$99 Cheap Flights from Chicago (ORD) to Jackson (MKL)

View $99 flight on Thu, Apr 16, 2026Opens in a new window

Popular airlines from Chicago O'Hare Intl. Airport (ORD) to Jackson, TN (MKL-McKellar-Sipes Regional)

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Cheap Flights from Chicago to Jackson (ORD-MKL)

Prices were available within the past 7 days and start at $99 for one-way flights and $199 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

KEY LIME AIR DBA DENVER AIR CONNECTION
Sun, Mar 22 - Sun, Mar 29
ORD
Chicago
MKL
Jackson
$199 Roundtrip, just found
$199
Roundtrip
just found
Select KEY LIME AIR DBA DENVER AIR CONNECTION flight, departing Sun, Mar 22 from Chicago to Jackson, returning Sun, Mar 29, priced at $199 just found
KEY LIME AIR DBA DENVER AIR CONNECTION
Tue, Dec 23 - Mon, Dec 29
ORD
Chicago
MKL
Jackson
$204 Roundtrip, found 4 hours ago
$204
Roundtrip
found 4 hours ago
Select KEY LIME AIR DBA DENVER AIR CONNECTION flight, departing Tue, Dec 23 from Chicago to Jackson, returning Mon, Dec 29, priced at $204 found 4 hours ago
KEY LIME AIR DBA DENVER AIR CONNECTION
Mon, Nov 24 - Sun, Dec 7
ORD
Chicago
MKL
Jackson
$223 Roundtrip, found 13 hours ago
$223
Roundtrip
found 13 hours ago
Select KEY LIME AIR DBA DENVER AIR CONNECTION flight, departing Mon, Nov 24 from Chicago to Jackson, returning Sun, Dec 7, priced at $223 found 13 hours ago
KEY LIME AIR DBA DENVER AIR CONNECTION
Mon, Nov 24 - Mon, Dec 1
ORD
Chicago
MKL
Jackson
$228 Roundtrip, found 1 day ago
$228
Roundtrip
found 1 day ago
Select KEY LIME AIR DBA DENVER AIR CONNECTION flight, departing Mon, Nov 24 from Chicago to Jackson, returning Mon, Dec 1, priced at $228 found 1 day ago
KEY LIME AIR DBA DENVER AIR CONNECTION
Sat, Nov 8 - Sun, Nov 23
ORD
Chicago
MKL
Jackson
$244 Roundtrip, found 12 hours ago
$244
Roundtrip
found 12 hours ago
Select KEY LIME AIR DBA DENVER AIR CONNECTION flight, departing Sat, Nov 8 from Chicago to Jackson, returning Sun, Nov 23, priced at $244 found 12 hours ago
KEY LIME AIR DBA DENVER AIR CONNECTION
Sat, Nov 15 - Mon, Dec 1
ORD
Chicago
MKL
Jackson
$248 Roundtrip, found 13 hours ago
$248
Roundtrip
found 13 hours ago
Select KEY LIME AIR DBA DENVER AIR CONNECTION flight, departing Sat, Nov 15 from Chicago to Jackson, returning Mon, Dec 1, priced at $248 found 13 hours ago
KEY LIME AIR DBA DENVER AIR CONNECTION
Wed, Dec 3 - Sat, Dec 6
ORD
Chicago
MKL
Jackson
$266 Roundtrip, found 11 hours ago
$266
Roundtrip
found 11 hours ago
Select KEY LIME AIR DBA DENVER AIR CONNECTION flight, departing Wed, Dec 3 from Chicago to Jackson, returning Sat, Dec 6, priced at $266 found 11 hours ago
KEY LIME AIR DBA DENVER AIR CONNECTION
Sat, Nov 8 - Sat, Nov 15
ORD
Chicago
MKL
Jackson
$268 Roundtrip, found 12 hours ago
$268
Roundtrip
found 12 hours ago
Select KEY LIME AIR DBA DENVER AIR CONNECTION flight, departing Sat, Nov 8 from Chicago to Jackson, returning Sat, Nov 15, priced at $268 found 12 hours ago
American Airlines
Mon, Dec 8 - Fri, Dec 12
ORD
Chicago
MKL
Jackson
$276 Roundtrip, found 2 days ago
$276
Roundtrip
found 2 days ago
Select American Airlines flight, departing Mon, Dec 8 from Chicago to Jackson, returning Fri, Dec 12, priced at $276 found 2 days ago
Delta
Tue, Dec 16 - Sun, Dec 28
ORD
Chicago
MKL
Jackson
$296 Roundtrip, found 13 hours ago
$296
Roundtrip
found 13 hours ago
Select Delta flight, departing Tue, Dec 16 from Chicago to Jackson, returning Sun, Dec 28, priced at $296 found 13 hours ago

Alternative airports near Jackson

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

Select flight to McKellar-Sipes Regional MKL. Cheapest and Closest option available. Average driving time to city center is 11 minutes. Flights from $223
MKL
McKellar-Sipes Regional
CheapestClosest
Average driving time to city center11 min
Flights from $223

