JAX - MDW

$117 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 4/14. 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
Travelers love KAYAK
41 299 237 searches in the past 7 days on KAYAK

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

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

Everything you should know

Cheapest round-trip
$256
Frontier
Thu 4/9Sat 4/11
JAX - MDW • 1 stop
Cheapest non-stop
$260
Typical prices: $323-$414
Southwest
Tue 4/28Thu 4/30
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 $256 (round-trip)
Best reviews • 8.0 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
Nonstop flights
You can fly direct with Southwest. Average duration is 2h 30m
Direct flights
Direct flights
+1
+1
Direct flights
Direct flights
+1
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KAYAK searches 100s of sites at once to find you the best travel deals.
We hope you love your trip to Midway!
Flight Deals
Booking Insights
Expert advice
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

Thu, Apr 9 - Sat, Apr 11
Frontier Logo
5:28 pm - 10:21 pm
JAX
-
MDW
5h 53m
1 stop
Frontier Logo
6:40 am - 3:37 pm
MDW
-
JAX
7h 57m
1 stop
$256Frontier
Tue, Apr 28 - Thu, Apr 30
Southwest Logo
7:20 am - 8:50 am
JAX
-
MDW
2h 30mnonstop
Southwest Logo
6:50 pm - 10:05 pm
MDW
-
JAX
2h 15mnonstop
$260Southwest
Wed, Apr 15 - Fri, Apr 17
Southwest Logo
7:20 am - 8:50 am
JAX
-
MDW
2h 30mnonstop
Southwest Logo
6:50 pm - 10:05 pm
MDW
-
JAX
2h 15mnonstop
$261Southwest
Fri, Apr 24 - Mon, Apr 27
Multiple Airlines Logo
8:27 pm - 6:37 pm
JAX
-
MDW
23h 10m
2 stops
Multiple Airlines Logo
6:00 am - 6:04 pm
MDW
-
JAX
11h 04m
1 stop
$265Multiple Airlines
Thu, Jun 4 - Mon, Jun 8
Southwest Logo
7:15 pm - 8:45 pm
JAX
-
MDW
2h 30mnonstop
Southwest Logo
7:20 pm - 10:35 pm
MDW
-
JAX
2h 15mnonstop
$267Southwest
Mon, Apr 13 - Mon, Apr 20
Frontier Logo
10:26 pm - 7:31 pm
JAX
-
MDW
22h 05m
2 stops
Frontier Logo
6:00 am - 6:04 pm
MDW
-
JAX
11h 04m
1 stop
$268Frontier
Tue, Apr 28 - Thu, Apr 30
Southwest Logo
11:50 am - 4:15 pm
JAX
-
MDW
5h 25m
1 stop
Southwest Logo
6:50 pm - 10:05 pm
MDW
-
JAX
2h 15mnonstop
$270Southwest
Wed, Apr 15 - Fri, Apr 17
Southwest Logo
7:20 am - 8:50 am
JAX
-
MDW
2h 30mnonstop
Southwest Logo
7:30 am - 4:20 pm
MDW
-
JAX
7h 50m
1 stop
$271Southwest
Mon, Apr 13 - Mon, Apr 20
Frontier Logo
8:18 pm - 7:31 pm
JAX
-
MDW
24h 13m
1 stop
Frontier Logo
6:00 am - 6:04 pm
MDW
-
JAX
11h 04m
1 stop
$272Frontier
Tue, Apr 28 - Thu, Apr 30
Southwest Logo
1:15 pm - 7:45 pm
JAX
-
MDW
7h 30m
2 stops
Southwest Logo
6:50 pm - 10:05 pm
MDW
-
JAX
2h 15mnonstop
$275Southwest
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.

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 Tuesdays for the best deals.

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 $340 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$117
Best time to beat the crowds with an average 41% drop in price.
Most popular time to fly and prices are also 8% lower on average.
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 $117 for a one-way ticket and $256 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 $372 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 $324 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 $199 or less one-way and $387 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 4321 reviews
8.6Crew
7.5Entertainment
7.0Food
8.0Comfort
8.1Boarding
Airline reviews

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

4.0 OkayKenny, Mar 2026
TPA - BWI
Read more Southwest reviews

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.

WiFi was not working and didn’t have a beverage service

An entire day of delays. Cost lots of money. Meals and a hotel.

I appreciate the staff who allowed me to board though I arrived a little late! Regarding the assigned seating, I had booked my flight before this change and wasn't aware of the change at the time, and so I didn't select a seat at booking as I didn't realize it was relevant. Better communication about the change would have been helpful for preparing.

All good except once again bags took an hour at Midway Airport Happens all the time. Ridiculous

The seats were comfortable, and the boarding process was pretty smooth.

Departure was delayed more than 1/2 hour while we waited for luggage (only) transfer from another flight/plane. Once approved for takeoff, the flight was excellent.

Flight was on time. Wi-fi was a little spotty/slow. Boarding and exit were efficient.

It was rough. The staff was unprofessional, the choice of on board drinks terrible, it was cramped in space at every airport, they always ran out of overhead bin space so they pressured people to check bags for free or we couldn’t leave on the plane— so I did check my bag to help, and they nearly lost my bag. My bag did not arrive on the luggage belt, another man on my flight and I had to waste our time going to the baggage office to search for our bags. I would only fly southwest again if it was my last choice. Also, my flights were consistently delayed over and over again— at one point they straight up told us we were waiting for the pilot to arrive.

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

Loved flying First Class. Very comfortable. The seat was amazing. Enjoyed a movie and was able to relax so much better than in coach.

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

There was an unruly family behind us that made the short flight miserable!!! The cabin crew did nothing to contain it.

An awesome flight crew. FC seat cushion just doesn’t cut it for a 3+ hour flight.

Delta continues to set the benchmark for traveler-friendly service with minimal disruption and clear communication within the mainland US (coast to coast). I am consistently pleased to be a Delta customer, and this experience once again met my expectations. There was a brief delay departing from MIA due to a technical issue that required the aircraft to return to the gate. However, the situation was handled professionally and transparently. Fortunately, my planned layover allowed ample buffer time, so the adjustment caused no stress. Overall, another smooth and reassuring experience.

Totally worth the miles to upgrade to Delta Comfort. Plenty of legroom.

This was my first time flying Delta ever and I had a great experience!

Flight delay was frustrating, also you cannot checkin online without delta app, web browser check-in throw errors

The flight was great as well as the airline staff

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.

The experience was good. No frills but I got there safe and sound and on time.

After boarding and un-boarding twice over 6+hours, the flight was canceled.

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

Information on your arrival and departure airports