$413+ 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 10/27. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — OAJ
Nov 19 — Nov 261
Round-trip
1 adult, Economy
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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
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Cheapest flights from Midway to JacksonvilleExplore 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 October 20, 2026.
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 October 20, 2026.
This Delta deal was found by Cheapflights users on 10/16. 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 11/186:00 am -
1 stop6h 42m
Sat 11/216:00 am -
2 stops11h 39m
Deal found 10/16![Delta logo]()
$434
This Delta deal was found by Cheapflights users on 10/20. 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.
Tue 11/175:13 pm -
1 stop4h 15m
Tue 11/246:00 am -
2 stops7h 51m
Deal found 10/20![Delta logo]()
$478
This Delta deal was found by Cheapflights users on 10/18. 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.
Mon 11/236:00 am -
1 stop4h 16m
Mon 11/3011:56 am -
1 stop5h 22m
Deal found 10/18![Delta logo]()
$537
This Delta deal was found by Cheapflights users on 10/18. 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.
Sun 11/226:00 am -
1 stop4h 16m
Mon 11/3011:56 am -
1 stop5h 22m
Deal found 10/18![Delta logo]()
$568
This Delta deal was found by Cheapflights users on 10/18. 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.
Tue 11/246:00 am -
1 stop4h 16m
Mon 11/3011:56 am -
1 stop5h 22m
Deal found 10/18![Delta logo]()
$606
This Delta deal was found by Cheapflights users on 10/20. 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.
Thu 10/226:04 am -
1 stop4h 05m
Sun 11/296:34 pm -
1 stop5h 20m
Deal found 10/20![Delta logo]()
$626
Best flights from Midway to JacksonvilleDiscover carefully curated flight deals from Midway to Jacksonville that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated October 20, 2026.
Discover carefully curated flight deals from Midway to Jacksonville that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated October 20, 2026.
This Delta deal was found by Cheapflights users on 10/16. 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 11/186:00 am -
1 stop6h 42m
Sat 11/216:00 am -
2 stops11h 39m
Deal found 10/16![Delta logo]()
$434
This Delta deal was found by Cheapflights users on 10/19. 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.
Sat 4/101:00 pm -
2 stops8h 15m
Sun 4/186:25 pm -
1 stop4h 45m
Deal found 10/19![Delta logo]()
$468
This Delta deal was found by Cheapflights users on 10/20. 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.
Tue 11/175:13 pm -
1 stop4h 15m
Tue 11/246:00 am -
2 stops7h 51m
Deal found 10/20![Delta logo]()
$478
This Delta deal was found by Cheapflights users on 10/18. 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.
Mon 11/236:00 am -
1 stop4h 16m
Mon 11/3011:56 am -
1 stop5h 22m
Deal found 10/18![Delta logo]()
$537
This Delta deal was found by Cheapflights users on 10/18. 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.
Sun 11/226:00 am -
1 stop4h 16m
Mon 11/3011:56 am -
1 stop5h 22m
Deal found 10/18![Delta logo]()
$568
This Delta deal was found by Cheapflights users on 10/20. 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.
Fri 2/1212:30 pm -
2 stops8h 45m
Mon 2/156:25 pm -
1 stop4h 45m
Deal found 10/20![Delta logo]()
$726
Last-minute flights from Midway to JacksonvilleDiscover last-minute flight deals from Midway to Jacksonville. Data last updated October 20, 2026 and is based on user searches.
Discover last-minute flight deals from Midway to Jacksonville. Data last updated October 20, 2026 and is based on user searches.
This Delta deal was found by Cheapflights users on 10/20. 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.
Thu 10/226:04 am -
1 stop4h 05m
Sun 11/296:34 pm -
1 stop5h 20m
Deal found 10/20![Delta logo]()
$626
This Delta deal was found by Cheapflights users on 10/20. 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.
Tue 11/175:13 pm -
1 stop4h 15m
Tue 11/246:00 am -
2 stops7h 51m
Deal found 10/20![Delta logo]()
$478
This Delta deal was found by Cheapflights users on 10/16. 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 11/186:00 am -
1 stop6h 42m
Sat 11/216:00 am -
2 stops11h 39m
Deal found 10/16![Delta logo]()
$434
This Delta deal was found by Cheapflights users on 10/18. 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.
