$236 Cheap Flights from Jackson (MKL) to Chicago (MDW)

View $236 flight on Sat, Apr 25, 2026Opens in a new window

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

Cheap Flights from Jackson to Chicago (MKL-MDW)

Prices were available within the past 7 days and start at $236 for one-way flights and $460 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

KEY LIME AIR DBA DENVER AIR CONNECTION
Sat, Apr 25 - Mon, Apr 27
MKL
Jackson
MDW
Chicago
$460 Roundtrip, found 2 days ago
$460
Roundtrip
found 2 days ago
Select KEY LIME AIR DBA DENVER AIR CONNECTION flight, departing Sat, Apr 25 from Jackson to Chicago, returning Mon, Apr 27, priced at $460 found 2 days ago
KEY LIME AIR DBA DENVER AIR CONNECTION
Sat, Apr 18 - Tue, Apr 21
MKL
Jackson
MDW
Chicago
$480 Roundtrip, found 1 day ago
$480
Roundtrip
found 1 day ago
Select KEY LIME AIR DBA DENVER AIR CONNECTION flight, departing Sat, Apr 18 from Jackson to Chicago, returning Tue, Apr 21, priced at $480 found 1 day ago
KEY LIME AIR DBA DENVER AIR CONNECTION
Thu, Jun 11 - Sun, Jun 14
MKL
Jackson
MDW
Chicago
$514 Roundtrip, found 3 days ago
$514
Roundtrip
found 3 days ago
Select KEY LIME AIR DBA DENVER AIR CONNECTION flight, departing Thu, Jun 11 from Jackson to Chicago, returning Sun, Jun 14, priced at $514 found 3 days ago
KEY LIME AIR DBA DENVER AIR CONNECTION
Mon, May 25 - Fri, May 29
MKL
Jackson
MDW
Chicago
$542 Roundtrip, found 1 day ago
$542
Roundtrip
found 1 day ago
Select KEY LIME AIR DBA DENVER AIR CONNECTION flight, departing Mon, May 25 from Jackson to Chicago, returning Fri, May 29, priced at $542 found 1 day ago
KEY LIME AIR DBA DENVER AIR CONNECTION
Thu, Apr 2 - Mon, Apr 6
MKL
Jackson
MDW
Chicago
$547 Roundtrip, found 4 days ago
$547
Roundtrip
found 4 days ago
Select KEY LIME AIR DBA DENVER AIR CONNECTION flight, departing Thu, Apr 2 from Jackson to Chicago, returning Mon, Apr 6, priced at $547 found 4 days ago
KEY LIME AIR DBA DENVER AIR CONNECTION
Thu, Apr 2 - Sun, Apr 5
MKL
Jackson
MDW
Chicago
$555 Roundtrip, found 6 days ago
$555
Roundtrip
found 6 days ago
Select KEY LIME AIR DBA DENVER AIR CONNECTION flight, departing Thu, Apr 2 from Jackson to Chicago, returning Sun, Apr 5, priced at $555 found 6 days ago
KEY LIME AIR DBA DENVER AIR CONNECTION
Thu, Apr 2 - Mon, Apr 6
MKL
Jackson
MDW
Chicago
$557 Roundtrip, found 4 days ago
$557
Roundtrip
found 4 days ago
Select KEY LIME AIR DBA DENVER AIR CONNECTION flight, departing Thu, Apr 2 from Jackson to Chicago, returning Mon, Apr 6, priced at $557 found 4 days ago
KEY LIME AIR DBA DENVER AIR CONNECTION
Tue, Mar 31 - Sat, Apr 4
MKL
Jackson
MDW
Chicago
$561 Roundtrip, found 3 days ago
$561
Roundtrip
found 3 days ago
Select KEY LIME AIR DBA DENVER AIR CONNECTION flight, departing Tue, Mar 31 from Jackson to Chicago, returning Sat, Apr 4, priced at $561 found 3 days ago
KEY LIME AIR DBA DENVER AIR CONNECTION
Sun, May 24 - Thu, May 28
MKL
Jackson
MDW
Chicago
$566 Roundtrip, found 1 day ago
$566
Roundtrip
found 1 day ago
Select KEY LIME AIR DBA DENVER AIR CONNECTION flight, departing Sun, May 24 from Jackson to Chicago, returning Thu, May 28, priced at $566 found 1 day ago
KEY LIME AIR DBA DENVER AIR CONNECTION
Thu, Sep 10 - Sun, Sep 13
MKL
Jackson
MDW
Chicago
$568 Roundtrip, found 6 days ago
$568
Roundtrip
found 6 days ago
Select KEY LIME AIR DBA DENVER AIR CONNECTION flight, departing Thu, Sep 10 from Jackson to Chicago, returning Sun, Sep 13, priced at $568 found 6 days ago

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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 $260
ORD
O'Hare Intl.
Cheapest
Average driving time to city center23 min
Flights from $260

