$155 Cheap Flights from Jackson (JAN) to Chicago (ORD)
Popular airlines from Evers Intl. Airport (JAN) to Chicago O'Hare Intl. Airport (ORD)
American AirlinesAmerican Airlines
DeltaDelta
UnitedUnited
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Cheap Flights from Jackson to Chicago (JAN-ORD)
Alternative airports near Chicago
Prices were available within the past 7 days. Prices and availability are subject to change.
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Jackson (JAN) to Chicago (ORD) at a glance
Travel from Jackson (JAN) to Chicago (ORD) with a selection of airlines offering weekly flights on this domestic short-haul route. Whether you're looking for cheap flights from Jackson or prefer full-service options, you can compare various itineraries to find one that aligns with your budget and travel plans. Discover essential details for your flights from Evers International Airport to O'Hare International Airport as you prepare to explore the vibrant sights and neighborhoods of Chicago.
- Fastest flight duration: around 4 hours in-flight, plus roughly 1h 15m layover with one stop
- Route distance: roughly 700 miles (1,130 km)
- Flights per week: around 12 departures on average
- Typical fares (one-way): economy tickets often range from $125–$410, depending on seasonality and how far ahead you book
Flights from Evers International Airport (JAN) to O'Hare International Airport (ORD)
Based on recent traveler preferences, here are the top airlines flying from Jackson to Chicago, often selected for one-stop and multi-stop journeys. Popular layovers include Hartsfield-Jackson Atlanta International Airport (ATL), Dallas-Fort Worth International Airport (DFW), and Charlotte-Douglas International Airport (CLT), each with approximately one-hour layovers. These options provide you with the flexibility to compare prices, total travel times, and cabin classes, helping you to craft the best itinerary for your trip.
- American Airlines: This full-service airline provides one-stop flights, with one-way ticket prices generally falling between $130 and $385. It operates around 45% of the departures on this route, featuring a flight duration of 4 hours and an overall travel time of approximately 5h 15m, including the layover.
- Delta: Another full-service option, Delta also offers one-stop service with one-way fares typically ranging from $125 to $455. It makes up about 41% of the departures for this route, with an in-flight time of 4 hours and a total journey time close to 5h 15m, factoring in the layover.
- United: As a full-service carrier, United provides one-stop service with one-way fares usually between $175 and $430. It accounts for around 9% of the route's departures, featuring a flight time of 4 hours and a complete travel duration of roughly 5h 15m, including layover time.
- Southwest Airlines: A budget-friendly choice, Southwest Airlines offers both one-stop and multi-stop options, with one-way fares that typically range from $125 to $360. This airline represents about 5% of the departures on this route, with a standard one-stop journey taking 4 hours in the air and about 5h 15m in total travel time.
Best time to fly from Jackson (JAN) to Chicago (ORD)
The most popular months for travelers flying from Jackson to Chicago are March, April, and August, when peak temperatures in Chicago reach up to 73°F in August. If you prefer quieter travel, consider May, the least busy and relatively cheaper time to visit with fewer crowds and temperatures around 57°F. For better deals, August usually offers the lowest average one-way fare around $219. Flight availability peaks in June, with approximately 18 flights per week, making it easier to find convenient departure times. February and November have the fewest flights, with approximately 10 flights per week.
- Cheapest time to fly: August usually offers good deals with average one-way fare around $219, roughly 18% cheaper than the yearly average.
- More budget-friendly months to fly: May and September typically offer average one-way fares of around $234.