Frequently asked questions

How much does a flight from O'Hare Intl. Airport (ORD) to McKellar-Sipes Regional Airport (MKL) cost?
Grab a cheap one-way flight from $99 or cheap return flight from $199 from O'Hare Intl. Airport (ORD) to McKellar-Sipes Regional Airport (MKL) 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 O'Hare Intl. Airport (ORD) to McKellar-Sipes Regional Airport (MKL)?
Planning your getaway for March is a great way to save, as it's the cheapest month for flights between ORD and MKL. You'll typically find the lowest fares during the off-season.
Which airlines fly direct from O'Hare Intl. Airport (ORD) to McKellar-Sipes Regional Airport (MKL)?
Catch a nonstop flight with Denver Air Connection and travel straight from O'Hare Intl. Airport (ORD) to McKellar-Sipes Regional Airport (MKL).
What is the cheapest airline that flies from O'Hare Intl. Airport (ORD) to McKellar-Sipes Regional Airport (MKL)?
To find the cheapest airline flying from ORD to MKL, use Expedia's filter tool. Tailor your search based on your travel needs, such as preferred carriers and seat class. You can then sort your results by "Price (lowest to highest)" to see the most affordable options first.
How many flights per day from O'Hare Intl. Airport (ORD) to McKellar-Sipes Regional Airport (MKL)?
On average, you can pick from 6 direct flights each week from O'Hare Intl. Airport (ORD) to McKellar-Sipes Regional Airport (MKL). For more flexibility, consider flights with layovers. Enter your dates on Expedia and then set the filters to include one stop or more.
What are the most popular departure times for flights from O'Hare Intl. Airport (ORD) to McKellar-Sipes Regional Airport (MKL)?
The 12 PM departures from ORD to MKL see the highest demand. Greater demand means you'll likely pay more for these departures. If you're looking to save, choose a less crowded time to fly.
What day of the week has the most flights from ORD to MKL?
Sunday offers the most flights from O'Hare Intl. Airport (ORD) to McKellar-Sipes Regional Airport (MKL). Consider jetting off on this day and you'll have the best chance of finding a departure that fits your plans.
What is the earliest flight from O'Hare Intl. Airport (ORD) to McKellar-Sipes Regional Airport (MKL)?
The earliest flight taking off from O'Hare Intl. Airport (ORD) is at around 12:40PM UTC-6. Hop on this flight and you'll arrive at McKellar-Sipes Regional Airport (MKL) at approximately 2:30PM UTC-6. The entire trip takes 1h 50m.
How long does it take to fly from O'Hare Intl. Airport (ORD) to McKellar-Sipes Regional Airport (MKL)?
Flights from ORD to MKL have an average travel time of 1 hour and 50 minutes. The distance between these two airports is 440 mi.
What is the best time to fly from O'Hare Intl. Airport (ORD) to McKellar-Sipes Regional Airport (MKL)?
Choose a flight from O'Hare Intl. Airport (ORD) to McKellar-Sipes Regional Airport (MKL) that takes off before 3 PM to reduce the risk of delays and cancellations. Departures after this hour are on average 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.
What airports do you fly into for Jackson from O'Hare Intl. Airport (ORD)?
If you're flying on a direct flight from O'Hare Intl. Airport (ORD) to Jackson, McKellar-Sipes Regional Airport (MKL) is the only airport you can touch down at.
Is it cheaper to buy a plane ticket from O'Hare Intl. Airport (ORD) to McKellar-Sipes Regional Airport (MKL) last-minute?
Waiting until right before your break to book your flight from ORD to MKL often results in higher prices. While you may find some last-minute deals, they're not always guaranteed. Be flexible with your itinerary for a better chance of snagging a bargain.
Is it cheaper to book an ORD to MKL flight and hotel package?
Booking an ORD to MKL flight and hotel package is typically cheaper than booking separately. With Expedia, you can enjoy the convenience of organizing your trip all in one place. Choose from our impressive range of accommodations 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 O'Hare Intl. Airport (ORD) to McKellar-Sipes Regional Airport (MKL)?
Usually, it's possible to reschedule or cancel your ORD to MKL flight. However, if it's been more than 24 hours since booking, additional charges may apply. Check your airline's policies in your itinerary to see what changes are allowed and whether any costs are involved. You'll also find more information on our Customer Service portal.

Travel information

Origin airport
O'Hare Intl.
Destination airport
McKellar-Sipes Regional
Airlines serving
KEY LIME AIR DBA DENVER AIR CONNECTION
Roundtrip price
$192
Distance
443 mi
Average flight time
1 hour 50 mins

Book with confidence

Chicago to Jackson Flights

The cheapest times to fly from Chicago to Jackson

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

 

The best time to book a flight from Chicago to Jackson

Sunday is one of the best days to book for cheap flights from Chicago to Jackson: 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 Chicago to Jackson

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 Chicago to Jackson in 2025. You can also book with separate airlines for your outbound and return journeys, from $99 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 Chicago to Jackson 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 Chicago to Jackson 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.

 

Chicago to Jackson Flights

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*Available to One Key members.