$169 Cheap Flights from Jackson (JAN) to Chicago (ORD)

View $169 flight on Sat, Apr 25, 2026Opens in a new window

Popular airlines from Evers Intl. Airport (JAN) to Chicago O'Hare Intl. Airport (ORD)

Cheap Flights from Jackson to Chicago (JAN-ORD)

Prices were available within the past 7 days and start at $169 for one-way flights and $315 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

American Airlines
Sat, May 16 - Tue, May 19
JAN
Jackson
ORD
Chicago
$315 Roundtrip, found 4 days ago
$315
Roundtrip
found 4 days ago
Select American Airlines flight, departing Sat, May 16 from Jackson to Chicago, returning Tue, May 19, priced at $315 found 4 days ago
American Airlines
Sat, May 16 - Tue, May 19
JAN
Jackson
ORD
Chicago
$320 Roundtrip, found 4 days ago
$320
Roundtrip
found 4 days ago
Select American Airlines flight, departing Sat, May 16 from Jackson to Chicago, returning Tue, May 19, priced at $320 found 4 days ago
American Airlines
Mon, Apr 27 - Wed, Apr 29
JAN
Jackson
ORD
Chicago
$322 Roundtrip, found 5 days ago
$322
Roundtrip
found 5 days ago
Select American Airlines flight, departing Mon, Apr 27 from Jackson to Chicago, returning Wed, Apr 29, priced at $322 found 5 days ago
American Airlines
Sat, Apr 11 - Wed, Apr 15
JAN
Jackson
ORD
Chicago
$323 Roundtrip, found 5 days ago
$323
Roundtrip
found 5 days ago
Select American Airlines flight, departing Sat, Apr 11 from Jackson to Chicago, returning Wed, Apr 15, priced at $323 found 5 days ago
American Airlines
Sat, Apr 11 - Wed, Apr 15
JAN
Jackson
ORD
Chicago
$324 Roundtrip, found 5 days ago
$324
Roundtrip
found 5 days ago
Select American Airlines flight, departing Sat, Apr 11 from Jackson to Chicago, returning Wed, Apr 15, priced at $324 found 5 days ago
American Airlines
Sat, Apr 11 - Wed, Apr 15
JAN
Jackson
ORD
Chicago
$327 Roundtrip, found 5 days ago
$327
Roundtrip
found 5 days ago
Select American Airlines flight, departing Sat, Apr 11 from Jackson to Chicago, returning Wed, Apr 15, priced at $327 found 5 days ago
American Airlines
Sat, Apr 11 - Wed, Apr 15
JAN
Jackson
ORD
Chicago
$328 Roundtrip, found 5 days ago
$328
Roundtrip
found 5 days ago
Select American Airlines flight, departing Sat, Apr 11 from Jackson to Chicago, returning Wed, Apr 15, priced at $328 found 5 days ago
Southwest Airlines
Wed, Apr 8 - Sat, Apr 11
JAN
Jackson
ORD
Chicago
$330 Roundtrip, found 5 days ago
$330
Roundtrip
found 5 days ago
Select Southwest Airlines flight, departing Wed, Apr 8 from Jackson to Chicago, returning Sat, Apr 11, priced at $330 found 5 days ago
Delta
Tue, Apr 28 - Sat, May 2
JAN
Jackson
ORD
Chicago
$337 Roundtrip, found 5 hours ago
$337
Roundtrip
found 5 hours ago
Select Delta flight, departing Tue, Apr 28 from Jackson to Chicago, returning Sat, May 2, priced at $337 found 5 hours ago
United
Sat, Mar 28 - Tue, Apr 14
JAN
Jackson
ORD
Chicago
$506 Roundtrip, found 3 days ago
$506
Roundtrip
found 3 days ago
Select United flight, departing Sat, Mar 28 from Jackson to Chicago, returning Tue, Apr 14, priced at $506 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 Midway Intl. MDW. Cheapest and Closest option available. Average driving time to city center is 16 minutes. Flights from $397
MDW
Midway Intl.
CheapestClosest
Average driving time to city center16 min
Flights from $397

Find the cheapest month to fly from Jackson (JAN) to Chicago (ORD)

August is typically the cheapest month to fly

From $182 - $538 per traveler.

