JAX - MDW

$131 Find Cheap Flights from Jacksonville to Chicago Midway Airport - Compare and Save

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Everything you should know

Cheapest round-trip
$280
Typical prices: $279-$411
Frontier
Sun 11/11Mon 11/12
JAX - MDW • 1 stop
Cheapest non-stop
$319
Typical prices: $302-$436
Southwest
Sun 12/2Sun 12/9
JAX - MDW • Non-stop
Nonstop flights
6 days a week
You can fly direct with Southwest. Average duration is 2h 29m
Direct flights
+1
Direct flights
+1
When to book
15 weeks
in advance
Our data shows that travelers who book at least 15 weeks in advance save around 47% compared to booking last minute.
Insights
Insights
When to travel
January
Cheapest • 14% price drop
July
Most popular
Good to know
+1
Good to know
+1
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We hope you love your trip to Chicago Midway Airport!
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Expert advice
Flight Deals

Cheap Flights from Jacksonville to Midway (JAX-MDW)

 
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Jacksonville to Midway

Wed, Nov 11 - Thu, Nov 12
Frontier Logo
7:03 pm - 11:47 pmJAX  Jacksonville-MDW Chicago Midway
5h 44m1 stop Atlanta Hartsfield-Jackson
Frontier Logo
6:08 am - 6:11 pmMDW  Chicago Midway-JAX Jacksonville
11h 03m1 stop Atlanta Hartsfield-Jackson
$280Frontier
Fri, Jan 22 - Sun, Jan 24
Frontier Logo
7:54 pm - 11:46 pmJAX  Jacksonville-MDW Chicago Midway
4h 52m1 stop Atlanta Hartsfield-Jackson
Frontier Logo
8:47 pm - 6:59 pmMDW  Chicago Midway-JAX Jacksonville
21h 12m2 stops Orlando Atlanta Hartsfield-Jackson
$288Frontier
Sat, Dec 26 - Mon, Dec 28
Frontier Logo
8:36 pm - 12:01 amJAX  Jacksonville-MDW Chicago Midway
4h 25m1 stop Atlanta Hartsfield-Jackson
Frontier Logo
1:11 pm - 7:51 pmMDW  Chicago Midway-JAX Jacksonville
5h 40m1 stop Atlanta Hartsfield-Jackson
$289Frontier
Mon, Nov 9 - Thu, Nov 12
Multiple Airlines Logo
7:03 pm - 11:47 pmJAX  Jacksonville-MDW Chicago Midway
5h 44m1 stop Atlanta Hartsfield-Jackson
Multiple Airlines Logo
6:08 am - 5:45 pmMDW  Chicago Midway-JAX Jacksonville
10h 37m2 stops Atlanta Hartsfield-Jackson Norfolk
$292Multiple Airlines
Thu, Nov 12 - Mon, Dec 7
Multiple Airlines Logo
8:45 pm - 2:26 pmJAX  Jacksonville-MDW Chicago Midway
18h 41m1 stop Knoxville McGhee Tyson
Multiple Airlines Logo
5:02 pm - 4:26 pmMDW  Chicago Midway-JAX Jacksonville
22h 24m2 stops Atlanta Hartsfield-Jackson Raleigh-Durham
$292Multiple Airlines
Wed, Dec 16 - Sun, Dec 20
Multiple Airlines Logo
3:39 pm - 10:24 pmJAX  Jacksonville-MDW Chicago Midway
7h 45m1 stop Atlanta Hartsfield-Jackson
Multiple Airlines Logo
6:52 am - 8:45 amMDW  Chicago Midway-JAX Jacksonville
24h 53m2 stops Atlanta Hartsfield-Jackson Fort Lauderdale
$293Multiple Airlines
Thu, Nov 26 - Thu, Dec 3
Southwest Logo
7:45 am - 9:10 amJAX  Jacksonville-MDW Chicago Midway
2h 25mnonstop
Southwest Logo
3:50 pm - 9:15 pmMDW  Chicago Midway-JAX Jacksonville
4h 25m1 stop Lambert-St Louis
$297Southwest
Thu, Dec 10 - Mon, Dec 14
Southwest Logo
5:40 pm - 9:30 pmJAX  Jacksonville-MDW Chicago Midway
4h 50m1 stop Baltimore/Washington
Southwest Logo
6:40 pm - 10:10 pmMDW  Chicago Midway-JAX Jacksonville
2h 30mnonstop
$297Southwest
Thu, Dec 3 - Mon, Dec 7
Delta Logo
7:00 am - 12:04 pmJAX  Jacksonville-MDW Chicago Midway
6h 04m1 stop Atlanta Hartsfield-Jackson
Delta Logo
5:12 pm - 12:09 amMDW  Chicago Midway-JAX Jacksonville
5h 57m1 stop Atlanta Hartsfield-Jackson
$307Delta
Thu, Dec 3 - Mon, Dec 7
Delta Logo
12:00 pm - 6:01 pmJAX  Jacksonville-MDW Chicago Midway
7h 01m1 stop Detroit Metropolitan Wayne County
Delta Logo
6:00 am - 11:53 amMDW  Chicago Midway-JAX Jacksonville
4h 53m1 stop Atlanta Hartsfield-Jackson
$307Delta
Booking Insights

