Cheap Flights from Jacksonville International (JAX) to Chicago Midway (MDW)

Compare Jacksonville International to Chicago Midway flight deals

Find the cheapest month or even day of the year to fly to Chicago Midway

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Flight deals from Jacksonville International to Chicago Midway

Looking for a cheap last-minute deal or the best return flight from Jacksonville International Airport to Chicago Midway Airport? If you want to travel next month, return fares start from £106. Find the lowest prices on one-way and return tickets right here.

Find the cheapest month to fly from Jacksonville International to Chicago Midway

We’re always keeping an eye on fares, so you can find the best one in seconds. It looks like Jacksonville International to Chicago Midway flights are currently cheapest in April.

Direct flights from Jacksonville International to Chicago Midway

Jacksonville International to Chicago Midway: Alternative routes

Compare routes from Jacksonville International to Chicago below. You may find an airport to fly into that's cheaper, faster, or easier than Chicago Midway.

Jacksonville to Chicago: Flight information

The things to know before you go.
Cheapest flight found£53
Cheapest month to flyMay
Average flight time2 hrs, 27 mins
Most popular airlineSouthwest Airlines
Average flights per week7

Finding cheap flights from Jacksonville International to Chicago Midway: Frequently asked questions

The best price we found for a return flight from Jacksonville International to Chicago Midway is £106. This is an estimate based on information collected from different airlines and travel providers over the last 4 days and is subject to change and availability.
2 hours and 27 minutes is the average flight time from Jacksonville International to Chicago Midway.
Southwest Airlines flies direct from Jacksonville International to Chicago Midway.
As of April 2026, there are 8 flights per week flying from Jacksonville International to Chicago Midway.
The cheapest month to fly from Jacksonville International to Chicago Midway is usually April.
After crunching the numbers on our flight calendar, we found that it's currently cheapest to fly from Jacksonville International Airport to Chicago Midway Airport on Thursday, 30 April 2026.
Yes – the average flight time is 2 hours and 27 minutes.
We show every price from over 1,200 airlines and travel agents, comparing them all so you don’t have to. If you know you want to fly to Chicago Midway but you’re not ready to book, set up a Price Alert. We’ll track prices for you, and let you know when they rise or fall.
We crunched all the numbers in our flight calendar and it looks like the cheapest time to book a flight to Chicago is around 40 days in advance, so don’t leave your flight to the last minute.
Currently, Frontier Airlines and Southwest Airlines offer the cheapest flight tickets to Chicago Midway.

Travelling from Jacksonville International Airport (JAX) to Chicago Midway International Airport (MDW): what you need to know

  • Around 2 hours 25 minutes is how long you can expect to be in the air on a direct flight from Jacksonville International Airport to Chicago Midway International Airport.

  • Chicago's timezone is UTC-5, making Chicago one hour behind Jacksonville.

  • Each week, there are seven Jacksonville International Airport to Chicago Midway International Airport flights. If you'd like to take off as early as possible, opt for the 05:45 Southwest Airlines flight. If you're eager to make the most of your day before you fly, the latest flight is at 20:35 with Southwest Airlines.

  • Your JAX to MDW flight won't wait if you're running late, so be at the airport on time. Arrive up to one hour in advance for domestic flights and two hours ahead when you're flying internationally.

  • During popular months like July, it's best to get to the airport well in advance. Plan to arrive two hours before domestic departures and four hours ahead for international flights whenever you're flying during a high season in general.

  • Southwest Airlines is your gateway to discovering Chicago (and perhaps some other exciting corners of United States!). Browse the direct flights from Jacksonville International Airport to Chicago Midway International Airport offered by this airline.

  • Most travellers choose to fly with Southwest Airlines on this route.

  • Southwest Airlines leads the way as the most punctual carrier for JAX to MDW flights, with 87.93% of services arriving on schedule.

