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MDW - JAX

$72 Find cheap flights from Chicago Midway Airport to Jacksonville

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Midway to Jacksonville departing on 7/31. 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
Wed 7/10
Wed 7/17

Search hundreds of travel sites at once for deals on flights to Jacksonville

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to Jacksonville, 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 Chicago to Jacksonville, as well as popular online travel agencies
In the last 7 days travelers have searched 42,898,604 times on KAYAK, and here is why:

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

Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Midway to Jacksonville 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 and deals for you by selecting your travel dates.
Choose your dates
10:59 am - 9:05 pmMDW-JAX
9h 06m1 stop
10:11 am - 3:59 pmJAX-MDW
6h 48m1 stop
$148Frontier
Find Deal
Tue, Aug 13 - Wed, Sep 4
10:28 am - 9:32 pmMDW-JAX
10h 04m1 stop
10:35 am - 10:30 pmJAX-MDW
12h 55m1 stop
$166Frontier
Find Deal
Thu, Jun 20 - Wed, Jun 26
10:59 am - 5:57 pmMDW-JAX
5h 58m1 stop
10:11 am - 3:59 pmJAX-MDW
6h 48m1 stop
$175Frontier
Find Deal
Fri, Aug 16 - Mon, Aug 19
10:28 am - 9:32 pmMDW-JAX
10h 04m1 stop
10:35 am - 10:30 pmJAX-MDW
12h 55m1 stop
$176Frontier
Find Deal
Thu, Jun 20 - Wed, Jun 26
9:18 am - 5:52 pmMDW-JAX
7h 34m1 stop
12:11 pm - 6:39 pmJAX-MDW
7h 28m1 stop
$236Delta
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Tue, Jul 9 - Wed, Jul 10
6:00 am - 11:54 amMDW-JAX
4h 54m1 stop
12:11 pm - 6:39 pmJAX-MDW
7h 28m1 stop
$266Delta
Find Deal
Wed, Jul 10 - Wed, Jul 17
7:31 pm - 3:25 pmMDW-JAX
18h 54m2 stops
3:25 pm - 8:17 pmJAX-MDW
5h 52m1 stop
$289Allegiant Air
Find Deal
Thu, Jul 4 - Mon, Jul 8
7:31 pm - 3:25 pmMDW-JAX
18h 54m2 stops
3:25 pm - 8:17 pmJAX-MDW
5h 52m1 stop
$297Allegiant Air
Find Deal
Thu, Jul 11 - Mon, Jul 15
10:35 pm - 10:35 amMDW-JAX
11h 00m2 stops
5:50 am - 3:20 pmJAX-MDW
10h 30m1 stop
$339Southwest
Find Deal
Mon, Jul 8 - Thu, Jul 11
10:35 pm - 10:35 amMDW-JAX
11h 00m2 stops
5:50 am - 5:35 pmJAX-MDW
12h 45m2 stops
$344Southwest
Find Deal
Mon, Jul 8 - Thu, Jul 11

Flights from Midway to Jacksonville - Travel Insights & Trends

Get data-powered insights and trends into flights from Midway to Jacksonville 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 Chicago Midway Airport to Jacksonville?

The average price of all flights from Chicago Midway Airport to Jacksonville clicked on KAYAK for each day over the last 12 months.
For Chicago Midway Airport to Jacksonville, Monday is the cheapest day to fly on average and Sunday is the most expensive. Flying from Jacksonville back to Chicago Midway Airport, the best deals are generally found on Friday, with Thursday being the most expensive.

What is the cheapest month to fly from Chicago Midway Airport to Jacksonville?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for flights from Chicago Midway Airport to Jacksonville, 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 Chicago Midway Airport to Jacksonville is January, where tickets cost $313 on average. On the other hand, the most expensive months are March and June, where the average cost of tickets is $430 and $367 respectively.

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

To calculate daily average prices, KAYAK takes all prices for each day before departure over the last year for flights from Chicago Midway Airport to Jacksonville, removes the top 0.1% to account for outliers, and then takes the average of all the values for each month.
To get a below average price on the flight from Chicago Midway Airport to Jacksonville, you should book around 1 week before departure. For the absolute cheapest price, our data suggests you should book 85 days before departure.

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

The cheapest price for the route for each airline clicked by KAYAK users in the last 72 hours.
The best deals for a one-way ticket found by KAYAK users over the last 3 days were on Frontier ($72) and Delta ($230). The cheapest round-trip tickets were found on Frontier ($148) and Delta ($236).

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

Each day, there are between 1 and 4 nonstop flights that take off from Chicago Midway Airport and land in Jacksonville, with an average flight time of 2h 15m. The most common departure time is 10:00 am and most flights take off in the morning. Each week, there are 19 flights. The most frequent day of departure is Friday, when 21% of all weekly flights depart. The fewest flights depart on a Sunday.

