$123 Cheap Flights from Chicago (MDW) to Jackson (JAN)

You can find cheap one-way flights from $123 and cheap return flights $245 Chicago, IL (MDW-Midway Intl.) to Jackson, MS (JAN-Evers Intl.) with Expedia. One-way flights generally range between $153 and $565, and roundtrip flights usually range from $360 to $1061. 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 Chicago, IL (MDW-Midway Intl.) to Jackson, MS (JAN-Evers 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.

April is the cheapest month to fly from Chicago, IL (MDW) to Jackson, MS (JAN), with average round-trip fares around $268. This price is about 34% lower than the average throughout the year, as spring travel often sees reduced demand. Other economical months to consider are January and February.

*Averages based on flights available on Expedia in the last year.

Enter MDW to JAN and your travel dates, then apply the 'Nonstop' filter to see only direct flights.

Southwest Airlines is one of the cheapest airlines offering connecting flights from Chicago (MDW) to Jackson (JAN), with round-trip tickets starting from around $223. This flight includes a layover in Love Field (DAL). Use Expedia's search tool to compare the prices and schedules of airlines that fly this route to find the best option for your plans and budget.

*Prices based on flights available on Expedia in the last year.

To find a cheap flight from Chicago, IL (MDW-Midway Intl.) to Jackson, MS (JAN-Evers 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.

The best time to fly from Chicago Midway (MDW) to Jackson (JAN) is typically in April or February. During these months, you can find return flights at around $268, making them the cheapest options. April offers pleasant spring weather, while February tends to have lower travel demand, allowing for better fares and a more relaxed travel experience.

*Prices based on flights available on Expedia in the last year.

The earliest flight from Midway International Airport (MDW) to Evers International Airport (JAN) usually departs at around 5:00 AM. Operated by Southwest Airlines, this early departure allows you to maximize your time in Jackson, Mississippi. To compare early flights on Expedia, select the "Early Morning" and "Morning" filters in your search.

The most popular departure times for flights from Chicago, IL (MDW) to Jackson, MS (JAN) are from 9am to noon. This accounts for around 37% of total traffic. Many major carriers, including Southwest Airlines and Delta, offer flights during this window. Many travelers prefer this time because it allows for a relaxed start to the day before heading to Jackson.

Flights from MDW to JAN with one stop typically take around 5 hours 30 minutes, covering approximately 667 miles. Keep in mind that actual flight times can vary due to wind patterns, weather, and air traffic.

First class seats are offered on the MDW to JAN route with Delta Air Lines.

It's easy to earn miles on a Chicago, IL (MDW-Midway Intl.) to Jackson, MS (JAN-Evers 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.

From Midway Intl. (MDW), you can fly into Evers Intl. (JAN) and McKellar-Sipes Regional (MKL) in Jackson. Some flights may connect through major hubs like Love Field (DAL), Orlando Intl. (MCO), Nashville Intl. (BNA) before reaching Jackson. Compare routes and airports on Expedia to find the best flight options for your travel plans.

Typically, booking a last minute flight from Chicago, IL (MDW-Midway Intl.) to Jackson, MS (JAN-Evers 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.

Securing a Chicago, IL (MDW-Midway Intl.) to Jackson, MS (JAN-Evers 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.

If you booked your Chicago, IL (MDW-Midway Intl.) to Jackson, MS (JAN-Evers 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.