Frequently asked questions

How much does a flight from Jackson, TN (MKL-McKellar-Sipes Regional) to Chicago, IL (MDW-Midway Intl.) cost?
You can find cheap one-way flights from $236 and cheap return flights from $460 MKL to MDW with Expedia. Flight prices vary based on the month and day of the week you want to travel, as well as the airline and how far in advance you book your ticket. Filter your search on Expedia by "Price (lowest to highest)" to see our cheapest fares first, and use the Price Tracking tool to receive alerts when MKL to MDW ticket fares go up or down.
What is the cheapest month to fly from Jackson, TN (MKL-McKellar-Sipes Regional) to Chicago, IL (MDW-Midway Intl.)?
The cheapest month to fly from MKL to MDW is April when demand is low. Traveling in off-peak or shoulder months is usually a good way to secure cheap tickets, just remember to avoid flying during holidays if you're able to. Use the calendar view in your search to see which months have low fares on this route.
Which airlines fly direct from Jackson, TN (MKL-McKellar-Sipes Regional) to Chicago, IL (MDW-Midway Intl.)?
Enter MKL to MDW and your travel dates, then apply the 'Nonstop' filter to see only direct flights.
What is the cheapest airline that flies from Jackson, TN (MKL-McKellar-Sipes Regional) to Chicago, IL (MDW-Midway Intl.)?
Key Lime Air is the only carrier that flies from Jackson, TN (MKL) to Chicago, IL (MDW). Use Expedia's flight search tool to compare airlines on this route and find our cheapest option for your trip. Use Expedia's search tool to compare the prices and schedules of airlines that fly this route to find the best option for your plans and budget.*Prices based on flights available on Expedia in the last year.
How do I find cheap flights from Jackson, TN (MKL-McKellar-Sipes Regional) to Chicago, IL (MDW-Midway Intl.)?
To find a cheap flight from Jackson, TN (MKL-McKellar-Sipes Regional) to Chicago, IL (MDW-Midway Intl.), be flexible with your dates. Traveling outside of peak vacation months and booking a mid-week flight can help you save. Early morning and late night flights are often more affordable, too. Expedia allows you to compare flight times, airlines and routes all in one place to find low fares. You can also set up Price Tracking and receive alerts when fares go up or down.
What is the best time to fly from Jackson, TN (MKL-McKellar-Sipes Regional) to Chicago, IL (MDW-Midway Intl.)?
The best time to fly is usually mid-week (Tuesday or Wednesday) and during early morning hours as flights tend to be cheaper, less crowded, and generally more on-time. Avoid major holidays and peak vacation seasons for smoother travel. Combining off-peak days and hours often gives the best combination of cost, comfort, and convenience.
What is the earliest flight from Jackson, TN (MKL-McKellar-Sipes Regional) to Chicago, IL (MDW-Midway Intl.)?
Sort flights by "Departure (earliest)" on Expedia to find the earliest flight from MKL to MDW. To compare more early flights, use the "Early Morning" and "Morning" filters in your search.
How long does it take to fly from Jackson, TN (MKL-McKellar-Sipes Regional) to Chicago, IL (MDW-Midway Intl.)?
Flights from MKL to MDW with one stop typically take around 4 hours, covering approximately 432 miles. Keep in mind that actual flight times can vary due to wind patterns, weather, and air traffic.
Can you fly business or first class from Jackson, TN (MKL-McKellar-Sipes Regional) to Chicago, IL (MDW-Midway Intl.)?
Select the "Business class" and "First class" filters when looking for MKL to MDW flights on Expedia. This is the easiest way to compare prices, routes and flight times for your trip.
How do I earn miles on a Jackson, TN (MKL-McKellar-Sipes Regional) to Chicago, IL (MDW-Midway Intl.) flight with Expedia?
It's easy to earn miles on a Jackson, TN (MKL-McKellar-Sipes Regional) to Chicago, IL (MDW-Midway Intl.) flight when you book with Expedia. Before you confirm your booking, simply select your frequent flyer program and enter your program number. As a member of One Key™, you can also earn OneKeyCash™* on top of your airline miles when you book with Expedia.*Excludes taxes and fees. OneKeyCash is not redeemable for cash and can only be used on Expedia and other participating brands.
What airports do you fly into for Chicago from McKellar-Sipes Regional (MKL)?
If you're planning to travel to Chicago from McKellar-Sipes Regional (MKL), you can fly into O'Hare Intl. (ORD) Some flights may connect through major hubs like Hartsfield-Jackson Atlanta Intl. (ATL) before reaching Chicago. Compare routes and airports on Expedia to find the best flight options for your travel plans.
Is it cheaper to buy a plane ticket from Jackson, TN (MKL-McKellar-Sipes Regional) to Chicago, IL (MDW-Midway Intl.) at the last minute?
Typically, booking a last minute flight from Jackson, TN (MKL-McKellar-Sipes Regional) to Chicago, IL (MDW-Midway Intl.) will be more expensive than booking in advance. As the departure date approaches, there are usually fewer seats available which can drive up the cost. However, if there's some wiggle room with your travel dates and times, you could bag a cheap last-minute fare.
Is it cheaper to book a Jackson, TN (MKL-McKellar-Sipes Regional) to Chicago, IL (MDW-Midway Intl.) flight and hotel package?
Securing a Jackson, TN (MKL-McKellar-Sipes Regional) to Chicago, IL (MDW-Midway Intl.) Chicago Vacation Packages is usually cheaper than booking separately. With Expedia, you can enjoy the ease of organizing your travels all in one place. Select from our extensive range of stays 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 Jackson, TN (MKL-McKellar-Sipes Regional) to Chicago, IL (MDW-Midway Intl.)?
If you booked your Jackson, TN (MKL-McKellar-Sipes Regional) to Chicago, IL (MDW-Midway Intl.) flight within the last 24 hours, you may be able to modify or cancel it without any 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'd like more information.

Travel information

Origin airport
McKellar-Sipes Regional
Destination airport
Midway Intl.
Roundtrip price
$460
Distance
432 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 April. 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 $236 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

*Flight schedules are subject to change.

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*Available to One Key members.