$152 Cheap Flights from Jackson (JAN) to Chicago (MDW)

View $152 flight on Wed, Apr 8, 2026Opens in a new window

Popular airlines from Evers Intl. Airport (JAN) to Chicago Midway Airport (MDW)

Cheap Flights from Jackson to Chicago (JAN-MDW)

Prices were available within the past 7 days and start at $152 for one-way flights and $265 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Southwest Airlines
Tue, Mar 31 - Thu, Apr 2
JAN
Jackson
MDW
Chicago
$265 Roundtrip, found 6 days ago
$265
Roundtrip
found 6 days ago
Select Southwest Airlines flight, departing Tue, Mar 31 from Jackson to Chicago, returning Thu, Apr 2, priced at $265 found 6 days ago
Southwest Airlines
Sat, May 9 - Tue, May 12
JAN
Jackson
MDW
Chicago
$290 Roundtrip, found 1 day ago
$290
Roundtrip
found 1 day ago
Select Southwest Airlines flight, departing Sat, May 9 from Jackson to Chicago, returning Tue, May 12, priced at $290 found 1 day ago
Southwest Airlines
Fri, May 15 - Wed, May 20
JAN
Jackson
MDW
Chicago
$290 Roundtrip, found 5 days ago
$290
Roundtrip
found 5 days ago
Select Southwest Airlines flight, departing Fri, May 15 from Jackson to Chicago, returning Wed, May 20, priced at $290 found 5 days ago
Southwest Airlines
Sat, May 9 - Tue, May 12
JAN
Jackson
MDW
Chicago
$295 Roundtrip, found 1 day ago
$295
Roundtrip
found 1 day ago
Select Southwest Airlines flight, departing Sat, May 9 from Jackson to Chicago, returning Tue, May 12, priced at $295 found 1 day ago
Delta
Tue, Apr 21 - Tue, Apr 28
JAN
Jackson
MDW
Chicago
$297 Roundtrip, found 6 days ago
$297
Roundtrip
found 6 days ago
Select Delta flight, departing Tue, Apr 21 from Jackson to Chicago, returning Tue, Apr 28, priced at $297 found 6 days ago
Southwest Airlines
Sat, Apr 25 - Tue, Apr 28
JAN
Jackson
MDW
Chicago
$300 Roundtrip, found 22 hours ago
$300
Roundtrip
found 22 hours ago
Select Southwest Airlines flight, departing Sat, Apr 25 from Jackson to Chicago, returning Tue, Apr 28, priced at $300 found 22 hours ago
Southwest Airlines
Sat, Apr 11 - Tue, Apr 14
JAN
Jackson
MDW
Chicago
$300 Roundtrip, found 1 day ago
$300
Roundtrip
found 1 day ago
Select Southwest Airlines flight, departing Sat, Apr 11 from Jackson to Chicago, returning Tue, Apr 14, priced at $300 found 1 day ago
Southwest Airlines
Fri, May 15 - Wed, May 20
JAN
Jackson
MDW
Chicago
$305 Roundtrip, found 5 days ago
$305
Roundtrip
found 5 days ago
Select Southwest Airlines flight, departing Fri, May 15 from Jackson to Chicago, returning Wed, May 20, priced at $305 found 5 days ago
Southwest Airlines
Sat, Apr 25 - Tue, Apr 28
JAN
Jackson
MDW
Chicago
$305 Roundtrip, found 22 hours ago
$305
Roundtrip
found 22 hours ago
Select Southwest Airlines flight, departing Sat, Apr 25 from Jackson to Chicago, returning Tue, Apr 28, priced at $305 found 22 hours ago
Southwest Airlines
Sat, Apr 25 - Tue, Apr 28
JAN
Jackson
MDW
Chicago
$310 Roundtrip, found 22 hours ago
$310
Roundtrip
found 22 hours ago
Select Southwest Airlines flight, departing Sat, Apr 25 from Jackson to Chicago, returning Tue, Apr 28, priced at $310 found 22 hours 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. Average driving time to city center is 23 minutes. Flights from $447
ORD
O'Hare Intl.
Average driving time to city center23 min
Flights from $447

