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Cheap flights from Chicago Midway Airport to Jacksonville from $114

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 6/3. 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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0 bags

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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.
Southwest Logo
6:50 pm - 10:05 pm
MDW
-
JAX
2h 15mnonstop
Southwest Logo
7:10 pm - 10:15 pm
JAX
-
MDW
4h 05m
1 stop
$252Southwest
Mon, May 11 - Tue, May 19
Frontier Logo
6:00 am - 5:35 pm
MDW
-
JAX
10h 35m
1 stop
Frontier Logo
6:30 pm - 11:09 am
JAX
-
MDW
17h 39m
1 stop
$255Frontier
Thu, May 28 - Thu, Jun 4
Southwest Logo
6:50 pm - 10:05 pm
MDW
-
JAX
2h 15mnonstop
Southwest Logo
11:50 am - 7:45 pm
JAX
-
MDW
8h 55m
2 stops
$257Southwest
Mon, May 11 - Tue, May 19
Southwest Logo
6:50 pm - 10:05 pm
MDW
-
JAX
2h 15mnonstop
Southwest Logo
1:15 pm - 8:00 pm
JAX
-
MDW
7h 45m
1 stop
$258Southwest
Mon, May 11 - Wed, May 20
Frontier Logo
12:04 pm - 5:35 pm
MDW
-
JAX
4h 31m
1 stop
Frontier Logo
6:30 pm - 10:02 pm
JAX
-
MDW
4h 32m
1 stop
$260Frontier
Fri, May 15 - Mon, May 18
Multiple Airlines Logo
2:48 pm - 4:14 pm
MDW
-
JAX
24h 26m
2 stops
Multiple Airlines Logo
6:28 pm - 11:12 am
JAX
-
MDW
17h 44m
1 stop
$261Multiple Airlines
Thu, Jul 16 - Mon, Jul 20
Southwest Logo
12:50 pm - 8:45 pm
MDW
-
JAX
6h 55m
2 stops
Southwest Logo
7:35 am - 1:10 pm
JAX
-
MDW
6h 35m
1 stop
$262Southwest
Wed, May 6 - Sat, May 9
Delta Logo
10:41 am - 5:53 pm
MDW
-
JAX
6h 12m
1 stop
Delta Logo
6:59 pm - 10:28 pm
JAX
-
MDW
4h 29m
1 stop
$265Delta
Tue, Apr 28 - Sat, May 2
Multiple Airlines Logo
12:04 pm - 5:35 pm
MDW
-
JAX
4h 31m
1 stop
Multiple Airlines Logo
9:03 pm - 10:02 pm
JAX
-
MDW
25h 59m
2 stops
$266Multiple Airlines
Fri, May 29 - Sun, May 31
Southwest Logo
12:50 pm - 8:45 pm
MDW
-
JAX
6h 55m
2 stops
Southwest Logo
5:45 am - 12:10 pm
JAX
-
MDW
7h 25m
2 stops
$267Southwest
Wed, May 6 - Sat, May 9

Southwest flights from Chicago Midway Airport to Jacksonville

Our best Southwest deals on Chicago Midway Airport to Jacksonville flight tickets
Southwest
May 11
MDW6:50 pmChicago Midway
2h 15m
JAX10:05 pmJacksonville
May 19
JAX7:10 pmJacksonville
4h 05m
1 stop
MDW10:15 pmChicago Midway
$252
Southwest
May 11
MDW6:50 pmChicago Midway
2h 15m
JAX10:05 pmJacksonville
May 19
JAX11:50 amJacksonville
8h 55m
2 stops
MDW7:45 pmChicago Midway
$257
Southwest
May 11
MDW6:50 pmChicago Midway
2h 15m
JAX10:05 pmJacksonville
May 20
JAX1:15 pmJacksonville
7h 45m
1 stop
MDW8:00 pmChicago Midway
$258

Frontier flights from Chicago Midway Airport to Jacksonville

Our best Frontier deals on Chicago Midway Airport to Jacksonville flight tickets
Frontier
May 28
MDW6:00 amChicago Midway
10h 35m
1 stop
JAX5:35 pmJacksonville
Jun 4
JAX6:30 pmJacksonville
17h 39m
1 stop
MDW11:09 amChicago Midway
$255
Frontier
May 15
MDW12:04 pmChicago Midway
4h 31m
1 stop
JAX5:35 pmJacksonville
May 18
JAX6:30 pmJacksonville
4h 32m
1 stop
MDW10:02 pmChicago Midway
$260
Frontier
May 8
MDW12:04 pmChicago Midway
4h 31m
1 stop
JAX5:35 pmJacksonville
May 11
JAX6:30 pmJacksonville
4h 32m
1 stop
MDW10:02 pmChicago Midway
$270

