JAX - MDW

$80 Find Cheap Flights from Jacksonville to Chicago Midway Airport - 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 Jacksonville to Midway departing on 10/26. 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.
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Everything you should know

Cheapest round-trip
$202
Typical prices: $218-$388
Southwest
Wed 8/26Mon 8/31
JAX - MDW • 2 stops
Cheapest non-stop
$251
Typical prices: $291-$336
Southwest
Wed 10/14Sat 10/17
JAX - MDW • Non-stop
Top airlines
Cheapest • from $202 (round-trip)
Best reviews • 8.0 score
Airline reviews
Airline reviews
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Airline reviews
Airline reviews
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Nonstop flights
You can fly direct with Southwest. Average duration is 2h 23m
Direct flights
Direct flights
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Direct flights
Direct flights
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When to travel
Cheapest • 100% price drop
Most popular
Good to know
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Flight Deals

Cheap Flights from Jacksonville to Midway (JAX-MDW)

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

Wed, Aug 26 - Mon, Aug 31
Southwest Logo
6:45 am - 3:20 pm
JAX
-
MDW
9h 35m
2 stops
Southwest Logo
6:45 pm - 10:00 pm
MDW
-
JAX
2h 15mnonstop
$202Southwest
Wed, Sep 9 - Thu, Sep 10
Southwest Logo
6:45 am - 3:20 pm
JAX
-
MDW
9h 35m
2 stops
Southwest Logo
6:45 pm - 10:05 pm
MDW
-
JAX
2h 20mnonstop
$202Southwest
Wed, Aug 19 - Sat, Aug 22
Southwest Logo
6:45 am - 3:25 pm
JAX
-
MDW
9h 40m
2 stops
Southwest Logo
12:45 pm - 4:00 pm
MDW
-
JAX
2h 15mnonstop
$202Southwest
Tue, Sep 22 - Thu, Sep 24
Delta Logo
6:00 am - 9:49 am
JAX
-
MDW
4h 49m
1 stop
Delta Logo
9:29 am - 5:22 pm
MDW
-
JAX
6h 53m
1 stop
$207Delta
Wed, Sep 9 - Mon, Sep 14
Delta Logo
11:59 am - 4:57 pm
JAX
-
MDW
5h 58m
1 stop
Delta Logo
5:10 pm - 11:58 pm
MDW
-
JAX
5h 48m
1 stop
$207Delta
Wed, Aug 19 - Mon, Aug 24
Delta Logo
6:00 am - 9:59 am
JAX
-
MDW
4h 59m
1 stop
Delta Logo
5:10 pm - 11:55 pm
MDW
-
JAX
5h 45m
1 stop
$207Delta
Thu, Sep 10 - Mon, Sep 14
Frontier Logo
7:46 pm - 11:44 pm
JAX
-
MDW
4h 58m
1 stop
Frontier Logo
6:25 am - 7:01 pm
MDW
-
JAX
11h 36m
1 stop
$222Frontier
Fri, Aug 21 - Mon, Aug 24
Frontier Logo
7:05 pm - 10:50 am
JAX
-
MDW
16h 45m
1 stop
Frontier Logo
11:50 am - 6:10 pm
MDW
-
JAX
5h 20m
1 stop
$226Frontier
Sun, Oct 4 - Wed, Oct 7
Multiple Airlines Logo
9:43 pm - 12:06 pm
JAX
-
MDW
15h 23m
1 stop
Multiple Airlines Logo
6:25 am - 5:51 pm
MDW
-
JAX
10h 26m
1 stop
$266Multiple Airlines
Thu, Oct 22 - Sun, Oct 25
Multiple Airlines Logo
4:13 pm - 1:36 pm
JAX
-
MDW
22h 23m
1 stop
Multiple Airlines Logo
12:03 pm - 5:51 pm
MDW
-
JAX
4h 48m
1 stop
$267Multiple Airlines
Booking Insights

KAYAK's insights & trends for Jacksonville to Midway flights

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

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

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

Flight prices are below average for this route right now.

Flights to Chicago Midway Airport from Jacksonville usually cost between $218 and $388 in August.
The lowest price found in the past 5 days was $202 on Southwest (Aug 19-Aug 22).