Price, demand and travel trends for Jacksonville to Chicago Midway Airport flights

Use KAYAK data on prices, travel dates, airlines and seasonal trends to compare options and book flights with more confidence.

How much is a round-trip flight from Jacksonville to Chicago Midway Airport?

Round-trip flights from Jacksonville to Chicago Midway Airport typically range from $279 to $411. The lowest price found in the past 5 days was $280, on Frontier.

What's the cheapest day of the week to fly from Jacksonville to Chicago Midway Airport?

Based on deals KAYAK users found in the last 12 months, Wednesday is the cheapest day of the week to fly from Jacksonville to Chicago Midway Airport. It’s 13% cheaper than the average day, while Monday is the most expensive, with prices 37% higher.

What’s the cheapest month to fly from Jacksonville to Chicago Midway Airport?

•January is the cheapest month to fly from Jacksonville to Chicago Midway Airport at $292 round-trip.
•November ($391) and October ($358) are the most expensive months.
•The price difference between flying in the cheapest and most expensive months is 33% on average.
This is based on KAYAK aggregated and averaged internal data over the past 12 months.

When are flights from Jacksonville to Chicago Midway Airport the cheapest?

Flights from Jacksonville to Chicago Midway Airport are cheapest 15 weeks before departure. Booking in this window typically costs about 47% less than the average last-minute fare (within 2 weeks of the flight), based on KAYAK data.

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Expert advice

Expert advice for your flight from Jacksonville to Midway

 
KAYAK teamed up with top travel experts to share the best tips for your journey.
Our travel experts
Marisa Garcia

Marisa Garcia

Expert on JAX

Marisa knows planes inside and out, spending 16 years working on aircraft in hangars at airports around the world. She is an aviation industry expert, specialized in airline interiors and regulations. Ten years ago, she pivoted to journalism. She shares her insights in leading aviation, travel, and business publications and on her site FlightChic.

Read more
Stefanie Waldek

Stefanie Waldek

Expert on MDW

Stefanie Waldek is a freelance space, travel, and design writer based in Saratoga Springs, NY. Her words have appeared in Space.com, Travel + Leisure, Condé Nast Traveler, Architectural Digest, and House Beautiful, among other publications. An expert in aviation and expedition cruising, Stefanie is frequently up in the air or on the sea, likely en route to Antarctica or the Arctic.

Read more

Key details for Jacksonville to Chicago Midway Airport flights

Low season

January

Cheapest flight

$131
Beat the crowds with an average 65% drop in travelers.
The most popular month to fly with an average 94% increase in travelers.
One-way flight from Jacksonville to Chicago Midway Airport

When to book flights from Jacksonville to Midway

Are your dates flexible? Find out the best times to travel from Jacksonville to Midway based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated round-trip price

Your Jacksonville to Chicago Midway Airport flight questions, answered

Find helpful answers about this route, including flight times, airports, airlines and booking tips.

