JAX - MDW

$71 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 10/19. 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

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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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, Oct 23 - Sun, Oct 26
Frontier Logo
9:42 pm - 4:09 pmJAX-MDW
19h 27m2 stops
Frontier Logo
8:25 am - 9:04 pmMDW-JAX
11h 39m1 stop
$193Frontier
Find Deal
Thu, Oct 30 - Sun, Nov 2
Frontier Logo
10:38 pm - 5:15 pmJAX-MDW
19h 37m2 stops
Frontier Logo
8:32 am - 9:53 pmMDW-JAX
12h 21m1 stop
$196Frontier
Find Deal
Sat, Oct 18 - Sun, Oct 19
Frontier Logo
11:46 am - 10:47 pmJAX-MDW
12h 01m2 stops
Frontier Logo
6:20 am - 5:10 pmMDW-JAX
9h 50m1 stop
$197Frontier
Find Deal
Thu, Oct 9 - Tue, Oct 14
Multiple Airlines Logo
6:03 pm - 11:46 pmJAX-MDW
6h 43m1 stop
Multiple Airlines Logo
8:05 am - 8:58 amMDW-JAX
23h 53m2 stops
$216Multiple Airlines
Find Deal
Thu, Oct 23 - Fri, Oct 24
Frontier Logo
6:03 pm - 11:46 pmJAX-MDW
6h 43m1 stop
Frontier Logo
12:03 pm - 10:51 amMDW-JAX
21h 48m2 stops
$219Frontier
Find Deal
Fri, Oct 10 - Tue, Oct 14
Multiple Airlines Logo
11:37 am - 11:20 pmJAX-MDW
12h 43m1 stop
Multiple Airlines Logo
8:05 am - 8:58 amMDW-JAX
23h 53m2 stops
$222Multiple Airlines
Find Deal
Wed, Oct 15 - Wed, Oct 22
Southwest Logo
2:50 pm - 4:10 pmJAX-MDW
2h 20mnonstop
Southwest Logo
7:35 am - 5:35 pmMDW-JAX
9h 00m2 stops
$292Southwest
Find Deal
Wed, Oct 8 - Wed, Oct 15
Southwest Logo
2:50 pm - 4:10 pmJAX-MDW
2h 20mnonstop
Southwest Logo
5:45 am - 11:10 amMDW-JAX
4h 25m1 stop
$297Southwest
Find Deal
Sat, Oct 11 - Wed, Oct 15
Delta Logo
7:10 pm - 10:14 pmJAX-MDW
4h 04m1 stop
Delta Logo
9:35 am - 5:30 pmMDW-JAX
6h 55m1 stop
$307Delta
Find Deal
Thu, Nov 6 - Wed, Nov 12
Delta Logo
6:10 am - 9:45 amJAX-MDW
4h 35m1 stop
Delta Logo
12:47 pm - 5:33 pmMDW-JAX
3h 46m1 stop
$308Delta
Find Deal

Everything you should know

Our travelers' advice
AI-generated summary based on content written by travel experts
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
Frontier
Cheapest • from $193 (round-trip)
Southwest
Best reviews • 8.0 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
When to book
4 weeks
in advance
Our data shows that travelers who book at least 4 weeks in advance save around 54% compared to booking last minute.
Insights
Insights
Insights
Insights
When to travel
August
Cheapest • 48% price drop
May
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
Cheapest round-trip
$193
Overall average: $354
Frontier
Thu 10/23Sun 10/26
JAX - MDW • 2 stops
Cheapest non-stop
$287
Typical prices: $523-706
Southwest
Wed 11/19Sat 11/22
JAX - MDW • Non-stop
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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!
Expert advice

Expert advice for your flight from Jacksonville to Midway

 
Snippets provided in this section are AI-generated based on a summarization of KAYAK-commissioned articles. The articles are presented as-is, for general informational purposes only, and may not be up-to-date. The opinions contained in the articles are original to the author and reflect their authentic experience, which may vary significantly from the experience of others.
KAYAK teamed up with top travel experts to share the best tips for your journey.
Airports
JAX

JAX offers free unlimited Wi-Fi throughout the terminal, making it easy to stay connected before your flight.

Read more about JAXby Marisa Garcia
MDW

The CTA Orange Line from MDW takes about 25-30 minutes to reach downtown Chicago, offering a convenient public transport option.

Read more about MDWby Stefanie Waldek
Our travel experts
Marisa Garcia

Marisa Garcia

Expert on JAX

Marisa Garcia

Marisa Garcia

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.

Read more
Stefanie Waldek

Stefanie Waldek

Expert on MDW

Stefanie Waldek

Stefanie Waldek

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.

Read more
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, Sunday is the most expensive day to fly from Jacksonville to Chicago Midway Airport. For your return ticket, we recommend flying on a Thursday 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 August, where tickets cost $218 (return) on average. On the other hand, the most expensive months are March and November, where the average cost of round-trip tickets is $763 and $597 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 $272, prices are generally cheapest when you fly direct.

How far in advance should I book a flight from Jacksonville to Chicago Midway Airport?

To calculate weekly average prices, KAYAK takes all prices for each week before departure 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 average of all the values for each week.

To get a below average price on the flight from Jacksonville to Chicago Midway Airport, you should book around 4 weeks before departure, which saves you about 54% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 9 weeks before departure.

