$235 Cheap Flights from Jackson (MKL) to Chicago (MDW)

View $235 flight on Sat, Nov 1, 2025Opens 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 $235 for one-way flights and $404 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

KEY LIME AIR DBA DENVER AIR CONNECTION
Tue, Nov 18 - Mon, Nov 24
MKL
Jackson
MDW
Chicago
$404 Roundtrip, found 1 day ago
$404
Roundtrip
found 1 day ago
Select KEY LIME AIR DBA DENVER AIR CONNECTION flight, departing Tue, Nov 18 from Jackson to Chicago, returning Mon, Nov 24, priced at $404 found 1 day ago
KEY LIME AIR DBA DENVER AIR CONNECTION
Sat, Nov 8 - Mon, Nov 10
MKL
Jackson
MDW
Chicago
$431 Roundtrip, found 2 days ago
$431
Roundtrip
found 2 days ago
Select KEY LIME AIR DBA DENVER AIR CONNECTION flight, departing Sat, Nov 8 from Jackson to Chicago, returning Mon, Nov 10, priced at $431 found 2 days ago
KEY LIME AIR DBA DENVER AIR CONNECTION
Tue, Nov 11 - Thu, Dec 4
MKL
Jackson
MDW
Chicago
$449 Roundtrip, found 3 days ago
$449
Roundtrip
found 3 days ago
Select KEY LIME AIR DBA DENVER AIR CONNECTION flight, departing Tue, Nov 11 from Jackson to Chicago, returning Thu, Dec 4, priced at $449 found 3 days ago
KEY LIME AIR DBA DENVER AIR CONNECTION
Tue, Nov 18 - Sat, Nov 22
MKL
Jackson
MDW
Chicago
$457 Roundtrip, found 1 day ago
$457
Roundtrip
found 1 day ago
Select KEY LIME AIR DBA DENVER AIR CONNECTION flight, departing Tue, Nov 18 from Jackson to Chicago, returning Sat, Nov 22, priced at $457 found 1 day ago
KEY LIME AIR DBA DENVER AIR CONNECTION
Fri, Nov 14 - Sat, Nov 15
MKL
Jackson
MDW
Chicago
$458 Roundtrip, found 3 days ago
$458
Roundtrip
found 3 days ago
Select KEY LIME AIR DBA DENVER AIR CONNECTION flight, departing Fri, Nov 14 from Jackson to Chicago, returning Sat, Nov 15, priced at $458 found 3 days ago
KEY LIME AIR DBA DENVER AIR CONNECTION
Tue, Nov 11 - Fri, Nov 28
MKL
Jackson
MDW
Chicago
$459 Roundtrip, found 3 days ago
$459
Roundtrip
found 3 days ago
Select KEY LIME AIR DBA DENVER AIR CONNECTION flight, departing Tue, Nov 11 from Jackson to Chicago, returning Fri, Nov 28, priced at $459 found 3 days ago
KEY LIME AIR DBA DENVER AIR CONNECTION
Tue, Nov 18 - Fri, Nov 21
MKL
Jackson
MDW
Chicago
$467 Roundtrip, found 1 day ago
$467
Roundtrip
found 1 day ago
Select KEY LIME AIR DBA DENVER AIR CONNECTION flight, departing Tue, Nov 18 from Jackson to Chicago, returning Fri, Nov 21, priced at $467 found 1 day ago
KEY LIME AIR DBA DENVER AIR CONNECTION
Fri, Nov 21 - Mon, Nov 24
MKL
Jackson
MDW
Chicago
$467 Roundtrip, found 1 day ago
$467
Roundtrip
found 1 day ago
Select KEY LIME AIR DBA DENVER AIR CONNECTION flight, departing Fri, Nov 21 from Jackson to Chicago, returning Mon, Nov 24, priced at $467 found 1 day ago
KEY LIME AIR DBA DENVER AIR CONNECTION
Sun, Nov 2 - Mon, Nov 17
MKL
Jackson
MDW
Chicago
$468 Roundtrip, found 3 days ago
$468
Roundtrip
found 3 days ago
Select KEY LIME AIR DBA DENVER AIR CONNECTION flight, departing Sun, Nov 2 from Jackson to Chicago, returning Mon, Nov 17, priced at $468 found 3 days ago
KEY LIME AIR DBA DENVER AIR CONNECTION
Sat, Nov 15 - Thu, Dec 4
MKL
Jackson
MDW
Chicago
$476 Roundtrip, found 3 days ago
$476
Roundtrip
found 3 days ago
Select KEY LIME AIR DBA DENVER AIR CONNECTION flight, departing Sat, Nov 15 from Jackson to Chicago, returning Thu, Dec 4, priced at $476 found 3 days ago

