A spacious airport terminal with high ceilings, check-in counters, and a Starbucks coffee shop.

CA $336 Cheap Flights from Jackson (JAN) to Chicago (ORD)

View CA $336 flight on Mon, Aug 10, 2026Opens in a new window

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

  • Be in the know

    Get alerts if flight prices drop or rise*

  • Book smarter

    Save up to 30% on select hotels after you book a flight*

  • Earn twice

    Earn your airline miles on top of our rewards
    Sign in

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

Prices were available within the past 7 days and start at CA $336 for one-way flights and CA $553 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

American Airlines
Mon, Aug 10 - Mon, Aug 17
JAN
Jackson
ORD
Chicago
CA $553 Roundtrip, found 5 days ago
CA $553
Roundtrip
found 5 days ago
Select American Airlines flight, departing Mon, Aug 10 from Jackson to Chicago, returning Mon, Aug 17, priced at CA $553 found 5 days ago
American Airlines
Mon, Aug 10 - Mon, Aug 17
JAN
Jackson
ORD
Chicago
CA $580 Roundtrip, found 5 days ago
CA $580
Roundtrip
found 5 days ago
Select American Airlines flight, departing Mon, Aug 10 from Jackson to Chicago, returning Mon, Aug 17, priced at CA $580 found 5 days ago
Delta
Mon, Aug 10 - Mon, Aug 17
JAN
Jackson
ORD
Chicago
CA $588 Roundtrip, found 5 days ago
CA $588
Roundtrip
found 5 days ago
Select Delta flight, departing Mon, Aug 10 from Jackson to Chicago, returning Mon, Aug 17, priced at CA $588 found 5 days ago
American Airlines
Mon, Aug 10 - Mon, Aug 17
JAN
Jackson
ORD
Chicago
CA $594 Roundtrip, found 5 days ago
CA $594
Roundtrip
found 5 days ago
Select American Airlines flight, departing Mon, Aug 10 from Jackson to Chicago, returning Mon, Aug 17, priced at CA $594 found 5 days ago
American Airlines
Mon, Aug 10 - Mon, Aug 17
JAN
Jackson
ORD
Chicago
CA $600 Roundtrip, found 5 days ago
CA $600
Roundtrip
found 5 days ago
Select American Airlines flight, departing Mon, Aug 10 from Jackson to Chicago, returning Mon, Aug 17, priced at CA $600 found 5 days ago
Delta
Sat, Aug 8 - Tue, Aug 18
JAN
Jackson
ORD
Chicago
CA $603 Roundtrip, found 5 days ago
CA $603
Roundtrip
found 5 days ago
Select Delta flight, departing Sat, Aug 8 from Jackson to Chicago, returning Tue, Aug 18, priced at CA $603 found 5 days ago
American Airlines
Mon, Aug 10 - Mon, Aug 17
JAN
Jackson
ORD
Chicago
CA $609 Roundtrip, found 5 days ago
CA $609
Roundtrip
found 5 days ago
Select American Airlines flight, departing Mon, Aug 10 from Jackson to Chicago, returning Mon, Aug 17, priced at CA $609 found 5 days ago
Delta
Mon, Aug 10 - Mon, Aug 17
JAN
Jackson
ORD
Chicago
CA $618 Roundtrip, found 5 days ago
CA $618
Roundtrip
found 5 days ago
Select Delta flight, departing Mon, Aug 10 from Jackson to Chicago, returning Mon, Aug 17, priced at CA $618 found 5 days ago
Delta
Mon, Aug 10 - Mon, Aug 17
JAN
Jackson
ORD
Chicago
CA $623 Roundtrip, found 5 days ago
CA $623
Roundtrip
found 5 days ago
Select Delta flight, departing Mon, Aug 10 from Jackson to Chicago, returning Mon, Aug 17, priced at CA $623 found 5 days ago
United
Mon, Aug 10 - Mon, Aug 17
JAN
Jackson
ORD
Chicago
CA $625 Roundtrip, found 5 days ago
CA $625
Roundtrip
found 5 days ago
Select United flight, departing Mon, Aug 10 from Jackson to Chicago, returning Mon, Aug 17, priced at CA $625 found 5 days ago

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 one-way and return flights from JAN to ORD 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 JAN to ORD ticket fares go up or down.
What is the cheapest month to fly from Jackson, MS (JAN-Evers Intl.) to Chicago, IL (ORD-O'Hare Intl.)?
If you're looking for the cheapest time to fly from Jackson, MS (JAN-Evers Intl.) to Chicago, IL (ORD-O'Hare Intl.), September is typically your best bet. You can expect average return fares around CA$432 during this month. September often sees lower prices as the summer travel rush ends and before the holiday season begins. Other budget-friendly months for this route include May and August.
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) to Chicago, IL (ORD)?
To find a cheap flight from Jackson, MS (JAN) to Chicago, IL (ORD), 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.)?
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 return flights costing around CA$432. These months offer a good balance of more affordable fares and pleasant weather for your trip.
How many flights per day from Jackson, MS (JAN-Evers Intl.) to Chicago, IL (ORD-O'Hare Intl.)?
There are around 26 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.) to Chicago, IL (ORD-O'Hare Intl.) typically departs at around 5:00 AM local time, operated by American Airlines. This is a seasonal service active in July. An early departure like this can help you make the most of 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 Friday, with around 20 flights available. This gives you a good selection for your travel plans. Major airlines on this route include American Airlines, Delta, and United. Flight schedules are consistent throughout the week, so you'll have plenty of options regardless of the day you choose to fly.
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. Many major carriers, including American Airlines, Delta and United, offer flights during this window. Many travellers prefer this time as it allows for an early start to their day in Chicago.
How long does it take to fly from Jackson, MS (JAN-Evers Intl.) to Chicago, IL (ORD-O'Hare Intl.)?
There are no nonstop flights from Jackson, MS (JAN-Evers Intl.) to Chicago, IL (ORD-O'Hare Intl.). The distance between these two cities is approximately 1,093 kilometres. For flights with one stop, you can expect the journey to typically take around 5 hours 18 minutes. If your flight has two or more stops, the travel time will be longer, usually around 7 hours 48 minutes. Keep in mind that these are average times, and your actual travel duration can vary depending on the specific routing, layover times, and even weather conditions.
Can you fly business or first class from Jackson, MS (JAN-Evers Intl.) to Chicago, IL (ORD-O'Hare Intl.)?
Yes, you can fly business class or first class between JAN and ORD.You can fly business class with Delta.First class cabins are available on Delta and American 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, IL (ORD) from Jackson, MS (JAN)?
If you're planning to travel to Chicago from Evers Intl. (JAN), you can fly directly into O'Hare Intl. (ORD). Some flights may connect through major hubs like George Bush Intercontinental (IAH), William P. Hobby (HOU), or 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) to Chicago, IL (ORD)?
If you booked your Jackson, MS (JAN) to Chicago, IL (ORD) 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.
Roundtrip price
CA $553
Distance
1085 km

Book with confidence

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 CA $553 rising to CA $625.  

Here are more money-saving tips: 

  • Fly in August 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

Explore a world of travel with Expedia

*Available to Expedia members.