$258 Cheap Flights from Chicago (MDW) to Jackson (MKL)

View $258 flight on Fri, Oct 10, 2025Opens in a new window

Popular airlines from Chicago Midway Airport (MDW) to Jackson, TN (MKL-McKellar-Sipes Regional)

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Cheap Flights from Chicago to Jackson (MDW-MKL)

Prices were available within the past 7 days and start at $258 for one-way flights and $459 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Delta
Sat, Aug 30 - Tue, Sep 2
MDW
Chicago
MKL
Jackson
$459 Roundtrip, found 5 days ago
$459
Roundtrip
found 5 days ago
Select Delta flight, departing Sat, Aug 30 from Chicago to Jackson, returning Tue, Sep 2, priced at $459 found 5 days ago
Delta
Thu, Oct 2 - Tue, Oct 7
MDW
Chicago
MKL
Jackson
$460 Roundtrip, found 6 hours ago
$460
Roundtrip
found 6 hours ago
Select Delta flight, departing Thu, Oct 2 from Chicago to Jackson, returning Tue, Oct 7, priced at $460 found 6 hours ago
Delta
Sat, Aug 16 - Sat, Aug 23
MDW
Chicago
MKL
Jackson
$464 Roundtrip, found 2 days ago
$464
Roundtrip
found 2 days ago
Select Delta flight, departing Sat, Aug 16 from Chicago to Jackson, returning Sat, Aug 23, priced at $464 found 2 days ago
Delta
Thu, Sep 11 - Sat, Sep 13
MDW
Chicago
MKL
Jackson
$470 Roundtrip, found 5 days ago
$470
Roundtrip
found 5 days ago
Select Delta flight, departing Thu, Sep 11 from Chicago to Jackson, returning Sat, Sep 13, priced at $470 found 5 days ago
Delta
Thu, Sep 4 - Sat, Sep 20
MDW
Chicago
MKL
Jackson
$474 Roundtrip, found 10 hours ago
$474
Roundtrip
found 10 hours ago
Select Delta flight, departing Thu, Sep 4 from Chicago to Jackson, returning Sat, Sep 20, priced at $474 found 10 hours ago
Delta
Thu, Sep 4 - Fri, Sep 5
MDW
Chicago
MKL
Jackson
$484 Roundtrip, found 10 hours ago
$484
Roundtrip
found 10 hours ago
Select Delta flight, departing Thu, Sep 4 from Chicago to Jackson, returning Fri, Sep 5, priced at $484 found 10 hours ago
Delta
Fri, Oct 31 - Thu, Nov 13
MDW
Chicago
MKL
Jackson
$484 Roundtrip, found 10 hours ago
$484
Roundtrip
found 10 hours ago
Select Delta flight, departing Fri, Oct 31 from Chicago to Jackson, returning Thu, Nov 13, priced at $484 found 10 hours ago
Delta
Tue, Aug 19 - Thu, Sep 4
MDW
Chicago
MKL
Jackson
$489 Roundtrip, found 10 hours ago
$489
Roundtrip
found 10 hours ago
Select Delta flight, departing Tue, Aug 19 from Chicago to Jackson, returning Thu, Sep 4, priced at $489 found 10 hours ago
Delta
Thu, Sep 4 - Thu, Sep 18
MDW
Chicago
MKL
Jackson
$494 Roundtrip, found 10 hours ago
$494
Roundtrip
found 10 hours ago
Select Delta flight, departing Thu, Sep 4 from Chicago to Jackson, returning Thu, Sep 18, priced at $494 found 10 hours ago
Delta
Fri, Sep 5 - Sat, Sep 20
MDW
Chicago
MKL
Jackson
$497 Roundtrip, found 10 hours ago
$497
Roundtrip
found 10 hours ago
Select Delta flight, departing Fri, Sep 5 from Chicago to Jackson, returning Sat, Sep 20, priced at $497 found 10 hours ago
Delta
Thu, Oct 2 - Tue, Oct 7
MDW
Chicago
MKL
Jackson
$500 Roundtrip, found 6 hours ago
$500
Roundtrip
found 6 hours ago
Select Delta flight, departing Thu, Oct 2 from Chicago to Jackson, returning Tue, Oct 7, priced at $500 found 6 hours ago
Delta
Fri, Oct 31 - Fri, Nov 14
MDW
Chicago
MKL
Jackson
$504 Roundtrip, found 10 hours ago
$504
Roundtrip
found 10 hours ago
Select Delta flight, departing Fri, Oct 31 from Chicago to Jackson, returning Fri, Nov 14, priced at $504 found 10 hours ago
Delta
Fri, Aug 29 - Tue, Sep 2
MDW
Chicago
MKL
Jackson
$505 Roundtrip, found 5 days ago
$505
Roundtrip
found 5 days ago
Select Delta flight, departing Fri, Aug 29 from Chicago to Jackson, returning Tue, Sep 2, priced at $505 found 5 days ago
Delta
Mon, Sep 29 - Tue, Oct 14
MDW
Chicago
MKL
Jackson
$514 Roundtrip, found 10 hours ago
$514
Roundtrip
found 10 hours ago
Select Delta flight, departing Mon, Sep 29 from Chicago to Jackson, returning Tue, Oct 14, priced at $514 found 10 hours ago
Delta
Fri, Sep 5 - Thu, Sep 18
MDW
Chicago
MKL
Jackson
$517 Roundtrip, found 10 hours ago
$517
Roundtrip
found 10 hours ago
Select Delta flight, departing Fri, Sep 5 from Chicago to Jackson, returning Thu, Sep 18, priced at $517 found 10 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 $489
MKL
McKellar-Sipes Regional
CheapestClosest
Average driving time to city center11 min
Flights from $489
Flights from Chicago (MDW) to Jackson (MKL)
Origin airport
Midway Intl.
Destination airport
McKellar-Sipes Regional
Roundtrip price
$459
Distance
432 mi

