JAX - MDW

$79 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 8/4. 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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Flights 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, Aug 21 - Mon, Aug 25
Southwest Logo
6:05 pm - 7:30 pmJAX-MDW
2h 25mnonstop
Southwest Logo
1:30 pm - 4:45 pmMDW-JAX
2h 15mnonstop
$157Southwest
Find Deal
Thu, Aug 7 - Wed, Aug 13
Southwest Logo
7:30 pm - 10:50 pmJAX-MDW
4h 20m1 stop
Southwest Logo
10:30 am - 1:45 pmMDW-JAX
2h 15mnonstop
$167Southwest
Find Deal
Thu, Aug 7 - Wed, Aug 13
Southwest Logo
11:20 am - 7:30 pmJAX-MDW
9h 10m2 stops
Southwest Logo
10:30 am - 1:45 pmMDW-JAX
2h 15mnonstop
$172Southwest
Find Deal
Mon, Aug 18 - Thu, Aug 21
Southwest Logo
7:30 pm - 10:50 pmJAX-MDW
4h 20m1 stop
Southwest Logo
2:35 pm - 10:20 pmMDW-JAX
6h 45m1 stop
$177Southwest
Find Deal
Thu, Sep 4 - Mon, Sep 8
Delta Logo
5:20 am - 9:16 amJAX-MDW
4h 56m1 stop
Delta Logo
9:30 am - 4:47 pmMDW-JAX
6h 17m1 stop
$197Delta
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Thu, Sep 25 - Sun, Sep 28
Frontier Logo
4:58 pm - 11:25 pmJAX-MDW
7h 27m1 stop
Frontier Logo
6:15 am - 3:58 pmMDW-JAX
8h 43m1 stop
$215Frontier
Find Deal
Thu, Aug 7 - Sun, Aug 10
Frontier Logo
7:49 pm - 11:17 pmJAX-MDW
4h 28m1 stop
Frontier Logo
6:20 am - 6:54 pmMDW-JAX
11h 34m1 stop
$225Frontier
Find Deal
Sat, Aug 16 - Tue, Aug 19
Delta Logo
5:01 pm - 9:12 pmJAX-MDW
5h 11m1 stop
Delta Logo
6:04 am - 1:29 pmMDW-JAX
6h 25m1 stop
$232Delta
Find Deal
Thu, Jul 31 - Sun, Aug 3
Allegiant Air Logo
4:18 pm - 1:56 pmJAX-MDW
22h 38m2 stops
Allegiant Air Logo
11:37 am - 2:29 pmMDW-JAX
25h 52m2 stops
$348Allegiant Air
Find Deal
Tue, Jul 8 - Fri, Jul 11
Allegiant Air Logo
11:16 am - 3:37 pmJAX-MDW
29h 21m2 stops
Allegiant Air Logo
8:03 am - 7:09 pmMDW-JAX
34h 06m2 stops
$360Allegiant Air
Find Deal
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
Useful Info

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 Monday 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 April, where tickets cost $340 (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 $543 respectively.

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 5 weeks before departure. For the absolute cheapest price, our data suggests you should book 9 weeks before departure.

Good to know

Low seasonJanuary
High seasonMay
Cheapest flight$79
Best time to beat the crowds with an average 5% drop in price.
Most popular time to fly and prices are also 21% 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 $79 for a one-way ticket and $157 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 Boeing 737-800 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 $399 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 $487 and an overall rating of 8.0.

  • 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 $198 or less one-way and $337 or less round-trip.

Prefer to fly direct from Jacksonville to Chicago Midway Airport?

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
See more direct flights

Top airlines flying 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 4287 reviews
8.2Boarding
7.1Food
8.6Crew
8.0Comfort
7.6Entertainment
Airline reviews

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.

6.0 GoodJennifer, Apr 2025FLL - RDU
Read more Southwest reviews

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

Planes are aged. The wifi is unreliable and on many fights, no-existent. The flight attendants were very good.

I had a wonderful flight, but the only thing that annoyed me was how crowded TSA was. I still believe airports and all planes work together to bunch everyone together to drive up cost.

Easy to book and to get check in and get on and off.

Everything worked well. Crew was as entertaining as is possible on a plane flight. Southwest still has good legroom:

I like that it was on time and the staff was friendly.

Glad flight made it out. So many delays due to hurricane. everyone did a great job.

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.

Newer plane, relatively easy boarding, not a full flight and was told that we could not be moved up because of weight and balance issues. Otherwise, a very good experience.

Everything was great. Great service, excellent communication, and early arrival

I sat in comfort plus. It was fine. Seats were comfortable. I got drinks and snacks.

Good and consistent Printer in lounge did not work for me :(

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

Information on your arrival and departure airports

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