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Cheap flights from Jacksonville to Chicago Midway Airport from $73

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Jacksonville to Chicago Midway Airport departing on 1/6. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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Find the cheapest flights from Jacksonville to Chicago

Cheap round-trip flights

These are some of the best round-trip flight deals from Jacksonville to Chicago that have been recently found on momondo from popular airlines, departing in the coming months.

Cheap one-way flights

Flying one-way? These are some of the best deals recently discovered on momondo for flights from Jacksonville to Chicago.

Cheap last minute flights

Planning a quick getaway from Jacksonville to Chicago? These are the last-minute flight deals available now.

Cheap direct flights

If you prefer a non-stop journey, check out our latest direct flight deals to Chicago, so you can enjoy a seamless trip without layovers.

Cheap bus & train deals from Jacksonville to Chicago

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

All round-trip flight deals to Chicago

The cheapest plane tickets to Chicago found on KAYAK recently.
5:59 pm - 12:20 amJAX-MDW
7h 21m1 stop
8:15 am - 4:59 pmMDW-JAX
7h 44m1 stop
$148Frontier
Find Deal
Fri, Dec 6 - Mon, Dec 16
5:59 pm - 12:20 amJAX-MDW
7h 21m1 stop
8:15 am - 4:59 pmMDW-JAX
7h 44m1 stop
$195Frontier
Find Deal
Fri, Dec 6 - Mon, Dec 9
6:57 pm - 10:20 pmJAX-MDW
4h 23m1 stop
6:00 am - 12:54 pmMDW-JAX
5h 54m1 stop
$236Delta
Find Deal
Wed, Jan 15 - Sun, Jan 19
4:20 pm - 6:00 pmJAX-MDW
2h 40mnonstop
12:45 pm - 4:00 pmMDW-JAX
2h 15mnonstop
$243Southwest
Find Deal
Mon, Feb 10 - Wed, Feb 26
5:35 am - 10:12 amJAX-MDW
5h 37m1 stop
6:00 am - 12:54 pmMDW-JAX
5h 54m1 stop
$246Delta
Find Deal
Thu, Jan 23 - Sun, Jan 26
4:35 pm - 6:15 pmJAX-MDW
2h 40mnonstop
12:45 pm - 4:00 pmMDW-JAX
2h 15mnonstop
$253Southwest
Find Deal
Wed, Jan 15 - Sun, Jan 19
12:23 pm - 6:14 pmJAX-MDW
6h 51m1 stop
6:00 am - 12:54 pmMDW-JAX
5h 54m1 stop
$256Delta
Find Deal
Thu, Jan 23 - Sun, Jan 26
6:33 pm - 12:46 pmJAX-MDW
19h 13m3 stops
1:26 pm - 5:03 pmMDW-JAX
26h 37m3 stops
$941WestJet
Find Deal
Thu, Jan 9 - Sun, Jan 12
9:34 am - 8:30 amJAX-MDW
23h 56m2 stops
2:15 pm - 11:38 amMDW-JAX
20h 23m3 stops
$1,618
Find Deal
Thu, Dec 5 - Sun, Dec 8
2:47 pm - 11:08 amJAX-MDW
21h 21m3 stops
11:48 am - 5:15 pmMDW-JAX
28h 27m3 stops
$2,304WestJet
Find Deal
Thu, Dec 19 - Sun, Dec 22
4:33 pm - 9:04 pmJAX-MDW
5h 31m1 stop
$73Frontier
Find Deal
Mon, Jan 6
7:50 pm - 6:39 amJAX-MDW
11h 49m1 stop
$80Frontier
Find Deal
Sat, Dec 21
4:35 pm - 6:15 pmJAX-MDW
2h 40mnonstop
$99Southwest
Find Deal
Tue, Jan 14
12:23 pm - 6:14 pmJAX-MDW
6h 51m1 stop
$108Delta
Find Deal
Tue, Jan 14
4:35 pm - 6:15 pmJAX-MDW
2h 40mnonstop
$109Southwest
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Thu, Jan 9
