$119 Cheap Flights from Jacksonville (OAJ) to Chicago (MDW)

View $119 flight on Mon, Nov 24, 2025Opens in a new window

Popular airlines from Albert J. Ellis Airport (OAJ) to Chicago Midway Airport (MDW)

Cheap Flights from Jacksonville to Chicago (OAJ-MDW)

Prices were available within the past 7 days and start at $119 for one-way flights and $280 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Delta
Tue, Dec 16 - Wed, Dec 31
OAJ
Jacksonville
MDW
Chicago
$280 Roundtrip, found 2 days ago
$280
Roundtrip
found 2 days ago
Select Delta flight, departing Tue, Dec 16 from Jacksonville to Chicago, returning Wed, Dec 31, priced at $280 found 2 days ago
Delta
Mon, Dec 15 - Wed, Dec 24
OAJ
Jacksonville
MDW
Chicago
$294 Roundtrip, found 2 days ago
$294
Roundtrip
found 2 days ago
Select Delta flight, departing Mon, Dec 15 from Jacksonville to Chicago, returning Wed, Dec 24, priced at $294 found 2 days ago
Delta
Mon, Nov 24 - Thu, Nov 27
OAJ
Jacksonville
MDW
Chicago
$297 Roundtrip, found 5 days ago
$297
Roundtrip
found 5 days ago
Select Delta flight, departing Mon, Nov 24 from Jacksonville to Chicago, returning Thu, Nov 27, priced at $297 found 5 days ago
Delta
Mon, Dec 22 - Wed, Dec 31
OAJ
Jacksonville
MDW
Chicago
$307 Roundtrip, found 2 days ago
$307
Roundtrip
found 2 days ago
Select Delta flight, departing Mon, Dec 22 from Jacksonville to Chicago, returning Wed, Dec 31, priced at $307 found 2 days ago
Delta
Wed, Dec 3 - Mon, Dec 15
OAJ
Jacksonville
MDW
Chicago
$317 Roundtrip, found 4 days ago
$317
Roundtrip
found 4 days ago
Select Delta flight, departing Wed, Dec 3 from Jacksonville to Chicago, returning Mon, Dec 15, priced at $317 found 4 days ago
Delta
Mon, Nov 24 - Tue, Dec 2
OAJ
Jacksonville
MDW
Chicago
$318 Roundtrip, found 5 days ago
$318
Roundtrip
found 5 days ago
Select Delta flight, departing Mon, Nov 24 from Jacksonville to Chicago, returning Tue, Dec 2, priced at $318 found 5 days ago
Delta
Mon, Nov 24 - Mon, Dec 1
OAJ
Jacksonville
MDW
Chicago
$322 Roundtrip, found 1 day ago
$322
Roundtrip
found 1 day ago
Select Delta flight, departing Mon, Nov 24 from Jacksonville to Chicago, returning Mon, Dec 1, priced at $322 found 1 day ago
Delta
Wed, Dec 3 - Sat, Dec 6
OAJ
Jacksonville
MDW
Chicago
$328 Roundtrip, found 4 days ago
$328
Roundtrip
found 4 days ago
Select Delta flight, departing Wed, Dec 3 from Jacksonville to Chicago, returning Sat, Dec 6, priced at $328 found 4 days ago
Delta
Tue, Dec 16 - Tue, Dec 30
OAJ
Jacksonville
MDW
Chicago
$331 Roundtrip, found 2 days ago
$331
Roundtrip
found 2 days ago
Select Delta flight, departing Tue, Dec 16 from Jacksonville to Chicago, returning Tue, Dec 30, priced at $331 found 2 days ago
Delta
Mon, Nov 24 - Mon, Dec 1
OAJ
Jacksonville
MDW
Chicago
$337 Roundtrip, found 5 days ago
$337
Roundtrip
found 5 days ago
Select Delta flight, departing Mon, Nov 24 from Jacksonville to Chicago, returning Mon, Dec 1, priced at $337 found 5 days ago

Alternative airports near Chicago

Prices were available within the past 7 days. Prices and availability are subject to change.

Select flight to O'Hare Intl. ORD. Average driving time to city center is 23 minutes. Flights from $374
ORD
O'Hare Intl.
Average driving time to city center23 min
Flights from $374
Flights from Jacksonville (OAJ) to Chicago (MDW)
Origin airport
Albert J. Ellis
Destination airport
Midway Intl.
Airlines serving
Delta
Roundtrip price
$279
Distance
729 mi

Jacksonville to Chicago Flights

The cheapest times to fly from Jacksonville to Chicago

On average, Thursday can be the cheapest time to fly, according to data from the Airlines Reporting Corporation (ARC), one of the world's biggest databases for global airline sales. The data reveals that you could save up to 16% by flying on a Thursday—the cheapest day to travel on average—instead of a Sunday—the most expensive. Some of the most affordable flights from Jacksonville to Chicago are during the month of December. You can find some of the cheapest flights from Jacksonville to Chicago with Expedia's search tool and vast selection of airlines.