  • What are the earliest and latest flights from Jacksonville to Chicago Midway Airport?

    These are the earliest and latest flight times available from Jacksonville to Chicago Midway Airport:

    • Earliest: departs at 7:00 am and lands at 9:29 am
    • Latest: departs at 7:55 pm and lands at 10:24 pm.

    The flight takes about 2h 29m.

  • What cabin classes can I book on flights from Jacksonville to Chicago Midway Airport?

    Only Economy Class is available on flights from Jacksonville to Chicago Midway Airport.

  • How long is a flight from Jacksonville to Chicago Midway Airport?

    A nonstop flight from Jacksonville to Chicago Midway Airport takes 2h 29m, covering 849 miles.

  • Do I need a passport to fly from Jacksonville to Chicago Midway Airport?

    No, a passport is not required for this domestic route, but you will need a real ID-compliant driver's license, a state ID or another TSA-accepted form of identification.

  • How much should I expect to pay for a Jacksonville to Chicago Midway Airport flight?

    Round-trip flights from Jacksonville to Chicago Midway Airport range from $279 to $411, with an average of $341 over the past 12 months. Anything below $279 counts as a good deal.

  • How expensive are last-minute Jacksonville to Chicago Midway Airport flights?

    Last-minute fares on this route (booked within two weeks of departure) run 39% above the $341 route average. Book 15 weeks before departure for the lowest fares.

  • How much can I save by taking a layover when flying from Jacksonville to Chicago Midway Airport?

    On this route, layover flights are cheaper than nonstop options on average. Layover fares average $297 round-trip via Atlanta Hartsfield-Jackson (ATL), compared to $356 for nonstop.

  • What is the standard checked-bag allowance on flights from Jacksonville to Chicago Midway Airport?

    There is no standard. Checked-bag policies vary by airline on this route. Most carriers charge $45–$90 for the first checked bag in economy. Premium fares and elite-status bookings typically include a free checked bag.

  • Which aircraft model is used most often on flights from Jacksonville to Chicago Midway Airport?

    The Boeing 737 MAX 8 family is used most often on this route, operated mainly by Southwest and United Airlines. Other aircraft seen on the route include Embraer 175 (Enhanced Winglets) variants.

  • How are flight departures from Jacksonville to Chicago Midway Airport spread across the day?

    Afternoon is the busiest departure period on Jacksonville to Chicago Midway Airport flights, with 100% of flights leaving in that window. Morning departures account for 0%, evening flights for 0%, and night flights for 0%.

  • Have flight prices from Jacksonville to Chicago Midway Airport changed much recently?

    Yes. Based on fares seen in the past 5 days, round-trip prices on this route showed a wide range, from about $289 to $1,985. That means the highest observed fare was about 7x higher than the lowest one.

  • Which airlines offer Wi-Fi on Jacksonville to Chicago Midway Airport flights?

    JetBlue is the only airline on the Jacksonville to Chicago Midway Airport route offering in-flight Wi-Fi. Pricing depends on fare class.

  • How are flight prices from Jacksonville to Chicago Midway Airport looking right now?

    One-way fares from Jacksonville to Chicago Midway Airport are currently lower than usual. Average one-way flight prices are about $146, which is 30% below the typical average for this route.

  • What car rental options are available at Chicago Midway Airport (MDW)?

    Chicago Midway Airport (MDW) hosts 5 major car rental companies, with daily rates averaging $84 for economy cars. Top options include:

    • Hertz
    • Dollar
    • Budget
    • Alamo
    • Rent-A-Wreck

  • Which airports can I use when flying from Jacksonville to Chicago Midway Airport?

    Flights from Jacksonville to Chicago Midway Airport usually depart from Jacksonville (JAX) and arrive at Chicago Midway (MDW).

  • Which airports do connecting flights from Jacksonville to Chicago Midway Airport pass through?