- Most flight options: June has the highest number of flights from Jackson to Chicago, with approximately 18 flights per week, giving you more flexibility in scheduling your trip.
| Month | Temperature | Demand | Weekly Flights | Average one-way Fare |
| January | 25.7°F (-3.5°C) | Average | 13 | $309 |
| February | 27.0°F (-2.8°C) | Average | 10 | $273 |
| March | 37.0°F (2.8°C) | Moderately High | 12 | $304 |
| April | 46.0°F (7.8°C) | Moderately High | 11 | $267 |
| May | 57.0°F (13.9°C) | Moderately Low | 12 | $232 |
| June | 67.3°F (19.6°C) | Average | 18 | $270 |
| July | 73.4°F (23.0°C) | Average | 15 | $251 |
| August | 73.0°F (22.8°C) | Moderately High | 14 | $219 |
| September | 67.1°F (19.5°C) | Average | 13 | $235 |
| October | 54.9°F (12.7°C) | Average | 12 | $256 |
| November | 42.3°F (5.7°C) | Moderately Low | 10 | $306 |
| December | 33.1°F (0.6°C) | Moderately Low | 12 | $291 |
*Average one-way fare is based on Expedia flight booking data from January 2025 to April 2026 for the specified route and travel class and may change depending on availability, dates, and demand.
Alternative route from Jackson (JAN) to Chicago (ORD)
- Jackson to Chicago (JAN-MDW): Midway International Airport (MDW) is located approximately 16 miles from O'Hare International Airport (ORD). One-way economy fares for this journey generally fall between $120 and $450, influenced by the time of year and how early you make your reservations. This route is mostly offered with one-stop flights, commonly featuring layovers at Hartsfield-Jackson Atlanta International Airport (ATL) and Nashville International Airport (BNA). Leading airlines on this route include Delta and the budget-friendly Southwest Airlines.
How to find the best prices for flights from Jackson (JAN) to Chicago (ORD)
Getting some of the best deals on flights from Jackson to Chicago is all about timing and flexibility. Here are some key tips to help you save:
- Best times to book and fly: cheaper fares are usually available when booking at least two months in advance, yet most travelers tend to book within two weeks. Departures in the morning, between 5 AM and 12 PM, generally offer lower prices and are also the most popular flight times. Additionally, flying on Thursday can provide both cheaper prices and popularity among travelers.
- Set up price alerts: stay updated on price changes by using Expedia's Price Tracker. Receive alerts when fares drop for your selected route.
- Bundle and save: bundle your flight and hotel to save on Expedia, or unlock a hotel deal after booking your flight.*
- Compare flight options: use Expedia's search tool to compare airlines, routes, direct vs. non-direct flights, and flight times. You can also sort by price to find the most affordable options.
- Stay flexible with dates: being open to different travel days can sometimes help you find better prices on flights and hotels.
- Think about luggage: nowadays, it's important to check the airline's baggage policies to find the best value. That may be paying for an additional carry-on bag or booking a ticket with checked luggage included. Either way, double-check your allowance before confirming your booking to avoid excess baggage fees at the airport.
*Members only. Savings vary and are not available on all bundles. Select hotels.
Arriving at O'Hare International Airport from Evers International Airport
Chicago welcomes travelers from Jackson with a range of transport options based on price, convenience, and proximity. For departures, Evers International Airport is roughly a 15-minute drive (covering about 13 miles) from central Jackson. Here's how to reach Chicago efficiently:
- Hotel transfer: Transfers offer a convenient way to reach your hotel in Chicago, with private rides that can be arranged in advance.
- Car rental: Renting a car from O'Hare International Airport is a great option if you plan to explore and sightsee beyond the city. Browse cheap car rentals at O'Hare International Airport on Expedia.
- Taxi/ride-hailing: Taxis and ride-hailing services may be available from designated pickup areas outside the terminal, check locally on arrival.
- Public transportation: From O'Hare International Airport, O'Hare Station, a metro station, is located about 0.1 miles away on foot, while Rosemont Station, a train station, is about 2.2 miles from the airport and typically reached by car.
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 October. 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 $155 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.
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 $155 and cheap return flights $281 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. Airport |
|---|---|
Destination airport | Chicago O'Hare Intl. Airport |
Distance | 678 miles away |
Airlines serving | American Airlines, Delta, United |
Popular airline | American Airlines |
Roundtrip price | $281 |