MDW - JAX

$88 Find Cheap Flights from Chicago Midway Airport to Jacksonville

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Midway to Jacksonville departing on 11/3. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
1 adult, Economy

KAYAK searches hundreds of travel sites at once for deals on flights to Jacksonville

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to Jacksonville, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to Jacksonville, as well as popular online travel agencies
Travelers love KAYAK
41,299,237 searches in the past 7 days on KAYAK

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Everything you should know

Cheapest round-trip
$286
Overall average: $339
Frontier
Thu 10/30Sun 11/2
MDW - JAX • 1 stop
Cheapest non-stop
$288
Typical prices: $328-$595
Southwest
Mon 11/10Sat 11/15
MDW - JAX • Non-stop
Our travelers' advice
AI-generated summary based on content written by travel experts
Midway's user-friendly experience simplifies navigation.
At JAX, car rentals are in the arrivals hall.
Expert advice
Expert advice
Expert advice
Expert advice
Top airlines
Frontier
Cheapest • from $286 (round-trip)
Southwest
Best reviews • 8.0 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
When to travel
August
Cheapest • 39% price drop
December
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
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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)

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Midway to Jacksonville that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Midway to Jacksonville

Thu, Oct 30 - Sun, Nov 2
Frontier Logo
6:20 am - 4:13 pmMDW-JAX
8h 53m1 stop
Frontier Logo
10:38 pm - 6:39 pmJAX-MDW
21h 01m2 stops
$286Frontier
Find Deal
Thu, Nov 20 - Mon, Nov 24
Delta Logo
6:00 am - 12:02 pmMDW-JAX
5h 02m1 stop
Delta Logo
5:00 am - 9:52 amJAX-MDW
5h 52m1 stop
$287Delta
Find Deal
Mon, Nov 10 - Sat, Nov 15
Southwest Logo
11:05 am - 2:20 pmMDW-JAX
2h 15mnonstop
Southwest Logo
5:35 am - 7:00 amJAX-MDW
2h 25mnonstop
$288Southwest
Find Deal
Thu, Nov 20 - Mon, Nov 24
Southwest Logo
9:20 am - 5:35 pmMDW-JAX
7h 15m1 stop
Southwest Logo
3:50 pm - 5:15 pmJAX-MDW
2h 25mnonstop
$290Southwest
Find Deal
Sat, Nov 8 - Sun, Nov 9
Multiple Airlines Logo
6:15 am - 10:38 amMDW-JAX
27h 23m2 stops
Multiple Airlines Logo
5:18 pm - 10:03 pmJAX-MDW
5h 45m1 stop
$293Multiple Airlines
Find Deal
Tue, Nov 11 - Wed, Nov 12
Southwest Logo
5:35 am - 12:25 pmMDW-JAX
5h 50m1 stop
Southwest Logo
11:10 am - 4:00 pmJAX-MDW
5h 50m1 stop
$297Southwest
Find Deal
Sat, Nov 8 - Mon, Nov 10
Southwest Logo
1:40 pm - 4:55 pmMDW-JAX
2h 15mnonstop
Southwest Logo
5:35 pm - 11:00 pmJAX-MDW
6h 25m1 stop
$298Southwest
Find Deal
Mon, Nov 10 - Sat, Nov 15
Frontier Logo
4:09 pm - 10:21 amMDW-JAX
17h 12m1 stop
Frontier Logo
10:38 pm - 7:30 amJAX-MDW
9h 52m1 stop
$299Frontier
Find Deal
Mon, Nov 10 - Wed, Nov 12
Southwest Logo
11:05 am - 2:20 pmMDW-JAX
2h 15mnonstop
Southwest Logo
7:00 am - 1:00 pmJAX-MDW
7h 00m2 stops
$303Southwest
Find Deal
Thu, Dec 11 - Tue, Dec 30
Multiple Airlines Logo
7:47 pm - 10:24 amMDW-JAX
13h 37m1 stop
Multiple Airlines Logo
8:01 pm - 9:56 amJAX-MDW
38h 55m2 stops
$307Multiple Airlines
Find Deal
Booking Insights

KAYAK's insights & trends for Midway to Jacksonville flights

Get data-powered insights and trends into flights from Midway to Jacksonville to help you find the cheapest flights, the best time to fly and much more.

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

The average price of all round-trip flights from Chicago Midway Airport to Jacksonville clicked on KAYAK for each day over the last 12 months.

Your flight ticket price will generally be cheaper if you fly to Jacksonville on a Thursday and more expensive on a Tuesday. On your return trip to Chicago Midway Airport, you should consider flying back on a Wednesday, and avoid Sundays for better deals.

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

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Chicago Midway Airport to Jacksonville, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.

The cheapest month for flights from Chicago Midway Airport to Jacksonville is August, where tickets cost $218 (return) on average. On the other hand, the most expensive months are March and December, where the average cost of round-trip tickets is $480 and $408 respectively.

Can I save money by flying with a layover from Chicago Midway Airport to Jacksonville?

The average round-trip price for all non-stop flights, flights with one layover, and flights with two layovers for the route found by users searching on KAYAK in the last 2 weeks.

No, with an average price for the route of $360, prices are generally cheapest when you fly direct.

