Beginning of main content
Round Trip Icon
Trip Type
Flight 1
Flight 2
Flight 3
Flight 4
Flight 5

Search over 1,000,000 properties worldwide and 550 airlines worldwide.

Search over a million flights, hotels, packages, and more

No Expedia cancellation fee to change or cancel almost any hotel reservation.

Cheap JAN to MDW Flights

Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

Jackson to Chicago route information

Origin Airport Evers Intl.
Destination Airport Midway Intl.
Airlines Serving Delta
Flight Price $356
Distance 667 mi

Chicago

$343.40

Cheap JAN to MDW Flights

  • How much is a plane ticket to Chicago (MDW) from Jackson (JAN)?

    Cost can range from $372 to $876, prices for JAN to MDW fluctuate less than the majority of routes in the United States. Prices are usually cheaper the further out you book.
  • What is the cheapest day to fly to Chicago?

    As of Oct 14th, the cheapest day to fly from Jackson to Chicago is Oct 31st. Tickets are presently being sold for $372, which is 24% below the average price.
  • Is there an alternative airport near Chicago?

    The other airport is O'Hare International Airport (ORD) which is 16 miles away and on average, flights are 14% cheaper for the coming two months. Save and put it towards your next trip.
  • How much time do people spend in Chicago?

    The average time spent in Chicago by travelers from Jackson is one week.
  • What is the cheapest day to fly?

    The cheapest day to fly from Jackson to Chicago is on Friday. If you want to save a bit of money on your next trip look for flights on Friday.
  • Which airline has the least delays from Jackson to Chicago?

    NetJets Aviation will have you to MDW on time 100% of the time. Spend as little time in an airport as necessary by flying with NetJets Aviation. Perfection is hard to come by, so hopefully it continues.
  • Can I change the date of my flight?

    Yes, you can switch your departure date. If you wish to save some funds in doing so, the lowest-cost day to fly in October is Friday. Flexibility is key when booking travel to help keep costs down.

Jackson to Chicago Flights

Sometimes you just need to get out of town or maybe you’re looking for a change of scenery. Regardless of the reason, a flight from Jackson to Chicago will do just the trick! Go on, plan to see all the famous landmarks and eat your weight in the local cuisine. Your trip is beckoning, so answer the call by packing your suitcase and filling your travel itinerary with exploring Chicago.

Whether you’re flying for business or jet-setting on your personal time, you’ve come to the right place. Here at Expedia.com, we’ll pair you up with JAN to MDW flights that won’t make your bank account wince. Ready to temporarily leave behind Jackson for new horizons? Browse through our cheap airfare, and filter by flight times and dates until you find just what you had in mind. From flights without layovers to ones that arrive early in the morning, you’ll come across plane tickets that suit your travel preferences. You can even bundle your flight to MDW with hotels and car rentals to score even bigger savings.

All set to hit the clouds? Book your travel arrangements with us today and have left-over money to put toward your travel outings and adventures.

Package Disclaimer

*Savings amount equal to 100% when flight + hotel are booked together. Prices based on searches conducted by fellow shoppers within the past 24 hours. There is no guarantee that these prices will be in effect at the time of your search. Vacation package savings are based on comparison to prices on Expedia.com of the same components booked separately. Savings vary based on origin/destination, length of trip, stay dates and travel partners, and aren't available on all packages.