Latest deals
Insights
When to book
FAQs
Reviews
Price Alerts

Cheap flights from Chicago Midway Airport to Jacksonville from $86

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 4/20. 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
0 bags

Save money when you book flights with momondo

Big names and deals

Big names and deals

Search 100s of travel sites to compare prices.

Filter for what you want

Filter for what you want

Free Wi-Fi? Stopover? Instantly customize your results.

Trusted and free

Trusted and free

We’re completely free to use - no hidden charges or fees.

Price Alerts

Price Alerts

Not ready to book? to track prices.
Search flight deals

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
4:50 pm - 8:05 pm
JAX
-
MDW
4h 15m
1 stop
$270Southwest
Mon, Apr 13 - Sat, Apr 25
Southwest Logo
7:25 am - 2:20 pm
MDW
-
JAX
5h 55m
1 stop
Southwest Logo
7:45 am - 3:50 pm
JAX
-
MDW
9h 05m
2 stops
$271Southwest
Sat, Apr 18 - Tue, Apr 21
Southwest Logo
6:00 pm - 9:15 pm
MDW
-
JAX
2h 15mnonstop
Southwest Logo
5:55 pm - 7:25 pm
JAX
-
MDW
2h 30mnonstop
$272Southwest
Tue, Mar 24 - Tue, Mar 31
Southwest Logo
5:40 am - 6:35 pm
MDW
-
JAX
11h 55m
1 stop
Southwest Logo
12:55 pm - 6:15 pm
JAX
-
MDW
6h 20m
1 stop
$274Southwest
Wed, May 20 - Sat, May 23
Multiple Airlines Logo
2:47 pm - 1:47 pm
MDW
-
JAX
22h 00m
1 stop
Multiple Airlines Logo
2:55 pm - 7:00 am
JAX
-
MDW
17h 05m
1 stop
$275Multiple Airlines
Thu, May 28 - Sun, May 31
Southwest Logo
6:00 pm - 9:15 pm
MDW
-
JAX
2h 15mnonstop
Southwest Logo
7:10 pm - 10:15 pm
JAX
-
MDW
4h 05m
1 stop
$276Southwest
Wed, Mar 25 - Wed, Apr 15
Frontier Logo
6:00 am - 6:35 pm
MDW
-
JAX
11h 35m
1 stop
Frontier Logo
6:49 pm - 10:14 pm
JAX
-
MDW
28h 25m
1 stop
$277Frontier
Fri, Apr 17 - Mon, Apr 20
Southwest Logo
4:50 pm - 9:30 pm
MDW
-
JAX
3h 40m
1 stop
Southwest Logo
7:20 am - 8:50 am
JAX
-
MDW
2h 30mnonstop
$278Southwest
Wed, Apr 8 - Wed, Apr 15
Delta Logo
12:47 pm - 7:02 pm
MDW
-
JAX
5h 15m
1 stop
Delta Logo
6:59 pm - 10:28 pm
JAX
-
MDW
4h 29m
1 stop
$279Delta
Tue, Mar 24 - Fri, Apr 17
Southwest Logo
6:50 pm - 10:05 pm
MDW
-
JAX
2h 15mnonstop
Southwest Logo
8:15 pm - 11:30 pm
JAX
-
MDW
4h 15m
1 stop
$280Southwest
Fri, Apr 17 - Mon, Apr 20

Southwest flights from Chicago Midway Airport to Jacksonville

Our best Southwest deals on Chicago Midway Airport to Jacksonville flight tickets
Southwest
Apr 13
MDW6:50 pmChicago Midway
2h 15m
JAX10:05 pmJacksonville
Apr 25
JAX4:50 pmJacksonville
4h 15m
1 stop
MDW8:05 pmChicago Midway
$270
Southwest
Apr 18
MDW7:25 amChicago Midway
5h 55m
1 stop
JAX2:20 pmJacksonville
Apr 21
JAX7:45 amJacksonville
9h 05m
2 stops
MDW3:50 pmChicago Midway
$271
Southwest
Mar 24
MDW6:00 pmChicago Midway
2h 15m
JAX9:15 pmJacksonville
Mar 31
JAX5:55 pmJacksonville
2h 30m
MDW7:25 pmChicago Midway
$272

