JAX - MDW

$125 Find Cheap Flights from Jacksonville to Chicago Midway Airport

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 6/1. 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 Chicago Midway Airport

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Jacksonville to Chicago, 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 Jacksonville to Chicago, as well as popular online travel agencies
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Everything you should know

Cheapest round-trip
$242
Typical prices: $386-$327
Southwest
Sat 5/23Tue 6/2
JAX - MDW • Non-stop
Cheapest non-stop
$242
Typical prices: $397-$347
Southwest
Sat 6/6Tue 6/9
JAX - MDW • Non-stop
Advice from real travelers
AI-powered summary based on content written by travel experts. AI can make mistakes.
JAX provides free unlimited Wi-Fi for all travelers.
The CTA Orange Line from MDW reaches downtown in 25-30 mins.
Expert advice
Expert advice
Expert advice
Expert advice
Top airlines
Cheapest • from $242 (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 30m
Direct flights
Direct flights
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Direct flights
Direct flights
+1
When to travel
Cheapest • 100% price drop
Most popular
Good to know
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We hope you love your trip to Midway!
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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

Sat, May 23 - Tue, Jun 2
Southwest Logo
3:05 pm - 4:35 pm
JAX
-
MDW
2h 30mnonstop
Southwest Logo
6:00 pm - 9:15 pm
MDW
-
JAX
2h 15mnonstop
$242Southwest
Fri, Jun 19 - Sun, Jun 21
Frontier Logo
6:28 pm - 11:04 am
JAX
-
MDW
17h 36m
1 stop
Frontier Logo
6:00 am - 5:33 pm
MDW
-
JAX
10h 33m
1 stop
$244Frontier
Fri, Jun 19 - Sun, Jun 21
Frontier Logo
6:28 pm - 11:04 am
JAX
-
MDW
17h 36m
1 stop
Frontier Logo
6:00 am - 5:33 pm
MDW
-
JAX
10h 33m
1 stop
$245Frontier
Fri, Jun 5 - Sun, Jun 7
Frontier Logo
6:30 pm - 10:02 pm
JAX
-
MDW
4h 32m
1 stop
Frontier Logo
6:00 am - 5:35 pm
MDW
-
JAX
10h 35m
1 stop
$246Frontier
Wed, May 27 - Wed, May 27
Southwest Logo
7:20 am - 8:50 am
JAX
-
MDW
2h 30mnonstop
Southwest Logo
10:25 am - 6:35 pm
MDW
-
JAX
7h 10m
1 stop
$247Southwest
Wed, Jun 3 - Sat, Jun 6
Southwest Logo
1:50 pm - 8:20 pm
JAX
-
MDW
7h 30m
1 stop
Southwest Logo
7:50 am - 11:15 am
MDW
-
JAX
2h 25mnonstop
$248Southwest
Fri, Jun 19 - Mon, Jun 22
Frontier Logo
6:28 pm - 10:11 pm
JAX
-
MDW
4h 43m
1 stop
Frontier Logo
6:00 am - 5:33 pm
MDW
-
JAX
10h 33m
1 stop
$250Frontier
Mon, Jun 8 - Wed, Jun 10
Southwest Logo
7:45 am - 9:05 am
JAX
-
MDW
2h 20mnonstop
Southwest Logo
3:10 pm - 9:05 pm
MDW
-
JAX
4h 55m
1 stop
$252Southwest
Fri, Jun 12 - Tue, Jun 16
Frontier Logo
6:28 pm - 11:04 am
JAX
-
MDW
17h 36m
1 stop
Frontier Logo
12:27 pm - 3:04 pm
MDW
-
JAX
25h 37m
2 stops
$254Frontier
Fri, Jun 12 - Tue, Jun 16
Frontier Logo
6:28 pm - 11:04 am
JAX
-
MDW
17h 36m
1 stop
Frontier Logo
12:27 pm - 3:04 pm
MDW
-
JAX
25h 37m
2 stops
$255Frontier
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 May.

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 Wednesday, 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 Wednesday and avoiding Sundays 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 July, where the average cost of round-trip tickets is $413 and $407 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.

Yes, flying with a layover may cost you more time, but you can also save money on the route, with a 1 stop layover the cheapest option at $341 on average.

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

Low seasonAugust
Cheapest flight$125
Best time to beat the crowds with an average 34% drop in price.
Most popular time to fly with an average 2% 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 3 days, the lowest price for a flight from Jacksonville to Chicago Midway Airport was $125 for a one-way ticket and $242 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 Boeing 737-800 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 $346 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 7.9.

  • 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 $175 or less one-way and $395 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 4314 reviews
8.1Boarding
7.0Food
8.6Crew
8.0Comfort
7.5Entertainment
Airline reviews

no service at all due to turbulence. they should've at least given us snacks, there were only 10 people on the entire flight.

4.0 OkayCrystal, Apr 2026
MSY - MDW
Read more Southwest reviews

no service at all due to turbulence. they should've at least given us snacks, there were only 10 people on the entire flight.

For the first time in a long time, the Wi-Fi actually worked the entire flight! The flight crew was amazing as usual.

Great flight. I didn't get a drink because I was asleep whole on the flight.

Communication about the delayed flight was poor. We were told to move gates three times but that was bad information. We went from gate 128 to gate 126 and then to gate 123 and back to gate 126. Communication about the delay was bad. Ended up being 1 1/2 hour late getting home.

Love them will get a Southwest card to track my points and keep flying with them. My family and I were pleased with the services.

