MDW - JAX

$99 Find Cheap Flights from Chicago Midway Airport to Jacksonville - Compare and Save

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 9/21. 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

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Everything you should know

Cheapest round-trip
$217
Typical prices: $203-$352
Delta
Sat 9/5Sat 9/12
MDW - JAX • 1 stop
Cheapest non-stop
$246
Typical prices: $213-$344
Southwest
Thu 8/20Thu 8/27
MDW - JAX • Non-stop
Top airlines
Cheapest • from $217 (round-trip)
Best reviews • 8.0 score
Airline reviews
Airline reviews
+1
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Airline reviews
Airline reviews
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Nonstop flights
You can fly direct with Southwest. Average duration is 2h 18m
Direct flights
Direct flights
+1
+1
Direct flights
Direct flights
+1
Top layover airports
Cheapest • Avg $285 (round-trip)
Shortest trip • 4h 15m (one-way)
Insights
Insights
Insights
Insights
When to travel
Cheapest • 37% price drop
Most popular
Good to know
Good to know
+1
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Good to know
Good to know
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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

Sat, Sep 5 - Sat, Sep 12
Delta Logo
4:39 pm - 11:55 pm
MDW
-
JAX
6h 16m
1 stop
Delta Logo
11:59 am - 4:57 pm
JAX
-
MDW
5h 58m
1 stop
$217Delta
Thu, Aug 13 - Sat, Aug 15
Southwest Logo
5:55 am - 1:20 pm
MDW
-
JAX
6h 25m
1 stop
Southwest Logo
6:15 am - 1:20 pm
JAX
-
MDW
8h 05m
2 stops
$222Southwest
Tue, Aug 18 - Sat, Aug 22
Frontier Logo
11:50 am - 6:10 pm
MDW
-
JAX
5h 20m
1 stop
Frontier Logo
7:05 pm - 10:55 am
JAX
-
MDW
16h 50m
1 stop
$223Frontier
Wed, Aug 12 - Sun, Aug 16
Frontier Logo
11:06 am - 5:34 pm
MDW
-
JAX
5h 28m
1 stop
Frontier Logo
6:29 pm - 9:51 am
JAX
-
MDW
16h 22m
1 stop
$225Frontier
Thu, Aug 13 - Mon, Aug 17
Southwest Logo
5:30 am - 3:15 pm
MDW
-
JAX
8h 45m
2 stops
Southwest Logo
4:30 pm - 11:20 pm
JAX
-
MDW
7h 50m
2 stops
$227Southwest
Tue, Aug 18 - Tue, Aug 25
Frontier Logo
11:50 am - 6:10 pm
MDW
-
JAX
5h 20m
1 stop
Frontier Logo
7:05 pm - 10:55 am
JAX
-
MDW
16h 50m
1 stop
$228Frontier
Fri, Aug 21 - Sun, Aug 23
Frontier Logo
11:50 am - 6:10 pm
MDW
-
JAX
5h 20m
1 stop
Frontier Logo
7:05 pm - 10:55 am
JAX
-
MDW
16h 50m
1 stop
$229Frontier
Tue, Aug 11 - Sun, Aug 16
Frontier Logo
11:06 am - 5:34 pm
MDW
-
JAX
5h 28m
1 stop
Frontier Logo
6:29 pm - 9:51 am
JAX
-
MDW
16h 22m
1 stop
$230Frontier
Fri, Sep 11 - Sun, Sep 13
Frontier Logo
12:03 pm - 5:51 pm
MDW
-
JAX
4h 48m
1 stop
Frontier Logo
6:46 pm - 10:58 am
JAX
-
MDW
17h 12m
1 stop
$231Frontier
Thu, Sep 10 - Sun, Sep 13
Frontier Logo
12:03 pm - 5:51 pm
MDW
-
JAX
4h 48m
1 stop
Frontier Logo
6:46 pm - 10:58 am
JAX
-
MDW
17h 12m
1 stop
$232Frontier
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.

How much is a round-trip flight from Chicago Midway Airport to Jacksonville?

This analysis is based on the cheapest round-trip price found on KAYAK in the last 12 months by searching for a flight from Chicago Midway Airport to Jacksonville departing in September.

Flight prices are below average for this route right now.

Flights to Jacksonville from Chicago Midway Airport usually cost between $288 and $420 in September.
The lowest price found in the past 5 days was $217 on Delta (Sep 5-Sep 12).

