MDW - JAX

$115 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 6/2. 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

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

Save 22% or moreCompare multiple travel sites with one search.

Track pricesNot ready to book? Create a price alert for when prices drop.

Bundle and saveSave money when you bundle your flight + hotel.

Filter your dealsChoose cabin class, free Wi-Fi and more.

Flights Deals
Useful Info
Flights Deals

Cheap Flight Deals 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.

Recent round-trip flight deals from Midway to Jacksonville

KAYAK's recommended round-trip deals from the most popular airlines that fly from Midway to Jacksonville.
Discover the best prices for you by selecting your travel dates on KAYAK.
Frontier Logo
7:40 am - 6:18 pmMDW-JAX
9h 38m1 stop
Frontier Logo
11:55 am - 7:52 pmJAX-MDW
8h 57m1 stop
$218Frontier
Find Deal
Mon, Jun 2 - Mon, Jun 9
Frontier Logo
7:40 am - 6:18 pmMDW-JAX
9h 38m1 stop
Frontier Logo
11:55 am - 7:52 pmJAX-MDW
8h 57m1 stop
$220Frontier
Find Deal
Mon, Jun 2 - Mon, Jun 9
Frontier Logo
7:40 am - 6:18 pmMDW-JAX
9h 38m1 stop
Frontier Logo
11:55 am - 7:52 pmJAX-MDW
8h 57m1 stop
$238Frontier
Find Deal
Fri, Jun 6 - Mon, Jun 9
Frontier Logo
7:45 am - 6:06 pmMDW-JAX
9h 21m1 stop
Frontier Logo
11:55 am - 7:52 pmJAX-MDW
8h 57m1 stop
$241Frontier
Find Deal
Fri, May 30 - Mon, Jun 2
Delta Logo
4:15 pm - 10:06 pmMDW-JAX
4h 51m1 stop
Delta Logo
5:37 pm - 9:13 pmJAX-MDW
4h 36m1 stop
$297Delta
Find Deal
Sat, May 24 - Sat, May 31
Southwest Logo
6:20 pm - 9:35 pmMDW-JAX
2h 15mnonstop
Southwest Logo
5:45 pm - 7:20 pmJAX-MDW
2h 35mnonstop
$300Southwest
Find Deal
Wed, May 28 - Mon, Jun 2
Delta Logo
6:00 am - 1:30 pmMDW-JAX
6h 30m1 stop
Delta Logo
5:35 pm - 9:41 pmJAX-MDW
5h 06m1 stop
$302Delta
Find Deal
Thu, Jul 3 - Tue, Jul 8
Southwest Logo
2:40 pm - 10:05 pmMDW-JAX
6h 25m1 stop
Southwest Logo
5:45 pm - 7:20 pmJAX-MDW
2h 35mnonstop
$310Southwest
Find Deal
Wed, May 28 - Mon, Jun 2
Southwest Logo
6:20 pm - 9:35 pmMDW-JAX
2h 15mnonstop
Southwest Logo
3:05 pm - 4:35 pmJAX-MDW
2h 30mnonstop
$312Southwest
Find Deal
Tue, May 20 - Sun, May 25
Allegiant Air Logo
10:48 am - 10:47 amMDW-JAX
22h 59m2 stops
Allegiant Air Logo
10:49 am - 8:52 amJAX-MDW
23h 03m2 stops
$406Allegiant Air
Find Deal
Sun, May 11 - Thu, May 15
Useful Info

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 August and March, where the average cost of round-trip tickets is $513 and $480 respectively.

Good to know

Low seasonJune
High seasonDecember
Cheapest flight$115
Best time to beat the crowds with an average 5% drop in price.
Most popular time to fly with an average 15% 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 $115 for a one-way ticket and $218 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 $401 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 $375 and an overall rating of 8.0.

  • 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 $161 or less one-way and $337 or less round-trip.

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
See more direct flights

Top 3 airlines serving 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 4294 reviews
8.0Comfort
7.1Food
8.6Crew
7.6Entertainment
8.2Boarding
Airline reviews

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

8.0 ExcellentJohn, Apr 2025PVD - FLL
Read more Southwest reviews

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!

Excellent experience. WiFi worked on this leg of My trip

Flight was great, but golf bag never made it until later in the day. Even though I had a nonstop flight it was placed on a different one. They made it right with flight credits and I was able to get it the same day.

Pretty standard flight. We left late, but arrived early. The wifi entertainment is always nice. The free snacks and beverages are simple, but appreciated. I'm tall and the seats are an issue. I can deal with a short flight, but any longer, I have to find another airline where I know beforehand I have extra legroom.

The flight attendant was proactive in helping with placing carry on in overhead bins. This was the first time I had ever been offered help without asking or obviously struggling. Many on the flight were older people like myself and vertically challenged. I would hope this would be the norm on all flights.