 

The best time to book a flight from Jacksonville to Chicago

Sunday is one of the best days to book for cheap flights from Jacksonville to Chicago: Tickets reserved on a Sunday cost between 6% and 13% less than those reserved on a Friday, according to ARC data. The data also suggests booking early can also lead to cheaper airfares. You could save 24% by buying your tickets for domestic flights at least a month in advance and 10% by booking international flights 2 months in advance.

 

How to find cheap round-trip tickets from Jacksonville to Chicago

Being flexible with your dates and using Expedia's Price Drop Protection and Price Tracking features are some of the best ways of finding a cheap ticket from Jacksonville to Chicago in 2025. You can also book with separate airlines for your outbound and return journeys, from $119 one-way. Expedia also offers Price Drop Protection, so if the cost of your airfare goes down after booking, you'll receive a credit for the difference*. This is available for a small fee, and is free to One Key Gold and Platinum tier members.

 

Expedia's Price Tracking feature means you can stay on top of airfares without manually checking every day. It sends you automated price alerts for cheap Jacksonville to Chicago flights and uses historical data to indicate when the best time to book is. Download Expedia's free app to activate this handy tool in a few easy taps.

 

You could also save big by booking one of Expedia's vacation packages. Bundling together your Jacksonville to Chicago airfare with your accommodations and car rental is often cheaper than booking everything separately. There’s also One Key, Expedia's generous rewards program. Join for free and you could earn One Key cash on most bookings to save on future adventures.

 

*Terms apply.

 

Disclaimer: ARC The statistics are based on average round-trip ticket prices between January and August 2023. The percentages you see are averages.

 

Frequently asked questions

How much does a flight from Albert J. Ellis Airport (OAJ) to Midway Intl. Airport (MDW) cost?
Grab a cheap one-way flight from $119 or cheap return flight from $280 from Albert J. Ellis Airport (OAJ) to Midway Intl. Airport (MDW) with Expedia. Enter your travel dates and sort by "Price (lowest to highest)" to find our cheapest flight offers on this route.
What is the cheapest month to fly from Albert J. Ellis Airport (OAJ) to Midway Intl. Airport (MDW)?
Planning your trip for December can help you save, as it's the cheapest month for flights between OAJ and MDW. You'll usually find the lowest fares during off-peak months.
What is the cheapest airline that flies from Albert J. Ellis Airport (OAJ) to Midway Intl. Airport (MDW)?
To find the cheapest airline that'll fly you from OAJ to MDW, use Expedia's filter tool. Customize your search based on what matters most to you, such as preferred carriers and ideal departure window. You can then sort your results by "Price (lowest to highest)" to see the cheapest flights first.
How many flights per day from Albert J. Ellis Airport (OAJ) to Midway Intl. Airport (MDW)?
You'll have to hop on a flight with a layover if you're traveling from Albert J. Ellis Airport (OAJ) to Midway Intl. Airport (MDW). Direct flights don't operate daily on this route. However, simply filter your search to include one or more stops to find the best option for your trip.
What day of the week has the most flights from OAJ to MDW?
Usually you'll find the widest variety of flight choices on a Friday. Tuesdays are often the quietest.* However, this can vary depending on the time of year, carrier and other factors.*Busiest/quietest day to travel is based on Expedia flight demand through January to December 2024.
What is the best time to fly from Albert J. Ellis Airport (OAJ) to Midway Intl. Airport (MDW)?
To avoid possible delays on the Albert J. Ellis Airport (OAJ) to Midway Intl. Airport (MDW) route, fly before 3 PM. Departures after this time are 22% more likely to be canceled.**Most reliable time of the day and month to travel recommendation is based on January through August 2024 flight status data sourced from OAG's global flight data platform.
Is it cheaper to buy a plane ticket from Albert J. Ellis Airport (OAJ) to Midway Intl. Airport (MDW) last-minute?
Booking your ticket from OAJ to MDW right before your journey is generally more expensive. However, if you're flexible with your travel dates and times, you could bag a cheap last-minute fare.
Is it cheaper to book an OAJ to MDW flight and hotel package?
Opting for an OAJ to MDW flight and hotel package is typically cheaper than booking separately. With Expedia, you can enjoy the convenience of organizing your travels all in one place. Select from our extensive range of hotels and then add flights, car rentals and activities to your booking. Bundle it all together, and you could save hundreds of dollars.
Can I cancel or change the date of my flight from Albert J. Ellis Airport (OAJ) to Midway Intl. Airport (MDW)?
If you reserved your OAJ to MDW flight in the last 24 hours, you may be able to cancel or modify it at no cost. Depending on the airline and the type of fare you purchased, additional charges may apply for changes beyond that time. Airline policies and contact information can be found in your itinerary or confirmation email. Or, head to our Customer Service portal for more details.

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*Available to One Key members.