Southwest continues to do less for more money. Flight attendants used to be fun and friendly. But now it’s like they don’t even see you. Such a shame.

I liked it better when you were truer to your roots Am paying more for less fun

I was supposed to be on a later flight. When I showed up at the gate, the woman working there was extremely helpful getting moved up to this earlier flight.

Long layover between flights to Long Island from BWI - need better coordination between flights

I realize they are still working out kinks with the new boarding process, but by the time I boarded in group 5, most of the bins were full. All airlines should better enforce small bags and jackets going under the seats until everyone has boarded.

Flight was delayed it was hot while sitting on the plane, one engine was working on the plane until they had to do some jimmy rigging down the runway in order for the other engine to charge up. It was ridiculous

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

Landed without a gate ready. Plane is extremely old and dirty.

All the amenities was wonderful, if they could keep their prices that low. I'd fly with them all the time.

The WiFi was horrific. I fly delta often and love their (usually reliable and free) WiFi. On this flight it was intermittent and when it did connect was extremely slow. I couldn’t get any work done while I was on the flight which was extremely frustrating. I was also in the exit row seat where there is now immediate seat in front of you, so while the leg room was nice, I couldn’t even watch the TV when the internet wasn’t working. Finally, for the last 20 mins of the flight, the announcement indicator came on the TV screens and took them over, even though no announcement was being made. Really disappointed.

Crew was great. Near on time departure and early arrival. Snacks are always meh. Not a fan of the "pay for everything including miles " proposal unless base flight rate going to be 100 bucks.

On the return flight, flight attendant Britt went out of her way to inform passengers that several of us had tight connections.

Too many people are taking up space in the overhead bins with their extra piece of luggage. Since they cannot fit their backpacks or extra luggage piece under the seat in front of them, they store it in the overheads and thus taking up room for other passengers. It wasn’t only one or two persons; more like 12 or 13 passengers.

Kayak botched up the booking, i had to call delta and fix. In the process Delta failed to honor my comfort plus seat assignment that i had previously.

Perhaps when you’re sitting in 1st class and the crew closes the bathroom for the pilots, there could be a notification other than holding your hands up as a blockade when you get there and you’re told the restrooms are closed please turn around … especially at night when visibility is poor and you’re met by a flight attendants with their arms up

The bag check, flight check-in, and onboard experience convinced my wife and me that we will actively go out of our way to avoid flying Frontier Airlines in the future. At bag check, we were informed that check-in could only be completed via the Frontier mobile app. Unfortunately, the app was extremely frustrating—sending us through repetitive, confusing loops that repeatedly forced us to decline add-on services with nearly every click. While most airline apps upsell, this one felt intentionally exhausting. As the process dragged on, we became genuinely concerned that my phone battery would die before check-in could be completed. We approached the bag check staff—who were standing together talking—and explained both our frustration and our predicament. They laughed. Later, my wife described the interaction as “gaslighting,” which felt accurate. We were then informed it would cost $25 per person simply to have our boarding passes printed. From that point forward, the tone of the experience was consistently hostile. The bag check employees were condescending and combative, behaving more like bullies than customer service staff. Unfortunately, that same attitude continued onboard. One flight attendant argued with me when I attempted to stow my backpack in the overhead bin. I explained that we had each paid $75 to check our bags specifically so we would not need to use carry-on space and could have adequate legroom. She demanded to see my ticket, pointed out that it said “no carry-on”—which I acknowledged—and I reiterated that this was precisely why we paid to check our bags. Her response was, “I don’t make the rules.” She then walked away, but not before asking if I “truly wanted to fly back to Chicago today?”—an unnecessary and unmistakable threat. It is also worth noting that despite booking our tickets together in the same transaction, we were not seated together. Upon our return to Chicago—where we could once again sit together—we compared onboard experiences. We both remarked on how unhappy the flight attendants appeared and how each of us was separately asked whether we would like to purchase a beverage. We declined. At no point was water mentioned as an option, leaving us with the clear impression that even water came at a cost—or that complimentary water, if available at all, was deliberately left unmentioned. Overall, the experience was shocking and deeply disappointing, but it was also a profound learning experience—one we will not forget and will not repeat. -Steve

It was an early flight and most people napped/slept and the crew let us which was nice.

Good for a budget airline! It was easy to get on, staff was really nice. Can’t say anything about the food or entertainment because it wasn’t available, which is fine.

It didn’t happen. I booked it and then was told it wasn’t available and then forced to pay far higher prices for a worse option

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.

Flight got delayed for 5 hours no good explanation was offered ;(

There was no one at the counter to assist with our check in. The app didn’t work, so I arrived at the airport with time to check in and I couldn’t because no employees were there. When I finally got someone on the phone, it was inside the 60min rule and they said I could no longer check in and they could sell me another ticket. We had to scramble and pay an additional $800 for tickets and THEN AFTER (about 60 min from my original convo with customer service and 10min after original departure time) I had boarded my new flight, there was email saying my original flight from Frontier was delayed and leaving 2hr 50min later, but I STILL wouldn’t have been able to check in. Which means customer service should have been able to see it and let me check in because I was well within my check in time. When I call Frontier, they hang up on me. So their app didn’t work and they employees left and they take zero responsibility or assistance with their “customer service”

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

Too many extra fees, uncomfortable, little leg room. Will not recommend this airline.

Everyone seemed to be in zone 1 for boarding. Maybe break it up a little. Otherwise, smooth flight.

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

Information on your arrival and departure airports