Sun 11/226:00 am -
1 stop4h 16m
Mon 11/3011:56 am -
1 stop5h 22m
Deal found 10/18![Delta logo]()
$568
This Delta deal was found by Cheapflights users on 10/18. 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.
Mon 11/236:00 am -
1 stop4h 16m
Mon 11/3011:56 am -
1 stop5h 22m
Deal found 10/18![Delta logo]()
$537
This Delta deal was found by Cheapflights users on 10/18. 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.
Tue 11/246:00 am -
1 stop4h 16m
Mon 11/3011:56 am -
1 stop5h 22m
Deal found 10/18![Delta logo]()
$606
One-way flights from Midway to JacksonvilleSearch for one-way flight options from Midway to Jacksonville. Find affordable one-way fares based on user searches. Data last updated October 20, 2026.
Search for one-way flight options from Midway to Jacksonville. Find affordable one-way fares based on user searches. Data last updated October 20, 2026.
This Delta deal was found by Cheapflights users on 10/17. 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 10/276:04 am -
1 stop6h 37m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/17![Delta logo]()
$413
This Delta deal was found by Cheapflights users on 10/17. 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 10/256:04 am -
1 stop4h 05m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/17![Delta logo]()
$465
This Delta deal was found by Cheapflights users on 10/17. 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 10/269:29 am -
2 stops11h 53m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/17![Delta logo]()
$470
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 October 20, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $434 (Delta) |
One-way from | $413 (Delta) |
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 7,457,451 searches. Data last updated October 20, 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
Cheapest round-trip
ChicagoJacksonville
MDW Chicago Midway - OAJ Jacksonville Albert J Ellis
MDWOAJ
Chicago Midway
Tue 10/27
6:04 am-1:41 pm
1 stop6h 37m
Jacksonville Albert J Ellis
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$413
ChicagoJacksonville
MDW Chicago Midway - OAJ Jacksonville Albert J Ellis
MDWOAJ
Chicago Midway
Wed 10/28
1:27 pm-10:22 pm
2 stops7h 55m
Jacksonville Albert J Ellis
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$418
ChicagoJacksonville
MDW Chicago Midway - OAJ Jacksonville Albert J Ellis
MDWOAJ
Chicago Midway
Wed 11/18
6:00 am-1:42 pm
1 stop6h 42m
Jacksonville Albert J Ellis
Sat 11/21
6:00 am-4:39 pm
2 stops11h 39m
$434
Quickest round-trip
ChicagoJacksonville
MDW Chicago Midway - OAJ Jacksonville Albert J Ellis
MDWOAJ
Chicago Midway
Sun 10/25
6:04 am-11:09 am
1 stop4h 05m
Jacksonville Albert J Ellis
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$465
ChicagoJacksonville
MDW Chicago Midway - OAJ Jacksonville Albert J Ellis
MDWOAJ
Chicago Midway
Sat 4/10
1:00 pm-10:15 pm
2 stops8h 15m
Jacksonville Albert J Ellis
Sun 4/18
6:25 pm-10:10 pm
1 stop4h 45m
$468
ChicagoJacksonville
MDW Chicago Midway - OAJ Jacksonville Albert J Ellis
MDWOAJ
Chicago Midway
Tue 11/17
5:13 pm-10:28 pm
1 stop4h 15m
Jacksonville Albert J Ellis
Tue 11/24
6:00 am-12:51 pm
2 stops7h 51m
$478
ChicagoJacksonville
MDW Chicago Midway - OAJ Jacksonville Albert J Ellis
MDWOAJ
Chicago Midway
Mon 11/23
6:00 am-11:16 am
1 stop4h 16m
Jacksonville Albert J Ellis
Mon 11/30
11:56 am-4:18 pm
1 stop5h 22m
$537
ChicagoJacksonville
MDW Chicago Midway - OAJ Jacksonville Albert J Ellis
MDWOAJ
Chicago Midway
Sun 11/22
6:00 am-11:16 am
1 stop4h 16m
Jacksonville Albert J Ellis
Mon 11/30
11:56 am-4:18 pm
1 stop5h 22m
$568
ChicagoJacksonville
MDW Chicago Midway - OAJ Jacksonville Albert J Ellis
MDWOAJ
Chicago Midway
Fri 2/12
12:30 pm-10:15 pm
2 stops8h 45m
Jacksonville Albert J Ellis
Mon 2/15
6:25 pm-10:10 pm
1 stop4h 45m
$726
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.
MDW-OAJ
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.
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