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 $248
ORD
O'Hare Intl.
Cheapest
Average driving time to city center23 min
Flights from $248

Frequently asked questions

How much does a flight from McKellar-Sipes Regional Airport (MKL) to Midway Intl. Airport (MDW) cost?
Secure a cheap one-way flight from $235 or cheap return flight from $404 from McKellar-Sipes Regional Airport (MKL) to Midway Intl. Airport (MDW) with Expedia. Enter your travel dates and sort by "Price (lowest to highest)" to see our cheapest flight deals on this route.
What is the cheapest month to fly from McKellar-Sipes Regional Airport (MKL) to Midway Intl. Airport (MDW)?
Traveling in November is a good way to save, as it's the cheapest month for flights between MKL and MDW. You'll typically find the lowest prices during off-peak months.
What is the cheapest airline that flies from McKellar-Sipes Regional Airport (MKL) to Midway Intl. Airport (MDW)?
Expedia's filter tool lets you easily compare different airlines, travel time 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 MKL to MDW flight.
How many flights per day from McKellar-Sipes Regional Airport (MKL) to Midway Intl. Airport (MDW)?
Direct flights from McKellar-Sipes Regional Airport (MKL) to Midway Intl. Airport (MDW) 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 select either "1 Stop" or "2+ Stops."
What day of the week has the most flights from MKL to MDW?
You'll generally find Tuesday the quietest day for flights, while Fridays are often the busiest.* However this can vary from season to season and during peak travel times or public holidays.*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 Midway Intl. Airport (MDW)?
To avoid potential delays on the McKellar-Sipes Regional Airport (MKL) to Midway Intl. Airport (MDW) route, travel before 3 PM. Flights after this time 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)?
O'Hare Intl. Airport (ORD) is the only airport in Chicago with direct flights from McKellar-Sipes Regional Airport (MKL). Browse the available options and discover cheap fares on Expedia.
Is it cheaper to buy a plane ticket from McKellar-Sipes Regional Airport (MKL) to Midway Intl. Airport (MDW) last-minute?
Booking your ticket from MKL to MDW just before your journey is typically more expensive. But if you're flexible with your itinerary, you could grab a cheap last-minute fare.
Is it cheaper to book a MKL to MDW flight and hotel package?
Booking a MKL to MDW flight and hotel package is usually cheaper than booking separately. With Expedia, you can enjoy the ease of organizing your trip all in one place. Select from our impressive range of stays and then add activities, car rentals 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 Midway Intl. Airport (MDW)?
It's usually possible to reschedule or cancel your MKL to MDW flight. However, if it's been more than 24 hours since booking, additional fees may apply. Check your airline's policies in your itinerary to see what changes are possible and whether any costs are involved. You'll also find more information on our Customer Service portal.

Travel information

Travel information

Origin airport
McKellar-Sipes Regional
Destination airport
Midway Intl.
Roundtrip price
$404
Distance
432 mi

Book with confidence

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 November. 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 $235 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

Explore a world of travel with Expedia

Explore a world of travel with Expedia

*Available to One Key members.