$324+ Cheap flights from Jacksonville, NC (OAJ) to Midway (MDW)
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 9/25. Fares are subject to change and may not be available on all flights or dates of travel.
OAJ — MDW
Sep 12 — Sep 191
Round-trip
1 adult, Economy
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Find cheap flights from Jacksonville to Midway 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 Jacksonville to Midway
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Cheapest flights from Jacksonville to MidwayExplore the most affordable flight options available from Jacksonville to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on August 13, 2026.
Explore the most affordable flight options available from Jacksonville to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on August 13, 2026.
This Delta deal was found by Cheapflights users on 8/10. 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 9/306:50 pm -
1 stop4h 54m
Sat 10/106:04 am -
1 stop4h 06m
Deal found 8/10![Delta logo]()
$389
This Delta deal was found by Cheapflights users on 8/12. 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 9/124:15 pm -
1 stop7h 29m
Mon 9/216:05 am -
1 stop4h 10m
Deal found 8/12![Delta logo]()
$423
This Delta deal was found by Cheapflights users on 8/10. 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 9/176:34 pm -
1 stop5h 11m
Sat 9/191:19 pm -
2 stops8h 03m
Deal found 8/10![Delta logo]()
$428
This Delta deal was found by Cheapflights users on 8/9. 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 10/104:06 pm -
1 stop7h 27m
Mon 10/126:04 am -
1 stop6h 47m
Deal found 8/9![Delta logo]()
$433
This Delta deal was found by Cheapflights users on 8/8. 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 9/54:15 pm -
1 stop7h 21m
Fri 9/116:05 am -
1 stop4h 10m
Deal found 8/8![Delta logo]()
$467
This Delta deal was found by Cheapflights users on 8/8. 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 9/176:34 pm -
1 stop5h 11m
Sun 9/206:05 am -
1 stop6h 36m
Deal found 8/8![Delta logo]()
$528
This Delta deal was found by Cheapflights users on 8/11. 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.
Fri 9/186:34 pm -
1 stop5h 10m
Sun 9/206:05 am -
1 stop4h 10m
Deal found 8/11![Delta logo]()
$538
This Delta deal was found by Cheapflights users on 8/9. 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 10/106:00 am -
2 stops7h 47m
Sat 10/106:44 pm -
2 stops18h 07m
Deal found 8/9![Delta logo]()
$545
This Delta deal was found by Cheapflights users on 8/9. 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 10/106:00 am -
2 stops7h 47m
Sun 10/116:44 pm -
2 stops18h 07m
Deal found 8/9![Delta logo]()
$551
Best flights from Jacksonville to MidwayDiscover carefully curated flight deals from Jacksonville to Midway that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated August 13, 2026.
Discover carefully curated flight deals from Jacksonville to Midway that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated August 13, 2026.
This Delta deal was found by Cheapflights users on 8/10. 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 9/3012:00 pm -
2 stops7h 33m
Sat 10/106:04 am -
1 stop4h 06m
Deal found 8/10![Delta logo]()
$394
This Delta deal was found by Cheapflights users on 8/10. 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 9/176:34 pm -
1 stop5h 11m
Sat 9/194:30 pm -
1 stop4h 52m
Deal found 8/10![Delta logo]()
$423
This Delta deal was found by Cheapflights users on 8/12. 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 9/124:15 pm -
1 stop7h 29m
Mon 9/216:05 am -
1 stop4h 10m
Deal found 8/12![Delta logo]()
$423
This Delta deal was found by Cheapflights users on 8/8. 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 9/54:15 pm -
1 stop7h 21m
Fri 9/116:05 am -
1 stop4h 10m
Deal found 8/8![Delta logo]()
$467
This Delta deal was found by Cheapflights users on 8/8. 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 9/176:34 pm -
1 stop5h 11m
Sun 9/206:05 am -
1 stop6h 36m
Deal found 8/8![Delta logo]()
$528
This Delta deal was found by Cheapflights users on 8/9. 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 10/96:33 pm -
2 stops15h 11m
Sat 10/104:19 pm -
1 stop5h 03m
Deal found 8/9![Delta logo]()
$577
This Delta deal was found by Cheapflights users on 8/9. 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 10/96:33 pm -
2 stops15h 11m
Sun 10/116:04 am -
1 stop4h 06m
Deal found 8/9![Delta logo]()
$611
This Delta deal was found by Cheapflights users on 8/10. 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 9/26:00 am -
2 stops11h 59m
Mon 9/76:05 am -
1 stop4h 25m
Deal found 8/10![Delta logo]()
$784
This Delta deal was found by Cheapflights users on 8/9. 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 8/246:48 pm -
1 stop4h 48m
Fri 8/281:25 pm -
2 stops8h 04m
Deal found 8/9![Delta logo]()
$790
This Delta deal was found by Cheapflights users on 8/10. 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.