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Expert advice

Expert advice for your flight from Midway to Jacksonville

 
Snippets provided in this section are AI-generated based on a summarization of KAYAK-commissioned articles. The articles are presented as-is, for general informational purposes only, and may not be up-to-date. The opinions contained in the articles are original to the author and reflect their authentic experience, which may vary significantly from the experience of others.
KAYAK teamed up with top travel experts to share the best tips for your journey.
Airports
MDW

Midway offers a user-friendly experience with a compact terminal, making it easy to navigate and explore dining options before your flight.

Read more about MDWby Stefanie Waldek
JAX

At JAX, car rentals are conveniently located in the arrivals hall, ideal for exploring Jacksonville and beyond.

Read more about JAXby Marisa Garcia
Our travel experts
Marisa Garcia

Marisa Garcia

Expert on JAX

Marisa Garcia

Marisa Garcia

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

Stefanie Waldek

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

Good to know

Low seasonAugust
Cheapest flight$88
Best time to beat the crowds with an average 40% drop in price.
Most popular time to fly with an average 13% increase in price.
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
KAYAK looks at all historical flight data for each date to provide a predicted price for one-way trips or round-trips with a duration up to 40 days. While we try to provide actual minimum prices for each date, some prices are predictions and actual prices may differ.

FAQs for booking Chicago Midway Airport to Jacksonville flights

  • What is the cheapest flight from Chicago Midway Airport to Jacksonville?

    In the last 3 days, the lowest price for a flight from Chicago Midway Airport to Jacksonville was $88 for a one-way ticket and $286 for a round-trip.

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

    No, a passport isn't needed to fly from Chicago Midway Airport to Jacksonville. However, local authorities might ask for an official ID.

  • Which airports will I be using when flying from Chicago Midway Airport to Jacksonville?

    Chicago Midway Airport airport is called Chicago Midway and the only airport in Jacksonville is Jacksonville.

  • Which airlines offer Wi-Fi service onboard planes from Chicago Midway Airport to Jacksonville?

    Only American Airlines offers inflight Wi-Fi service on the Chicago Midway Airport to Jacksonville flight route.

  • Which aircraft models fly most regularly from Chicago Midway Airport to Jacksonville?

    The Airbus A319 is the aircraft model that flies most regularly on the Chicago Midway Airport to Jacksonville flight route.

  • On which days can I fly direct from Chicago Midway Airport to Jacksonville?

    There are nonstop flights from Chicago Midway Airport to Jacksonville on a daily basis.

  • How does KAYAK find such low prices on flights from Chicago Midway Airport to Jacksonville?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Chicago Midway Airport to Jacksonville.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Chicago Midway Airport to Jacksonville?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Jacksonville from Chicago Midway Airport is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Chicago Midway Airport to Jacksonville?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Jacksonville with an airline and back to Chicago Midway Airport with another airline. Booking your flights between Chicago Midway Airport and JAX can sometimes prove cheaper using this method.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Chicago Midway Airport to Jacksonville?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Jacksonville from Chicago Midway Airport up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

KAYAK’s top tips for finding a cheap flight from Chicago Midway Airport to Jacksonville

  • Looking for a cheap flight? 25% of our users found flights on this route for $164 or less one-way and $288 or less round-trip.

Prefer to fly direct from Chicago Midway Airport to Jacksonville?

 
Direct data is based off flight results for the next 60 days. Find direct flights from all airlines flying direct from Chicago Midway 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

Reviews of the top airline flying from Midway to Jacksonville

 
See real verified KAYAK customer reviews for airlines flying from Chicago to Jacksonville. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with from Midway to Jacksonville? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
8.0
SouthwestOverall score based on 4241 reviews
8.6Crew
8.0Comfort
7.5Entertainment
7.0Food
8.1Boarding
Airline reviews

Better and more food and drinks. Put msnbc and free speech tv on the news channel selection list.

10.0 ExcellentKevin, Jul 2025MDW - PUJ
Read more Southwest reviews

Better and more food and drinks. Put msnbc and free speech tv on the news channel selection list.

The quality of Southwest Airlines continues to degrade each time I fly with them. If it were not for the free luggage, I would probably choose another airline. Their prices are a little bit competitive, but way too high for the quality of the service. Southwest is not unique in this way. Domestic flight in the United States of America has continued to be a lower and lower quality product. Very sad when you compare the quality of domestic airlines to that of many international airlines around the world.

after landing, we stay 2 hours on the taxi way before reaching the gate The airline and the crew were good though

I'm not a fan of Southwest's model. I don't like the herding style of boarding.

It is southwest seat was ok. Not the most comfortable seat

Plz don't take away free bags and free seating

My flight to Chicago left and landed early. My return flight left two minutes late and arrived 2 minutes late. My seat selections were ideal! There were no snacks going to Chicago and no snacks on the return trip. There are no charging outlets on board.

Excellent! Only question is how we check in at exactly 24 hours in advance and end up at the end of the B boarding group

It went well. Plane wasn't full. Will be great when assigned seating is in place

One of the crew performed a hilarious skit to accompany the standard instructions. Passengers enjoyed it so much they applauded at the end!

Everything you need to know for your flight from Midway to Jacksonville

Information on your arrival and departure airports

Chicago Midway Airport (MDW)
Jacksonville (JAX)

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