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 Wednesday and more expensive on a Sunday. On your return trip to Chicago Midway Airport, you should consider flying back on a Saturday, and avoid Mondays 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 July and June, where the average cost of round-trip tickets is $470 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 $406, prices are generally cheapest when you fly direct.

Expert advice

Expert advice for your flight from Midway to Jacksonville

 
AI-powered summary based on content written by travel experts. AI can make mistakes.
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.

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.

Good to know

Low season

January

Cheapest flight

$99
Best time to beat the crowds with an average 20% drop in price.
Most popular time to fly with an average 35% 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 5 days, the lowest price for a flight from Chicago Midway Airport to Jacksonville was $99 for a one-way ticket and $217 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?

    American Airlines, and JetBlue offer 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 Embraer 175 (Enhanced Winglets) 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 Frontier?

    The two airlines most popular with KAYAK users for flights from Chicago to Jacksonville are Southwest and Frontier. With an average price for the route of $369 and an overall rating of 8.0, Southwest is the most popular choice. Frontier is also a great choice for the route, with an average price of $272 and an overall rating of 5.6.

  • 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 $187 or less one-way and $406 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 4238 reviews
8.6Crew
8.1Boarding
7.0Food
8.0Comfort
7.5Entertainment
Airline reviews

Overall good, just screaming kids in the area the whole flight.

8.0 ExcellentAnonymous, Jul 2026
MDW - MHT
Read more Southwest reviews

Overall good, just screaming kids in the area the whole flight.

OKay. I sat in the back of the plane and it was really loud between babies and little kids, and adults who.like to talk a lot and loudly most of the flight.

The first time I flew in the extra legroom section. It was difficult to notice a difference. I had bad luck with my neighbors. The crew was okay. Southwest has reduced the live TV options.

I flew twice this week on Southwest, was delayed over 2 hours both ways. From Pittsburgh to Chicago it was due to weather but the gate agents, pilot etc were great at updating everyone. Today from Midway to Pittsburgh the plane had come from an international location, kept getting delayed, no information was given until we were delayed for the third time. It was ridiculous, whoever scheduled that plane to fly to Pittsburgh after didn’t consider a lot of things.

The staff was very friendly, professional, and courteous. The overall flight was a great experience.

All was good. I just had a hard time getting connected to the WiFi/internet during the flight

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.

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 experience. WiFi worked on this leg of My trip

Flight was canceled. Most upsetting was message from Kayak, stating that the flight was canceled and click with Kayak for details regarding rebook, refund details. THERE'S NO INFORMATION PROVIDED BY KAYAK EXCEPT THAT FLIGHT IS CANCELED. AND NOW THIS SURVEY TO FIND OUT HOW WAS THE FLIGHT !!!!!!!

Better than expected. Staff were friendly and nice on both flights.

Just know that everything, and I mean everything is “ala cart”. 60$ just to put something in the overhead bin. I will never fly Frontier again nor do I recommend them to anyone else.

Great for the price. No wifi or entertainment, but gate agents and crew were fantastic and we boarded quickly and left on time.

Our flight was canceled for no known reason. We weren’t told until we were checking in at 5:00 am. This was after our last flight with Frontier where we sat on the plane for three hours (not an exaggeration) before we took off because of a mechanical issue. We won’t be flying Frontier again.

I didn’t have enough time to catch my connecting flight and had to use a different Airline. I will be requesting a refund.

I brought a ticket and car rental through Travelocity. There was no where to add a KTN. So I thought i’d add it by looking up ticket on frontier website. I tried 3 times with the frontier chat bot to add my KTN it never updated my boarding pass. So then I tried showing up early to do it in person at the airport. The first employee update my ktn in the system and gave me a new boarding pass. I was sent back by tsa to join regular line. Then I was told to add my Ktn. It would cost me $25 extra. Given the length of the cue I did pay. Congratulations! BUT I will NEVER fly frontier again. Plus the plane was very old. It had actual ashtrays and old looking tray backs. Worst travel experience ever. Im warning my friends and family not to use frontier ever.

It was delayed 9 hours for operational reasons, despite the plane arriving to the airport on time.

Was just ok with over selling I guess. A lot of people in a short space and when we finally arrive i20 minutes, waiting to get out from the plain because we were waiting authorization for out boarding? Something like that.

They changed my flight and did not want to accommodate me or try to help me in any way. They do not care about their customers.

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

Information on your arrival and departure airports