
$149 Cheap flight deals from Jackson (JAN) to Chicago (CHI)
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This Weekend's Flight Deals from Jackson to Chicago
This weekend's flight prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.
Airfares from $149 One Way, $297 Round Trip from Jackson to Chicago
Prices starting at $297 for return flights and $149 for one-way flights to Chicago were the cheapest prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.
Chicago economy flight packages

Sable at Navy Pier Chicago, Curio Collection by Hilton
Dec 13 - Dec 16
Jackson (JAN) to Chicago (ORD)
Chicago (ORD) to Jackson (JAN)
Reviewed on Nov 3, 2025

Park Hyatt Chicago
Dec 23 - Dec 26
Jackson (JAN) to Chicago (ORD)
Chicago (ORD) to Jackson (JAN)
Reviewed on Sep 13, 2024

Trump International Hotel & Tower Chicago
Jan 2 - Jan 4
Jackson (JAN) to Chicago (ORD)
Chicago (ORD) to Jackson (JAN)
Reviewed on Oct 13, 2025
More About Flying To Chicago from Jackson
Route Information for Flights from Jackson to Chicago
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Destination Airport IATA Code | CHI |
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Flights from Jackson to Chicago
Jackson-Medgar Wiley Evers International Airport
Planning a trip on a budget is easy with Orbitz.com, which can help travelers locate cheap flights from Jackson. The Jackson-Medgar Wiley Evers International Airport is located nine miles from downtown Jackson, Mississippi on International Drive. Five airlines provide service to the airport, including American Eagle, Delta, United, US Airways and Southwest Airlines.
Parking at the Airport
Jackson-Medgar Wiley Evers International Airport offers a variety of parking options. The parking garage is located adjacent to the main terminal. The surface lot is adjacent to the parking garage, and both lots charge fees by the day. The cell phone lot is available on a first-come, first-served basis and is free for those dropping off and picking up passengers. The long-term lot is located on South Hangar Drive at discount prices. Courtesy shuttle services are provided from the long-term lot to the main terminal every 15 minutes.
Transportation to the Airport
Orbitz.com provides assistance in locating cheap rental car services in the Jackson area. The rental car counter is located on the first floor of terminal one for convenient drop-off service. Several taxis provide metered services to and from the airport, including Citicab, Deluxe and Yellow Cab. Limos can be rented by the hour or by the day, and the city bus system offers rides to the airport from various locations throughout the city.
Restaurants at Jackson-Medgar Wiley Evers International Airport
For passengers who want a snack or a quick cup of coffee before their flight, Starbucks offers a variety of blended coffees and pastry items. In Jackson, the Mayflower café provides a sit-down breakfast menu for those who prefer a quick meal. Orbitz.com can help locate cheap flights from Jackson.
Airports in Chicago
Chicago O'Hare International Airport is located on West O'Hare, approximately 18 miles from downtown Chicago. It has hubs for every major airline that offers flights to Chicago, including American Airlines, British Airways and JetBlue. The Chicago Midway International Airport is located on South Cicero Avenue, approximately 12 miles from downtown Chicago. Seven airlines service Midway airport, including Air Tran, Delta and Southwest Airlines. Orbitz.com searches flights arriving at both airports so you get the best prices.
Transportation from the Airport
Both airports offer public transportation via Chicago's elevated train system. The tickets cost $2.25, or you can purchase an all-day pass for $5.75. Taxi services are also available from both airports. Cab fares to downtown Chicago range from $35 to $45. If you want to rent a car for the duration of your stay, Orbitz.com can reserve a vehicle for you. Both airports have onsite rental car facilities.
Weather in Chicago
Summer temperatures in Chicago range from 66 to 84 degrees Fahrenheit, and the temperatures during the winter months range from 18 to 35 degrees Fahrenheit. Chicago is prone to heavy snowfall during the winter months, so most vacationers travel to Chicago during the summer. However, if you use Orbitz.com and schedule your trip during the off-peak travel season, it's easy to find cheap flights to Chicago.
Highlights and Attractions
Orbitz.com not only helps you find cheap flights to Chicago, but can also help you purchase tickets to the Sears Tower or make reservations for guided city tours.
Frequently asked questions
Flights to Chicago
- New York to Chicago
- Dallas to Chicago
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Flights from Jackson
- Jackson to Atlanta
- Jackson to Dallas
- Jackson to Houston
- Jackson to Chicago
- Jackson to Orlando
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- Jackson to Los Angeles
- Jackson to Detroit
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- Jackson to New Orleans
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- Jackson to Hartford
- Jackson to Killeen
- Jackson to Roanoke
- Jackson to Midland
- Jackson to Augusta
- Jackson to Accra
Jackson Airports
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Fare, taxes & fees: Fares include all taxes and fees, except baggage fees. Rates shown reflect fares found by other Orbitz users over the past 7 days. Due to rapidly changing airline prices & seat availability, these fares may no longer be available.
Refunds/changes/cancellations: Itinerary changes, if permitted for the fare, will have a $30 service fee charged by Orbitz. Additional airline charges may apply.
Other conditions: Schedules, fares and rules are subject to change without notice. Seats are limited and may not be available on all flights/dates or in all markets. Lower fares may be available. Fares will not be honored retroactively or in exchange for any wholly/partially unused ticket. Tickets are non-transferable and non-refundable. Fare rules are provided for the selected itinerary before booking.
