MDW - JAX

$146 Find Cheap Flights from Chicago Midway Airport to Jacksonville - Compare and Save

1 adult
1 adult, Economy, 0 bags

Save 25% or more on flights. Compare deals from all over the web.

Never overpay with our price tracking tools.

Filter searches by price, airline and more to find your best flights.

Everything you should know

Cheapest round-trip
$269
Typical prices: $281-$447
Frontier
Thu 11/15Mon 11/19
MDW - JAX • 1 stop
Cheapest non-stop
$280
Typical prices: $303-$474
Southwest
Mon 11/12Thu 11/15
MDW - JAX • Non-stop
Nonstop flights
Every day
You can fly direct with Southwest. Average duration is 2h 20m
Direct flights
+1
Direct flights
+1
When to book
14 weeks
in advance
Our data shows that travelers who book at least 14 weeks in advance save around 48% compared to booking last minute.
Insights
Insights
When to travel
October
Cheapest • 24% price drop
June
Most popular
Good to know
+1
Good to know
+1
Top layover airports
Atlanta Hartsfield-Jackson (ATL)
Cheapest • Avg $316 (round-trip)
Lambert-St Louis (STL)
Shortest trip • 4h 15m (one-way)
Insights
Insights
Start a new search
KAYAK searches 100s of sites at once to find you the best travel deals.
We hope you love your trip to Jacksonville!
Flight Deals
Booking Insights
Expert advice
Flight Deals

Cheap Flights from Midway to Jacksonville (MDW-JAX)

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

Recent round-trip flight deals from Midway to Jacksonville

Sat, Nov 14 - Sat, Nov 21
Multiple Airlines Logo
7:15 am - 6:31 pmMDW  Chicago Midway-JAX Jacksonville
10h 16m1 stop Atlanta Hartsfield-Jackson
Multiple Airlines Logo
3:55 pm - 8:14 amJAX  Jacksonville-MDW Chicago Midway
17h 19m2 stops Fort Lauderdale Atlanta Hartsfield-Jackson
$268Multiple Airlines
Sun, Nov 15 - Thu, Nov 19
Frontier Logo
6:08 am - 6:11 pmMDW  Chicago Midway-JAX Jacksonville
11h 03m1 stop Atlanta Hartsfield-Jackson
Frontier Logo
8:08 pm - 11:47 pmJAX  Jacksonville-MDW Chicago Midway
4h 39m1 stop Atlanta Hartsfield-Jackson
$269Frontier
Thu, Dec 10 - Mon, Dec 14
Southwest Logo
6:40 pm - 10:10 pmMDW  Chicago Midway-JAX Jacksonville
2h 30mnonstop
Southwest Logo
6:05 am - 12:05 pmJAX  Jacksonville-MDW Chicago Midway
7h 00m1 stop Lambert-St Louis
$269Southwest
Thu, Dec 3 - Mon, Dec 7
Southwest Logo
6:40 pm - 10:10 pmMDW  Chicago Midway-JAX Jacksonville
2h 30mnonstop
Southwest Logo
3:45 pm - 9:30 pmJAX  Jacksonville-MDW Chicago Midway
6h 45m1 stop Baltimore/Washington
$269Southwest
Mon, Nov 2 - Fri, Nov 6
Frontier Logo
6:42 pm - 6:08 pmMDW  Chicago Midway-JAX Jacksonville
22h 26m1 stop Atlanta Hartsfield-Jackson
Frontier Logo
8:10 pm - 5:47 pmJAX  Jacksonville-MDW Chicago Midway
22h 37m1 stop Atlanta Hartsfield-Jackson
$272Frontier
Wed, Jan 6 - Mon, Jan 11
Southwest Logo
8:05 am - 6:00 pmMDW  Chicago Midway-JAX Jacksonville
8h 55m2 stops Lambert-St Louis Nashville Intl
Southwest Logo
1:30 pm - 3:00 pmJAX  Jacksonville-MDW Chicago Midway
2h 30mnonstop
$272Southwest
Fri, Nov 6 - Sat, Nov 7
Frontier Logo
6:08 am - 7:25 pmMDW  Chicago Midway-JAX Jacksonville
12h 17m1 stop Atlanta Hartsfield-Jackson
Frontier Logo
7:16 pm - 11:47 pmJAX  Jacksonville-MDW Chicago Midway
5h 31m1 stop Atlanta Hartsfield-Jackson
$273Frontier
Tue, Nov 3 - Sat, Nov 7
Multiple Airlines Logo
6:16 am - 8:30 amMDW  Chicago Midway-JAX Jacksonville
25h 14m2 stops Atlanta Hartsfield-Jackson Fort Lauderdale
Multiple Airlines Logo
7:16 pm - 11:47 pmJAX  Jacksonville-MDW Chicago Midway
5h 31m1 stop Atlanta Hartsfield-Jackson
$276Multiple Airlines
Tue, Nov 17 - Thu, Nov 26
Delta Logo
11:27 am - 5:49 pmMDW  Chicago Midway-JAX Jacksonville
5h 22m1 stop Atlanta Hartsfield-Jackson
Delta Logo
11:23 am - 3:15 pmJAX  Jacksonville-MDW Chicago Midway
4h 52m1 stop Atlanta Hartsfield-Jackson
$277Delta
Wed, Nov 18 - Thu, Nov 26
Delta Logo
6:00 am - 1:20 pmMDW  Chicago Midway-JAX Jacksonville
6h 20m1 stop Atlanta Hartsfield-Jackson
Delta Logo
11:23 am - 3:15 pmJAX  Jacksonville-MDW Chicago Midway
4h 52m1 stop Atlanta Hartsfield-Jackson
$277Delta
Booking Insights