5:35 am - 10:12 amJAX-MDW
5h 37m1 stop
$118Delta
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Thu, Jan 30
8:34 pm - 8:45 amJAX-MDW
37h 11m3 stops
Mon, Feb 10
9:31 am - 5:32 pmJAX-MDW
33h 01m3 stops
Wed, Feb 12
6:33 pm - 12:46 pmJAX-MDW
19h 13m3 stops
$485WestJet
Find Deal
Tue, Jan 14
6:33 pm - 12:46 pmJAX-MDW
19h 13m3 stops
$486WestJet
Find Deal
Wed, Jan 8
10:31 am - 5:56 pmJAX-MDW
8h 25m1 stop
10:28 am - 6:27 pmMDW-JAX
6h 59m1 stop
$547Frontier
Find Deal
Sun, Nov 24 - Thu, Nov 28
10:13 am - 9:59 pmJAX-MDW
12h 46m1 stop
8:18 am - 2:45 pmMDW-JAX
5h 27m1 stop
$688Frontier
Find Deal
Mon, Nov 25 - Sat, Nov 30
5:55 pm - 7:25 pmJAX-MDW
2h 30mnonstop
6:10 am - 4:40 pmMDW-JAX
9h 30m1 stop
$712Southwest
Find Deal
Sun, Nov 24 - Thu, Nov 28
5:55 am - 9:05 amJAX-MDW
4h 10m1 stop
6:45 am - 5:30 pmMDW-JAX
9h 45m2 stops
$726Southwest
Find Deal
Sun, Nov 24 - Thu, Nov 28
5:55 am - 1:40 pmJAX-MDW
8h 45m2 stops
6:00 am - 5:30 pmMDW-JAX
10h 30m2 stops
$731Southwest
Find Deal
Sun, Nov 24 - Thu, Nov 28
9:57 am - 1:53 pmJAX-MDW
4h 56m1 stop
9:31 am - 5:23 pmMDW-JAX
6h 52m1 stop
$911Delta
Find Deal
Sat, Nov 23 - Sat, Nov 30
5:55 pm - 7:25 pmJAX-MDW
2h 30mnonstop
1:45 pm - 5:00 pmMDW-JAX
2h 15mnonstop
$998Southwest
Find Deal
Thu, Nov 21 - Sun, Nov 24
7:10 am - 11:58 amJAX-MDW
5h 48m1 stop
12:43 pm - 5:26 pmMDW-JAX
3h 43m1 stop
$1,016Delta
Find Deal
Thu, Nov 21 - Sun, Nov 24
8:25 am - 1:53 pmJAX-MDW
6h 28m1 stop
3:19 pm - 8:58 pmMDW-JAX
4h 39m1 stop
$1,171Delta
Find Deal
Sat, Nov 23 - Wed, Nov 27
11:18 am - 5:02 pmJAX-MDW
6h 44m2 stops
6:00 am - 12:10 pmMDW-JAX
5h 10m1 stop
$1,393Delta
Find Deal
Mon, Nov 25 - Sat, Nov 30
4:20 pm - 6:00 pmJAX-MDW
2h 40mnonstop
12:45 pm - 4:00 pmMDW-JAX
2h 15mnonstop
$243Southwest
Find Deal
Mon, Feb 10 - Wed, Feb 26
4:35 pm - 6:15 pmJAX-MDW
2h 40mnonstop
12:45 pm - 4:00 pmMDW-JAX
2h 15mnonstop
$253Southwest
Find Deal
Wed, Jan 15 - Sun, Jan 19
7:00 am - 8:30 amJAX-MDW
2h 30mnonstop
1:15 pm - 4:30 pmMDW-JAX
2h 15mnonstop
$263Southwest
Find Deal
Sat, Feb 15 - Sun, Feb 16
4:35 pm - 6:15 pmJAX-MDW
2h 40mnonstop
9:00 am - 12:15 pmMDW-JAX
2h 15mnonstop
$308Southwest
Find Deal
Mon, Jan 13 - Fri, Jan 17
5:55 pm - 7:25 pmJAX-MDW
2h 30mnonstop
12:45 pm - 4:00 pmMDW-JAX
2h 15mnonstop
$341Southwest
Find Deal
Fri, Jan 3 - Wed, Jan 8
4:35 pm - 6:05 pmJAX-MDW
2h 30mnonstop
12:35 pm - 3:50 pmMDW-JAX
2h 15mnonstop
$350Southwest
Find Deal
Fri, Dec 6 - Mon, Dec 16
11:35 am - 1:10 pmJAX-MDW
2h 35mnonstop
5:00 pm - 8:15 pmMDW-JAX
2h 15mnonstop
$418Southwest
Find Deal
Fri, Mar 14 - Mon, Mar 17
4:35 pm - 6:05 pmJAX-MDW
2h 30mnonstop
12:35 pm - 3:50 pmMDW-JAX
2h 15mnonstop
$440Southwest
Find Deal
Thu, Dec 5 - Thu, Dec 12
5:55 pm - 7:25 pmJAX-MDW
2h 30mnonstop
9:50 am - 1:05 pmMDW-JAX
2h 15mnonstop
$443Southwest
Find Deal
Thu, Dec 19 - Sun, Dec 22
5:55 pm - 7:25 pmJAX-MDW
2h 30mnonstop
9:50 am - 1:05 pmMDW-JAX
2h 15mnonstop
$474Southwest
Find Deal
Thu, Dec 19 - Sun, Dec 22

