Cheap Flights from Chicago Midway to Jacksonville International

Compare Chicago Midway to Jacksonville International flight deals

Find the cheapest month or even day of the year to fly to Jacksonville International

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Flight deals from Chicago Midway to Jacksonville International

Looking for a cheap last-minute deal or the best return flight from Chicago Midway Airport to Jacksonville International Airport? If you want to travel next month, return fares start from Rs39,018. Find the lowest prices on one-way and return tickets right here.

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

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

Direct flights from Chicago Midway to Jacksonville International

Chicago Midway to Jacksonville International: Alternative routes

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

Chicago to Jacksonville: Flight information

The things to know before you go.
Cheapest flight foundRs18,083
Cheapest month to flyJune
Average flight time2 hrs, 18 mins
Most popular airlineSouthwest Airlines
Average flights per week10

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

The best price we found for a return flight from Chicago Midway to Jacksonville International is Rs36,681. 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 18 minutes is the average flight time from Chicago Midway to Jacksonville International.
Southwest Airlines flies direct from Chicago Midway to Jacksonville International.
As of April 2026, there are 10 flights per week flying from Chicago Midway to Jacksonville International.
The cheapest month to fly from Chicago Midway to Jacksonville International is usually June.
After crunching the numbers on our flight calendar, we found that it's currently cheapest to fly from Chicago Midway Airport to Jacksonville International Airport on Tuesday, 2 June 2026.
Yes – the average flight time is 2 hours and 18 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 Jacksonville International 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 Jacksonville 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 Jacksonville International.

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

  • Around 2 hours 15 minutes is how long you can expect to be travelling on a direct flight from Chicago Midway International Airport to Jacksonville International Airport.

  • Jacksonville is one hour ahead of Chicago and observes the UTC-4 timezone.

  • Every week, there are seven Chicago Midway International Airport to Jacksonville International Airport flights. If you want to get going as soon as possible, jump on the 08:35 Southwest Airlines flight. If you're eager to make the most of your day before you fly, the last flight is at 21:30 with Southwest Airlines.

  • Arrive at the airport on time so you don't miss your MDW to JAX flight. Be there at least two hours ahead for international flights and an hour early for domestic departures to avoid sprinting to your gate.

  • Be prepared for bigger queues in popular months like July. Arriving up to four hours ahead of an international flight and two hours for domestic departures is a smart move.

  • Southwest Airlines offers direct flights from Chicago Midway International Airport to Jacksonville International Airport. Book with this popular carrier, then get ready to check out the sights in Jacksonville — and maybe even more of United States if time allows.

  • Southwest Airlines has the highest passenger demand on this route.

  • With 79.66% of services landing as planned, Southwest Airlines is the most punctual carrier operating MDW to JAX flights.

  • If you'd like to split up your journey, simply deselect 'Direct flights only' when searching for your ticket from Chicago Midway International Airport to Jacksonville International Airport. Here are the top stopovers between MDW and JAX:

    • McGhee Tyson Airport

    • Nashville International Airport

    • Hartsfield-Jackson Atlanta International Airport

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

  • The lowest price we've seen for a one-way Chicago Midway International Airport to Jacksonville International Airport flight is Rs18,083. A round-trip plane ticket right now is Rs36,681. Depending on the availability and when you book, these fares may change.

  • To pick up cheap tickets from MDW to JAX, reserve your trip six months before your planned departure.

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

  • You don't need to check back in every day to see if fares have gone down when you create a Price Alert. We'll send you an update the moment there's a better deal on cheap flights from MDW to JAX.

  • Select your ideal departure and arrival times, airlines and number of stops with the filters. Alternatively, sort your results by 'Cheapest' to find the best deals on flights from Chicago Midway International Airport to Jacksonville International Airport.

Handy information about Chicago Midway International Airport (MDW)

  • The address for MDW is 5700 South Cicero.

  • 77.88% of flights that take off from Chicago Midway International Airport reach their destination on time.

  • Central Chicago to Chicago Midway International Airport is around 19 kilometres. Depending on traffic, it'll take about 20 minutes to get there if you're ride-sharing, catching a cab or driving.

  • Expect a trip time of roughly 45 minutes on public transport.

  • Get your journey off to a hassle-free start by staying near MDW. Whether you're boarding an early flight from Chicago Midway International Airport to Jacksonville International Airport or want to avoid feeling rushed, these hotels are the answer:

Arriving at Jacksonville International Airport (JAX)

Getting from Jacksonville International Airport (JAX) to central Jacksonville

  • JAX is located at 2400 Yankee Clipper Drive.

  • From Jacksonville International Airport, Jacksonville is approximately 23 kilometres away. It takes around 15 minutes to drive to the centre.

  • If you're travelling by public transport, expect a journey of roughly 1 hour 20 minutes.

When to fly to Jacksonville International Airport (JAX)

  • It's time to pick your trip dates for your flight from Chicago Midway International Airport to Jacksonville International Airport. July is the busiest month to visit Jacksonville. If you're after a more low-key vibe, go in May.

  • When reserving your flight from Chicago Midway International Airport to Jacksonville International Airport, think about the kind of weather you like. July is the warmest month in Jacksonville, with the temperature ranging from 23ºC to 34ºC.

  • January has average temperatures of between 5ºC and 21ºC. Look for cheap tickets from MDW to JAX around that time if you like cooler conditions.

Explore more of United States

  • Jacksonville has loads to offer, but there are so many other corners of United States waiting to be explored. Around 467 kilometres north-west of Jacksonville, a trip to Atlanta will keep you on the move. Check out popular attractions like Georgia Aquarium, Centennial Olympic Park and Piedmont Park.

  • Tampa is another must-experience destination in United States and is around 274 kilometres south of Jacksonville. No journey is complete without a visit to Ybor City Tattoo Company, Tampa Riverwalk and The Florida Aquarium.

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