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

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

If your flying dates are flexible, you should consider flying to Chicago Midway Airport on a Saturday, as we generally find the cheapest rates on that day for this route. On the other hand, Monday is the most expensive day to fly from Jacksonville to Chicago Midway Airport. For your return ticket, we recommend flying on a Tuesday and avoiding Thursdays for the best deals.

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

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Jacksonville to Chicago Midway Airport, 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 Jacksonville to Chicago Midway Airport is February, where tickets cost $0 (return) on average. On the other hand, the most expensive months are November and December, where the average cost of round-trip tickets is $499 and $402 respectively.

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

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 $356, prices are generally cheapest when you fly direct.

Expert advice

Expert advice for your flight from Jacksonville to Midway

 
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

Cheapest flight

$80
Most popular time to fly with an average 13% increase in price.
Flight from Jacksonville to Chicago Midway Airport

When to book flights from Jacksonville to Midway

Are your dates flexible? Find out the best times to travel from Jacksonville to Midway 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 Jacksonville to Chicago Midway Airport flights

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

    In the last 5 days, the lowest price for a flight from Jacksonville to Chicago Midway Airport was $80 for a one-way ticket and $202 for a round-trip.

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

    Even though you are not required to have a passport, keep in mind that an official ID is needed to board the airplane.

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

    On your way to Chicago Midway Airport, you’ll fly out from Jacksonville. You’ll be landing at Chicago Midway.

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

    American Airlines, JetBlue, and Delta offer inflight Wi-Fi service on the Jacksonville to Chicago Midway Airport flight route.

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

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

  • Which airline alliances offer flights from Jacksonville to Chicago Midway Airport?

    SkyTeam is the only airline alliance operating flights between Jacksonville and Chicago Midway Airport.

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

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

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

    The two airlines most popular with KAYAK users for flights from Jacksonville to Chicago are Southwest and Delta. With an average price for the route of $357 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 $321 and an overall rating of 7.8.

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

    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 Jacksonville to Chicago Midway Airport.

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Chicago Midway Airport from Jacksonville 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 Jacksonville to Chicago Midway Airport?

    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 Chicago Midway Airport with an airline and back to Jacksonville with another airline. Booking your flights between Jacksonville and MDW 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 Jacksonville to Chicago Midway Airport?

    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 Chicago Midway Airport from Jacksonville 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 Jacksonville to Chicago Midway Airport

  • Looking for a cheap flight? 25% of our users found flights on this route for $202 or less one-way and $317 or less round-trip.

Prefer to fly direct from Jacksonville to Chicago Midway Airport?

 
Direct data is based off flight results for the next 60 days. Find direct flights from all airlines flying direct from Jacksonville to Chicago Midway.
Find which airlines fly direct from Jacksonville Airport to Chicago Midway Airport, which days they fly and book direct flights.

Direct departures

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

Direct returns

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

Reviews of the top 3 airlines serving from Jacksonville to Midway

 
See real verified KAYAK customer reviews for airlines flying from Jacksonville to Chicago. 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 Jacksonville to Midway? 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 4227 reviews
8.1Boarding
7.0Food
8.0Comfort
8.6Crew
7.5Entertainment
Airline reviews

Flight was delayed over 3 hours. Planes were dirty. Staff indifferent. And they serve vegan pretzels as snacks.

2.0 MediocreMatthew, Jun 2026
CVG - MDW
Read more Southwest reviews

Flight was delayed over 3 hours. Planes were dirty. Staff indifferent. And they serve vegan pretzels as snacks.

The flight was smooth. The Southwest experience has degraded overall, but this one was okay.

The checking experience in Orlando was terrible, almost missed the flight. Too many travelers and Southwest completely understaffed.

Everything was on time. I was disappointed by the front section female, African American flight attendant. I did not see her name tag or would have identified by name not race. As passengers moved to the bathroom early in flight, she would say with a disdainful tone “I have to say the seat belt light is on” then go back to her book. Better trained flight attendants say something like be careful the seat belt light is on.

Flight was awfully bumpy and landing was a bit jolting. I was in the restroom when snacks and drinks were served and was not asked if i wanted any. I had to ask for water finally.