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 August. 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 $258 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.

 

Frequently asked questions

How much does a flight from Midway Intl. Airport (MDW) to McKellar-Sipes Regional Airport (MKL) cost?
Snag a cheap one-way flight from $258 or cheap return flight from $459 from Midway Intl. Airport (MDW) 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 Midway Intl. Airport (MDW) to McKellar-Sipes Regional Airport (MKL)?
August is the most affordable month to fly from MDW to MKL. Avoiding peak travel times is often the key to landing a great deal.
Which airlines fly direct from Midway Intl. Airport (MDW) to McKellar-Sipes Regional Airport (MKL)?
Although Chicago, IL (MDW-Midway Intl.) has no direct flights to McKellar-Sipes Regional Airport (MKL), other airports have nonstop routes. Taking off from O'Hare Intl. Airport (ORD) will get you to Jackson without any detours.
What is the cheapest airline that flies from Midway Intl. Airport (MDW) to McKellar-Sipes Regional Airport (MKL)?
Expedia's filter tool lets you easily compare different airlines, flight durations and fares all in one place. Tailor the search to your trip, then sort by "Price (lowest to highest)" to find the carrier with the cheapest MDW to MKL flight.
How many flights per day from Midway Intl. Airport (MDW) to McKellar-Sipes Regional Airport (MKL)?
Nonstop flights from Midway Intl. Airport (MDW) to McKellar-Sipes Regional Airport (MKL) aren't available daily, so you'll have to take a flight with a layover. Explore your options with Expedia's filters. Enter your travel dates and pick either "1 Stop" or "2+ Stops."
What day of the week has the most flights from MDW to MKL?
You'll usually find Tuesday the quietest day for flights, while Fridays tend to be the busiest.* However this can vary from season to season and during public holidays or peak travel times.*Busiest/quietest day to travel is based on Expedia flight demand through January to December 2024.
What is the best time to fly from Midway Intl. Airport (MDW) to McKellar-Sipes Regional Airport (MKL)?
To avoid potential delays on the Midway Intl. Airport (MDW) to McKellar-Sipes Regional Airport (MKL) route, aim to travel before 3 PM. Later departures have a 22% higher chance of cancellation.**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 Midway Intl. Airport (MDW) to McKellar-Sipes Regional Airport (MKL) last-minute?
Waiting until right before your break to book a flight from MDW to MKL often results in higher prices. While you may come across some last-minute discounts, they aren't always guaranteed. Be flexible with your travel plans to maximize your chances of scoring a bargain.
Is it cheaper to book a MDW to MKL flight and hotel package?
Opting for a MDW to MKL flight and hotel package tends to be cheaper than booking separately. With Expedia, you can enjoy the ease of organizing your travels all in one place. Select from our wide range of accommodations and then add flights, car rentals and activities to your booking. Bundle everything together, and you could save hundreds of dollars.
Can I cancel or change the date of my flight from Midway Intl. Airport (MDW) to McKellar-Sipes Regional Airport (MKL)?
Typically, you can reschedule or cancel your MDW to MKL flight. However, there may be additional charges, especially if your booking was made over 24 hours ago. Double-check your itinerary for the airline's policies and fees on flight changes, or if you want further information, go to our Customer Service portal.

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*Available to One Key members.