Frequently asked questions

How much does a flight from Jackson, MS (JAN-Evers Intl.) to Chicago, IL (MDW-Midway Intl.) cost?
You can find cheap one-way flights from $152 and cheap return flights from $265 Jackson, MS (JAN-Evers Intl.) to Chicago, IL (MDW-Midway Intl.) with Expedia. One-way flights typically cost between $154 and $527, and return flights often range between $292 and $810. 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 the cheapest fares first, and use the Price Tracking tool to receive alerts when Jackson, MS (JAN-Evers Intl.) to Chicago, IL (MDW-Midway Intl.) ticket fares go up or down.*Typical price ranges based on flights available on Expedia in the last year. Prices include multi-airline options.
What is the cheapest month to fly from Jackson, MS (JAN-Evers Intl.) to Chicago, IL (MDW-Midway Intl.)?
September is the cheapest month to fly from Jackson, MS (JAN) to Chicago, IL (MDW), with average return fares around $286. This is about 30% lower than the average price throughout the year, as travel demand tends to drop after the summer. Other budget-friendly months include January and February.*Averages based on flights available on Expedia in the last year.
Which airlines fly direct from Jackson, MS (JAN-Evers Intl.) to Chicago, IL (MDW-Midway Intl.)?
Enter JAN 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, MS (JAN-Evers Intl.) to Chicago, IL (MDW-Midway Intl.)?
Southwest Airlines is one of the cheapest airlines offering connecting flights from Jackson, MS (JAN) to Chicago, IL (MDW) with a layover in William P. Hobby (HOU) starting from around $500. 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, MS (JAN-Evers Intl.) to Chicago, IL (MDW-Midway Intl.)?
To find a cheap flight from Jackson, MS (JAN-Evers Intl.) 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, MS (JAN-Evers Intl.) to Chicago, IL (MDW-Midway Intl.)?
For flights from Jackson (JAN) to Chicago (MDW), September and January are the best months to travel, with average return flight prices around $286. These months offer lower fares and a comfortable travel experience. If you're looking for popular travel times, August and July are also great options, providing plenty of flight choices.*Prices based on flights available on Expedia in the last year.
What is the earliest flight from Jackson, MS (JAN-Evers Intl.) to Chicago, IL (MDW-Midway Intl.)?
The earliest flight from Jackson, MS (JAN-Evers Intl.) to Chicago, IL (MDW-Midway Intl.) typically departs at around 5:10 AM, operated by Southwest Airlines. This seasonal service is available during the summer months, giving you an early start to your day in Chicago. To compare early flights on Expedia, select the "Early Morning" and "Morning" filters in your search.
What are the most popular departure times for flights from Jackson, MS (JAN-Evers Intl.) to Chicago, IL (MDW-Midway Intl.)?
For flights from Jackson, MS (JAN) to Chicago, IL (MDW), the most popular departure times are in the early afternoon, from noon to 3pm. About 26% of passengers prefer this time window. Southwest Airlines and Delta Air Lines offer flights during this window. This timing works well because it allows you to have a relaxed morning before your flight.
How long does it take to fly from Jackson, MS (JAN-Evers Intl.) to Chicago, IL (MDW-Midway Intl.)?
Flying from JAN to MDW with a connection usually takes about 4 hours 20 minutes, traveling roughly 667 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, MS (JAN-Evers Intl.) to Chicago, IL (MDW-Midway Intl.)?
Select the "Business class" and "First class" filters when looking for JAN 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, MS (JAN-Evers Intl.) to Chicago, IL (MDW-Midway Intl.) flight with Expedia?
It's easy to earn miles on a Jackson, MS (JAN-Evers Intl.) 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 Evers Intl. (JAN)?
When traveling from Evers Intl. (JAN) to Chicago, you can fly into O'Hare Intl. (ORD) and Midway Intl. (MDW). Some flights may connect through major hubs like George Bush Intercontinental (IAH), William P. Hobby (HOU), Dallas-Fort Worth Intl. (DFW) 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, MS (JAN-Evers Intl.) to Chicago, IL (MDW-Midway Intl.) at the last minute?
Typically, booking a last minute flight from Jackson, MS (JAN-Evers Intl.) 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, MS (JAN-Evers Intl.) to Chicago, IL (MDW-Midway Intl.) flight and hotel package?
Securing a Jackson, MS (JAN-Evers Intl.) 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, MS (JAN-Evers Intl.) to Chicago, IL (MDW-Midway Intl.)?
If you booked your Jackson, MS (JAN-Evers Intl.) 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
Evers Intl.
Destination airport
Midway Intl.
Airlines serving
Delta, Southwest Airlines
Roundtrip price
$264
Distance
667 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 March. 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 $152 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.