JAX to MDW (Jacksonville to Chicago) Flights

Last Minute Flights from JAX to MDW

Best airfare and ticket deals for JAX to MDW flights are based on recent deals found by Expedia.com customers within the past 7 days.

OriginDestinationTravel DatesFlights From*
JAXChicagoApril 27 to May 4$311
*Prices include taxes and fees

Cheapest JAX to MDW Flights

Best airfare and ticket deals for JAX to MDW flights are based on recent deals found by Expedia.com customers within the past 7 days.

OriginDestinationTravel DatesFlights From*
JAXChicagoMay 18 to May 22$108
JAXChicagoMay 18 to May 21$134
JAXChicagoMay 18 to May 25$139
JAXChicagoMay 25 to May 31$237
*Prices include taxes and fees
JAX to MDW Flight Details
Origin airport
Jacksonville Intl.
Origin airport IATA code
JAX
Destination airport
Midway Intl.
Destination airport IATA code
MDW
Distance
849 mi

Frequently asked questions

Which airlines with flights from Jacksonville International Airport to MDW allow free cancellation due to COVID-19?
Air carriers offering flexible fares from JAX to MDW are a cinch to find with our handy filter tool. Exactly what kinds of COVID-19 related changes are permitted is defined in the fare’s policies. Simply enter your trip details, then check the “No change fee” box. You’ll find it to the left of your screen below the “Flexible change policies” heading.
What airlines fly direct from Jacksonville, FL Airport (JAX-Jacksonville Intl.) to Chicago, IL Airport (MDW-Midway Intl.)?
Southwest Airlines (WN) does. Book a fare on one of the 21 flights a month that take off from JAX and journey straight to MDW. Avoiding a tiresome stopover is a top way to begin your Chicago adventure.
How many flights are there from JAX to MDW?
About 21 every day. If you’re in a big hurry to fly to Chicago, see if you can grab an awesome last-minute deal from Jacksonville, FL Airport (JAX-Jacksonville Intl.) to Chicago, IL Airport (MDW-Midway Intl.) and then secure it right away!
How long does it take to fly from Jacksonville, FL Airport (JAX-Jacksonville Intl.) to Chicago, IL Airport (MDW-Midway Intl.)?
This flight from Jacksonville, FL Airport (JAX-Jacksonville Intl.) to Chicago, IL Airport (MDW-Midway Intl.) will take some 3 hours and 58 minutes. Use the time to get stuck into the novel that’s been sitting on your bookshelf for ages or catch up on some sleep.
What is the flight distance from Jacksonville, FL Airport (JAX-Jacksonville Intl.) to Chicago, IL Airport (MDW-Midway Intl.)?
Jacksonville, FL Airport (JAX-Jacksonville Intl.) to Chicago, IL Airport (MDW-Midway Intl.) is a short-haul trip of 850 miles (1350 km). You’ll have barely enough time to settle into your seat before touching down in Chicago.
How many morning flights are there from JAX to MDW?
With 66 morning flights from JAX to MDW each week, you have plenty of choice.
  • Buckle up and fly off with Delta (DL). It offers 34 weekly flights with morning departures. The first one leaves at 5:34AM.
  • As another option, reserve a ticket with Southwest Airlines (WN) and take off as early as 5:35AM. This company has 32 morning flights each week between JAX and MDW.
How many afternoon flights are there from JAX to MDW?
If you’re not an early riser, jump on one of the 84 afternoon and evening flights available weekly from JAX to MDW.
  • Book an airfare with Delta (DL). This airline has 44 afternoon and evening flights every week scheduled to depart from 12:03PM onward.
  • Alternatively, Southwest Airlines (WN) lists 40 afternoon and evening flights each week, with the earliest leaving the gate at 12:40PM.
What is the earliest departure time out of Jacksonville to Chicago?
Fly out of JAX at 5:34AM and hit the tarmac at MDW at 12:40AM. This is the earliest departure you can book on this route.
What is the latest departure time out of Jacksonville to Chicago?
Lock in a seat on the 8:15PM flight out of JAX, landing at MDW at 8:00PM, and allow yourself time to carry out any last-minute vacation preparations. This is the latest flight available on this route.
What is the average price from Jacksonville to Chicago?
Flights from JAX to MDW begin at around $108. You’ll want to act fast, because fantastic fares don’t hang around forever! This price was available on Flights.com within the past 7 days, for flights departing within the next year. Prices and availability are subject to change. Additional terms apply.

Jacksonville to Chicago Flights

Whether it’s for an obligation or the sake of your sanity, sometimes you need to get away. Maybe you need flights from Jacksonville to Chicago to attend your cousin’s wedding, to pitch a business idea to your boss, or perhaps simply to treat yourself to a mini vacation. Regardless of the reasons behind packing your bags and needing to find the cheapest flights from JAX to MDW, we’ve got you covered here at Flights.com.

We present you with some of the hottest deals on airfare so stop that Google flights search. We want you to spend less on your flight from Jacksonville to Chicago, so you can spend more during your getaway. With Flights.com, you’ll find it simple to land airline tickets with itineraries matching your travel schedule. What’s more, we provide you with all the information you need to confidently make reservations on your family, business, or personal trip.