$155 Cheap Flights from Chicago (ORD) to Jackson (JAN)

Chicago (ORD) to Jackson (JAN) at a glance

Travel from Chicago (ORD) to Jackson (JAN) with a range of airlines offering convenient short-haul flights. You can compare options from both full-service and budget airlines to find the best itinerary that suits your needs in terms of budget and schedule. As you prepare to explore the iconic sights and neighborhoods of Jackson, be sure to check out the key details for flights from O'Hare International Airport to Evers International Airport.

• 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 $130–$415, depending on seasonality and how far ahead you book

Flights from O'Hare International Airport (ORD) to Evers International Airport (JAN)

Based on recent traveler bookings, here are the most popular airlines flying from Chicago to Jackson, primarily favored for their one-stop services. Common layover locations include Hartsfield-Jackson Atlanta International Airport (ATL) with an approximate 1 hour and 15-minute layover, Charlotte-Douglas International Airport (CLT) with around a 1-hour layover, and George Bush Intercontinental Airport (IAH) also offering about a 1-hour layover. This variety allows you to compare prices, total travel times, and cabin classes to find the ideal itinerary.

• American Airlines: This major airline provides full-service options with one-stop routes. One-way ticket prices generally range from $130 to $405. It operates nearly 39% of flights for this journey, featuring an in-flight duration of 4 hours and a total travel time of about 5 hours and 15 minutes, including layover.
• Delta: Another prominent full-service airline, Delta offers one-stop flights with typical one-way fares between $135 and $415. It handles around 38% of departures on this route, with an in-air travel time of 4 hours, and the overall journey takes about 5 hours and 15 minutes, factoring in layovers.
• United: As a full-service carrier, United features one-stop options, with one-way fares ranging widely from $160 to $960. This airline makes up roughly 15% of flights on this route, maintaining a flight duration of 4 hours, while the total trip time is approximately 5 hours and 15 minutes, including the layover period.
• Southwest Airlines: Known for its budget-friendly services, Southwest provides one-stop flights with one-way fares typically between $145 and $405. It accounts for about 8% of departures on this route, with a flight time of 4 hours and a total journey length of around 5 hours and 15 minutes, including layover.

Travelers flying from Chicago to Jackson can enhance their journey by upgrading to Delta's premium economy class service on this route for a more comfortable experience.

Best time to fly from Chicago (ORD) to Jackson (JAN)

The most popular months for travelers flying from Chicago to Jackson are January, March, and April, when peak temperatures in Jackson reach up to 64.6°F in April. If you prefer quieter travel, consider November, the least busy and relatively cheaper time to visit with fewer crowds and temperatures around 55.6°F. For better deals, May usually offers the lowest average one-way fare around $220. Flight availability peaks in August, with approximately 15 flights per week, making it easier to find convenient departure times. May and December have the fewest flights, with approximately 10 flights per week.

• Cheapest time to fly: May usually offers good deals with average one-way fare around $220, roughly 19% cheaper than the yearly average.
• More budget-friendly months to fly: September and June typically offer average one-way fares of around $245.
• Most flight options: August has the highest number of flights from Chicago to Jackson, with approximately 15 flights per week, giving you more flexibility in scheduling your trip.

*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 Chicago (ORD) to Jackson (JAN)

• Chicago to Jackson (MDW-JAN): Midway International Airport (MDW) is located approximately 16 miles from O'Hare International Airport (ORD). On this route, one-way economy prices generally fall between $120 and $410, influenced by the season and how far in advance you book. Typically, flights on this route involve at least one stop, with popular layover cities including Hartsfield-Jackson Atlanta International Airport (ATL) and Nashville International Airport (BNA). Major airlines operating on this route are Southwest Airlines, known for its budget-friendly options, and Delta. Additionally, first class is offered on this route.

How to find the best prices for flights from Chicago (ORD) to Jackson (JAN)

Getting some of the best deals on flights from Chicago to Jackson is all about timing and flexibility. Here are some key tips to help you save:

1. Best times to book and fly: cheaper fares are usually available when booking 2 to 8 weeks in advance, though most travelers tend to book within 2 weeks. Morning departures from 5 am to 12 pm often provide cheaper prices and are also the most popular. Additionally, flying on Tuesday generally offers lower prices, while Friday remains the busiest travel day.
2. Set up price alerts: stay updated on price changes by using Expedia's Price Tracker. Receive alerts when fares drop for your selected route.
3. Bundle and save: bundle your flight and hotel to save on Expedia, or unlock a hotel deal after booking your flight.*
4. 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.
5. Stay flexible with dates: being open to different travel days can sometimes help you find better prices on flights and hotels.
6. 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 Evers International Airport from O'Hare International Airport

Jackson welcomes travelers from Chicago with a range of transport options based on price, convenience, and proximity. Jackson city center is approximately a 15-minute drive (covering about 13 miles) from Evers International Airport, depending on traffic. Here's how to reach Jackson efficiently:

• Hotel transfer: Transfers offer a convenient way to reach your hotel in Jackson, with options including free hotel shuttles and private rides, which can be arranged in advance with your hotel.
• Car rental: Renting a car from Evers International Airport is a great option if you plan to explore and sightsee beyond the city. Browse cheap car rentals at Evers 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 Evers International Airport, Jackson Station, a train station, is located about 6.8 miles from the airport, providing convenient access for travelers.

Chicago to Jackson Flights

The cheapest times to fly from Chicago to Jackson

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 Chicago to Jackson are during the month of November. You can find some of the cheapest flights from Chicago to Jackson with Expedia's search tool and vast selection of airlines.

The best time to book a flight from Chicago to Jackson

Sunday is one of the best days to book for cheap flights from Chicago to Jackson: 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 Chicago to Jackson

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 Chicago to Jackson 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 Chicago to Jackson 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 Chicago to Jackson 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.