$149 Cheap Delta flights Jacksonville (OAJ) to Chicago (MDW)

View $149 flight on Sat, Aug 30, 2025Opens in a new window

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$149 Cheap Delta flights Jacksonville (OAJ) to Chicago (MDW)

Prices were available within the past 7 days and start at $149 for one-way flights and $257 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Delta
Sat, Oct 18 - Mon, Oct 20
OAJ
Jacksonville
MDW
Chicago
$257 Roundtrip, found 4 days ago
$257
Roundtrip
found 4 days ago
Select Delta flight, departing Sat, Oct 18 from Jacksonville to Chicago, returning Mon, Oct 20, priced at $257 found 4 days ago
Delta
Wed, Sep 24 - Sun, Sep 28
OAJ
Jacksonville
MDW
Chicago
$268 Roundtrip, found 4 days ago
$268
Roundtrip
found 4 days ago
Select Delta flight, departing Wed, Sep 24 from Jacksonville to Chicago, returning Sun, Sep 28, priced at $268 found 4 days ago
Delta
Sun, Aug 31 - Fri, Sep 5
OAJ
Jacksonville
MDW
Chicago
$279 Roundtrip, found 5 days ago
$279
Roundtrip
found 5 days ago
Select Delta flight, departing Sun, Aug 31 from Jacksonville to Chicago, returning Fri, Sep 5, priced at $279 found 5 days ago
Delta
Sat, Oct 18 - Mon, Oct 20
OAJ
Jacksonville
MDW
Chicago
$288 Roundtrip, found 4 days ago
$288
Roundtrip
found 4 days ago
Select Delta flight, departing Sat, Oct 18 from Jacksonville to Chicago, returning Mon, Oct 20, priced at $288 found 4 days ago
Delta
Wed, Sep 3 - Sat, Sep 13
OAJ
Jacksonville
MDW
Chicago
$297 Roundtrip, just found
$297
Roundtrip
just found
Select Delta flight, departing Wed, Sep 3 from Jacksonville to Chicago, returning Sat, Sep 13, priced at $297 just found
Delta
Thu, Oct 16 - Sun, Oct 26
OAJ
Jacksonville
MDW
Chicago
$298 Roundtrip, found 5 days ago
$298
Roundtrip
found 5 days ago
Select Delta flight, departing Thu, Oct 16 from Jacksonville to Chicago, returning Sun, Oct 26, priced at $298 found 5 days ago
Flights from Jacksonville (OAJ) to Chicago (MDW)
Origin airport
Albert J. Ellis
Destination airport
Midway Intl.
Airlines serving
Delta
Popular airline
Delta
Distance
729 mi

Frequently asked questions

How much is a Delta Air Lines flight from Albert J. Ellis Airport (OAJ) to Midway Intl. Airport (MDW)?
Set the "Price (lowest to highest)" filter on Expedia to look for cheap Delta Air Lines return flights from $257 from OAJ to MDW. Affordable one-way tickets from $149 are also available.**These prices were available on Expedia within the past 7 days, for flights departing within the next year. Prices and availability are subject to change. Additional terms apply.
What is the cheapest month to fly from OAJ to MDW with Delta Air Lines?
Delta Air Lines flights to Chicago tend to be cheaper in the off-peak months of January and February. Whether you need a one-way or round-trip ticket, you could find a better deal then.
Does Delta Air Lines fly nonstop from Albert J. Ellis Airport (OAJ) to Midway Intl. Airport (MDW)?
To figure out if there's a direct journey from OAJ to MDW with Delta Air Lines or other carriers, check the "Nonstop" filter when looking for tickets.
What is the earliest Delta Air Lines flight from OAJ to MDW?
Search Delta Air Lines's earliest flights from OAJ to MDW by selecting our "Morning" and "Early Morning" filters. Not only will you get to your destination sooner, early departures also experience 20% fewer cancellations.**Most reliable time of the day recommendation is based on January through August 2024 flight status data sourced from OAG's global flight data platform.
What airports does Delta Air Lines fly into in Chicago?
Delta Air Lines flights from Albert J. Ellis Airport (OAJ) to Chicago come in to land at Midway Intl. Airport (MDW). This is the main entry point here.
Why fly with Delta Air Lines from OAJ to MDW?
Offering a rewarding loyalty program and an excellent in-flight experience, Delta Air Lines is the leading choice for many passengers flying from OAJ to MDW. Plus, if you're a Delta SkyMiles and One Key™ member booking through Expedia, you could earn OneKeyCash™* on eligible flights on top of your airline miles, which can go toward future trips.*OneKeyCash™ disclaimer - OneKeyCash™ is not redeemable for cash and can only be used on Expedia, Hotels.com and Vrbo.
Can I change or cancel my Delta Air Lines flight from Albert J. Ellis Airport (OAJ) to Midway Intl. Airport (MDW)?
You can usually cancel or modify your flight, although there may be additional fees if your booking was made more than 24 hours ago. Need to keep your options open? Make use of Expedia's "No cancel fee" and "Changes included" filters to find flights that won't charge extra if you have to revise your plans. To update your itinerary, go to "Trips," select your flight and click on "Manage Booking" for further information.
*Available to One Key members.