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Cheap flights from Chicago Midway Airport to Jacksonville from $80

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Chicago Midway Airport to Jacksonville departing on 11/16. 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 Chicago Midway Airport to Jacksonville

Cheap round-trip flights

Enter your travel dates to find the best prices.
Multiple Airlines Logo
6:20 am - 5:10 pmMDW-JAX
9h 50m1 stop
Multiple Airlines Logo
9:38 am - 8:32 amJAX-MDW
47h 54m2 stops
$270Multiple Airlines
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Sun, Oct 26 - Wed, Oct 29
Delta Logo
6:00 am - 1:42 pmMDW-JAX
6h 42m1 stop
Delta Logo
11:47 am - 4:43 pmJAX-MDW
5h 56m1 stop
$276Delta
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Mon, Nov 24 - Wed, Dec 3
Southwest Logo
5:35 pm - 8:45 pmMDW-JAX
2h 10mnonstop
Southwest Logo
5:00 pm - 6:25 pmJAX-MDW
2h 25mnonstop
$281Southwest
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Fri, Oct 31 - Mon, Nov 3
Delta Logo
6:00 am - 12:02 pmMDW-JAX
5h 02m1 stop
Delta Logo
1:14 pm - 4:18 pmJAX-MDW
4h 04m1 stop
$286Delta
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Mon, Nov 24 - Tue, Dec 2
Delta Logo
10:47 am - 4:23 pmMDW-JAX
4h 36m1 stop
Delta Logo
6:10 am - 9:54 amJAX-MDW
4h 44m1 stop
$287Delta
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Thu, Nov 27 - Thu, Dec 4
Southwest Logo
11:05 am - 2:20 pmMDW-JAX
2h 15mnonstop
Southwest Logo
5:00 pm - 6:25 pmJAX-MDW
2h 25mnonstop
$288Southwest
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Mon, Nov 10 - Tue, Nov 11
Southwest Logo
5:35 pm - 8:45 pmMDW-JAX
2h 10mnonstop
Southwest Logo
7:00 am - 1:45 pmJAX-MDW
7h 45m1 stop
$291Southwest
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Fri, Oct 31 - Mon, Nov 3
Multiple Airlines Logo
6:06 pm - 8:58 amMDW-JAX
37h 52m2 stops
Multiple Airlines Logo
5:18 pm - 6:39 pmJAX-MDW
26h 21m1 stop
$292Multiple Airlines
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Mon, Nov 3 - Sun, Nov 9
Frontier Logo
5:30 am - 8:49 pmMDW-JAX
14h 19m1 stop
Frontier Logo
11:19 am - 7:42 pmJAX-MDW
9h 23m1 stop
$325Frontier
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Mon, Dec 1 - Fri, Dec 5
Frontier Logo
4:03 pm - 10:04 amMDW-JAX
17h 01m1 stop
Frontier Logo
9:28 pm - 7:42 pmJAX-MDW
23h 14m2 stops
$327Frontier
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Tue, Nov 25 - Thu, Dec 4

Southwest flights from Chicago Midway Airport to Jacksonville

Our best Southwest deals on Chicago Midway Airport to Jacksonville flight tickets
Southwest
Oct 31
MDW5:35 pmChicago Midway
2h 10m
JAX8:45 pmJacksonville
Nov 3
JAX5:00 pmJacksonville
2h 25m
MDW6:25 pmChicago Midway
$281
Find similar
Southwest
Nov 10
MDW11:05 amChicago Midway
2h 15m
JAX2:20 pmJacksonville
Nov 11
JAX5:00 pmJacksonville
2h 25m
MDW6:25 pmChicago Midway
$288
Find similar
Southwest
Oct 31
MDW5:35 pmChicago Midway
2h 10m
JAX8:45 pmJacksonville
Nov 3
JAX7:00 amJacksonville
7h 45m
1 stop
MDW1:45 pmChicago Midway
$291
Find similar

