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

View $99 flight on Sat, Aug 23, 2025Opens in a new window

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

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Cheap Flights from Jackson to Chicago (MKL-ORD)

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
Thu, Sep 25 - Thu, Oct 2
MKL
Jackson
ORD
Chicago
$199 Roundtrip, found 1 hour ago
$199
Roundtrip
found 1 hour ago
Select KEY LIME AIR DBA DENVER AIR CONNECTION flight, departing Thu, Sep 25 from Jackson to Chicago, returning Thu, Oct 2, priced at $199 found 1 hour ago
KEY LIME AIR DBA DENVER AIR CONNECTION
Sun, Sep 28 - Mon, Sep 29
MKL
Jackson
ORD
Chicago
$204 Roundtrip, found 1 hour ago
$204
Roundtrip
found 1 hour ago
Select KEY LIME AIR DBA DENVER AIR CONNECTION flight, departing Sun, Sep 28 from Jackson to Chicago, returning Mon, Sep 29, priced at $204 found 1 hour ago
KEY LIME AIR DBA DENVER AIR CONNECTION
Sat, Aug 30 - Mon, Sep 15
MKL
Jackson
ORD
Chicago
$209 Roundtrip, found 3 hours ago
$209
Roundtrip
found 3 hours ago
Select KEY LIME AIR DBA DENVER AIR CONNECTION flight, departing Sat, Aug 30 from Jackson to Chicago, returning Mon, Sep 15, priced at $209 found 3 hours ago
KEY LIME AIR DBA DENVER AIR CONNECTION
Thu, Aug 14 - Thu, Aug 21
MKL
Jackson
ORD
Chicago
$223 Roundtrip, found 1 hour ago
$223
Roundtrip
found 1 hour ago
Select KEY LIME AIR DBA DENVER AIR CONNECTION flight, departing Thu, Aug 14 from Jackson to Chicago, returning Thu, Aug 21, priced at $223 found 1 hour ago
KEY LIME AIR DBA DENVER AIR CONNECTION
Thu, Aug 14 - Fri, Aug 22
MKL
Jackson
ORD
Chicago
$228 Roundtrip, found 1 hour ago
$228
Roundtrip
found 1 hour ago
Select KEY LIME AIR DBA DENVER AIR CONNECTION flight, departing Thu, Aug 14 from Jackson to Chicago, returning Fri, Aug 22, priced at $228 found 1 hour ago
KEY LIME AIR DBA DENVER AIR CONNECTION
Tue, Aug 12 - Thu, Aug 21
MKL
Jackson
ORD
Chicago
$244 Roundtrip, found 1 hour ago
$244
Roundtrip
found 1 hour ago
Select KEY LIME AIR DBA DENVER AIR CONNECTION flight, departing Tue, Aug 12 from Jackson to Chicago, returning Thu, Aug 21, priced at $244 found 1 hour ago
KEY LIME AIR DBA DENVER AIR CONNECTION
Fri, Aug 15 - Sat, Aug 16
MKL
Jackson
ORD
Chicago
$248 Roundtrip, found 1 hour ago
$248
Roundtrip
found 1 hour ago
Select KEY LIME AIR DBA DENVER AIR CONNECTION flight, departing Fri, Aug 15 from Jackson to Chicago, returning Sat, Aug 16, priced at $248 found 1 hour ago
KEY LIME AIR DBA DENVER AIR CONNECTION
Sat, Dec 6 - Sun, Dec 7
MKL
Jackson
ORD
Chicago
$267 Roundtrip, found 13 hours ago
$267
Roundtrip
found 13 hours ago
Select KEY LIME AIR DBA DENVER AIR CONNECTION flight, departing Sat, Dec 6 from Jackson to Chicago, returning Sun, Dec 7, priced at $267 found 13 hours ago
KEY LIME AIR DBA DENVER AIR CONNECTION
Tue, Aug 12 - Thu, Aug 14
MKL
Jackson
ORD
Chicago
$268 Roundtrip, found 1 hour ago
$268
Roundtrip
found 1 hour ago
Select KEY LIME AIR DBA DENVER AIR CONNECTION flight, departing Tue, Aug 12 from Jackson to Chicago, returning Thu, Aug 14, priced at $268 found 1 hour ago
KEY LIME AIR DBA DENVER AIR CONNECTION
Sat, Aug 2 - Wed, Aug 20
MKL
Jackson
ORD
Chicago
$273 Roundtrip, found 6 hours ago
$273
Roundtrip
found 6 hours ago
Select KEY LIME AIR DBA DENVER AIR CONNECTION flight, departing Sat, Aug 2 from Jackson to Chicago, returning Wed, Aug 20, priced at $273 found 6 hours ago