    Most connecting flights from Jacksonville to Chicago Midway Airport pass through Atlanta Hartsfield-Jackson (ATL), which handles 100% of one-stop traffic on this route.

  • Can I save money by using flexible dates for flights from Jacksonville to Chicago Midway Airport?

    Yes. Flexible dates can save you up to 37% on flights from Jacksonville to Chicago Midway Airport. Wednesday is the cheapest departure day at $297 round-trip on average, while Monday is the most expensive at $469, a difference of $172.

    KAYAK's flexible dates feature shows options up to 3 days before and after your selected dates, making it easier to compare nearby fares.

  • What airlines fly from Jacksonville to Chicago Midway Airport?

    Only Southwest operates flights between Jacksonville and Chicago Midway Airport.

  • What is the time difference between Jacksonville and Chicago Midway Airport?

    Chicago Midway Airport is 1 hour behind Jacksonville (Central Time vs Eastern Time). Plan for the time shift when scheduling connections or first-day activities.

  • What popular places can I visit in Chicago Midway Airport?

    Some of the most popular sights in Chicago Midway Airport are Magnificent Mile, Grant Park and Soldier Field. These are among the most viewed places in Chicago Midway Airport on KAYAK.

  • Which airlines offer extra legroom and free seat selection on Jacksonville to Chicago Midway Airport flights?

    Among airlines operating Jacksonville to Chicago Midway Airport flights:

    • Southwest: offers free seat selection

    Extra legroom and free seat selection availability depends on fare class and route.

  • Which airlines include bags at no extra cost on Jacksonville to Chicago Midway Airport flights?

    Here are some options for this route, based on selected ticket types and cabin classes:

    • Southwest: a cabin bag in Economy Class class
    • JetBlue: a cabin bag in Economy Class class

    Bag allowance can vary by ticket type, cabin class, route and airline, so always check the fare details before booking.

Your guide to booking Jacksonville to Chicago Midway Airport flights

Get tips on when to book, when to fly and what to know before your trip.
  • If your dates are flexible, aim for a Wednesday departure and avoid flying on Monday. On this route, Wednesday flights average $297, about $172 less than Monday fares (37% savings) based on the last 12 months.
  • For the best chance at a low fare, aim to book around 15 weeks before you fly. On this route, that window historically saves about 47% versus last-minute pricing (KAYAK booking data, last 12 months).
  • If you can choose when to travel, plan your Jacksonville to Chicago Midway Airport trip for January. Fares historically average $292 round-trip in that month - typically $99 less than the most expensive month, which is November (based on the last 12 months).
  • If you have the time, taking a 1-stop flight through Atlanta Hartsfield-Jackson Airport (ATL) can be cheaper than flying direct. The cheapest layover option averages $297 round-trip on this route - about $60 less than direct flights (based on the last 12 months).
  • If you're arriving late at night and need somewhere to stay, check out these hotels close to Chicago Midway Airport.

    • DoubleTree by Hilton Chicago Midway Airport
    • Holiday Inn Chicago - Midway Airport S by IHG
    • Skylark Motel Chicago Midway Airport

Prefer to fly direct from Jacksonville to Chicago Midway Airport?

 
Find which airlines fly direct from Jacksonville Airport to Chicago Midway Airport, which days they fly and book direct flights.

Direct departures

Jacksonville to Chicago Midway

Monday

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Tuesday

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Southwest

Wednesday

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Thursday

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Friday

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Saturday

Southwest

Southwest

Sunday

Southwest

Southwest

See more direct flights

Direct returns

Chicago Midway to Jacksonville

Monday

Southwest

Southwest

Tuesday

Southwest

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Wednesday

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Thursday

Southwest

Southwest

Friday

Southwest

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Saturday

Southwest

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Sunday

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See more direct flights

More options for your flight from Jacksonville to Midway

Complete your trip to Chicago with a hotel stay or car rental

Car rentals in Chicago
Hotels in Chicago
Vacations in Chicago