Delta flights from Chicago Midway Airport to Jacksonville

Our best Delta deals on Chicago Midway Airport to Jacksonville flight tickets
Delta
Nov 24
MDW6:00 amChicago Midway
6h 42m
1 stop
JAX1:42 pmJacksonville
Dec 3
JAX11:47 amJacksonville
5h 56m
1 stop
MDW4:43 pmChicago Midway
$276
Find similar
Delta
Nov 24
MDW6:00 amChicago Midway
5h 02m
1 stop
JAX12:02 pmJacksonville
Dec 2
JAX1:14 pmJacksonville
4h 04m
1 stop
MDW4:18 pmChicago Midway
$286
Find similar
Delta
Nov 27
MDW10:47 amChicago Midway
4h 36m
1 stop
JAX4:23 pmJacksonville
Dec 4
JAX6:10 amJacksonville
4h 44m
1 stop
MDW9:54 amChicago Midway
$287
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momondo Fare Finder

 
Customize your flight search to find flights from Chicago Midway Airport to Jacksonville that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, momondo users made 832,500 searches. Data last updated October 14, 2025.
Use the filters below to find and compare flights from Chicago Midway Airport to Jacksonville that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

ChicagoJacksonville

MDW - JAX

MDWJAX

Chicago Midway

Sun 10/26

6:20 am-5:10 pm

1 stop9h 50m

Jacksonville

Wed 10/29

9:38 am-8:32 am

2 stops47h 54m

$270

ChicagoJacksonville

MDW - JAX

MDWJAX

Chicago Midway

Mon 11/24

6:00 am-1:42 pm

1 stop6h 42m

Jacksonville

Wed 12/3

11:47 am-4:43 pm

1 stop5h 56m

$276

ChicagoJacksonville

MDW - JAX

MDWJAX

Chicago Midway

Fri 10/31

5:35 pm-8:45 pm

Nonstop2h 10m

Jacksonville

Mon 11/3

5:00 pm-6:25 pm

Nonstop2h 25m

$281

ChicagoJacksonville

MDW - JAX

MDWJAX

Chicago Midway

Mon 11/24

6:00 am-12:02 pm

1 stop5h 02m

Jacksonville

Tue 12/2

1:14 pm-4:18 pm

1 stop4h 04m

$286

ChicagoJacksonville

MDW - JAX

MDWJAX

Chicago Midway

Thu 11/27

10:47 am-4:23 pm

1 stop4h 36m

Jacksonville

Thu 12/4

6:10 am-9:54 am

1 stop4h 44m

$287

ChicagoJacksonville

MDW - JAX

MDWJAX

Chicago Midway

Mon 11/10

11:05 am-2:20 pm

Nonstop2h 15m

Jacksonville

Tue 11/11

5:00 pm-6:25 pm

Nonstop2h 25m

$288

ChicagoJacksonville

MDW - JAX

MDWJAX

Chicago Midway

Fri 10/31

5:35 pm-8:45 pm

Nonstop2h 10m

Jacksonville

Mon 11/3

7:00 am-1:45 pm

1 stop7h 45m

$291

ChicagoJacksonville

MDW - JAX

MDWJAX

Chicago Midway

Mon 11/3

6:06 pm-8:58 am

2 stops37h 52m

Jacksonville

Sun 11/9

5:18 pm-6:39 pm

1 stop26h 21m

$292

ChicagoJacksonville

MDW - JAX

MDWJAX

Chicago Midway

Mon 12/1

5:30 am-8:49 pm

1 stop14h 19m

Jacksonville

Fri 12/5

11:19 am-7:42 pm

1 stop9h 23m

$325

ChicagoJacksonville

MDW - JAX

MDWJAX

Chicago Midway

Tue 11/25

4:03 pm-10:04 am

1 stop17h 01m

Jacksonville

Thu 12/4

9:28 pm-7:42 pm

2 stops23h 14m

$327

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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See travel insights to Jacksonville from

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

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 typical price of a round-trip flight between Chicago Midway Airport and Jacksonville?

What is the cheapest month to fly to Jacksonville?

If you are unable to visit Jacksonville during the month of August, then departing from Chicago Midway Airport during the month September is also very affordable. Most momondo users find prices during this month for around $257.

What is the cheapest day to depart on your flight to Jacksonville?

