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JAX - MDW

$74 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 6/10. 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
0 bags
Mon 7/1
Mon 7/8

Search 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
In the last 7 days travelers have searched 42,335,261 times on KAYAK, and here is why:

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Cheap flight deals from Jacksonville to Midway (JAX-MDW)

 
These are the cheapest deals for flights from Jacksonville to Midway currently on KAYAK along with options from the most popular airlines KAYAK users selected for this route. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.

Recent round-trip flight deals from Jacksonville to Midway

Recommended round-trip deals departing in the coming months from the most popular airlines that fly from Jacksonville to Midway.

Recent one-way flight deals from Jacksonville to Midway

Only flying one-way? Below are some of the best one-way flight deals from Jacksonville to Midway found on KAYAK recently.

Recent last minute flight deals from Jacksonville to Midway

Leaving soon but still want a bargain? Check out these latest deals for last minute flights from Jacksonville to Midway.

Recent direct flight deals from Jacksonville to Midway

The latest deals for direct flights from Jacksonville to Midway so you can sit back and relax without the need for a layover.

Cheap bus & train deals from Jacksonville to Midway

Find recent round-trip train or bus tickets from Jacksonville to Midway.

All round-trip flight deals to Midway

The cheapest plane tickets to Midway found on KAYAK recently.
Discover the best prices and deals for you by selecting your travel dates.
Choose your dates
12:11 pm - 6:39 pmJAX-MDW
7h 28m1 stop
6:00 am - 11:54 amMDW-JAX
4h 54m1 stop
$236Delta
Find Deal
Tue, Jul 9 - Wed, Jul 10
10:35 am - 10:30 pmJAX-MDW
12h 55m1 stop
8:53 am - 8:22 pmMDW-JAX
10h 29m1 stop
$238Frontier
Find Deal
Wed, Jun 12 - Sat, Jun 15
12:11 pm - 6:39 pmJAX-MDW
7h 28m1 stop
6:00 am - 1:26 pmMDW-JAX
6h 26m1 stop
$264Delta
Find Deal
Tue, Jul 16 - Tue, Jul 23
10:35 am - 10:30 pmJAX-MDW
12h 55m1 stop
8:53 am - 8:22 pmMDW-JAX
10h 29m1 stop
$268Frontier
Find Deal
Wed, Jun 12 - Sat, Jun 15
12:14 pm - 9:13 pmJAX-MDW
9h 59m1 stop
7:59 pm - 7:22 amMDW-JAX
10h 23m1 stop
$279Frontier
Find Deal
Sat, Sep 7 - Thu, Sep 12
12:11 pm - 6:39 pmJAX-MDW
7h 28m1 stop
6:55 pm - 12:08 amMDW-JAX
4h 13m1 stop
$284Delta
Find Deal
Sun, Aug 4 - Tue, Aug 6
7:10 am - 8:35 amJAX-MDW
2h 25mnonstop
9:30 pm - 12:45 amMDW-JAX
2h 15mnonstop
$345Southwest
Find Deal
Tue, Jul 9 - Thu, Jul 11
6:20 am - 4:55 pmJAX-MDW
11h 35m2 stops
7:05 am - 2:30 pmMDW-JAX
6h 25m1 stop
$346Southwest
Find Deal
Tue, Jul 9 - Thu, Jul 11
9:48 pm - 11:18 amJAX-MDW
14h 30m2 stops
7:31 pm - 3:25 pmMDW-JAX
18h 54m2 stops
$418Allegiant Air
Find Deal
Thu, Jul 11 - Sun, Jul 14
4:10 pm - 11:18 amJAX-MDW
20h 08m2 stops
7:31 pm - 3:25 pmMDW-JAX
18h 54m2 stops
$476Allegiant Air