Delta is my preferred airline. I've traveled with them for years. On time in most cases, good communication, easy to use app. Most planes are pretty nice. I was on a CRJ 700/900 however, which was pretty badly aged inside and needed a refresh. No infotainment, unreliable wifi, best to download before boarding or bring a book. Food choices are really just snacks on this flight, nice variety but about what you'd expect. Great staff and prompt in departure and early arrival too. Overall quite satisfied.

Crew was friendly Love the entertainment in the seat head rest.

Delta flight was on time, seats were comfortable, and crew was nice.

Other then mechanical/ computer problem and 3.5 hours flight delay the flight was great. I guess that what happened when you fly an old airplane now a day.

This was a code share Latam Airlines flight - everything very good except there was no seatback entertainment

Don't waste your money or points on first class. Delta first class is a joke. The seats were rickety, the food was awful, and nothing worked, wifi, my light, the power plug - and it was dirty - the fold out table was gross. For 2-3 hours, tough it out in Economy.

Loyal Delta traveler, but last nights flight was a train wreck. Seated in 1B after multiple delays. Then we couldn’t takeoff because of an issue with the passenger that was ‘not in compliance’ and had to deplane along with the threat if they did not deplane, all the passengers would be required to do so. Finally they were escorted off, but the experience threw off the crew. Disruptive for everyone. Service was a mess, televisions didn’t work, bathroom door kept swinging open during the entire flight whenever empty …

My flight was cancelled twice and the third time I tried to rebook it online I cancelled the flight because it looked like I would get a refund to my credit card. Instead I now have a credit. I was also on hold for three hours waiting for a representative and then disconnected. I will never fly delta again.

It was very cold because the air conditioner was on high power, and my son got sick.

Awful. Flight was continuously getting delayed and gates kept changing without any reason. Flight was delayed for more then 3 hours

Not very good. Paid in excess of $400 for assigned seating for my family and that was not provided. I want that money back.

I chose the seats when booked the flight and paid for them. However after checking in I found we were assigned different seats!

It was a no frills flight. Would have liked to be able to charge my device

Seats were extremely uncomfortable and it was very hot on the plane.

Since they are a budget airline, I wasn’t expecting too much but they did some things well. They were on time, the plane was clean, boarding was fairly straightforward and the staff was cheerful and friendly. The only downside was comfort. The seats were fairly hard and after a 2 hour flight your rear end is not feeling so great. Maybe a little more cushion in the seats, Frontier!

Check in at Philadelphia international was absolutely terrible! I fly 2 to 3 times a month and avoid frontier at all cost and will never fly Frontier again! The night before travel, I tried checking in however, the app was giving me an error, so I went to the desktop, which instructed you that you need to use the app. The next day I presented at the check-in gate after trying at least a half dozen times prior to getting into the airport and continuing to getting the error in the app. I actually had rebooted my phone numerous times and reinstall the app just in case. My phone is only one generation older than the current model. It has no problems completing a frontier flight purchase or any other app issues. There was only three frontier employees working at check-in and a huge line while I was in line I continued to try and check in via the app. As I approach the desk, I was dreading dealing with the agent. He was extremely unprofessional, anti-semantic & very ignorant, and mean to the people in front of me, as well as the people who ended up being behind me. He literally told people “Man I don’t care bout y’all” in his native dialect! Maintaining my composure I approached and explained the situation. To which he replied, you’re gonna have to pay then! I don’t understand. It’s an issue with their app not allowing me to check in! Not my issue! He told me if I pay cash it would be $15, $25 if I pay credit card. I don’t understand a $10 difference for paying with a credit card? I am completely cashless so I continued to try using the app to avoid the $25 fee, Which I still don’t believe that I should be responsible for since it was Frontier’s technical issue!!! I continued to check in via the app a couple more times after he verified I was doing everything right he proceeded to continue to belittle the people behind me. Yelling at them saying I don’t care about you people! I cannot believe that this is the way that businesses would treat its customers! Unfortunately, the black mail with dreadlocks did not have a name tag all he had was a frontier sweater on! For the $25 fee that I ended up getting charged on my credit card. I should’ve just booked originally with Spirit or any other carrier! I have no problem paying fees that I should be responsible for, but when it’s due to a technical failure of a company, the customer should not be responsible for it! I cannot believe that it’s not frontier going out of business!

they delayed my flight which ended up, causing my layover flight to leave without me, resulting in me missing a flight and having to stay overnight in Houston international. I got no compensation other than a flight to my original location only a day later. i’ve never experienced such a unprofessional situation

Our flight was suppose to leave at 9pm and we didn’t board until after 3am. We lost a whole day at our hotel and half a day at a park we paid a lot of money for.

Boarding was organized and flight was on time. Overall very satisfied with my flight.

The boarding gate was in Terminal D, but the Frontier counter was in Terminal E. So I had to move back and forth between terminals to check in my luggage. This was the worst experience that I had in terms of flights.

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

Information on your arrival and departure airports

Not what you’re looking for? Find thousands of other hotels, flights, car rentals and package deals with KAYAK.