$128 Cheap Flights from Jackson (JAN) to Chicago (ORD)

View $128 flight on Sun, Jan 18, 2026Opens in a new window

Popular airlines from Evers Intl. Airport (JAN) to Chicago O'Hare Intl. Airport (ORD)

Cheap Flights from Jackson to Chicago (JAN-ORD)

Prices were available within the past 7 days and start at $128 for one-way flights and $255 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Delta
Sat, Jan 17 - Tue, Jan 20
JAN
Jackson
ORD
Chicago
$255 Roundtrip, found 1 hour ago
$255
Roundtrip
found 1 hour ago
Select Delta flight, departing Sat, Jan 17 from Jackson to Chicago, returning Tue, Jan 20, priced at $255 found 1 hour ago
American Airlines
Sat, Jan 10 - Sat, Jan 17
JAN
Jackson
ORD
Chicago
$276 Roundtrip, found 1 hour ago
$276
Roundtrip
found 1 hour ago
Select American Airlines flight, departing Sat, Jan 10 from Jackson to Chicago, returning Sat, Jan 17, priced at $276 found 1 hour ago
American Airlines
Wed, Feb 18 - Sat, Feb 21
JAN
Jackson
ORD
Chicago
$277 Roundtrip, found 5 days ago
$277
Roundtrip
found 5 days ago
Select American Airlines flight, departing Wed, Feb 18 from Jackson to Chicago, returning Sat, Feb 21, priced at $277 found 5 days ago
American Airlines
Wed, Feb 11 - Sat, Feb 14
JAN
Jackson
ORD
Chicago
$277 Roundtrip, found 4 days ago
$277
Roundtrip
found 4 days ago
Select American Airlines flight, departing Wed, Feb 11 from Jackson to Chicago, returning Sat, Feb 14, priced at $277 found 4 days ago
Delta
Thu, Jan 15 - Tue, Jan 20
JAN
Jackson
ORD
Chicago
$279 Roundtrip, found 1 hour ago
$279
Roundtrip
found 1 hour ago
Select Delta flight, departing Thu, Jan 15 from Jackson to Chicago, returning Tue, Jan 20, priced at $279 found 1 hour ago
American Airlines
Wed, Feb 11 - Sat, Feb 14
JAN
Jackson
ORD
Chicago
$279 Roundtrip, found 4 days ago
$279
Roundtrip
found 4 days ago
Select American Airlines flight, departing Wed, Feb 11 from Jackson to Chicago, returning Sat, Feb 14, priced at $279 found 4 days ago
American Airlines
Wed, Jan 14 - Sat, Jan 17
JAN
Jackson
ORD
Chicago
$280 Roundtrip, found 6 days ago
$280
Roundtrip
found 6 days ago
Select American Airlines flight, departing Wed, Jan 14 from Jackson to Chicago, returning Sat, Jan 17, priced at $280 found 6 days ago
American Airlines
Wed, Feb 18 - Sat, Feb 21
JAN
Jackson
ORD
Chicago
$281 Roundtrip, found 5 days ago
$281
Roundtrip
found 5 days ago
Select American Airlines flight, departing Wed, Feb 18 from Jackson to Chicago, returning Sat, Feb 21, priced at $281 found 5 days ago
Southwest Airlines
Mon, Jan 12 - Sat, Jan 17
JAN
Jackson
ORD
Chicago
$298 Roundtrip, found 3 hours ago
$298
Roundtrip
found 3 hours ago
Select Southwest Airlines flight, departing Mon, Jan 12 from Jackson to Chicago, returning Sat, Jan 17, priced at $298 found 3 hours ago
United
Sat, Jan 10 - Tue, Jan 13
JAN
Jackson
ORD
Chicago
$478 Roundtrip, found 1 day ago
$478
Roundtrip
found 1 day ago
Select United flight, departing Sat, Jan 10 from Jackson to Chicago, returning Tue, Jan 13, priced at $478 found 1 day ago

Find the cheapest month to fly from Jackson (JAN) to Chicago (ORD)

August is typically the cheapest month to fly

From $182 - $538 per traveler.