Find Deal
Thu, Jul 4 - Sun, Jul 7
8:11 am - 1:38 pmJAX-MDW
6h 27m1 stop
$74Frontier
Find Deal
Mon, Jun 10
12:14 pm - 9:13 pmJAX-MDW
9h 59m1 stop
$84Frontier
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Sat, Sep 14
3:25 pm - 8:17 pmJAX-MDW
5h 52m1 stop
$88Allegiant Air
Find Deal
Mon, Jul 15
8:11 am - 1:38 pmJAX-MDW
6h 27m1 stop
$100Frontier
Find Deal
Mon, Jun 17
8:11 am - 1:38 pmJAX-MDW
6h 27m1 stop
$105Frontier
Find Deal
Mon, Jun 17
5:15 pm - 9:44 pmJAX-MDW
5h 29m1 stop
$118Delta
Find Deal
Tue, Oct 8
8:36 am - 7:13 pmJAX-MDW
11h 37m1 stop
$133Frontier
Find Deal
Thu, Aug 22
5:29 pm - 9:46 pmJAX-MDW
5h 17m1 stop
$136Delta
Find Deal
Mon, Jul 1
4:15 pm - 11:13 amJAX-MDW
19h 58m2 stops
$181Allegiant Air
Find Deal
Sun, Jun 16
7:17 pm - 9:37 pmJAX-MDW
27h 20m3 stops
Mon, Jul 15
6:45 pm - 10:01 pmJAX-MDW
4h 16m1 stop
6:00 am - 11:40 amMDW-JAX
4h 40m1 stop
$569Delta
Find Deal
Tue, Jun 4 - Tue, Jun 18
7:20 am - 11:52 amJAX-MDW
5h 32m1 stop
3:45 pm - 9:02 pmMDW-JAX
4h 17m1 stop
$577Delta
Find Deal
Wed, Jun 5 - Sat, Jun 15
3:28 pm - 11:50 pmJAX-MDW
9h 22m1 stop
10:28 am - 9:32 pmMDW-JAX
10h 04m1 stop
$629Frontier
Find Deal
Mon, Jun 3 - Thu, Jun 13
10:35 am - 10:30 pmJAX-MDW
12h 55m1 stop
8:53 am - 8:22 pmMDW-JAX
10h 29m1 stop
$637Frontier
Find Deal
Wed, Jun 5 - Sat, Jun 8
11:24 am - 7:45 pmJAX-MDW
9h 21m1 stop
10:16 am - 8:49 pmMDW-JAX
9h 33m1 stop
$658Frontier
Find Deal
Sun, Jun 2 - Tue, Jun 4
11:59 am - 5:06 pmJAX-MDW
6h 07m1 stop
6:00 am - 12:13 pmMDW-JAX
5h 13m1 stop
$660Delta
Find Deal
Tue, Jun 4 - Thu, Jun 6
5:20 am - 7:55 amJAX-MDW
3h 35m1 stop
3:45 pm - 10:12 pmMDW-JAX
5h 27m1 stop
$678Delta
Find Deal
Tue, Jun 4 - Fri, Jun 7
6:45 pm - 10:01 pmJAX-MDW
4h 16m1 stop
6:00 am - 11:40 amMDW-JAX
4h 40m1 stop
$683Delta
Find Deal
Mon, Jun 3 - Tue, Jun 11
5:20 am - 7:55 amJAX-MDW
3h 35m1 stop
9:29 am - 4:52 pmMDW-JAX
6h 23m1 stop
$713Delta
Find Deal
Tue, Jun 4 - Fri, Jun 7
11:59 am - 5:06 pmJAX-MDW
6h 07m1 stop
6:00 am - 1:36 pmMDW-JAX
6h 36m1 stop
$736Delta
Find Deal
Thu, Jun 6 - Sun, Jun 9
7:10 am - 8:35 amJAX-MDW
2h 25mnonstop
9:30 pm - 12:45 amMDW-JAX
2h 15mnonstop
$345Southwest
Find Deal
Tue, Jul 9 - Thu, Jul 11
4:30 pm - 5:55 pmJAX-MDW
2h 25mnonstop
9:30 pm - 12:45 amMDW-JAX
2h 15mnonstop
$557Southwest
Find Deal
Tue, Jun 11 - Thu, Jun 13

Flights from Jacksonville to Midway - Travel Insights & Trends

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 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 Friday, as we generally find the cheapest rates on that day for this route. On the other hand, Saturday 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 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 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 September, where tickets cost $271 on average. On the other hand, the most expensive months are December and July, where the average cost of tickets is $772 and $546 respectively.

Which airlines provide the cheapest flights from Jacksonville to Chicago Midway Airport?