  • If you want to explore another city along the way, just deselect 'Direct flights only' when searching for your ticket from Jacksonville International Airport to Chicago Midway International Airport. These are the top stopovers between JAX and MDW:

    • Nashville International Airport

    • Hartsfield-Jackson Atlanta International Airport

    • John Glenn Columbus International Airport

How to find the cheapest flights from Jacksonville International Airport (JAX) to Chicago Midway International Airport (MDW)

  • The cheapest price we've found for a one-way Jacksonville International Airport to Chicago Midway International Airport flight is £53. A return ticket right now is £106. Depending on the availability and when you book, these fares could change.

  • Book six months before travelling. After looking at the numbers on our calendar, this is how far you should book ahead to secure cheap tickets from JAX to MDW.

  • The cheapest month for flights from Jacksonville International Airport to Chicago Midway International Airport is May. Use the 'Whole month' tool to see the lowest airfares if you have a flexible schedule.

  • Stay on top of deals for cheap flights from JAX to MDW by setting up a Price Alert. You'll get an email or notification through the app when a new low fare is offered.

  • Secure the right flight for you with the help of the filters. To see the 'Fastest,' 'Cheapest' or 'Best' flights from Jacksonville International Airport to Chicago Midway International Airport, use the 'Sort by' tool. You can also filter by departure and arrival times, airline, and journey duration.

Handy information about Jacksonville International Airport (JAX)

  • You'll find JAX at 2400 Yankee Clipper Drive.

  • 80.42% of flights leaving Jacksonville International Airport arrive at their destination on schedule. With its strong on-time performance, you're unlikely to face delays when flying out of JAX.

  • Central Jacksonville to Jacksonville International Airport is around 14 miles. Depending on traffic, it'll take you about 15 minutes to get there if you're catching a cab, ride-sharing or driving.

  • You can expect a trip time of about 1 hour 20 minutes when using public transport.

  • Catching an early flight from Jacksonville International Airport to Chicago Midway International Airport? Avoid rushing to the terminal (and catch some extra z's) by choosing one of these hotels near JAX:

Arriving at Chicago Midway International Airport (MDW)

  • If you have a late Jacksonville International Airport to Chicago Midway International Airport flight, few things top the convenience of being close to the terminal. Pick up your bags from the carousel and then be showered and sleeping soon after at one of these hotels near MDW:

  • Travel at your own pace with a Chicago Midway International Airport rental car. Book your wheels from Dollar, Hertz or Budget and experience more of Chicago and beyond.

  • Get the best deal by reserving your ride from Chicago Midway International Airport around four weeks ahead of your departure.

Getting from Chicago Midway International Airport (MDW) to central Chicago

  • MDW is located at 5700 South Cicero.

  • Chicago Midway International Airport to the centre of Chicago has a drive time of about 20 minutes. It's approximately 12 miles away.

  • Travelling to the centre by public transport will take you roughly 45 minutes.

When to fly to Chicago Midway International Airport (MDW)

  • July is the busiest month for flights from Jacksonville International Airport to Chicago Midway International Airport. For smaller crowds, go to Chicago in May.

  • Lock in your flight from Jacksonville International Airport to Chicago Midway International Airport for July if you'd like to go to Chicago during its warmest month. You can expect temperatures of between 15ºC (59ºF) and 29ºC (84ºF).

  • For cooler conditions, search for a cheap ticket from JAX to MDW in January. Average temperatures are between -12ºC (10ºF) and 3ºC (37ºF) then.

Explore more of United States

  • Columbus is just one of the many places in United States waiting to be discovered once you've seen the sights of Chicago. Around 280 miles away to the south-east, check out popular attractions including Franklin Park Conservatory and Botanical Gardens, Ohio Statehouse and German Village.

  • Indianapolis is another favourite destination in United States and is around 160 miles south-east of Chicago. No journey is complete without seeing The Children's Museum of Indianapolis, Indianapolis Museum of Art and Indianapolis Zoo.

Prices shown on this page are estimated lowest prices only. Found in the last 45 days.