Good to know

Low seasonJanuary
Cheapest flight$71
Best time to beat the crowds with an average 0% drop in price.
Most popular time to fly and prices are also 15% 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 $71 for a one-way ticket and $193 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, Delta, and JetBlue 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.

  • 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 $397 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 $402 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 $176 or less one-way and $282 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 4242 reviews
8.6Crew
8.1Boarding
8.0Comfort
7.0Food
7.5Entertainment
Airline reviews

Near 4 hour flight with only 1 service. Had to use call button to request water. Internet and power not working until into flight. Internet would stop working during flight.

6.0 GoodDavid, Aug 2025MCO - DEN
Read more Southwest reviews

Near 4 hour flight with only 1 service. Had to use call button to request water. Internet and power not working until into flight. Internet would stop working during flight.

My flight was delayed 50 minutes and we were rushed to board to then sit for 15 minutes until the pilot arrived. Unacceptable since we could have waited to board. Also the delayed flight was updated AFTER we boarded to more than the 10 minutes as originally stated.

If we are going to have to pay for luggage, make it easier to do. Put something on the app during check-in so I don't need to do it at the kiosk. I've done it twice recently and I ended up having to pay at the desk because something went wrong at the kiosk in Tampa.

Worst experience I had on Southwest. Still better than most, but the seating was barely tolerable.

It was okay. The plane was delayed from earlier in the day, but they kept updating the departure time, sometimes later, sometimes earlier. That was stressful. Once we finally got on and took off, it was fine. I was supposed to have a connection in Chicago to Los Angeles, and the time for so late I was rebooked to arrive in LA 3 hours late. The departure time to Chicago later became early enough to have taken my original connection and arrive earlier but that wasn't an option.

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.

The price of the tickets isn't matching the flight experience. No matter how long the flight is, you're only getting pretzels. The flight attendants looked unkept and over it.

WiFi on the flight was not working. Thus, entertainment options were limited.

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.

Crew was great flight was great baggage claim was a failure. It took over 1 hour for bags to arrive. Poor communication poor effort when I spoke to the supervisor about the delay

Really low quality food especially for an international flight. The crew also was surprisingly unpleasant except couple of ladies. I know we were not in first class but that’s no reason to treat customers as less.

For a 69 year old with health problems I had the worse experience, no wheelchair when I entered a lady told me to sit and wait while a gentleman told me I had to walk to the Delta station, which I did. I had a carry on and a bag, and I was traveling with my service dog, which was on his carrier and the lady charged me for my carry on luggage, beside all the waiting cause of the delay, I had to walk to get my luggage cause no wheelchair showed up, I am so disappointed. I will get in touch with the company. I got home at 3:00 am, not good for my health situation.

Flight was an hour late, who knows why. It was OK, nothing outstanding.

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

This had nothing to do with Delta… The flights were on time and flawless. The service was excellent. We purchased seats in (aisle/middle) comfort plus since this was a cross country flight. Unfortunately, the woman seated at the window was 300+ pounds and, as might be expected, covered up about a third of the middle seat also. there was absolutely nothing that Delta could have done about that… I just don’t know what the answer should be. If you purchase a seat, you should should be able to use the entire seat and not just the portion that someone else is not sitting/oozing in. Disappointing…there should be something that could be done….I'm just not sure what solution could be.

The worst part was I was NOT allowed in the lounge even though I was holding a first class ticket and have a premium American Express card. I have flown Business or First Class with many airlines. Delta is the ONLY one who does not extend this courtesy to anyone except people who hold the very expensive American Express card. As a result, I won’t fly Delta if I have any other choice.

The Dekta Rep that checked us in was great. She's very personable, pleasant, and can tell she enjoys her job.

The young man who was our flight attendant in first class was lazy and did not do his job well at all. Never offered drinks upon boarding - actually I take that back... said "are you okay with water" as if I do not want to get you anything else, only passed the snacks around once, got my drink order wrong and then never offered a second round of drinks. He was the worst I have ever seen on Delta and we fly a lot.

Flight left early and arrived early. the whole trip was excellent.

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.

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

Boarding in Orlando was not good. Giant mob at the gate, should have been lines.

My flight was delayed by two hours which made it so that I would miss my layover flight. I stood in line for customer service for over an hour and when I reached the agent she told me to scan a QR code and it'll give me options. I wasn't offered any help, guidance or compensation, only told that I have options but that I had to figure it all out myself. I was refunded part of the trip and had to buy an expensive same day ticket from another airline in order to get home. I will never fly Frontier again.

We were delayed three times ,and that destroyed my plans, and reservations

The confirmation # CK8GNW and my name was not recognized/in Frontier system. I was able to check in on Frintier app so i went to the Frontier ticket agent, at time they told me that my name/ confirmation did not show up as a purchased ticket. I had to purchase a new ticket that cost $289.00 one way.

Although an hour and a half early was told by staff at check in they had overbooked and could not check us in for the flight.

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

Worst airline experience. They were rude and kept changing our seats and/or giving our seats away so our family didn’t get to sit with each other. Almost everyone we dealt with at both airports with this airline was rude. The app kept giving us wrong information making things take longer. Dealing with them before TSA can take close to an hour…longer than I’ve ever had to deal with before. Never using this airline again.

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

Information on your arrival and departure airports

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