Cheap Flights from Jackson (JXN) to Chicago (MDW)

Popular airlines from Jackson, MI (JXN-Reynolds Field) to Chicago Midway Airport (MDW)

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Frequently asked questions

How much does a flight from Jackson, MI (JXN-Reynolds Field) to Midway Intl. Airport (MDW) cost?
Get a cheap one-way flight or cheap return flight from Jackson, MI (JXN-Reynolds Field) to Midway Intl. Airport (MDW) with Expedia. Enter your travel dates and sort by "Price (lowest to highest)" to find our cheapest flight deals on this route.
What is the cheapest month to fly from Jackson, MI (JXN-Reynolds Field) to Midway Intl. Airport (MDW)?
The cheapest month to fly from JXN to MDW is , when there's less demand. Off-peak season is often when airlines offer better prices between these airports.
What is the cheapest airline that flies from Jackson, MI (JXN-Reynolds Field) to Midway Intl. Airport (MDW)?
Expedia's filter tool lets you easily compare different airlines, departure times and fares all in one place. Choose your preferences, then sort by "Price (lowest to highest)" to find out which carrier offers the cheapest JXN to MDW flight.
How many flights per day from Jackson, MI (JXN-Reynolds Field) to Midway Intl. Airport (MDW)?
Direct flights from Jackson, MI (JXN-Reynolds Field) to Midway Intl. Airport (MDW) aren't available daily, so you'll need to take a flight with a layover. Explore your options with our filter tool. Enter your travel dates and click on either "1 Stop" or "2+ Stops."
What day of the week has the most flights from JXN to MDW?
Typically you'll have the most choice when it comes to flights on a Friday. Tuesdays tend to be the quietest.* However, this can vary depending on the time of year, airline and other factors.*Busiest/quietest day to travel is based on Expedia flight demand through January to December 2024.
What is the best time to fly from Jackson, MI (JXN-Reynolds Field) to Midway Intl. Airport (MDW)?
To avoid possible delays on the Jackson, MI (JXN-Reynolds Field) to Midway Intl. Airport (MDW) route, aim to fly before 3 PM. Later departures have a 22% higher chance of being canceled.**Most reliable time of the day and month to travel recommendation is based on January through August 2024 flight status data sourced from OAG's global flight data platform.
Is it cheaper to buy a plane ticket from Jackson, MI (JXN-Reynolds Field) to Midway Intl. Airport (MDW) last-minute?
Waiting until just before your departure to book a flight from JXN to MDW generally means paying more. While you might find some last-minute offers, they aren't always guaranteed. Be flexible with your travel plans for a better chance of scoring a bargain.
Is it cheaper to book a JXN to MDW flight and hotel package?
You can save money by booking a JXN to MDW flight and hotel package compared to booking separately. In fact, travelers could save hundreds of dollars by bundling with Expedia. And it's easy to manage everything in one place. Once you've chosen your preferred accommodations and flights, you can add extras such as car rentals, tours and activities.
Can I cancel or change the date of my flight from Jackson, MI (JXN-Reynolds Field) to Midway Intl. Airport (MDW)?
In most instances, you can modify or cancel your JXN to MDW flight. However, additional charges may apply, especially if your booking was made over 24 hours ago. Check your itinerary for the airline's policies and fees on flight changes, or if you want more information, head to our Customer Service portal.

Travel information

Origin airport
Reynolds Field
Destination airport
Midway Intl.
Distance
171 mi

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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 . 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 2025. You can also book with separate airlines for your outbound and return journeys, from 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.

 

Jackson to Chicago Flights

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*Available to One Key members.