Cheap Flights from Jackson (MKL) to Chicago (PWK)

Popular airlines from Jackson, TN (MKL-McKellar-Sipes Regional) to Chicago, IL (PWK-Chicago Executive)

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. Cheapest option available. Average driving time to city center is 23 minutes. Flights from $223
ORD
O'Hare Intl.
Cheapest
Average driving time to city center23 min
Flights from $223
Select flight to Midway Intl. MDW. Closest option available. Average driving time to city center is 16 minutes. Flights from $534
MDW
Midway Intl.
Closest
Average driving time to city center16 min
Flights from $534

Frequently asked questions

How much does a flight from McKellar-Sipes Regional Airport (MKL) to Chicago Executive Airport (PWK) cost?
Get a cheap one-way flight or cheap return flight from McKellar-Sipes Regional Airport (MKL) to Chicago Executive Airport (PWK) 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 McKellar-Sipes Regional Airport (MKL) to Chicago Executive Airport (PWK)?
Planning your getaway for may help you find better deals, as it's the cheapest month for flights between MKL and PWK. You'll typically find the lowest fares during off-peak months.
What is the cheapest airline that flies from McKellar-Sipes Regional Airport (MKL) to Chicago Executive Airport (PWK)?
Expedia's filter tool lets you easily compare airlines, flight times and fares all in one place. Select your preferences, then sort by "Price (lowest to highest)" to find out which carrier offers the cheapest MKL to PWK flight.
How many flights per day from McKellar-Sipes Regional Airport (MKL) to Chicago Executive Airport (PWK)?
There are no daily direct flights departing from McKellar-Sipes Regional Airport (MKL) to Chicago Executive Airport (PWK). But you can opt for flights with layovers. Filter your search on Expedia to include one or two stops, and you'll be on your way before you know it.
What day of the week has the most flights from MKL to PWK?
Friday is usually the busiest day for flights, while Tuesday is often the quietest.* Just remember that flight schedules can change depending on a range of factors, including the season and airline.*Busiest/quietest day to travel is based on Expedia flight demand through January to December 2024.
What is the best time to fly from McKellar-Sipes Regional Airport (MKL) to Chicago Executive Airport (PWK)?
To avoid potential delays on the McKellar-Sipes Regional Airport (MKL) to Chicago Executive Airport (PWK) route, fly 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.
What airports do you fly into for Chicago from McKellar-Sipes Regional Airport (MKL)?
If you're taking a direct flight from McKellar-Sipes Regional Airport (MKL) to Chicago, O'Hare Intl. Airport (ORD) is the only airport you can land at.
Is it cheaper to buy a plane ticket from McKellar-Sipes Regional Airport (MKL) to Chicago Executive Airport (PWK) last-minute?
Booking your ticket from MKL to PWK just before your trip is generally more expensive. However, if you're flexible with your travel dates and times, you could snag a cheap last-minute fare.
Is it cheaper to book a MKL to PWK flight and hotel package?
Booking a MKL to PWK flight and hotel package is usually 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 stays and then add car rentals, activities and flights 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 Chicago Executive Airport (PWK)?
If you booked your MKL to PWK flight in the last 24 hours, you may be able to cancel or modify it without fees. Depending on the airline and the type of ticket you have, additional charges may apply for changes beyond this timeframe. Airline policies and contact information can be found in your itinerary or confirmation email. Or, head to our Customer Service portal if you want more information.

Travel information

Origin airport
McKellar-Sipes Regional
Destination airport
Chicago Executive
Distance
453 mi

Book with confidence

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 . 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 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.

 

Jackson to Chicago Flights

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*Available to One Key members.