CA $219 Cheap Flights from Jackson (JAN) to Chicago (ORD)

View CA $219 flight on Tue, May 26, 2026Opens in a new window

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

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Cheap flights from Jackson (JAN) to Chicago (ORD)

Prices were available within the past 7 days and start at CA $219 for one-way flights and for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Frequently asked questions

What is the cheapest month to fly from Jackson, MS (JAN-Evers Intl.) to Chicago, IL (ORD-O'Hare Intl.)?
September is typically the cheapest month to fly from Jackson, MS (JAN-Evers Intl.) to Chicago, IL (ORD-O'Hare Intl.), with average round-trip fares around 756 CAD. This is about 23% lower than the average price throughout the year. September often sees lower prices as the summer travel rush ends and before the holiday season begins, leading to reduced demand. Other cheap months to fly from Jackson, MS (JAN-Evers Intl.) to Chicago, IL (ORD-O'Hare Intl.) include May and August.
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.)?
Based on booking data from the past year, the cheapest months to fly from Jackson, MS (JAN-Evers Intl.) to Chicago, IL (ORD-O'Hare Intl.) are typically September and May, with average prices around 756 CAD. June is the most popular month for this route, meaning you'll find plenty of flight options, though prices might be higher. If you're looking for the best balance of value and availability, consider traveling in September or May for a good deal, or June if your priority is a wide selection of flights.
How many flights per day from Jackson, MS (JAN-Evers Intl.) to Chicago, IL (ORD-O'Hare Intl.)?
There are approximately 27 connecting flights per day from Jackson, MS (JAN-Evers Intl.) to Chicago, IL (ORD-O'Hare Intl.). Some common connection points include George Bush Intercontinental (IAH), Hartsfield-Jackson Atlanta Intl. (ATL), and Dallas-Fort Worth Intl. (DFW).
What is the earliest flight from Jackson, MS (JAN-Evers Intl.) to Chicago, IL (ORD-O'Hare Intl.)?
The earliest flight from Jackson, MS (JAN-Evers Intl.) (JAN) to Chicago, IL (ORD-O'Hare Intl.) (ORD) typically departs at approximately 5:00 AM local time, operated by American Airlines. This is a seasonal service active in July. An early departure like this can help maximize your time at your destination. To compare early flights on Expedia, select the "Early Morning" and "Morning" filters in your search.
What day of the week has the most flights from Jackson, MS (JAN-Evers Intl.) to Chicago, IL (ORD-O'Hare Intl.)?
You'll typically find the most flights from Jackson, MS (JAN-Evers Intl.) to Chicago, IL (ORD-O'Hare Intl.) on a Wednesday, with around 20 flights available. This gives you plenty of options for your travel plans. Major airlines on this route include American Airlines, Delta Air Lines, and United Airlines. Flight schedules are consistent throughout the week.
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 Jackson, MS (JAN-Evers Intl.) to Chicago, IL (ORD-O'Hare Intl.) are in the early morning, from 6am to 9am. About 25% of passengers prefer this time. Many major carriers, including American Airlines, Delta Air Lines and United Airlines, offer flights during this window. This timing works well because it allows you to get an early start on your travel day and arrive at your destination with plenty of time.
How long does it take to fly from Jackson, MS (JAN-Evers Intl.) to Chicago, IL (ORD-O'Hare Intl.)?
Flights from JAN to ORD with one stop typically take around 5 hours 30 minutes, covering approximately 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.)?
Select the "Business class" and "First class" filters when looking for JAN to ORD 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 (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)?
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), 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, 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.) 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 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.
Distance
1085 km

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Pearl to Chicago Flights

The easy way to book your flights from Jackson to Chicago 

With Expedia, it’s simple to find and book flights to Chicago from Jackson whether you’re traveling for business or pleasure. Enter your travel dates, hit search, and choose your flight from 20 airlines that cover this route. There are nonstop flights to O'Hare Intl., too.  

Choose your preferred carrier and cabin class with the advanced search tool and select your ideal departure time. Then, if you want, you can see just nonstop or refundable flights. And if you’re traveling last minute, just enter the date to check out flights from Jackson to Chicago today, tomorrow, or this week.  

 

Save dollars with cheap flights from Evers Intl., JAN to O'Hare Intl., ORD 

Sort your search results by price to find great deals on your flight from Jackson to Chicago—you get all your cheapest options first. Grab yourself a bargain now—the lowest price on flights to Chicago from Jackson currently is just rising to .  

Here are more money-saving tips: 

  • Fly in when flight prices are normally at their lowest 
  • Book about a month to 6 weeks before you travel for the best prices to Chicago  
  • Avoid peak season and weekends when flights can cost more
  • Early morning and late-night flights are sometimes cheaper, so try varying your travel times 
  • One surefire way to save money on your flight is to book your flight and hotel together with Expedia. Sometimes, the savings are so large that the flight is basically free! 

 

Reasons to choose Expedia for your flight to Chicago from Jackson 

Whatever your destination, budget, or reason to travel, in just one quick search, you can choose from loads of flights, airlines, and cabin classes. The filters make it quick and easy to find your ideal flights, and if you choose one of the flexible options, you won’t be charged to change your flight. So book your flight to Chicago with Expedia today.

Pearl to Chicago Flights

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