Frequently asked questions

How much does a flight from Jackson, MS (JAN-Evers Intl.) to Chicago, IL (ORD-O'Hare Intl.) cost?
You can find cheap one-way flights from $169 and cheap return flights from $315 Jackson, MS (JAN-Evers Intl.) to Chicago, IL (ORD-O'Hare Intl.) with Expedia. One-way flights typically cost between $216 and $734, and return flights often range between $377 and $1088. 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 (ORD-O'Hare 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 (ORD-O'Hare Intl.)?
September is the cheapest month to fly from Jackson (JAN) to Chicago (ORD), with average return fares around $311. This is about 23% lower than the average price throughout the year, as September often sees a lull in travel after the busy summer months. Other cheap months to fly from Jackson to Chicago include May and August.*Averages based on flights available on Expedia in the last year.
Which airlines fly direct from Jackson, MS (JAN-Evers Intl.) to Chicago, IL (ORD-O'Hare Intl.)?
Enter JAN to ORD and your travel dates, then apply the 'Nonstop' filter to see only direct flights.
How do I find cheap flights from Jackson, MS (JAN-Evers Intl.) to Chicago, IL (ORD-O'Hare Intl.)?
To find a cheap flight from Jackson, MS (JAN-Evers Intl.) to Chicago, IL (ORD-O'Hare 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 (ORD-O'Hare Intl.)?
When flying from Jackson (JAN) to Chicago (ORD), September and May are the best months to travel. Average return flight prices are around $311, making these months affordable. September allows you to enjoy the early fall atmosphere, while May brings pleasant spring weather, perfect for exploring the Windy City.*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 (ORD-O'Hare Intl.)?
The earliest flight from Evers International (JAN) to O'Hare International (ORD) usually leaves at around 5:00 AM, operated by American Airlines. This seasonal service is active in July, giving you a great opportunity to reach Chicago early in the day. 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 (ORD-O'Hare Intl.)?
The most popular departure times for flights from Evers Intl. (JAN) to O'Hare Intl. (ORD) are in the early morning, from 6am to 9am. About 24% of passengers prefer this time window. Many major carriers, including American Airlines, Delta, and United Airlines, offer flights during this window. This timing is favored as it allows travelers to arrive in Chicago with plenty of time to start their day.
How long does it take to fly from Jackson, MS (JAN-Evers Intl.) to Chicago, IL (ORD-O'Hare Intl.)?
Flying from JAN to ORD with a connection usually takes about 5 hours, traveling roughly 679 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 (ORD-O'Hare Intl.)?
First class is available on flights from JAN to ORD. First class cabins are available on:

  • American Airlines
  • Delta Air Lines
  • United Airlines

How do I earn miles on a Jackson, MS (JAN-Evers Intl.) to Chicago, IL (ORD-O'Hare Intl.) flight with Expedia?
It's easy to earn miles on a Jackson, MS (JAN-Evers Intl.) to Chicago, IL (ORD-O'Hare 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)?
From Evers Intl. (JAN), you can fly into Midway Intl. (MDW) and O'Hare Intl. (ORD) in Chicago. Some flights may connect through major hubs like William P. Hobby (HOU), Nashville Intl. (BNA), Baltimore Washington Intl. Thurgood Marshall (BWI) 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 (ORD-O'Hare Intl.) at the last minute?
Typically, booking a last minute flight from Jackson, MS (JAN-Evers Intl.) to Chicago, IL (ORD-O'Hare 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 (ORD-O'Hare Intl.) flight and hotel package?
Securing a Jackson, MS (JAN-Evers Intl.) to Chicago, IL (ORD-O'Hare 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 (ORD-O'Hare Intl.)?
If you booked your Jackson, MS (JAN-Evers Intl.) to Chicago, IL (ORD-O'Hare 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
O'Hare Intl.
Airlines serving
American Airlines, Delta, Southwest Airlines, United
Roundtrip price
$314
Distance
678 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 May. 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 $169 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.