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 $464
MDW
Midway Intl.
Closest
Average driving time to city center16 min
Flights from $464
Flights from Jackson (MKL) to Chicago (ORD)
Origin airport
McKellar-Sipes Regional
Destination airport
O'Hare Intl.
Airlines serving
KEY LIME AIR DBA DENVER AIR CONNECTION
Roundtrip price
$198
Distance
443 mi
Average flight time
1 hour 40 mins

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 September. 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 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 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 McKellar-Sipes Regional Airport (MKL) to O'Hare Intl. Airport (ORD) cost?
Score cheap return tickets from McKellar-Sipes Regional Airport (MKL) to O'Hare Intl. Airport (ORD) starting from $199. Reserve your seat and get ready to go. This information is based on the cheapest price found on Expedia for this return journey departing within the next three months. This airfare is for a Key Lime DBA Denver Air Connection flight leaving MKL on August 14 2025 and touching down at ORD. The price was last updated on July 23 2025 and has not changed since.
What is the cheapest month to fly from MKL to ORD?
The cheapest flights from MKL to ORD are usually during off-peak season, when demand is lower. To save money, avoid flying during public holidays, school breaks and major local events.
Which airlines fly direct from McKellar-Sipes Regional Airport (MKL) to O'Hare Intl. Airport (ORD)?
Fly directly from McKellar-Sipes Regional Airport (MKL) to O'Hare Intl. Airport (ORD) on a Denver Air Connection flight.
What is the cheapest airline that flies from MKL to ORD?
With prices as low as $99 for a one-way flight from MKL to ORD, Key Lime DBA Denver Air Connection is currently the cheapest carrier operating this route. This fare is based on the lowest price found on Expedia departing within the next three months. The flight takes off from MKL on September 4 2025. Prices were last updated on July 23 2025 and have not changed since.
How many flights per day from McKellar-Sipes Regional Airport (MKL) to O'Hare Intl. Airport (ORD)?
On average you can take your pick of 6 direct flights each week from McKellar-Sipes Regional Airport (MKL) to O'Hare Intl. Airport (ORD). For more options, consider flights with layovers. Enter your dates on Expedia and then set the filter tool to include one or two stops.
What are the most popular departure times for flights from McKellar-Sipes Regional Airport (MKL) to O'Hare Intl. Airport (ORD)?
The 11 AM departures from MKL to ORD are the most sought after. Prices can be higher for these popular slots. If you want to save on your fare, book during off-peak hours.
What day of the week has the most flights from MKL to ORD?
If you jet off on a Friday, you'll get the largest range of choices for flights from McKellar-Sipes Regional Airport (MKL) to O'Hare Intl. Airport (ORD).
What is the earliest flight from McKellar-Sipes Regional Airport (MKL) to O'Hare Intl. Airport (ORD)?
The first flight of the day jetting off from McKellar-Sipes Regional Airport (MKL) is at around 11:15AM UTC-6. Board this plane and you'll touch down at O'Hare Intl. Airport (ORD) at approximately 12:55PM UTC-6. The entire trip takes 1h 40m.
How long does it take to fly from McKellar-Sipes Regional Airport (MKL) to O'Hare Intl. Airport (ORD)?
Typically, it takes 1 hour and 40 minutes to cover the 440 mi from MKL to ORD.
What is the best time to fly from McKellar-Sipes Regional Airport (MKL) to O'Hare Intl. Airport (ORD)?
To avoid potential delays on the McKellar-Sipes Regional Airport (MKL) to O'Hare Intl. Airport (ORD) route, aim to fly before 3 PM. Later departures have a 22% higher chance of being 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 Chicago from McKellar-Sipes Regional Airport (MKL)?
O'Hare Intl. Airport (ORD) is the only airport in Chicago with direct flights from McKellar-Sipes Regional Airport (MKL). Consider your options and find cheap fares on Expedia.
Is it cheaper to buy a plane ticket from McKellar-Sipes Regional Airport (MKL) to O'Hare Intl. Airport (ORD) last-minute?
Waiting until just before your departure to book a ticket from MKL to ORD generally means paying more. Although you may find some last-minute deals, they aren't always guaranteed. Be flexible with your itinerary for the best chance of snagging a bargain.
Is it cheaper to book a MKL to ORD flight and hotel package?
Securing a MKL to ORD flight and hotel package is generally cheaper than booking separately. With Expedia, you can enjoy the convenience of organizing your travels all in one place. Select from our wide range of accommodations and then add flights, activities and car rentals to your booking. Bundle everything together, and you could save hundreds of dollars.
Can I cancel or change the date of my flight from McKellar-Sipes Regional Airport (MKL) to O'Hare Intl. Airport (ORD)?
Typically, you can modify or cancel your MKL to ORD flight. However, there may be additional fees, especially if you made your booking more than 24 hours ago. Check your itinerary for the airline's fees and rules on flight changes, or if you want more information, visit our Customer Service portal.

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