$333+ Cheap flights from Midway (MDW) to Jacksonville, NC (OAJ)
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 9/30. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — OAJ
Sep 20 — Sep 271
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
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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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Best
Last-minute
One-way
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 August 21, 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 August 21, 2026.
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.
Sat 9/126:05 am -
1 stop4h 10m
Sat 9/194:15 pm -
1 stop7h 29m
Deal found 8/18![Delta logo]()
$389
This Delta deal was found by Cheapflights users on 8/17. 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 12/36:00 am -
1 stop6h 47m
Thu 12/1011:55 am -
1 stop5h 19m
Deal found 8/17![Delta logo]()
$457
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.
Mon 9/285:10 pm -
1 stop4h 12m
Fri 10/26:00 am -
1 stop4h 49m
Deal found 8/18![Delta logo]()
$665
This Delta deal was found by Cheapflights users on 8/17. 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.
Wed 10/712:49 pm -
1 stop4h 04m
Wed 10/146:00 am -
2 stops7h 47m
Deal found 8/17![Delta logo]()
$818
This Delta deal was found by Cheapflights users on 8/17. 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 10/110:48 am -
1 stop6h 06m
Thu 10/86:33 pm -
1 stop5h 00m
Deal found 8/17![Delta logo]()
$848
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 August 21, 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 August 21, 2026.
This Delta deal was found by Cheapflights users on 8/17. 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.
Wed 10/710:59 am -
1 stop5h 54m
Wed 10/146:33 pm -
1 stop5h 00m
Deal found 8/17![Delta logo]()
$389
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.
Sat 9/126:05 am -
1 stop4h 10m
Sat 9/194:15 pm -
1 stop7h 29m
Deal found 8/18![Delta logo]()
$389
This Delta deal was found by Cheapflights users on 8/17. 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 12/36:00 am -
1 stop6h 47m
Thu 12/1011:55 am -
1 stop5h 19m
Deal found 8/17![Delta logo]()
$457
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.
Mon 9/285:10 pm -
1 stop4h 12m
Fri 10/26:00 am -
1 stop4h 49m
Deal found 8/18![Delta logo]()
$665
This Delta deal was found by Cheapflights users on 8/16. 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.
Mon 8/314:39 pm -
1 stop4h 27m
Fri 9/46:00 am -
1 stop4h 59m
Deal found 8/16![Delta logo]()
$972
Last-minute flights from Midway to JacksonvilleDiscover last-minute flight deals from Midway to Jacksonville. Data last updated August 21, 2026 and is based on user searches.
Discover last-minute flight deals from Midway to Jacksonville. Data last updated August 21, 2026 and is based on user searches.
This Delta deal was found by Cheapflights users on 8/16. 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.
Mon 8/314:39 pm -
1 stop4h 27m
Fri 9/46:00 am -
1 stop4h 59m
Deal found 8/16![Delta logo]()
$972
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.
Sat 9/126:05 am -
1 stop4h 10m
Sat 9/194:15 pm -
1 stop7h 29m
Deal found 8/18![Delta logo]()
$389
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.
Mon 9/285:10 pm -
1 stop4h 12m
Fri 10/26:00 am -
1 stop4h 49m
Deal found 8/18![Delta logo]()
$665
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 August 21, 2026.
Search for one-way flight options from Midway to Jacksonville. Find affordable one-way fares based on user searches. Data last updated August 21, 2026.
This Delta deal was found by Cheapflights users on 8/16. 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 9/306:05 am -
1 stop6h 36m
Deal found 8/16![Delta logo]()
$333
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 August 21, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $389 (Delta) |
One-way from | $333 (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 August 21, 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
Wed 10/7
10:59 am-5:53 pm
1 stop5h 54m
Jacksonville Albert J Ellis
Wed 10/14
6:33 pm-10:33 pm
1 stop5h 00m
$389
ChicagoJacksonville
MDW Chicago Midway - OAJ Jacksonville Albert J Ellis
MDWOAJ
Chicago Midway
Sat 9/12
6:05 am-11:15 am
1 stop4h 10m
Jacksonville Albert J Ellis
Sat 9/19
4:15 pm-10:44 pm
1 stop7h 29m
$389
ChicagoJacksonville
MDW Chicago Midway - OAJ Jacksonville Albert J Ellis
MDWOAJ
Chicago Midway
Thu 12/3
6:00 am-1:47 pm
1 stop6h 47m
Jacksonville Albert J Ellis
Thu 12/10
11:55 am-4:14 pm
1 stop5h 19m
$457
Quickest round-trip
ChicagoJacksonville
MDW Chicago Midway - OAJ Jacksonville Albert J Ellis
MDWOAJ
Chicago Midway
Mon 9/28
5:10 pm-10:22 pm
1 stop4h 12m
Jacksonville Albert J Ellis
Fri 10/2
6:00 am-9:49 am
1 stop4h 49m
$665
ChicagoJacksonville
MDW Chicago Midway - OAJ Jacksonville Albert J Ellis
MDWOAJ
Chicago Midway
Mon 8/31
4:39 pm-10:06 pm
1 stop4h 27m
Jacksonville Albert J Ellis
Fri 9/4
6:00 am-9:59 am
1 stop4h 59m
$972
Cheapest one-way
Quickest one-way
ChicagoJacksonville
MDW Chicago Midway - OAJ Jacksonville Albert J Ellis
MDWOAJ
Chicago Midway
Wed 9/30
6:05 am-1:41 pm
1 stop6h 36m
$333
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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