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$285+ 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 7/30. Fares are subject to change and may not be available on all flights or dates of travel.
OAJ — MDW
Aug 16 — Aug 231
Sun 8/16
Sun 8/23
1 adult, Economy
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Cheap flight deals from Jacksonville to Midway

Cheapest flights from Jacksonville to Midway
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 July 17, 2026.

This Delta deal was found by Cheapflights users on 7/14. 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 8/2812:10 pm
OAJ
-
MDW
1 stop5h 05m
Delta
Sat 8/296:11 am
MDW
-
OAJ
1 stop4h 19m
Delta
Deal found 7/14$398
This Delta deal was found by Cheapflights users on 7/14. 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 8/136:00 am
OAJ
-
MDW
1 stop4h 59m
Delta
Mon 8/176:05 am
MDW
-
OAJ
1 stop4h 25m
Delta
Deal found 7/14$417
This Delta deal was found by Cheapflights users on 7/13. 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 8/812:10 pm
OAJ
-
MDW
1 stop4h 28m
Delta
Sat 8/156:11 am
MDW
-
OAJ
1 stop4h 19m
Delta
Deal found 7/13$423
This Delta deal was found by Cheapflights users on 7/12. 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 7/236:44 pm
OAJ
-
MDW
1 stop4h 31m
Delta
Fri 8/712:46 pm
MDW
-
OAJ
1 stop4h 21m
Delta
Deal found 7/12$526
This Delta deal was found by Cheapflights users on 7/13. 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 7/206:44 pm
OAJ
-
MDW
1 stop4h 31m
Delta
Tue 7/286:00 am
MDW
-
OAJ
1 stop4h 19m
Delta
Deal found 7/13$530
This Delta deal was found by Cheapflights users on 7/14. 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 8/14:35 pm
OAJ
-
MDW
1 stop6h 40m
Delta
Sat 8/86:11 am
MDW
-
OAJ
1 stop4h 19m
Delta
Deal found 7/14$537
This Delta deal was found by Cheapflights users on 7/13. 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 7/206:44 pm
OAJ
-
MDW
1 stop4h 31m
Delta
Mon 7/276:00 am
MDW
-
OAJ
1 stop4h 19m
Delta
Deal found 7/13$556

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 July 17, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$398
(Delta)

One-way from

$285
(Delta)
Provider with most accurate pricing for Jacksonville Albert J Ellis-Chicago Midway flight deals.
Search Deals
Provider most trusted by Cheapflights users for Jacksonville Albert J Ellis-Chicago Midway flights.
Search Deals
From Jacksonville Albert J Ellis to Chicago Midway
Search Deals
One-way flight from Jacksonville Albert J Ellis to Chicago Midway
Search Deals

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 July 17, 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

Price

Cheapest round-trip

JacksonvilleChicago

OAJ - MDW

OAJMDW

Jacksonville Albert J Ellis

Fri 8/28

12:10 pm-4:15 pm

1 stop5h 05m

Chicago Midway

Sat 8/29

6:11 am-11:30 am

1 stop4h 19m

$398
Quickest round-trip

JacksonvilleChicago

OAJ - MDW

OAJMDW

Jacksonville Albert J Ellis

Sat 8/8

12:10 pm-3:38 pm

1 stop4h 28m

Chicago Midway

Sat 8/15

6:11 am-11:30 am

1 stop4h 19m

$423

JacksonvilleChicago

OAJ - MDW

OAJMDW

Jacksonville Albert J Ellis

Sat 8/1

4:35 pm-10:15 pm

1 stop6h 40m

Chicago Midway

Sat 8/8

6:11 am-11:30 am

1 stop4h 19m

$537

JacksonvilleChicago

OAJ - MDW

OAJMDW

Jacksonville Albert J Ellis

Thu 8/13

6:00 am-12:39 pm

2 stops7h 39m

Chicago Midway

Mon 8/17

9:24 am-10:29 pm

2 stops12h 05m

$1,029
Cheapest one-way
Quickest one-way

JacksonvilleChicago

OAJ - MDW

OAJMDW

Jacksonville Albert J Ellis

Thu 7/30

6:44 pm-10:15 pm

1 stop4h 31m

$285

JacksonvilleChicago

OAJ - MDW

OAJMDW

Jacksonville Albert J Ellis

Thu 7/23

6:44 pm-10:15 pm

1 stop4h 31m

$440

JacksonvilleChicago

OAJ - MDW

OAJMDW

Jacksonville Albert J Ellis

Mon 7/27

6:44 pm-10:15 pm

1 stop4h 31m

$488

JacksonvilleChicago

OAJ - MDW

OAJMDW

Jacksonville Albert J Ellis

Fri 7/24

4:43 pm-10:15 pm

1 stop6h 32m

$488

JacksonvilleChicago

OAJ - MDW

OAJMDW

Jacksonville Albert J Ellis

Sat 7/25

4:35 pm-10:15 pm

1 stop6h 40m

$488

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/16

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 July.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • 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.
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.

  • What airport do you fly from for flights from Jacksonville to Chicago Midway?

    Located just 11.3 mi from the city center, Jacksonville Albert J Ellis is the airport most travelers will use when flying to Chicago Midway from Jacksonville. Booking flights from Albert J Ellis (OAJ) to Chicago Midway should be relatively easy as there are 0 daily outbound flights to Chicago Midway from 0 different airlines.

  • How long is the flight from Jacksonville, North Carolina to Chicago Midway Airport?

    Departing from Jacksonville, North Carolina to Chicago Midway Airport will take you 5h 05m. The distance between Jacksonville, North Carolina and Chicago Midway Airport is about 729 mi.

  • Can I find deals for flights from Jacksonville to Midway that include hotel bookings?

    Yes. In addition to deals on Jacksonville to Midway flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Jacksonville to Midway?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Jacksonville to Midway.

  • Can I find deals for business class flights from Jacksonville to Midway?

    Yes. Cheapflights offers flight deals from Jacksonville to Midway by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

See more FAQs

Traveling to a place near Chicago Midway Airport?

Book flights to Chicago Midway Airport if you plan to visit one of these locations
Benton Harbor
Lansing
Merrillville
Valparaiso
Hammond
Saint Joseph
Porter

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