According to our data, Wednesday is the cheapest day to fly to Jacksonville from Chicago Midway Airport. The lowest ticket price found for a Wednesday departure recently was $372. Keep in mind that prices can always vary depending on your route and whether or not you are flying domestic or international. On the other hand, Sunday is the most expensive day to depart from Chicago Midway Airport because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $425.

What is the cheapest time of day to depart on your flight to Jacksonville?

Flying to Jacksonville from Chicago Midway Airport at noon is the least expensive time of day to depart. momondo users have found prices as low as $328 when looking at flights departing at noon. Flights to Jacksonville are more costly in the evening, with an average ticket price of $414. Departure times in the evening fall within the peak daily travel times, which is why tickets can be more expensive.

What is the cheapest Chicago Midway to Jacksonville flight route?

Fly from Chicago Midway to Jacksonville for the best Chicago Midway - Jacksonville flight prices

What cabin class options are available on Chicago Midway to Jacksonville flights?

There is only 1 cabin class available to choose from on Chicago Midway to Jacksonville flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

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

You could potentially save up to 13% on your flight if you consider stops on a Chicago Midway Airport to Jacksonville flight.

When to book flights from Chicago Midway Airport to Jacksonville

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

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

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

Best Price Found

$164

Fastest flight time

2h 10m

Direct flights

Every day

Airports in Jacksonville

1 airport
The best one-way flight to Jacksonville from Chicago Midway Airport in the past 72 hours is $164. The best round-trip flight deal from Chicago Midway Airport to Jacksonville found on momondo in the last 72 hours is $288.
The fastest flight from Chicago Midway Airport to Jacksonville takes 2h 10m
Direct flights go from Chicago Midway Airport to Jacksonville every day.
There is 1 airport near Jacksonville: Jacksonville (JAX)
Search flight deals

  • How far is Chicago Midway to Jacksonville by plane?

    Jacksonville is 860.2 mi away from Chicago Midway. Flights usually cover this in 2h 10m, depending on flying conditions and air traffic around both airports.

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

    Prices for flights from Chicago Midway Airport to Jacksonville Airport are updated daily.

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

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

    The minimum age for a child to fly alone is five, but airlines that offer an unaccompanied minor (UNMR) service may have their own age limitations. Flight duration, scheduling, and layovers are among the considerations that may influence age limits. We recommend that you double-check with the airline you are booking with for travel from Chicago Midway Airport to Jacksonville Airport.

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

    The necessary travel and health documents for your Jacksonville Airport trip may vary depending on your travel plans and individual circumstances. Generally, you should have various documents, such as a national ID card or driver's license and a passport that is valid for six months beyond your scheduled arrival date. We recommend seeking advice from your airline or a trusted third party, such as IATA.

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

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

Best airlines flying from Chicago Midway Airport to Jacksonville

Compare and see reviews for airlines that fly from Chicago Midway Airport to Jacksonville with momondo
Airline
Rating
Free Cancellation
Price
SouthwestPriceFrom $203Free CancellationRating
8.0
4,238 reviews
Search Southwest flights

  • Southwest Flights From Chicago Midway Airport to Jacksonville

    Southwest flies from Chicago Midway Airport to Jacksonville around 5 times per week, with 4,238 momondo users rating the airline 8.0/10. The cheapest Southwest deal from Chicago Midway Airport to Jacksonville in the last 72 hours was $203 (round-trip), much lower than the average airfare cost of $390 for Southwest flights on this route.

Traveling to a place near Jacksonville?

Book flights to Jacksonville if you plan to visit one of these locations
Fernandina Beach
Jacksonville Beach
Orange Park
Ponte Vedra Beach
Kingsland
Waycross
Atlantic Beach
Neptune Beach
St Johns
Yulee
Cumberland Island

Why use momondo?

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

momondo collates all your flight options in one place and lets you filter them to find the perfect flight from Chicago to Jacksonville. momondo saves you time and could save you money on your trip.

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

Flights from Chicago to Jacksonville 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 Chicago to Jacksonville?

Once all potential Chicago to Jacksonville 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 Chicago to Jacksonville right now. Can momondo alert me if prices change?

Price alerts on flights to Jacksonville from Chicago 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.

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