Delta flights from Jacksonville to Chicago Midway Airport

Our best Delta deals on Jacksonville to Chicago Midway Airport flight tickets
Delta
Jan 15
JAX6:57 pmJacksonville
4h 23m
1 stop
MDW10:20 pmChicago Midway
Jan 19
MDW6:00 amChicago Midway
5h 54m
1 stop
JAX12:54 pmJacksonville
Delta
Jan 23
JAX5:35 amJacksonville
5h 37m
1 stop
MDW10:12 amChicago Midway
Jan 26
MDW6:00 amChicago Midway
5h 54m
1 stop
JAX12:54 pmJacksonville
Delta
Jan 23
JAX12:23 pmJacksonville
6h 51m
1 stop
MDW6:14 pmChicago Midway
Jan 26
MDW6:00 amChicago Midway
5h 54m
1 stop
JAX12:54 pmJacksonville

Frontier flights from Jacksonville to Chicago Midway Airport

Our best Frontier deals on Jacksonville to Chicago Midway Airport flight tickets
Frontier
Dec 6
JAX5:59 pmJacksonville
7h 21m
1 stop
MDW12:20 amChicago Midway
Dec 16
MDW8:15 amChicago Midway
7h 44m
1 stop
JAX4:59 pmJacksonville
Frontier
Dec 6
JAX5:59 pmJacksonville
7h 21m
1 stop
MDW12:20 amChicago Midway
Dec 9
MDW8:15 amChicago Midway
7h 44m
1 stop
JAX4:59 pmJacksonville
Frontier
Dec 5
JAX11:36 amJacksonville
7h 36m
1 stop
MDW6:12 pmChicago Midway
Dec 9
MDW8:15 amChicago Midway
7h 44m
1 stop
JAX4:59 pmJacksonville

See travel insights to Chicago from

How to get the cheapest flight ticket from Jacksonville to Chicago Midway Airport

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

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

May. The cheapest time of year to fly to Chicago Midway Airport from Jacksonville is May. Most expensive is November

What is the cheapest day to depart Jacksonville for Chicago Midway Airport?

Wednesday. The cheapest day of the week is typically Wednesday. The most expensive is typically Sunday

When is the cheapest time to fly from Jacksonville to Chicago Midway Airport?

At noon. Jacksonville to Chicago Midway Airport flights are approximately 22% more expensive in the afternoon than at noon

Can stopping save me money on Jacksonville to Chicago Midway Airport flights?

You could potentially save up to 35% on your flight if you consider stops on a Jacksonville to Chicago Midway Airport flight.

How have Jacksonville to Chicago Midway Airport flight prices changed over time?