The flight was great. We were not offered any beverages though. And there was no real turbulence, so not sure why.

Not good.,At first delayed due to weather, then still had to load all the luggage, then a mechanical issue. Upon finally arriving, clothes wet as suitcases sat out in the rain. In a hard side suitcase! Ruined some paper items inside. Not happy!

The flight itself was good. We were delayed 1 1/2 hours which was not good.

Flight was fine but new boarding policy was a drag Xtra time passenger group And Waiting until entire bridge empties before calling a list preferred... Waste of time

Wish that they would space out the boarding a little. COVID is still around and is real. No entertainment. Miss the peanuts.

It was as good as it could be. Flying is not a pleasant experience these days.

Aside from a completely packed plane, I really have no complaints.

The flight was very good and the staff was very friendly and helpful!

We landed and sat on the tarmac for 45 minutes because they only have one gate at the airport and there was another plane running late so we had to wait

Got on the plane and sat there for an hour before departure.

The food is terrible. The staff is wonderful. Comfort is good.

Cramped seating for me. Luckily it wasn’t a long flight

Excellent check-in. Crew was good. Excellent communication from flight deck.

Amazing flight! I have never noticed the uniforms of the attendants before in twenty years of flying except today when one female had the most amazing dress on. It was beautifully designed and showed she was in charge. I never dreamed I would google who designed Delta uniforms . The ultimate compliment is when another woman admires your outfit. . I hope your designer puts it on the market

Flight was on time, the staff was personable & professional, & the plane arrived on time.

This company socks. It's fraud. They canceled our flight yesterday, and today we were late because of a really long line at the check in bag. At the rebook station, there was ton of people. The workers were all rude. I am gonna make a report to FTC.

The single worst check in experience I could imagine. I’ll never do any business with Frontier or any affiliated company

Severe turbulence. Captain never came on to reassure passengers after things settled down.

The crew was delayed because they came on another flight that was delayed due to weather 10pm flight left at 1.30 am The airline made no effort to align alternate crew

The flight itself was ok and the pilot was very communicative. However, our flight was delayed for almost 3 hours, the gate was changed 3 times and there was no communication as we were waiting. The flight staff was overall a little crabby...I understand as they probably had a long day but we all did.

After waiting several minutes to be acknowledged by 3 employees on their phones, was told we had missed our flight because the doors were closed at that literal moment. Had they given any actual service or help while we were standing there we would have been on with time to spare. More than 10 people were turned away in this fashion claiming there was no way they could let us on the plane, even though it was still sitting connected to the terminal. After the desk agents let us know they didn't care about the situation we were forced to pay more than twice the price of our original tickets as no credits were given for the price of the "missed" flight. And the icing on the cake was after being treated poorly, fleeced for another few hundred dollars for new tickets? We waited on the next plane for 25 minutes passed the "doors closed" time, letting almost an extra dozen passengers on board. You're company has lazy, disinterested employees and your lack of any real help will ensure this was the first and last time we fly Frontier. Awful.

terrible cascading delays and unhelpful customer service. uncomfortable plane. crew was great, however!

The trip was unremarkable which is good. Crew was very professional and courteous.

I was singled out for being a Latina flying solo and the attendants took me out of line to put my luggage in the personal item bin to see if it would fly. Keep In mind I had just flown with the same luggage with no problem not even 5 days ago. The tag was sticking out a bit and the attendant was belligerent about charging me $100. I could not refuse because I didn’t wanna cause a scene. But today I felt targeted and embarrassed. I went online and found out that this happens a lot with this airline and to many minority women.

Nothing I missed my first flight because my boarding pass said one thing and another passenger on the same flight said another. I didn’t get notified of a gate change until 8:39 pm which was one minute before the flight departed at 8:40pm when we explained this to gate agent Dorsey prior to the flight departing she was extremely short and had nasty attitude. Some of the passengers in my party including myself needed to catch that flight due work the next which included presentations and court litigation. We were deeply saddened and frustrated how Frontier handled this situation. We were told that the flight was over booked by 19 seats and they constantly change gates to make people miss their flight. If that is true I will ensure there will be a class action lawsuit against frontier airlines.

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

Information on your arrival and departure airports