Alternative airports near Chicago

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

Select flight to Midway Intl. MDW. Closest option available. Average driving time to city center is 16 minutes. Flights from $417
MDW
Midway Intl.
Closest
Average driving time to city center16 min
Flights from $417
Flights from Jackson (JAN) to Chicago (ORD)
Origin airport
Evers Intl.
Destination airport
O'Hare Intl.
Airlines serving
American Airlines, Delta, Southwest Airlines, United
Roundtrip price
$254
Distance
678 mi

Jackson to Chicago Flights

The cheapest times to fly from Jackson 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 Jackson to Chicago are during the month of January. You can find some of the cheapest flights from Jackson to Chicago with Expedia's search tool and vast selection of airlines.

 

The best time to book a flight from Jackson to Chicago

Sunday is one of the best days to book for cheap flights from Jackson 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 Jackson 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 Jackson to Chicago in 2026. You can also book with separate airlines for your outbound and return journeys, from $128 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 Jackson 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 Jackson 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 Evers Intl. Airport (JAN) to O'Hare Intl. Airport (ORD) cost?
Snag a cheap one-way flight from $128 or cheap return flight from $255 from Evers Intl. Airport (JAN) to O'Hare Intl. Airport (ORD) with Expedia. Enter your travel dates and sort by "Price (lowest to highest)" to see our cheapest flight deals on this route.
What is the cheapest month to fly from Evers Intl. Airport (JAN) to O'Hare Intl. Airport (ORD)?
Planning your trip for January is a good way to save, as it's the cheapest month for flights between JAN and ORD. You'll often find the lowest fares during the off-season.
What is the cheapest airline that flies from Evers Intl. Airport (JAN) to O'Hare Intl. Airport (ORD)?
To find the cheapest airline that'll fly you from JAN to ORD, use Expedia's filter tool. Tailor your search based on what matters most to you, such as preferred carriers and flight duration. You can then sort your results by "Price (lowest to highest)" to discover the cheapest flight right away.
How many flights per day from Evers Intl. Airport (JAN) to O'Hare Intl. Airport (ORD)?
There are no daily direct flights departing from Evers Intl. Airport (JAN) to O'Hare Intl. Airport (ORD). But you can choose flights with layovers. Filter your search on Expedia to include one or two stops, and you'll be soaring above the clouds before you know it.
What day of the week has the most flights from JAN to ORD?
Typically you'll have the most choice when it comes to flights on a Friday. Tuesdays are often the quietest.* But this can vary based 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 Evers Intl. Airport (JAN) to O'Hare Intl. Airport (ORD)?
To reach O'Hare Intl. Airport (ORD) on schedule, select a flight that takes off from Evers Intl. Airport (JAN) before 3 PM. The chance of cancellations is 22% higher, on average, for departures after this time.**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 Evers Intl. Airport (JAN) to O'Hare Intl. Airport (ORD) last-minute?
Booking your plane ticket from JAN to ORD shortly before your journey is usually more expensive. However, if you're flexible with your schedule, you could score a cheap last-minute fare.
Is it cheaper to book a JAN to ORD flight and hotel package?
You'll generally save money by booking a JAN to ORD flight and hotel package compared to booking separately. In fact, you could save hundreds of dollars by bundling with Expedia. And it's easy to manage it all in one place. Once you've selected your preferred flights and accommodations, consider adding extras like activities, tours and car rentals.
Can I cancel or change the date of my flight from Evers Intl. Airport (JAN) to O'Hare Intl. Airport (ORD)?
If you booked your JAN to ORD flight in the last 24 hours, you may be able to modify or cancel it without fees. Depending on the airline and the type of ticket 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, visit our Customer Service portal for more details.

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*Available to One Key members.