The cheapest price for the route for each airline clicked by KAYAK users in the last 72 hours.
In the last 3 days, Frontier offered the best one-way deal for that route, at $74. KAYAK users also found Jacksonville to Chicago Midway Airport round-trip flights on Delta from $236 and on Frontier from $238.

How many flights are there between Jacksonville and Chicago Midway Airport per day?

Each day, there are between 1 and 4 nonstop flights that take off from Jacksonville and land in Chicago Midway Airport, with an average flight time of 2h 25m. The most common departure time is 7:00 am and most flights take off in the morning. Each week, there are 14 flights. The most frequent day of departure is Monday, when 29% of all weekly flights depart. The fewest flights depart on a Saturday.

How long does a flight from Jacksonville to Chicago Midway Airport take?

A direct flight to Chicago Midway Airport will take on average 2h 25m to travel the 849 miles flying distance from Jacksonville.

What’s the earliest departure time from Jacksonville to Chicago Midway Airport?

Early birds can take the earliest flight from Jacksonville at 7:00 am and will be landing in Chicago Midway Airport at 8:25 am.

What’s the latest departure time from Jacksonville to Chicago Midway Airport?

If you prefer to fly at night, the latest flight from Jacksonville to Chicago Midway Airport jets off at 5:10 pm and lands at 6:35 pm.

Good to know

Low season

July

High season

June

Cheapest flight

$74
Best time to beat the crowds but there is an average 32% increase 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 $74 for a one-way ticket and $236 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?

    Only American Airlines offers 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 MAX 8 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, Delta or Frontier?

    The two airlines most popular with KAYAK users for flights from Jacksonville to Chicago are Delta and Frontier. With an average price for the route of $384 and an overall rating of 8.0, Delta is the most popular choice. Frontier is also a great choice for the route, with an average price of $251 and an overall rating of 6.2.

  • 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.

See more FAQs

Prefer to fly non-stop from Jacksonville to Chicago Midway Airport?

Find which airlines fly direct from Jacksonville to Midway, which days they fly and book direct flights.

Nonstop 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

Nonstop 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
DeltaOverall score based on 10410 reviews
8.6Crew
8.0Entertainment
7.4Food
8.2Boarding
7.9Comfort
Airline reviews

Rated entertainment as Mediocre as there were major problems with the Infotainment system that took probably a half hour for them to fix.

8.0 Excellentrghinftl, May 2024FLL - BOS
Read more about Delta reviews

Rated entertainment as Mediocre as there were major problems with the Infotainment system that took probably a half hour for them to fix.

Delta crushed it. Flight attendant in first was attentive and just never stopped. Honestly one of the best domestic flights I’ve been on.

The 1st class male crew member was very pleasant - the short female with round glasses , maybe in 50’s had no personality- never spoke when delivering my food, drink, & never smiled the whole trip! In fact looked annoyed when the boarding proses was happening- I would never hire this woman - unfriendly . Have never dealt with a crew member like her-

Best airline! Always friendly and welcoming. Skyclub was great and loved the fast free wifi on board. I also love that you can pre-order your meal on the app!

Delayed due to an ill passenger after loading. Not preventable on Delta's part. Was in first class. The seats are becoming worn and detaching from their velcro attachments. Only got snacks on flight. The attendant was not the friendliest.

I liked the ease of checking in, luggage check in, wheel chair assistance, boarding and flight.

I usually have a positive experience with Delta. Complimentary upgrades are always nice!

The main person that was coordinating everything was a short white/light skin Spanish man and he was very rude. It honestly made me feel like it was everyone’s First day at work. His announcements were very not reasonable and they did not make sense. The stewardess on the flight that made the announcements she didn’t even know what she was talking about she sounded inebriated. There were no snacks or drinks on our flight there wasn’t even much turbulence. This flight was not enjoyable nor was it what a Delta flight should be and just this past week I flew with Delta 3 times.

nothing Delta could do... the person sitting next to me was huge and overflowing into my seat

Crew was great! I need wheelchair assistance and they knew who I was and updated me that my chair was on its way and to just hang tight. There was some turbulence but the captain announced we would be going thru it and he handled the plane well. Landing was soft and his.

Good for the price. My only complaint is that the pilot should keep the air flowing while passengers are waiting to getting out of airplane.