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 April 18, 2026.
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

Cheapest round-trip
Quickest round-trip

ChicagoJacksonville

MDW - JAX

MDWJAX

Chicago Midway

Mon 5/11

6:50 pm-10:05 pm

Nonstop2h 15m

Jacksonville

Tue 5/19

7:10 pm-10:15 pm

1 stop4h 05m

$252

ChicagoJacksonville

MDW - JAX

MDWJAX

Chicago Midway

Thu 5/28

6:00 am-5:35 pm

1 stop10h 35m

Jacksonville

Thu 6/4

6:30 pm-11:09 am

1 stop17h 39m

$255

ChicagoJacksonville

MDW - JAX

MDWJAX

Chicago Midway

Mon 5/11

6:50 pm-10:05 pm

Nonstop2h 15m

Jacksonville

Tue 5/19

11:50 am-7:45 pm

2 stops8h 55m

$257

ChicagoJacksonville

MDW - JAX

MDWJAX

Chicago Midway

Mon 5/11

6:50 pm-10:05 pm

Nonstop2h 15m

Jacksonville

Wed 5/20

1:15 pm-8:00 pm

1 stop7h 45m

$258

ChicagoJacksonville

MDW - JAX

MDWJAX

Chicago Midway

Fri 5/15

12:04 pm-5:35 pm

1 stop4h 31m

Jacksonville

Mon 5/18

6:30 pm-10:02 pm

1 stop4h 32m

$260

ChicagoJacksonville

MDW - JAX

MDWJAX

Chicago Midway

Thu 7/16

2:48 pm-4:14 pm

2 stops24h 26m

Jacksonville

Mon 7/20

6:28 pm-11:12 am

1 stop17h 44m

$261

ChicagoJacksonville

MDW - JAX

MDWJAX

Chicago Midway

Wed 5/6

12:50 pm-8:45 pm

2 stops6h 55m

Jacksonville

Sat 5/9

7:35 am-1:10 pm

1 stop6h 35m

$262

ChicagoJacksonville

MDW - JAX

MDWJAX

Chicago Midway

Tue 4/28

10:41 am-5:53 pm

1 stop6h 12m

Jacksonville

Sat 5/2

6:59 pm-10:28 pm

1 stop4h 29m

$265

ChicagoJacksonville

MDW - JAX

MDWJAX

Chicago Midway

Fri 5/29

12:04 pm-5:35 pm

1 stop4h 31m

Jacksonville

Sun 5/31

9:03 pm-10:02 pm

2 stops25h 59m

$266

ChicagoJacksonville

MDW - JAX

MDWJAX

Chicago Midway

Wed 5/6

12:50 pm-8:45 pm

2 stops6h 55m

Jacksonville

Sat 5/9

5:45 am-12:10 pm

2 stops7h 25m

$267

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 March, 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, Saturday is the cheapest day to fly to Jacksonville from Chicago Midway Airport. The lowest ticket price found for a Saturday departure recently was $336. 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 $389.

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 $352 when looking at flights departing at noon. Flights to Jacksonville are more costly in the evening, with an average ticket price of $369. 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 15% on your flight if you consider stops on a Chicago Midway Airport to Jacksonville flight.

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

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

$170

Fastest flight time

2h 15m

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 $170. The best round-trip flight deal from Chicago Midway Airport to Jacksonville found on momondo in the last 72 hours is $300.
The fastest flight from Chicago Midway Airport to Jacksonville takes 2h 15m
Direct flights go from Chicago Midway Airport to Jacksonville every day.
There is 1 airport in Jacksonville. From Chicago Midway Airport there are direct flights to Jacksonville (JAX).
Search flight deals

Frequently asked questions about flying from Chicago Midway Airport to Jacksonville

  • How far is Chicago Midway to Jacksonville by plane?

    Jacksonville is 860.2 mi away from Chicago Midway. Flights usually cover this in 2h 15m, 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
4,330 reviews
Search Southwest flights

  • Southwest Flights From Chicago Midway Airport to Jacksonville

    Southwest flies from Chicago Midway Airport to Jacksonville around 4 times per week, with 4,330 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 $345 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
Kingsland
Ponte Vedra Beach
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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