$414+ 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 11/14. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — OAJ
Nov 11 — Nov 181
Round-trip
1 adult, Economy
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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
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 12, 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 12, 2026.
This Delta deal was found by Cheapflights users on 10/9. 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 11/144:13 pm -
1 stop5h 15m
Sat 11/216:00 am -
2 stops7h 51m
Deal found 10/9![Delta logo]()
$414
This Delta deal was found by Cheapflights users on 10/8. 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 12/45:12 pm -
1 stop4h 16m
Sun 12/66:00 am -
1 stop7h 04m
Deal found 10/8![Delta logo]()
$477
This Delta deal was found by Cheapflights users on 10/8. 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.
Sat 10/1710:12 am -
2 stops11h 10m
Tue 10/206:33 pm -
1 stop5h 00m
Deal found 10/8![Delta logo]()
$510
This Delta deal was found by Cheapflights users on 10/8. 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 12/46:00 am -
1 stop4h 17m
Mon 12/76:35 pm -
1 stop5h 19m
Deal found 10/8![Delta logo]()
$685
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 12, 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 12, 2026.
This Delta deal was found by Cheapflights users on 10/11. 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 11/144:13 pm -
1 stop5h 15m
Sat 11/216:00 am -
2 stops7h 51m
Deal found 10/11![Delta logo]()
$414
This Delta deal was found by Cheapflights users on 10/8. 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 2/46:00 am -
1 stop10h 44m
Sat 2/611:58 am -
1 stop5h 27m
Deal found 10/8![Delta logo]()
$420
This Delta deal was found by Cheapflights users on 10/8. 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 2/56:00 am -
1 stop4h 12m
Sat 2/65:40 am -
1 stop5h 12m
Deal found 10/8![Delta logo]()
$443
This Delta deal was found by Cheapflights users on 10/8. 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 12/45:12 pm -
1 stop4h 16m
Sun 12/66:00 am -
1 stop7h 04m
Deal found 10/8![Delta logo]()
$477
This Delta deal was found by Cheapflights users on 10/8. 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 12/46:00 am -
1 stop4h 17m
Mon 12/76:35 pm -
1 stop5h 19m
Deal found 10/8![Delta logo]()
$685
This Delta deal was found by Cheapflights users on 10/10. 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.
Mon 10/2612:49 pm -
1 stop4h 04m
Fri 10/3012:00 pm -
1 stop5h 14m
Deal found 10/10![Delta logo]()
$805
Last-minute flights from Midway to JacksonvilleDiscover last-minute flight deals from Midway to Jacksonville. Data last updated October 12, 2026 and is based on user searches.
Discover last-minute flight deals from Midway to Jacksonville. Data last updated October 12, 2026 and is based on user searches.
This Delta deal was found by Cheapflights users on 10/8. 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.
Sat 10/1710:12 am -
2 stops11h 10m
Tue 10/206:33 pm -
1 stop5h 00m
Deal found 10/8![Delta logo]()
$510
This Delta deal was found by Cheapflights users on 10/9. 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 11/144:13 pm -
1 stop5h 15m
Sat 11/216:00 am -
2 stops7h 51m
Deal found 10/9![Delta logo]()
$414
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 12, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $414 (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 12, 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
Sat 11/14
4:13 pm-10:28 pm
1 stop5h 15m
Jacksonville Albert J Ellis
Sat 11/21
6:00 am-12:51 pm
2 stops7h 51m
$414
ChicagoJacksonville
MDW Chicago Midway - OAJ Jacksonville Albert J Ellis
MDWOAJ
Chicago Midway
Thu 2/4
6:00 am-5:44 pm
1 stop10h 44m
Jacksonville Albert J Ellis
Sat 2/6
11:58 am-4:25 pm
1 stop5h 27m
$420
ChicagoJacksonville
MDW Chicago Midway - OAJ Jacksonville Albert J Ellis
MDWOAJ
Chicago Midway
Fri 2/5
6:00 am-11:12 am
1 stop4h 12m
Jacksonville Albert J Ellis
Sat 2/6
5:40 am-9:52 am
1 stop5h 12m
$443
ChicagoJacksonville
MDW Chicago Midway - OAJ Jacksonville Albert J Ellis
MDWOAJ
Chicago Midway
Fri 12/4
5:12 pm-10:28 pm
1 stop4h 16m
Jacksonville Albert J Ellis
Sun 12/6
6:00 am-12:04 pm
1 stop7h 04m
$477
ChicagoJacksonville
MDW Chicago Midway - OAJ Jacksonville Albert J Ellis
MDWOAJ
Chicago Midway
Fri 12/4
6:00 am-11:17 am
1 stop4h 17m
Jacksonville Albert J Ellis
Mon 12/7
6:35 pm-10:54 pm
1 stop5h 19m
$685
Quickest round-trip
ChicagoJacksonville
MDW Chicago Midway - OAJ Jacksonville Albert J Ellis
MDWOAJ
Chicago Midway
Mon 10/26
12:49 pm-5:53 pm
1 stop4h 04m
Jacksonville Albert J Ellis
Fri 10/30
12:00 pm-4:14 pm
1 stop5h 14m
$805
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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