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

Nonstop flights from Chicago Midway Airport generally make it to Jacksonville in 2h 15m. The flying distance between the two cities is 849 miles.

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

Early birds can take the earliest flight from Chicago Midway Airport at 10:40 am and will be landing in Jacksonville at 1:55 pm.

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

If you prefer to fly at night, the latest flight from Chicago Midway Airport to Jacksonville jets off at 9:30 pm and lands at 12:45 am.

Good to know

Low season

January

High season

February

Cheapest flight

$72
Best time to beat the crowds with an average 20% drop in price.
Most popular time to fly and prices are also 10% lower on average.
Flight from Chicago Midway Airport to Jacksonville

When to book flights from Midway to Jacksonville

Are your dates flexible? Find out the best times to travel from Midway to Jacksonville 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 Chicago Midway Airport to Jacksonville flights

  • What is the cheapest flight from Chicago Midway Airport to Jacksonville?

    In the last 3 days, the lowest price for a flight from Chicago Midway Airport to Jacksonville was $72 for a one-way ticket and $148 for a round-trip.

  • Do I need a passport to fly between Chicago Midway Airport and Jacksonville?

    No, a passport isn't needed to fly from Chicago Midway Airport to Jacksonville. However, local authorities might ask for an official ID.

  • Which airports will I be using when flying from Chicago Midway Airport to Jacksonville?

    Chicago Midway Airport airport is called Chicago Midway and the only airport in Jacksonville is Jacksonville.

  • Which aircraft models fly most regularly from Chicago Midway Airport to Jacksonville?

    We unfortunately don’t have that data for this specific route.

  • On which days can I fly direct from Chicago Midway Airport to Jacksonville?

    There are nonstop flights from Chicago Midway Airport to Jacksonville on a daily basis.

  • Which is the best airline for flights from Chicago to Jacksonville, Delta or Frontier?

    The two airlines most popular with KAYAK users for flights from Chicago to Jacksonville are Delta and Frontier. With an average price for the route of $349 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 $202 and an overall rating of 6.2.

  • How does KAYAK find such low prices on flights from Chicago Midway Airport to Jacksonville?

    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 Chicago Midway Airport to Jacksonville.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Chicago Midway Airport to Jacksonville?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Jacksonville from Chicago Midway Airport 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 Chicago Midway Airport to Jacksonville?

    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 Jacksonville with an airline and back to Chicago Midway Airport with another airline. Booking your flights between Chicago Midway Airport and JAX 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 Chicago Midway Airport to Jacksonville?

    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 Jacksonville from Chicago Midway Airport 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 Chicago Midway Airport to Jacksonville?

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

Nonstop departures

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

Nonstop returns

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
See more direct flights

Top airlines flying from Midway to Jacksonville

 
See real verified KAYAK customer reviews for airlines flying from Chicago to Jacksonville. 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 Midway to Jacksonville? 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 10295 reviews
7.4Food
7.9Comfort
8.2Boarding
8.6Crew
8.0Entertainment
Airline reviews

Awful. Flight was continuously getting delayed and gates kept changing without any reason. Flight was delayed for more then 3 hours

2.0 MediocreNairan, May 2024JFK - FLL
Read more about Delta reviews

Awful. Flight was continuously getting delayed and gates kept changing without any reason. Flight was delayed for more then 3 hours

5-hour delay due to storms in Tanoa and airspace restricted by Miami traffic controllers.

I would fly again the whole experience was great. The only feed back I can give that they don't do that American Airlines does is the crew there is more humorous with boarding and thank their passengers. It makes it more fun to fly with them. I would however fly Delta again.

Horrible. This was not first class. This was a connecting flight whi h was late. My original flight never came. I hated the fact that delta gave me a connecting flight from New York to Orlando Florida. No meals and the television screens were not working. There wasn't even any power to charge your phones. This is NOT FIRST CLASS DELTA!!! Do better next time!

They did a fine job. Can't wait to use Delta in the future.

Seat back monitors and outlets were dead and not working.

The experience was good and the flight departed on time and landed early

The flight was delayed but we got to our final destination.

public website still broken for years randomly blocking browsers with privacy options active after loading a page maybe once. check-in on laptop was almost impossible but eventually randomly worked. had to print pass at airport since couldn't get back in to load digital pass on mobile firefox or chrome. red eye flight so smooth onboarding, plenty of room to spread out, easy offboarding. onboard wifi instructions mention vpn can cause problems connecting but fails to also mention private dns. no printed or built in menu list, seems weird to require personal device to point at qr code link for menu which does not even allow direct ordering. people with health condition risk related dietary restrictions trying to avoid for example cholesterol and sugar are left guessing what they can order either way without nutritional info highlights (cranberry juice was minute maid cocktail with as much suger as typical can of soda). tap to pay wasn't working and always seems sketchy to manually enter card info. good movie variety, so limited tv was okay.

