MDW - JAX

$72 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 9/15. 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
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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

Sun, Oct 12 - Fri, Oct 17
Frontier Logo
8:25 am - 9:04 pmMDW-JAX
11h 39m1 stop
Frontier Logo
11:37 am - 11:20 pmJAX-MDW
12h 43m1 stop
$181Frontier
Find Deal
Thu, Sep 18 - Sun, Sep 21
Frontier Logo
6:20 am - 11:43 amMDW-JAX
4h 23m1 stop
Frontier Logo
12:38 pm - 3:58 pmJAX-MDW
4h 20m1 stop
$189Frontier
Find Deal
Fri, Sep 26 - Sun, Sep 28
Frontier Logo
8:15 am - 3:21 pmMDW-JAX
6h 06m1 stop
Frontier Logo
12:38 pm - 3:58 pmJAX-MDW
4h 20m1 stop
$192Frontier
Find Deal
Sun, Sep 7 - Sun, Sep 14
Frontier Logo
8:06 am - 2:39 pmMDW-JAX
5h 33m1 stop
Frontier Logo
12:38 pm - 3:58 pmJAX-MDW
4h 20m1 stop
$206Frontier
Find Deal
Wed, Sep 17 - Sun, Sep 21
 Logo
9:00 am - 11:43 amMDW-JAX
25h 43m1 stop
 Logo
5:27 pm - 7:00 pmJAX-MDW
26h 33m1 stop
Wed, Sep 24 - Wed, Oct 1
Southwest Logo
10:30 am - 1:45 pmMDW-JAX
2h 15mnonstop
Southwest Logo
1:20 pm - 7:15 pmJAX-MDW
6h 55m1 stop
$251Southwest
Find Deal
Wed, Sep 24 - Wed, Oct 1
Southwest Logo
10:30 am - 1:45 pmMDW-JAX
2h 15mnonstop
Southwest Logo
7:20 am - 1:25 pmJAX-MDW
7h 05m2 stops
$256Southwest
Find Deal
Wed, Sep 17 - Mon, Sep 22
 Logo
9:00 am - 11:43 amMDW-JAX
25h 43m1 stop
 Logo
8:35 am - 3:58 pmJAX-MDW
32h 23m2 stops
Tue, Dec 2 - Wed, Dec 10
Delta Logo
1:05 pm - 8:39 pmMDW-JAX
6h 34m1 stop
Delta Logo
7:30 am - 11:55 amJAX-MDW
5h 25m1 stop
$261Delta
Find Deal
Wed, Sep 17 - Sat, Sep 20
Delta Logo
6:00 am - 1:25 pmMDW-JAX
6h 25m1 stop
Delta Logo
9:45 am - 3:26 pmJAX-MDW
6h 41m1 stop
$278Delta
Find Deal
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
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 Monday and more expensive on a Sunday. 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 September, where tickets cost $259 (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 $440 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 $222, prices are generally cheapest when you fly direct.

Good to know

Low seasonJune
Cheapest flight$72
Best time to beat the crowds but there is an average 1% increase in price.
Most popular time to fly with an average 18% 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 $72 for a one-way ticket and $181 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 Boeing 737-800 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.

  • Which is the best airline for flights from Chicago to Jacksonville, Southwest or Delta?

    The two airlines most popular with KAYAK users for flights from Chicago to Jacksonville are Southwest and Delta. With an average price for the route of $394 and an overall rating of 8.0, Southwest is the most popular choice. Delta is also a great choice for the route, with an average price of $346 and an overall rating of 7.9.

  • 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 $89 or less one-way and $203 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 airlines 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 4242 reviews
8.1Boarding
8.0Comfort
8.6Crew
7.0Food
7.5Entertainment
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!

This route with Delta always has delays or is cancelled. Aircrafts seem smaller and older. I fly Delta quite a bit - haven’t had issues with the international flights. But this route has always been the troublesome one

Three seats in first class were broken and while they were able to still acommodate us it was looking very touch and go and they had others they could not acommodate

Mechanic delay in addition to a 2 hour change in takeoff time was frustrating.

Delayed due to thunderstorms and no in-flight service due to rough weather — both of which are out of Delta’s control. Flight was good overall.

The flight attendants in SLC were rude. I arrived 40 minutes early to gate. Ticket said I needed check in for seat assignments and tried check in and attendants said they weren’t doing it. And proceeded to never call me to give me a ticket so when time to board I received the very last seat. Please relay to employees to do their job better..,

Always good but we must do something about people in rows ahead of you that don't put their seats back up when they are suppose to. And It's rough to not be able to even lean over to get something out of my purse.

this crew didn't care much. bumping carts into seats more times than i care to remember

Everything was fine except the entertainment was not working for half of the flight.

Easy boarding with an extremely kind attendant. Seats were spacious and we had 3 seats for 2 people so we could stretch out. Comfortable air flow and very attentive and hospital attendants. Bathrooms and food were the only negative. Bathrooms were so small you could hardly get in and close the door. I don’t think an obese person would fit or a person with a movement disability. Food was the trending food for flights, nonexistent. We spent $40 getting sandwich and snack at airport for our 6 hour flught.

I am very bothered by the events today. I can't believe the flight attendants allowed someone to take my seat and made me move. It was embarrassing. I was in the right. The lady just didn't want move. I can't believe delta would allow this to stand and disrespect my rights as a passenger. The lady complained about her leg and that she couldn't move. Firstly somehow she was able to make it to row 24. Not sure how much her leg could have hurt. Secondly, I'm in plenty of pain myself. I just finished chemotherapy a several weeks ago. My body is constantly sore. Yet deltas flight attendants didn't appropriately protect my rights. In the end they found me a seat on the plane but I want to understand how delta can operate this way. They in essence allowed a bully to get their way.

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

Information on your arrival and departure airports

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