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Cheap flights from Chicago Midway Airport to Jacksonville from $90

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 7/9. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
1 adult, Economy, 0 bags

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
6:20 pm - 9:45 pm
MDW
-
JAX
2h 25mnonstop
Southwest Logo
11:05 am - 5:55 pm
JAX
-
MDW
7h 50m
1 stop
$227Southwest
Tue, Jul 7 - Tue, Jul 14
Frontier Logo
6:05 am - 5:34 pm
MDW
-
JAX
10h 29m
1 stop
Frontier Logo
6:29 pm - 10:03 pm
JAX
-
MDW
4h 34m
1 stop
$230Frontier
Tue, Aug 4 - Wed, Aug 12
Southwest Logo
7:50 am - 4:55 pm
MDW
-
JAX
8h 05m
2 stops
Southwest Logo
6:50 pm - 8:15 pm
JAX
-
MDW
2h 25mnonstop
$232Southwest
Wed, Jul 1 - Tue, Jul 14
Southwest Logo
5:35 am - 7:35 pm
MDW
-
JAX
13h 00m
1 stop
Southwest Logo
7:25 am - 8:50 am
JAX
-
MDW
2h 25mnonstop
$233Southwest
Wed, Jul 1 - Tue, Jul 14
Frontier Logo
6:05 am - 5:34 pm
MDW
-
JAX
10h 29m
1 stop
Frontier Logo
6:29 pm - 10:03 pm
JAX
-
MDW
4h 34m
1 stop
$236Frontier
Thu, Aug 6 - Tue, Aug 11
Delta Logo
6:00 am - 12:00 pm
MDW
-
JAX
5h 00m
1 stop
Delta Logo
4:14 pm - 10:15 pm
JAX
-
MDW
7h 01m
1 stop
$237Delta
Tue, Jun 30 - Wed, Jul 8
Frontier Logo
12:03 pm - 5:51 pm
MDW
-
JAX
4h 48m
1 stop
Frontier Logo
6:46 pm - 10:58 am
JAX
-
MDW
17h 12m
1 stop
$238Frontier
Thu, Sep 24 - Sun, Sep 27
Frontier Logo
11:06 am - 5:34 pm
MDW
-
JAX
5h 28m
1 stop
Frontier Logo
6:29 pm - 11:12 am
JAX
-
MDW
17h 43m
1 stop
$239Frontier
Thu, Aug 13 - Mon, Aug 17
Southwest Logo
5:55 pm - 9:15 pm
MDW
-
JAX
2h 20mnonstop
Southwest Logo
7:00 am - 8:25 am
JAX
-
MDW
2h 25mnonstop
$240Southwest
Tue, Aug 18 - Mon, Aug 24
Southwest Logo
12:45 pm - 4:00 pm
MDW
-
JAX
2h 15mnonstop
Southwest Logo
5:25 pm - 6:50 pm
JAX
-
MDW
2h 25mnonstop
$241Southwest
Sat, Aug 8 - Tue, Aug 11

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Frontier flights from Chicago Midway Airport to Jacksonville

Our best Frontier deals on Chicago Midway Airport to Jacksonville flight tickets
Frontier
Aug 4
MDW6:05 amChicago Midway
10h 29m
1 stop
JAX5:34 pmJacksonville
Aug 12
JAX6:29 pmJacksonville
4h 34m
1 stop
MDW10:03 pmChicago Midway
$230
Frontier
Aug 6
MDW6:05 amChicago Midway
10h 29m
1 stop
JAX5:34 pmJacksonville
Aug 11
JAX6:29 pmJacksonville
4h 34m
1 stop
MDW10:03 pmChicago Midway
$236
Frontier
Sep 24
MDW12:03 pmChicago Midway
4h 48m
1 stop
JAX5:51 pmJacksonville
Sep 27
JAX6:46 pmJacksonville
17h 12m
1 stop
MDW10:58 amChicago Midway
$238