Horrible. Flight ORD to CGH was okay, but Paris was a nightmare. Old planes, delays, involuntary downgrades, broken planes, terrible communication. CGH to CPT was my worst flight ever.

It was delayed 9 hours for operational reasons, despite the plane arriving to the airport on time.

I am very disappointed with Frontier Airlines. They cancelled our flight because they couldn't find a crew member, and then didn't get us to our connecting flight. We had to cancel our whole vacation. We were promised flight and hotel vouchers, but they never sent them.

I fly Frontier because it’s affordable. I understand that the seats are tight and not the most comfortable…but that’s part of it. The problem with this flight was that there was a group of travelers directly behind me at the back of the plane who were ridiculously loud and obnoxious the entire flight. I’m pretty sure they were drunk and I could periodically smell an odd odor that I believe was one of them using a smokeless vape pen. The stewards had to remind them to keep quiet during the pre-flight instruction, but that was it. They never said another thing to them for the rest of the flight. It was a miserable.

Six hour delay. Poor customer service. No voucher. Bad communication. Missed important appointments.

I purchased a carry on bag online…was supposed to cost $72 but after a whole slew of bs charges, the total was over $175.00. Because of these hidden charges, I will not even consider flying Frontier ever again. It’s just not worth the hassle. I’m scratching this company off my list forever.

Flight delayed 3 times, resulting in late arrival, rental car place gave car away resulting in increased BS charges because I was late. Frontier blows.

It was impossible to change a carry-on for a checked bag after the initial selection. The flight was delayed 14 hours "to allow for a late arriving aircraft." The seats were shockingly uncomfortable. This was only the second time I've seen seats that didn't recline in an airline. The first was in an East Bloc airline before the fall if the Iron Curtain.

Was just ok with over selling I guess. A lot of people in a short space and when we finally arrive i20 minutes, waiting to get out from the plain because we were waiting authorization for out boarding? Something like that.

First time flying Frontier, I am not sure the Ala Carte menu of options is for me.

I liked getting off the plane. Everything else was well below standards. Not even offering a bag of peanuts for free for a 4 hours flight is ridiculous.

Book cheap flights from Chicago to Jacksonville

Recent one-way flight deals

 
Only flying one-way? Below are some of the best one-way flight deals from Chicago to Jacksonville found on KAYAK in the last 72 hours.
7/31Wed
1 stopFrontier
5h 41mMDW-JAX
$72
6/29Sat
1 stopFrontier
10h 29mMDW-JAX
$114
6/22Sat
1 stopFrontier
10h 29mMDW-JAX
$145
9/12Thu
1 stopFrontier
5h 27mMDW-JAX
$208
7/14Sun
1 stopFrontier
9h 52mMDW-JAX
$210
6/28Fri
1 stopDelta
6h 23mMDW-JAX
$230
6/15Sat
1 stopFrontier
10h 29mMDW-JAX
$250
6/16Sun
2 stopsAllegiant Air
17h 32mMDW-JAX
$287
7/9Tue
1 stopDelta
7h 34mMDW-JAX
$303
9/12Thu
3 stopsWestJet
27h 23mMDW-JAX
$609

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Last minute flights from Midway to Jacksonville

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 Chicago to Jacksonville that are departing in the next 10 days.
6/13Thu
multi-stopAllegiant Air
17h 42mMDW-JAX
6/16Sun
multi-stopAllegiant Air
19h 58mJAX-MDW
$535
6/12Wed
multi-stopDelta
4h 19mMDW-JAX
6/17Mon
multi-stopDelta
3h 56mJAX-MDW
$678
6/13Thu
multi-stopDelta
4h 33mMDW-JAX
6/16Sun
multi-stopDelta
3h 56mJAX-MDW
$871
6/15Sat
multi-stopDelta
4h 43mMDW-JAX
6/22Sat
multi-stopDelta
8h 10mJAX-MDW
$1,055
6/13Thu
multi-stopDelta
8h 16mMDW-JAX
6/16Sun
multi-stopDelta
5h 36mJAX-MDW
$1,277

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Chicago Midway Airport - Jacksonville Flights

Departure:

Chicago Midway Airport (MDW)United States

Destination:

Jacksonville (JAX)United States

Return flight deals:

Jacksonville - Chicago Midway Airport

Cabin classes: