MSN - OAJ

$355 Find Cheap Flights from Madison to Jacksonville

This is the cheapest round-trip flight price found by a KAYAK user in the last 72 hours by searching for a flight from Madison to Jacksonville departing on 5/26. 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, 0 bags

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 Madison 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 Madison to Jacksonville, as well as popular online travel agencies
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Everything you should know

Cheapest round-trip
$355
Delta
Tue 5/26Sat 5/30
MSN - OAJ • 2 stops
Cheapest one-way
$388
Delta
Wed 5/6
MSN - OAJ • 1 stop
Top airlines
Delta
Cheapest • from $355 (round-trip)
American Airlines
Best reviews • 7.1 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
Nonstop flights
Not available
There are currently no direct flights between Madison and Jacksonville. You'll need at least 1 connection.
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Flight Deals
Booking Insights
Flight Deals

Cheap Flights from Madison to Jacksonville (MSN-OAJ)

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Madison 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 Madison to Jacksonville

Tue, May 26 - Sat, May 30
Delta Logo
7:00 am - 3:27 pm
MSN
-
OAJ
7h 27m
2 stops
Delta Logo
11:46 am - 9:27 pm
OAJ
-
MSN
10h 41m
2 stops
$355Delta
Tue, May 26 - Sat, May 30
American Airlines Logo
7:00 am - 12:49 pm
MSN
-
OAJ
4h 49m
1 stop
American Airlines Logo
6:41 am - 1:33 pm
OAJ
-
MSN
7h 52m
2 stops
$384American Airlines
Tue, May 26 - Sat, May 30
American Airlines Logo
7:00 am - 12:49 pm
MSN
-
OAJ
4h 49m
1 stop
American Airlines Logo
6:11 pm - 12:09 am
OAJ
-
MSN
6h 58m
1 stop
$433American Airlines
Fri, Jun 26 - Mon, Jun 29
American Airlines Logo
5:00 am - 2:35 pm
MSN
-
OAJ
8h 35m
2 stops
American Airlines Logo
6:11 pm - 11:59 pm
OAJ
-
MSN
6h 48m
1 stop
$448American Airlines
Fri, Jun 26 - Mon, Jun 29
American Airlines Logo
5:00 am - 2:35 pm
MSN
-
OAJ
8h 35m
2 stops
American Airlines Logo
5:00 am - 12:03 pm
OAJ
-
MSN
8h 03m
2 stops
$453American Airlines
Fri, Jun 26 - Mon, Jun 29
American Airlines Logo
5:00 am - 2:35 pm
MSN
-
OAJ
8h 35m
2 stops
American Airlines Logo
6:11 pm - 11:59 pm
OAJ
-
MSN
6h 48m
1 stop
$465American Airlines
Fri, Jun 26 - Mon, Jun 29
American Airlines Logo
5:00 am - 2:35 pm
MSN
-
OAJ
8h 35m
2 stops
American Airlines Logo
5:00 am - 12:03 pm
OAJ
-
MSN
8h 03m
2 stops
$471American Airlines
Fri, Jun 26 - Mon, Jun 29
American Airlines Logo
5:00 am - 2:35 pm
MSN
-
OAJ
8h 35m
2 stops
American Airlines Logo
5:00 am - 12:03 pm
OAJ
-
MSN
8h 03m
2 stops
$487American Airlines
Mon, Jun 1 - Fri, Jun 5
Delta Logo
11:04 am - 6:05 pm
MSN
-
OAJ
6h 01m
1 stop
Delta Logo
6:47 pm - 10:44 pm
OAJ
-
MSN
4h 57m
1 stop
$525Delta
Fri, Jun 26 - Mon, Jun 29
American Airlines Logo
7:00 am - 2:35 pm
MSN
-
OAJ
6h 35m
1 stop
American Airlines Logo
6:11 pm - 11:59 pm
OAJ
-
MSN
6h 48m
1 stop
$540American Airlines
Booking Insights

KAYAK's insights & trends for Madison to Jacksonville flights

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

Which airlines provide the cheapest flights from Madison to Jacksonville?

The cheapest round-trip price for the route for each airline clicked by KAYAK users in the last 72 hours.

In the past 3 days, the cheapest round-trip tickets from Madison to Jacksonville were found on Delta ($355) and American Airlines ($384).

Find deals

Good to know

Cheapest flight$355
Flight from Madison to Jacksonville

When to book flights from Madison to Jacksonville

Are your dates flexible? Find out the best times to travel from Madison 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 flights from Madison to Jacksonville

  • What is the cheapest flight from Madison to Jacksonville?

    In the last 3 days, the lowest price for a flight from Madison to Jacksonville was $388 for a one-way ticket and $355 for a round-trip.

  • Do I need a passport to fly between Madison and Jacksonville?

    A passport is not required to fly from Madison to Jacksonville.

  • Which aircraft models fly most regularly from Madison to Jacksonville?

    We unfortunately don’t have that data for this specific route.

  • Which airline alliances offer flights from Madison to Jacksonville?

    oneworld is the only airline alliance operating flights between Madison and Jacksonville.

  • How does KAYAK find such low prices on flights from Madison 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 Madison to Jacksonville.

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Jacksonville from Madison 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 Madison 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 Madison with another airline. Booking your flights between Madison and OAJ 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 Madison 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 Madison up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

Reviews of the top airline flying from Madison to Jacksonville

 
See real verified KAYAK customer reviews for airlines flying from Madison 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 Madison 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.
7.1
American AirlinesOverall score based on 11681 reviews
7.5Boarding
6.4Food
6.9Entertainment
7.2Comfort
7.9Crew
Airline reviews

Had to wait for a gate for a long time, then waited on the run way for a long time before leaving. The actual flights part was good.

6.0 GoodSarah, Apr 2026
ILM - CLT
Read more American Airlines reviews

Had to wait for a gate for a long time, then waited on the run way for a long time before leaving. The actual flights part was good.

The staff was nice. I appreciated that I was able to take an earlier flight, even though it was last minute. The boarding process felt rather chaotic.

Overall a good experience, however Wifi was not working on the flight.

Delayed flight. Missed connection, AA put us on a later connecting flight. The connection flight was delayed 4 times and we had to deplane. Didnt get home until 3am, when I was supposed to be home at 8:30p. Zero compensation offered from American. I would not fly them again.

No gate in Rome. Had stairs. Got separated from my wife in a wheel chair. Customs was a zoo. If AA doesnt have landing rights, it should be advertised.

The captain announced to the cabin there would be a delay because they observed a "cut" on a tire during precheck that needed to be cleared by maintenance. We were delayed during this inspection and allowed to proceed after maintenance "measured the cut and decided it was acceptable". My complaint is not about the delay or due diligence. I wish the captain had been more generic when making his announcement. I was a nervous wreck all the way to Charlotte worried that we would have a blowout when landing!

Flight was delayed and they gave up my seat on my connection, even when I could still make the flight

Flight was delayed. No urgency by American Airlines team to assist those with connecting flights. It was basically you are on your own to run through the terminals to try and make your connection. Thanks, Mary

I have never been assaulted they way I was today in Charlotte - shame on American

One of our group members was struggling to walk. In Charlotte we asked for a wheelchair and she was accompanied by Desmond. I was impressed by his patience and attention. In Boston she received the same service. I didn’t get the name of the helper but she went above and beyond in assisting us. A great AA service

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

Information on your arrival and departure airports

Madison (MSN)
Jacksonville (OAJ)