$437+ 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 9/5. Fares are subject to change and may not be available on all flights or dates of travel.
OAJ — MDW
Sep 25 — Oct 21
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
One-way
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 26, 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 26, 2026.
This Delta deal was found by Cheapflights users on 8/21. 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
Wed 9/96:05 am -
1 stop4h 10m
Deal found 8/21![Delta logo]()
$437
This Delta deal was found by Cheapflights users on 8/23. 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 9/206:34 pm -
1 stop5h 10m
Sun 9/276:05 am -
1 stop6h 36m
Deal found 8/23![Delta logo]()
$477
This Delta deal was found by Cheapflights users on 8/24. 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 10/812:00 pm -
1 stop5h 14m
Sat 10/104:19 pm -
1 stop5h 03m
Deal found 8/24![Delta logo]()
$754
This Delta deal was found by Cheapflights users on 8/23. 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 9/76:00 am -
1 stop4h 59m
Fri 9/116:05 am -
1 stop4h 10m
Deal found 8/23![Delta logo]()
$785
This Delta deal was found by Cheapflights users on 8/25. 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 9/94:15 pm -
1 stop7h 29m
Sun 9/136:05 am -
1 stop4h 10m
Deal found 8/25![Delta logo]()
$1,285
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 26, 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 26, 2026.
This Delta deal was found by Cheapflights users on 8/21. 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
Wed 9/96:05 am -
1 stop4h 10m
Deal found 8/21![Delta logo]()
$437
This Delta deal was found by Cheapflights users on 8/23. 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 9/206:34 pm -
1 stop5h 10m
Sun 9/276:05 am -
1 stop6h 36m
Deal found 8/23![Delta logo]()
$477
This Delta deal was found by Cheapflights users on 8/24. 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 10/812:00 pm -
1 stop5h 14m
Sat 10/104:19 pm -
1 stop5h 03m
Deal found 8/24![Delta logo]()
$754
This Delta deal was found by Cheapflights users on 8/23. 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 9/76:00 am -
1 stop4h 59m
Fri 9/116:05 am -
1 stop4h 10m
Deal found 8/23![Delta logo]()
$785
This Delta deal was found by Cheapflights users on 8/25. 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 9/94:15 pm -
1 stop7h 29m
Sun 9/136:05 am -
1 stop4h 10m
Deal found 8/25![Delta logo]()
$1,285
Last-minute flights from Jacksonville to MidwayDiscover last-minute flight deals from Jacksonville to Midway. Data last updated August 26, 2026 and is based on user searches.
Discover last-minute flight deals from Jacksonville to Midway. Data last updated August 26, 2026 and is based on user searches.
This Delta deal was found by Cheapflights users on 8/21. 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
Wed 9/96:05 am -
1 stop4h 10m
Deal found 8/21![Delta logo]()
$437
This Delta deal was found by Cheapflights users on 8/23. 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 9/76:00 am -
1 stop4h 59m
Fri 9/116:05 am -
1 stop4h 10m
Deal found 8/23![Delta logo]()
$785
This Delta deal was found by Cheapflights users on 8/25. 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 9/94:15 pm -
1 stop7h 29m
Sun 9/136:05 am -
1 stop4h 10m
Deal found 8/25![Delta logo]()
$1,285
This Delta deal was found by Cheapflights users on 8/23. 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 9/206:34 pm -
1 stop5h 10m
Sun 9/276:05 am -
1 stop6h 36m
Deal found 8/23![Delta logo]()
$477
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 26, 2026.
Search for one-way flight options from Jacksonville to Midway. Find affordable one-way fares based on user searches. Data last updated August 26, 2026.
This Delta deal was found by Cheapflights users on 8/25. 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 9/312:10 pm -
1 stop5h 05m
Deal found 8/25![Delta logo]()
$445
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 26, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $433 (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 August 26, 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 9/5
4:15 pm-10:36 pm
1 stop7h 21m
Chicago Midway
Wed 9/9
6:05 am-11:15 am
1 stop4h 10m
$437
JacksonvilleChicago
OAJ Jacksonville Albert J Ellis - MDW Chicago Midway
OAJMDW
Jacksonville Albert J Ellis
Sun 9/20
6:34 pm-10:44 pm
1 stop5h 10m
Chicago Midway
Sun 9/27
6:05 am-1:41 pm
1 stop6h 36m
$477
JacksonvilleChicago
OAJ Jacksonville Albert J Ellis - MDW Chicago Midway
OAJMDW
Jacksonville Albert J Ellis
Thu 10/8
12:00 pm-4:14 pm
1 stop5h 14m
Chicago Midway
Sat 10/10
4:19 pm-10:22 pm
1 stop5h 03m
$754
Quickest round-trip
JacksonvilleChicago
OAJ Jacksonville Albert J Ellis - MDW Chicago Midway
OAJMDW
Jacksonville Albert J Ellis
Mon 9/7
6:00 am-9:59 am
1 stop4h 59m
Chicago Midway
Fri 9/11
6:05 am-11:15 am
1 stop4h 10m
$785
JacksonvilleChicago
OAJ Jacksonville Albert J Ellis - MDW Chicago Midway
OAJMDW
Jacksonville Albert J Ellis
Wed 9/9
4:15 pm-10:44 pm
1 stop7h 29m
Chicago Midway
Sun 9/13
6:05 am-11:15 am
1 stop4h 10m
$1,285
Cheapest one-way
Quickest one-way
JacksonvilleChicago
OAJ Jacksonville Albert J Ellis - MDW Chicago Midway
OAJMDW
Jacksonville Albert J Ellis
Thu 9/3
12:10 pm-4:15 pm
1 stop5h 05m
$445
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 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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