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$475+ 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 7/11. Fares are subject to change and may not be available on all flights or dates of travel.
OAJ — MDW
Jul 28 — Aug 41
Tue 7/28
Tue 8/4
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 June 28, 2026.

This Delta deal was found by Cheapflights users on 6/25. 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.
Sat 7/114:35 pm
OAJ
-
MDW
1 stop6h 40m
Delta
Wed 7/1511:05 am
MDW
-
OAJ
1 stop5h 57m
Delta
Deal found 6/25$475
This Delta deal was found by Cheapflights users on 6/24. 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.
Fri 7/106:44 pm
OAJ
-
MDW
1 stop4h 31m
Delta
Mon 7/136:00 am
MDW
-
OAJ
1 stop4h 19m
Delta
Deal found 6/24$527
This Delta deal was found by Cheapflights users on 6/26. 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 12/235:40 am
OAJ
-
MDW
2 stops11h 42m
Delta
Sat 12/266:00 am
MDW
-
OAJ
1 stop4h 12m
Delta
Deal found 6/26$554
This Delta deal was found by Cheapflights users on 6/27. 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 7/126:44 pm
OAJ
-
MDW
1 stop4h 31m
Delta
Thu 7/166:00 am
MDW
-
OAJ
1 stop4h 19m
Delta
Deal found 6/27$569
This Delta deal was found by Cheapflights users on 6/24. 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 7/96:44 pm
OAJ
-
MDW
1 stop4h 31m
Delta
Mon 7/136:00 am
MDW
-
OAJ
1 stop4h 19m
Delta
Deal found 6/24$582
This Delta deal was found by Cheapflights users on 6/26. 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 12/245:40 am
OAJ
-
MDW
2 stops11h 42m
Delta
Sat 12/266:00 am
MDW
-
OAJ
1 stop4h 12m
Delta
Deal found 6/26$616
This Delta deal was found by Cheapflights users on 6/23. 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.
Thu 6/254:45 pm
OAJ
-
MDW
1 stop6h 32m
Delta
Thu 7/26:00 am
MDW
-
OAJ
1 stop4h 21m
Delta
Deal found 6/23$702

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 June 28, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$475
(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

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 June 28, 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

Sat 7/11

4:35 pm-10:15 pm

1 stop6h 40m

Chicago Midway

Wed 7/15

11:05 am-6:02 pm

1 stop5h 57m

$475
Quickest round-trip

JacksonvilleChicago

OAJ - MDW

OAJMDW

Jacksonville Albert J Ellis

Fri 7/10

6:44 pm-10:15 pm

1 stop4h 31m

Chicago Midway

Mon 7/13

6:00 am-11:19 am

1 stop4h 19m

$527

JacksonvilleChicago

OAJ - MDW

OAJMDW

Jacksonville Albert J Ellis

Sun 7/12

6:44 pm-10:15 pm

1 stop4h 31m

Chicago Midway

Thu 7/16

6:00 am-11:19 am

1 stop4h 19m

$569

JacksonvilleChicago

OAJ - MDW

OAJMDW

Jacksonville Albert J Ellis

Thu 7/9

6:44 pm-10:15 pm

1 stop4h 31m

Chicago Midway

Mon 7/13

6:00 am-11:19 am

1 stop4h 19m

$582

JacksonvilleChicago

OAJ - MDW

OAJMDW

Jacksonville Albert J Ellis

Wed 12/23

11:06 am-4:25 pm

1 stop6h 19m

Chicago Midway

Sat 12/26

6:00 am-11:12 am

1 stop4h 12m

$611

JacksonvilleChicago

OAJ - MDW

OAJMDW

Jacksonville Albert J Ellis

Thu 12/24

5:40 am-4:22 pm

2 stops11h 42m

Chicago Midway

Sat 12/26

11:20 am-10:15 pm

2 stops9h 55m

$801

JacksonvilleChicago

OAJ - MDW

OAJMDW

Jacksonville Albert J Ellis

Wed 7/8

6:44 pm-10:15 pm

1 stop4h 31m

Chicago Midway

Sun 7/12

6:00 am-11:19 am

1 stop4h 19m

$829

JacksonvilleChicago

OAJ - MDW

OAJMDW

Jacksonville Albert J Ellis

Sat 7/18

4:35 pm-10:15 pm

1 stop6h 40m

Chicago Midway

Sun 7/26

12:41 pm-6:02 pm

1 stop4h 21m

$903

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/25

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 June.
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 6h 40m. 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
Hammond
Lansing
Merrillville
Valparaiso
Porter

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