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

Round-trip flights from Chicago Midway Airport to Jacksonville typically range from $281 to $447. The lowest price found in the past 5 days was $269, on Frontier.

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

Based on deals KAYAK users found in the last 12 months, Tuesday is the cheapest day of the week to fly from Chicago Midway Airport to Jacksonville. It’s 20% cheaper than the average day, while Monday is the most expensive, with prices 29% higher.

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

•October is the cheapest month to fly from Chicago Midway Airport to Jacksonville at $263 round-trip.
•July ($470) and December ($427) are the most expensive months.
•The price difference between flying in the cheapest and most expensive months is 78% on average.
This is based on KAYAK aggregated and averaged internal data over the past 12 months.

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

Flights from Chicago Midway Airport to Jacksonville are cheapest 14 weeks before departure. Booking in this window typically costs about 48% less than the average last-minute fare (within 2 weeks of the flight), based on KAYAK data.

Find deals
Expert advice

Expert advice for your flight from Midway to Jacksonville

 
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 Chicago Midway Airport to Jacksonville flights

Low season

October

Cheapest flight

$147
Beat the crowds with an average 46% drop in travelers.
The most popular month to fly with an average 51% increase in travelers.
One-way flight from Chicago Midway Airport to Jacksonville

When to book flights from Midway to Jacksonville

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

Your Chicago Midway Airport to Jacksonville 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 Chicago Midway Airport to Jacksonville?

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

    • Earliest: departs at 8:00 am and lands at 10:20 am
    • Latest: departs at 9:10 pm and lands at 11:30 pm.

    The flight takes about 2h 20m.

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

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

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

    A nonstop flight from Chicago Midway Airport to Jacksonville takes 2h 20m, covering 849 miles.

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

    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 Chicago Midway Airport to Jacksonville flight?

    Round-trip flights from Chicago Midway Airport to Jacksonville range from $281 to $447, with an average of $347 over the past 12 months. Anything below $281 counts as a good deal.

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

    Last-minute fares on this route (booked within two weeks of departure) run 29% above the $347 route average. Book 14 weeks before departure for the lowest fares.

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

    On this route, layover flights are cheaper than nonstop options on average. Layover fares average $316 round-trip via Atlanta Hartsfield-Jackson (ATL), compared to $365 for nonstop.