I arrived 1 hour prior to boarding, and they said I was too late for a domestic flight. First time I heard that :-(

Frontier is a crappy airline nothing about it is honest

Crew members are very rude and not cooperate with passengers.

30 minute delay due to boarding and settling of a family.

I am HIGHLY unhappy with the amount of money I spent on the flight. Paid in advance only to find the flight at a discount price a week or so before the flight. I will not fly frontier again and have bad mouthed your business since to anyone I have spoken with about flying (which has been many a people). Crew was mediocre and instead of moving me to a spot where I could gain some leg room they sat their flight attendant there. Won’t be flying frontier in the future.

Well, I didn’t have food! So NA wasn’t an option. I’ll be back!

First time flying with Frontier . From buying tickets ,getting boarding pass and boarding plane was super easy. Definitely would fly again with Frontier .

Our flight was on time and unremarkable which I'm grateful for, as it is not the norm traveling these days. Frontier is a low-cost carrier and it really shows when compared to other "normal" carriers. They don't even give you water during the flight. The coach seats are decent, however it was not as clean as it should be. We had crumbs all over the floor by our seats.

They lost my baggage on my connection flight, it’s been 24 hours since I put my claim in and still no update on my bags.

Book cheap flights from Jacksonville to Chicago

Recent one-way flight deals

 
Only flying one-way? Below are some of the best one-way flight deals from Jacksonville to Chicago found on KAYAK in the last 72 hours.
6/10Mon
1 stopFrontier
6h 27mJAX-MDW
$74
9/14Sat
1 stopFrontier
9h 59mJAX-MDW
$84
7/15Mon
1 stopAllegiant Air
5h 52mJAX-MDW
$88
6/17Mon
1 stopFrontier
6h 27mJAX-MDW
$100
6/17Mon
1 stopFrontier
6h 27mJAX-MDW
$105
10/8Tue
1 stopDelta
5h 29mJAX-MDW
$118
8/22Thu
1 stopFrontier
11h 37mJAX-MDW
$133
7/1Mon
1 stopDelta
5h 17mJAX-MDW
$136
6/16Sun
2 stopsAllegiant Air
19h 58mJAX-MDW
$181
7/15Mon
3 stops
27h 20mJAX-MDW
$357

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Last minute flights from Jacksonville to Midway

Last minute flight, train and bus deals

 
These last-minute flight deals are the cheapest flights found on KAYAK in the last 72 hours for flights from Jacksonville to Chicago that are departing in the next 10 days.
6/4Tue
multi-stopDelta
4h 16mJAX-MDW
6/18Tue
multi-stopDelta
4h 40mMDW-JAX
$569
6/5Wed
multi-stopDelta
5h 32mJAX-MDW
6/15Sat
multi-stopDelta
4h 17mMDW-JAX
$577
6/3Mon
multi-stopFrontier
9h 22mJAX-MDW
6/13Thu
multi-stopFrontier
10h 04mMDW-JAX
$629
6/5Wed
multi-stopFrontier
12h 55mJAX-MDW
6/8Sat
multi-stopFrontier
10h 29mMDW-JAX
$637
6/2Sun
multi-stopFrontier
9h 21mJAX-MDW
6/4Tue
multi-stopFrontier
9h 33mMDW-JAX
$658
6/4Tue
multi-stopDelta
6h 07mJAX-MDW
6/6Thu
multi-stopDelta
5h 13mMDW-JAX
$660
6/4Tue
multi-stopDelta
3h 35mJAX-MDW
6/7Fri
multi-stopDelta
5h 27mMDW-JAX
$678
6/3Mon
multi-stopDelta
4h 16mJAX-MDW
6/11Tue
multi-stopDelta
4h 40mMDW-JAX
$683
6/4Tue
multi-stopDelta
3h 35mJAX-MDW
6/7Fri
multi-stopDelta
6h 23mMDW-JAX
$713
6/6Thu
multi-stopDelta
6h 07mJAX-MDW
6/9Sun
multi-stopDelta
6h 36mMDW-JAX
$736

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Jacksonville - Chicago Midway Airport Flights

Departure:

Jacksonville (JAX)United States

Destination:

Chicago Midway Airport (MDW)United States

Return flight deals:

Chicago Midway Airport - Jacksonville

Cabin classes:

$384