrust Score*
FlightHubPrice Accuracy3 starsTrust Score*1 star
eDreamsPrice Accuracy3 starsTrust Score*3 stars

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: When it comes to deals on Chicago Midway Airport-Jacksonville, North Carolina flights, users find the pricing of eDreams to be most consistent on Cheapflights vs. eDreams Users can find the same prices on Chicago Midway Airport-Jacksonville, North Carolina flight deals on Cheapflights vs. eDreams >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 eDreams the most. eDreams 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 6h 40m. 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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