$414+ Cheap flights from Jacksonville, NC (OAJ) to Midway (MDW)
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 11/21. Fares are subject to change and may not be available on all flights or dates of travel.
OAJ — MDW
Nov 11 — Nov 181
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
Cheapest
Best
Last-minute
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 October 12, 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 October 12, 2026.
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 11/216:00 am -
2 stops7h 51m
Tue 11/246:00 am -
1 stop4h 16m
Deal found 10/8![Delta logo]()
$414
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.
Fri 11/136:34 pm -
1 stop5h 20m
Mon 11/166:00 am -
1 stop4h 16m
Deal found 10/10![Delta logo]()
$477
This Delta deal was found by Cheapflights users on 10/12. 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.
Tue 10/276:00 am -
1 stop6h 54m
Sat 10/316:04 am -
1 stop4h 54m
Deal found 10/12![Delta logo]()
$691
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.
Wed 11/2511:56 am -
1 stop5h 22m
Mon 11/305:13 pm -
1 stop4h 15m
Deal found 10/8![Delta logo]()
$838
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 10/156:33 pm -
1 stop5h 00m
Fri 10/1612:27 pm -
2 stops8h 55m
Deal found 10/8![Delta logo]()
$954
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 October 12, 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 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 11/216:00 am -
2 stops7h 51m
Tue 11/2411:27 am -
1 stop5h 27m
Deal found 10/11![Delta logo]()
$414
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.
Fri 11/136:34 pm -
1 stop5h 20m
Mon 11/166:00 am -
1 stop4h 16m
Deal found 10/10![Delta logo]()
$477
This Delta deal was found by Cheapflights users on 10/12. 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.
Tue 10/276:00 am -
1 stop6h 54m
Sat 10/316:04 am -
1 stop4h 54m
Deal found 10/12![Delta logo]()
$691
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.
Wed 11/2511:56 am -
1 stop5h 22m
Mon 11/305:13 pm -
1 stop4h 15m
Deal found 10/8![Delta logo]()
$838
This Delta deal was found by Cheapflights users on 10/12. 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.
Thu 12/246:10 am -
2 stops12h 14m
Sun 12/2712:55 pm -
1 stop4h 09m
Deal found 10/12![Delta logo]()
$1,247
Last-minute flights from Jacksonville to MidwayDiscover last-minute flight deals from Jacksonville to Midway. Data last updated October 12, 2026 and is based on user searches.
Discover last-minute flight deals from Jacksonville to Midway. 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.
Thu 10/156:33 pm -
1 stop5h 00m
Fri 10/1612:27 pm -
2 stops8h 55m
Deal found 10/8![Delta logo]()
$954
This Delta deal was found by Cheapflights users on 10/12. 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.
Tue 10/276:00 am -
1 stop6h 54m
Sat 10/316:04 am -
1 stop4h 54m
Deal found 10/12![Delta logo]()
$691
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.
Fri 11/136:34 pm -
1 stop5h 20m
Mon 11/166:00 am -
1 stop4h 16m
Deal found 10/10![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 11/216:00 am -
2 stops7h 51m
Tue 11/246:00 am -
1 stop4h 16m
Deal found 10/8![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.
Wed 11/2511:56 am -
1 stop5h 22m
Mon 11/305:13 pm -
1 stop4h 15m
Deal found 10/8![Delta logo]()
$838
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 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 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 7,457,451 searches. Data last updated October 12, 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
Sat 11/21
6:00 am-12:51 pm
2 stops7h 51m
Chicago Midway
Tue 11/24
11:27 am-5:54 pm
1 stop5h 27m
$414
Quickest round-trip
JacksonvilleChicago
OAJ Jacksonville Albert J Ellis - MDW Chicago Midway
OAJMDW
Jacksonville Albert J Ellis
Fri 11/13
6:34 pm-10:54 pm
1 stop5h 20m
Chicago Midway
Mon 11/16
6:00 am-11:16 am
1 stop4h 16m
$477
JacksonvilleChicago
OAJ Jacksonville Albert J Ellis - MDW Chicago Midway
OAJMDW
Jacksonville Albert J Ellis
Tue 10/27
6:00 am-11:54 am
1 stop6h 54m
Chicago Midway
Sat 10/31
6:04 am-11:58 am
1 stop4h 54m
$691
JacksonvilleChicago
OAJ Jacksonville Albert J Ellis - MDW Chicago Midway
OAJMDW
Jacksonville Albert J Ellis
Wed 11/25
11:56 am-4:18 pm
1 stop5h 22m
Chicago Midway
Mon 11/30
5:13 pm-10:28 pm
1 stop4h 15m
$838
JacksonvilleChicago
OAJ Jacksonville Albert J Ellis - MDW Chicago Midway
OAJMDW
Jacksonville Albert J Ellis
Thu 12/24
6:10 am-5:24 pm
2 stops12h 14m
Chicago Midway
Sun 12/27
12:55 pm-6:04 pm
1 stop4h 09m
$1,247
Sorted 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 October.
| 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
Merrillville
Lansing
Valparaiso
Hammond
Saint Joseph
Porter
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