Southwest flights from Chicago Midway Airport to Jacksonville

Our best Southwest deals on Chicago Midway Airport to Jacksonville flight tickets
Southwest
Jul 7
MDW6:20 pmChicago Midway
2h 25m
JAX9:45 pmJacksonville
Jul 14
JAX11:05 amJacksonville
7h 50m
1 stop
MDW5:55 pmChicago Midway
$227
Southwest
Jul 1
MDW6:20 pmChicago Midway
2h 20m
JAX9:40 pmJacksonville
Jul 15
JAX2:55 pmJacksonville
8h 05m
2 stops
MDW10:00 pmChicago Midway
$232
Southwest
Jul 1
MDW5:35 amChicago Midway
13h 00m
1 stop
JAX7:35 pmJacksonville
Jul 14
JAX7:25 amJacksonville
2h 25m
MDW8:50 amChicago Midway
$233

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 June 13, 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

ChicagoJacksonville

MDW - JAX

MDWJAX

Chicago Midway

Tue 7/7

6:20 pm-9:45 pm

Nonstop2h 25m

Jacksonville

Tue 7/14

11:05 am-5:55 pm

1 stop7h 50m

$227

ChicagoJacksonville

MDW - JAX

MDWJAX

Chicago Midway

Tue 8/4

6:05 am-5:34 pm

1 stop10h 29m

Jacksonville

Wed 8/12

6:29 pm-10:03 pm

1 stop4h 34m

$230

ChicagoJacksonville

MDW - JAX

MDWJAX

Chicago Midway

Wed 7/1

7:50 am-4:55 pm

2 stops8h 05m

Jacksonville

Tue 7/14

6:50 pm-8:15 pm

Nonstop2h 25m

$232

ChicagoJacksonville

MDW - JAX

MDWJAX

Chicago Midway

Wed 7/1

5:35 am-7:35 pm

1 stop13h 00m

Jacksonville

Tue 7/14

7:25 am-8:50 am

Nonstop2h 25m

$233

ChicagoJacksonville

MDW - JAX

MDWJAX

Chicago Midway

Thu 8/6

6:05 am-5:34 pm

1 stop10h 29m

Jacksonville

Tue 8/11

6:29 pm-10:03 pm

1 stop4h 34m

$236

ChicagoJacksonville

MDW - JAX

MDWJAX

Chicago Midway

Tue 6/30

6:00 am-12:00 pm

1 stop5h 00m

Jacksonville

Wed 7/8

4:14 pm-10:15 pm

1 stop7h 01m

$237

ChicagoJacksonville

MDW - JAX

MDWJAX

Chicago Midway

Thu 9/24

12:03 pm-5:51 pm

1 stop4h 48m

Jacksonville

Sun 9/27

6:46 pm-10:58 am

1 stop17h 12m

$238

ChicagoJacksonville

MDW - JAX

MDWJAX

Chicago Midway

Thu 8/13

11:06 am-5:34 pm

1 stop5h 28m

Jacksonville

Mon 8/17

6:29 pm-11:12 am

1 stop17h 43m

$239

ChicagoJacksonville

MDW - JAX

MDWJAX

Chicago Midway

Tue 8/18

5:55 pm-9:15 pm

Nonstop2h 20m

Jacksonville

Mon 8/24

7:00 am-8:25 am

Nonstop2h 25m

$240
Quickest round-trip

ChicagoJacksonville

MDW - JAX

MDWJAX

Chicago Midway

Sat 8/8

12:45 pm-4:00 pm

Nonstop2h 15m

Jacksonville

Tue 8/11

5:25 pm-6:50 pm

Nonstop2h 25m

$241

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 March is also very affordable. Most momondo users find prices during this month for around $238.

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 $340. 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 $390.

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 $337 when looking at flights departing at noon. Flights to Jacksonville are more costly in the evening, with an average ticket price of $370. 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 Airport to Jacksonville flights?

There is only 1 cabin class available to choose from on Chicago Midway Airport 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?

No. A direct flight is the cheapest option for a flight between Chicago Midway Airport to Jacksonville.

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

$148

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 $148. The best round-trip flight deal from Chicago Midway Airport to Jacksonville found on momondo in the last 72 hours is $290.
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
7.9
4,234 reviews
Search Southwest flights

  • Southwest Flights From Chicago Midway Airport to Jacksonville

    Southwest flies from Chicago Midway Airport to Jacksonville around 7 times per week, with 4,234 momondo users rating the airline 7.9/10. 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 $357 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
Waycross
Ponte Vedra Beach
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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