HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Jacksonville

$281+ 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 4/27. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — OAJ
Apr 9 — Apr 161
Thu 4/9
Thu 4/16
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Midway to Jacksonville with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

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 March 10, 2026.

This Delta deal was found by Cheapflights users on 3/5. 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 4/276:00 am
MDW
-
OAJ
1 stop4h 18m
Delta
Thu 4/306:49 pm
OAJ
-
MDW
1 stop4h 39m
Delta
Deal found 3/5$281
This Delta deal was found by Cheapflights users on 3/9. 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.
Fri 4/176:00 am
MDW
-
OAJ
1 stop6h 40m
Delta
Mon 4/206:49 pm
OAJ
-
MDW
1 stop4h 39m
Delta
Deal found 3/9$351
This Delta deal was found by Cheapflights users on 3/10. 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 4/236:00 am
MDW
-
OAJ
1 stop6h 40m
Delta
Sat 4/2512:05 pm
OAJ
-
MDW
1 stop5h 24m
Delta
Deal found 3/10$419
This Delta deal was found by Cheapflights users on 3/8. 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 6/196:00 am
MDW
-
OAJ
1 stop6h 40m
Delta
Sun 6/215:40 am
OAJ
-
MDW
1 stop5h 11m
Delta
Deal found 3/8$489
This Delta deal was found by Cheapflights users on 3/6. 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 3/196:00 am
MDW
-
OAJ
1 stop6h 40m
Delta
Sun 3/226:51 pm
OAJ
-
MDW
1 stop4h 40m
Delta
Deal found 3/6$562
This Delta deal was found by Cheapflights users on 3/10. 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 3/2510:45 am
MDW
-
OAJ
1 stop6h 23m
Delta
Sun 3/296:51 pm
OAJ
-
MDW
1 stop4h 40m
Delta
Deal found 3/10$642
This Delta deal was found by Cheapflights users on 3/8. 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 5/2112:51 pm
MDW
-
OAJ
1 stop4h 55m
Delta
Sun 5/244:07 pm
OAJ
-
MDW
1 stop6h 02m
Delta
Deal found 3/8$664
This Delta deal was found by Cheapflights users on 3/6. 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 3/306:00 am
MDW
-
OAJ
1 stop6h 40m
Delta
Sat 4/44:40 pm
OAJ
-
MDW
1 stop6h 51m
Delta
Deal found 3/6$692
This Delta deal was found by Cheapflights users on 3/6. 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 3/266:00 am
MDW
-
OAJ
1 stop4h 12m
Delta
Fri 4/36:51 pm
OAJ
-
MDW
1 stop4h 40m
Delta
Deal found 3/6$828
This Delta deal was found by Cheapflights users on 3/6. 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 3/2010:45 am
MDW
-
OAJ
1 stop6h 23m
Delta
Sun 3/226:51 pm
OAJ
-
MDW
1 stop4h 40m
Delta
Deal found 3/6$864
This Delta deal was found by Cheapflights users on 3/7. 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 5/45:21 pm
MDW
-
OAJ
1 stop4h 30m
Delta
Wed 5/65:40 am
OAJ
-
MDW
2 stops8h 03m
Delta
Deal found 3/7$909

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 March 10, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$281
(Delta)
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

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 March 10, 2026.
Use the filters below to find and compare flights from Chicago Midway Airport to Jacksonville that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip
Quickest round-trip

ChicagoJacksonville

MDW - OAJ

MDWOAJ

Chicago Midway

Mon 4/27

6:00 am-11:18 am

1 stop4h 18m

Jacksonville Albert J Ellis

Thu 4/30

6:49 pm-10:28 pm

1 stop4h 39m

$281

ChicagoJacksonville

MDW - OAJ

MDWOAJ

Chicago Midway

Mon 5/4

6:00 am-11:18 am

1 stop4h 18m

Jacksonville Albert J Ellis

Wed 5/6

12:05 pm-4:26 pm

1 stop5h 21m

$351

ChicagoJacksonville

MDW - OAJ

MDWOAJ

Chicago Midway

Fri 4/17

6:00 am-1:40 pm

1 stop6h 40m

Jacksonville Albert J Ellis

Mon 4/20

6:49 pm-10:28 pm

1 stop4h 39m

$351

ChicagoJacksonville

MDW - OAJ

MDWOAJ

Chicago Midway

Thu 5/21

12:51 pm-6:46 pm

1 stop4h 55m

Jacksonville Albert J Ellis

Sun 5/24

4:07 pm-9:09 pm

1 stop6h 02m

$664

ChicagoJacksonville

MDW - OAJ

MDWOAJ

Chicago Midway

Mon 3/23

12:47 pm-6:08 pm

1 stop4h 21m

Jacksonville Albert J Ellis

Fri 3/27

11:58 am-5:22 pm

1 stop6h 24m

$939

ChicagoJacksonville

MDW - OAJ

MDWOAJ

Chicago Midway

Thu 4/23

6:00 am-11:18 am

1 stop4h 18m

Jacksonville Albert J Ellis

Sat 4/25

5:40 am-12:43 pm

2 stops8h 03m

$987

ChicagoJacksonville

MDW - OAJ

MDWOAJ

Chicago Midway

Mon 3/30

1:10 pm-10:33 pm

2 stops8h 23m

Jacksonville Albert J Ellis

Sat 4/4

4:40 pm-10:31 pm

1 stop6h 51m

$1,090

ChicagoJacksonville

MDW - OAJ

MDWOAJ

Chicago Midway

Sat 5/16

9:22 am-10:04 pm

2 stops11h 42m

Jacksonville Albert J Ellis

Mon 5/18

4:07 pm-9:09 pm

1 stop6h 02m

$1,187

ChicagoJacksonville

MDW - OAJ

MDWOAJ

Chicago Midway

Wed 3/25

9:35 am-6:08 pm

2 stops7h 33m

Jacksonville Albert J Ellis

Sun 3/29

6:51 pm-10:31 pm

1 stop4h 40m

$1,427
Cheapest one-way
Quickest one-way

ChicagoJacksonville

MDW - OAJ

MDWOAJ

Chicago Midway

Sat 3/28

4:30 pm-10:33 pm

1 stop5h 03m

$470

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/8

Sorted by cheapest first
  • Most accurate provider: When it comes to deals on Chicago Midway Airport-Jacksonville, North Carolina flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Chicago Midway Airport-Jacksonville, North Carolina flight deals on Cheapflights vs. FlightHub >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 FlightHub the most. FlightHub 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 4h 18m. 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

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.