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

    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 Chicago Midway Airport to Jacksonville?

    The Airbus A319 family is used most often on this route, operated mainly by American Airlines and United Airlines. Other aircraft seen on the route include Boeing 737 MAX 8 variants.

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

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

  • Have flight prices from Chicago Midway Airport to Jacksonville 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 $269 to $1,819. That means the highest observed fare was about 7x higher than the lowest one.

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

    One-way fares from Chicago Midway Airport to Jacksonville are currently lower than usual. Average one-way flight prices are about $155, which is 18% below the typical average for this route.

  • What car rental options are available at Jacksonville Airport (JAX)?

    Jacksonville Airport (JAX) hosts 5 major car rental companies, with daily rates starting from around $21 for economy cars. Top options include:

    • Easirent
    • Hertz
    • Dollar
    • Thrifty
    • Budget

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

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

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

    One-stop flights from Chicago Midway Airport to Jacksonville most commonly connect through:

    • Atlanta Hartsfield-Jackson (ATL) - 93% of one-stop connections
    • Nashville Intl (BNA) - 4% of one-stop connections
    • Lambert-St Louis (STL) - 2% of one-stop connections

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

    Yes. Flexible dates can save you up to 38% on flights from Chicago Midway Airport to Jacksonville. Tuesday is the cheapest departure day at $279 round-trip on average, while Monday is the most expensive at $450, a difference of $171.

    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 Chicago Midway Airport to Jacksonville?

    Only Southwest operates flights between Chicago Midway Airport and Jacksonville.

  • How much time can I save by choosing a different layover airport from Chicago Midway Airport to Jacksonville?

    Flying via Lambert-St Louis (STL) gives the shortest average 1-stop total travel time at 4h 15m, compared with 4h 38m via Nashville Intl (BNA) and 6h 14m via Atlanta Hartsfield-Jackson (ATL).

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

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

  • What popular places can I visit in Jacksonville?

    Some of the most popular sights in Jacksonville are Mayo Clinic- Kinne Auditorium, EverBank Field and Veterans Memorial Arena. These are among the most viewed places in Jacksonville on KAYAK.

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

    Among airlines operating Chicago Midway Airport to Jacksonville 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 Chicago Midway Airport to Jacksonville 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 Chicago Midway Airport to Jacksonville 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 Tuesday departure and avoid flying on Monday. On this route, Tuesday flights average $279, about $171 less than Monday fares (38% savings) based on the last 12 months.
  • For the best chance at a low fare, aim to book around 14 weeks before you fly. On this route, that window historically saves about 48% versus last-minute pricing (KAYAK booking data, last 12 months).
  • If you can choose when to travel, plan your Chicago Midway Airport to Jacksonville trip for October. Fares historically average $263 round-trip in that month - typically $207 less than the most expensive month, which is July (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 $316 round-trip on this route - about $50 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 Jacksonville Airport.

    • DoubleTree by Hilton Jacksonville Airport
    • SpringHill Suites by Marriott Jacksonville North I-95 Area
    • Microtel Inn & Suites by Wyndham Jacksonville Airport

Prefer to fly direct from Chicago Midway Airport to Jacksonville?

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

Direct departures

Chicago Midway to Jacksonville

Monday

Southwest

Southwest

Tuesday

Southwest

Southwest

Wednesday

Southwest

Southwest

Thursday

Southwest

Southwest

Friday

Southwest

Southwest

Saturday

Southwest

Southwest

Sunday

Southwest

Southwest

See more direct flights

Direct returns

Jacksonville to Chicago Midway

Monday

Southwest

Southwest

Tuesday

Southwest

Southwest

Wednesday

Southwest

Southwest

Thursday

Southwest

Southwest

Friday

Southwest

Southwest

Saturday

Southwest

Southwest

Sunday

Southwest

Southwest

See more direct flights

More options for your flight from Midway to Jacksonville

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

Car rentals in Jacksonville
Hotels in Jacksonville
Vacations in Jacksonville