When to book flights from Jacksonville to Chicago Midway Airport

Are you open to changing your travel dates? Check out the ideal times to fly from Jacksonville to Chicago Midway Airport according to our flight data. Find out which month and days have the cheapest flights.
Estimated round-trip price

Cheap Jacksonville to Chicago Midway Airport (JAX to MDW) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Jacksonville to Chicago Midway Airport

Best Price Found

$73

Fastest flight time

2h 25m

Direct flights

Every day
The best one-way flight to Chicago Midway Airport from Jacksonville in the past 72 hours is $73. The best round-trip flight deal from Jacksonville to Chicago Midway Airport found on momondo in the last 72 hours is $148.
The fastest flight from Jacksonville to Chicago Midway Airport takes 2h 25m
Direct flights go from Jacksonville to Chicago Midway Airport every day.

  • How far is Jacksonville to Chicago Midway by plane?

    A flight from Jacksonville to Chicago Midway will travel around 860.2 mi. A reasonable flight in good conditions will take 2h 25m.

  • When did momondo last update prices for flights from Jacksonville Airport to Chicago Midway Airport?

    Prices for flights from Jacksonville Airport to Chicago Midway Airport were last updated today.

  • How many operators does momondo search for flights from Jacksonville Airport to Chicago Midway Airport?

  • How old do you have to be to fly from Jacksonville Airport to Chicago Midway Airport?

    Although the minimum age for a child to fly alone is five, airlines that offer an unaccompanied minor (UMNR) service may have their own age limits, which could be impacted by factors such as flight length, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Jacksonville Airport to Chicago Midway Airport.

  • What documentation or ID do you need to fly to Chicago Midway Airport?

    The travel and health documents required for your trip to Chicago Midway Airport can vary based on your itinerary and personal situation. As a rule, consider having multiple documents such as a national ID card or driver’s license, and a passport valid for six-months after you plan to arrive at Chicago Midway Airport. We always recommend checking with your airline or a trusted third party such as IATA to get advice.

  • What is the most popular plane model from Jacksonville to Chicago Midway Airport?

  • What is the most popular airline from Jacksonville to Chicago Midway Airport?


Best airlines flying from Jacksonville to Chicago Midway Airport

Compare and see reviews for airlines that fly from Jacksonville to Chicago Midway Airport with momondo
Airline
Rating
Free Cancellation
Price
FrontierPriceFrom $143Free CancellationRating
6.1
3,539 reviews
Search Frontier flights
DeltaPriceFrom $251Free CancellationRating
8.0
8,759 reviews
Search Delta flights
SouthwestPriceFrom $268Free CancellationRating
8.1
5,015 reviews
Search Southwest flights
  • Southwest Flights From Jacksonville to Chicago Midway Airport

    Southwest flight deals from Jacksonville to Chicago Midway Airport start from $268 round-trip. Over the 4 Southwest flights for this route in a normal week, average airfare is usually $439 round-trip - but some users have found much cheaper deals with momondo.


Why use momondo?

Why should I use momondo to find a flight deal from Jacksonville to Chicago?

Finding the right flight to Chicago from Jacksonville is quick and easy when you have a range of options in front of you, from reputable agents and recognisable airlines. Options that can then be filtered down to find the best fit. That is what momondo does. We make finding flights to Chicago quick and easy, saving you time and money.

Can I find flights from Jacksonville to Chicago with flexible booking policies on momondo?

Flights from Jacksonville to Chicago with flexible booking policies can be found by using the search form above and then selecting our dedicated flexible booking filter, which will highlight only the flights where this policy is applied.

How can momondo help me find flights from Jacksonville to Chicago?

Once all potential Jacksonville to Chicago flight options are in front of you, momondo lets you sort and filter flights based on preferences such as airline, price and flight times amongst many other options.

I’m not ready to book a flight from Jacksonville to Chicago right now. Can momondo alert me if prices change?

Price alerts on flights to Chicago from Jacksonville are quick and easy to set up on momondo. Simply perform a search and select the price alert feature. It is as simple as that.


An easier way to manage your Chicago Midway Airport trip

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