Sat 12/126:00 am -
1 stop5h 33m
Thu 12/176:00 am -
1 stop4h 11m
Deal found 8/10![Delta logo]()
$803
Last-minute flights from Jacksonville to MidwayDiscover last-minute flight deals from Jacksonville to Midway. Data last updated August 13, 2026 and is based on user searches.
Discover last-minute flight deals from Jacksonville to Midway. Data last updated August 13, 2026 and is based on user searches.
This Delta deal was found by Cheapflights users on 8/12. 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 8/146:48 pm -
1 stop4h 48m
Mon 8/176:05 am -
1 stop6h 41m
Deal found 8/12![Delta logo]()
$595
This Delta deal was found by Cheapflights users on 8/11. 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.
Sun 8/166:48 pm -
1 stop4h 48m
Mon 8/316:05 am -
1 stop4h 25m
Deal found 8/11![Delta logo]()
$566
This Delta deal was found by Cheapflights users on 8/10. 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 9/24:15 pm -
1 stop7h 21m
Mon 9/76:05 am -
1 stop4h 25m
Deal found 8/10![Delta logo]()
$718
This Delta deal was found by Cheapflights users on 8/8. 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 9/54:15 pm -
1 stop7h 21m
Fri 9/116:05 am -
1 stop4h 10m
Deal found 8/8![Delta logo]()
$467
This Delta deal was found by Cheapflights users on 8/12. 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 9/124:15 pm -
1 stop7h 29m
Mon 9/216:05 am -
1 stop4h 10m
Deal found 8/12![Delta logo]()
$423
This Delta deal was found by Cheapflights users on 8/10. 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 9/176:34 pm -
1 stop5h 11m
Sat 9/191:19 pm -
2 stops8h 03m
Deal found 8/10![Delta logo]()
$428
This Delta deal was found by Cheapflights users on 8/8. 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 9/176:34 pm -
1 stop5h 11m
Sun 9/206:05 am -
1 stop6h 36m
Deal found 8/8![Delta logo]()
$528
This Delta deal was found by Cheapflights users on 8/10. 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.
Fri 9/186:34 pm -
1 stop5h 10m
Sun 9/206:05 am -
1 stop4h 10m
Deal found 8/10![Delta logo]()
$538
This Delta deal was found by Cheapflights users on 8/10. 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 9/306:50 pm -
1 stop4h 54m
Sat 10/106:04 am -
1 stop4h 06m
Deal found 8/10![Delta logo]()
$389
One-way flights from Jacksonville to MidwaySearch for one-way flight options from Jacksonville to Midway. Find affordable one-way fares based on user searches. Data last updated August 13, 2026.
Search for one-way flight options from Jacksonville to Midway. Find affordable one-way fares based on user searches. Data last updated August 13, 2026.
This Delta deal was found by Cheapflights users on 8/10. 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.
Fri 9/252:26 pm -
1 stop25h 58m
Deal found 8/10![Delta logo]()
$324
This Delta deal was found by Cheapflights users on 8/9. 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 9/186:34 pm -
1 stop5h 10m
Deal found 8/9![Delta logo]()
$333
This Delta deal was found by Cheapflights users on 8/7. 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.
Tue 11/36:00 am -
2 stops11h 47m
Deal found 8/7![Delta logo]()
$338
This Delta deal was found by Cheapflights users on 8/10. 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 9/242:26 pm -
2 stops29h 07m
Deal found 8/10![Delta logo]()
$425
This Delta deal was found by Cheapflights users on 8/12. 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 8/224:15 pm -
1 stop7h 21m
Deal found 8/12![Delta logo]()
$583
Find flight deals from Jacksonville to Midway
Discover tips and strategies to find the most affordable flight options for your journey from Jacksonville (OAJ) to Midway (MDW). 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 13, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $389 (Delta) |
One-way from | $324 (Delta) |
Cheapflights Fare Finder
Customize your flight search to find flights from Jacksonville to Midway 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 August 13, 2026.
Use the filters below to find and compare flights from Jacksonville to Chicago Midway Airport that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
JacksonvilleChicago
OAJ Jacksonville Albert J Ellis - MDW Chicago Midway
OAJMDW
Jacksonville Albert J Ellis
Wed 9/30
12:00 pm-6:33 pm
2 stops7h 33m
Chicago Midway
Sat 10/10
6:04 am-11:10 am
1 stop4h 06m
$394
JacksonvilleChicago
OAJ Jacksonville Albert J Ellis - MDW Chicago Midway
OAJMDW
Jacksonville Albert J Ellis
Thu 9/17
6:34 pm-10:45 pm
1 stop5h 11m
Chicago Midway
Sat 9/19
4:30 pm-10:22 pm
1 stop4h 52m
$423
JacksonvilleChicago
OAJ Jacksonville Albert J Ellis - MDW Chicago Midway
OAJMDW
Jacksonville Albert J Ellis
Sat 9/12
4:15 pm-10:44 pm
1 stop7h 29m
Chicago Midway
Mon 9/21
6:05 am-11:15 am
1 stop4h 10m
$423
JacksonvilleChicago
OAJ Jacksonville Albert J Ellis - MDW Chicago Midway
OAJMDW
Jacksonville Albert J Ellis
Sat 9/5
4:15 pm-10:36 pm
1 stop7h 21m
Chicago Midway
Fri 9/11
6:05 am-11:15 am
1 stop4h 10m
$467
JacksonvilleChicago
OAJ Jacksonville Albert J Ellis - MDW Chicago Midway
OAJMDW
Jacksonville Albert J Ellis
Thu 9/17
6:34 pm-10:45 pm
1 stop5h 11m
Chicago Midway
Sun 9/20
6:05 am-1:41 pm
1 stop6h 36m
$528
JacksonvilleChicago
OAJ Jacksonville Albert J Ellis - MDW Chicago Midway
OAJMDW
Jacksonville Albert J Ellis
Fri 10/9
6:33 pm-8:44 am
2 stops15h 11m
Chicago Midway
Sat 10/10
4:19 pm-10:22 pm
1 stop5h 03m
$577
JacksonvilleChicago
OAJ Jacksonville Albert J Ellis - MDW Chicago Midway
OAJMDW
Jacksonville Albert J Ellis
Fri 10/9
6:33 pm-8:44 am
2 stops15h 11m
Chicago Midway
Sun 10/11
6:04 am-11:10 am
1 stop4h 06m
$611
JacksonvilleChicago
OAJ Jacksonville Albert J Ellis - MDW Chicago Midway
OAJMDW
Jacksonville Albert J Ellis
Wed 9/2
6:00 am-4:59 pm
2 stops11h 59m
Chicago Midway
Mon 9/7
6:05 am-11:30 am
1 stop4h 25m
$784
JacksonvilleChicago
OAJ Jacksonville Albert J Ellis - MDW Chicago Midway
OAJMDW
Jacksonville Albert J Ellis
Mon 8/24
6:48 pm-10:36 pm
1 stop4h 48m
Chicago Midway
Fri 8/28
1:25 pm-10:29 pm
2 stops8h 04m
$790
Quickest round-trip
JacksonvilleChicago
OAJ Jacksonville Albert J Ellis - MDW Chicago Midway
OAJMDW
Jacksonville Albert J Ellis
Sat 12/12
6:00 am-10:33 am
1 stop5h 33m
Chicago Midway
Thu 12/17
6:00 am-11:11 am
1 stop4h 11m
$803
Showing 1-10 of 15 resultsSorted by cheapest first
Compare providers for flights from Jacksonville to Midway
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 Jacksonville to Midway in August.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars |
- Most accurate provider: When it comes to deals on Jacksonville, North Carolina-Chicago Midway Airport flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Jacksonville, North Carolina-Chicago Midway Airport flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Jacksonville, North Carolina-Chicago Midway Airport flight searches over the past month and is updated monthly.
- Most trusted provider: When it comes to deals on Jacksonville, North Carolina-Chicago Midway Airport 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 Jacksonville, North Carolina-Chicago Midway Airport 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 Jacksonville to Midway
Have a flexible travel schedule? Discover the best time to fly to Midway from Jacksonville with our price prediction graph.
OAJ-MDW
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 Jacksonville to Midway. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
Traveling to a place near Chicago Midway Airport?
Book flights to Chicago Midway Airport if you plan to visit one of these locationsBenton Harbor
Lansing
Merrillville
Valparaiso
Hammond
Saint Joseph
Porter
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