Delta flights from Chicago Midway Airport to Jacksonville

Our best Delta deals on Chicago Midway Airport to Jacksonville flight tickets
Delta
Mar 24
MDW12:47 pmChicago Midway
5h 15m
1 stop
JAX7:02 pmJacksonville
Apr 17
JAX6:59 pmJacksonville
4h 29m
1 stop
MDW10:28 pmChicago Midway
$279
Delta
May 7
MDW6:23 amChicago Midway
4h 22m
1 stop
JAX11:45 amJacksonville
May 11
JAX5:38 pmJacksonville
4h 31m
1 stop
MDW9:09 pmChicago Midway
$303
Delta
Mar 24
MDW12:47 pmChicago Midway
5h 15m
1 stop
JAX7:02 pmJacksonville
Mar 28
JAX5:30 amJacksonville
5h 26m
1 stop
MDW9:56 amChicago Midway
$308

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 February 26, 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

ChicagoJacksonville

MDW - JAX

MDWJAX

Chicago Midway

Mon 4/13

6:50 pm-10:05 pm

Nonstop2h 15m

Jacksonville

Sat 4/25

4:50 pm-8:05 pm

1 stop4h 15m

$270

ChicagoJacksonville

MDW - JAX

MDWJAX

Chicago Midway

Sat 4/18

7:25 am-2:20 pm

1 stop5h 55m

Jacksonville

Tue 4/21

7:45 am-3:50 pm

2 stops9h 05m

$271

ChicagoJacksonville

MDW - JAX

MDWJAX

Chicago Midway

Tue 3/24

6:00 pm-9:15 pm

Nonstop2h 15m

Jacksonville

Tue 3/31

5:55 pm-7:25 pm

Nonstop2h 30m

$272

ChicagoJacksonville

MDW - JAX

MDWJAX

Chicago Midway

Wed 5/20

5:40 am-6:35 pm

1 stop11h 55m

Jacksonville

Sat 5/23

12:55 pm-6:15 pm

1 stop6h 20m

$274

ChicagoJacksonville

MDW - JAX

MDWJAX

Chicago Midway

Thu 5/28

2:47 pm-1:47 pm

1 stop22h 00m

Jacksonville

Sun 5/31

2:55 pm-7:00 am

1 stop17h 05m

$275

ChicagoJacksonville

MDW - JAX

MDWJAX

Chicago Midway

Wed 3/25

6:00 pm-9:15 pm

Nonstop2h 15m

Jacksonville

Wed 4/15

7:10 pm-10:15 pm

1 stop4h 05m

$276

ChicagoJacksonville

MDW - JAX

MDWJAX

Chicago Midway

Fri 4/17

6:00 am-6:35 pm

1 stop11h 35m

Jacksonville

Mon 4/20

6:49 pm-10:14 pm

1 stop28h 25m

$277

ChicagoJacksonville

MDW - JAX

MDWJAX

Chicago Midway

Wed 4/8

4:50 pm-9:30 pm

1 stop3h 40m

Jacksonville

Wed 4/15

7:20 am-8:50 am

Nonstop2h 30m

$278

ChicagoJacksonville

MDW - JAX

MDWJAX

Chicago Midway

Tue 3/24

12:47 pm-7:02 pm

1 stop5h 15m

Jacksonville

Fri 4/17

6:59 pm-10:28 pm

1 stop4h 29m

$279

ChicagoJacksonville

MDW - JAX

MDWJAX

Chicago Midway

Fri 4/17

6:50 pm-10:05 pm

Nonstop2h 15m

Jacksonville

Mon 4/20

8:15 pm-11:30 pm

1 stop4h 15m

$280

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
1
2

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 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, Saturday is the cheapest day to fly to Jacksonville from Chicago Midway Airport. The lowest ticket price found for a Saturday departure recently was $332. 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 $398.

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 $346 when looking at flights departing at noon. Flights to Jacksonville are more costly in the afternoon, with an average ticket price of $373. Departure times in the afternoon 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 49% 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?

As of February 2026, prices for Chicago Midway Airport to Jacksonville flights are approximately 40% more expensive when compared to flights at the same time last year.

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

$308

Fastest flight time

2h 15m

Direct flights

Every day

Airports in Jacksonville

1 airport
The best flight deal from Chicago Midway Airport to Jacksonville found on momondo in the last 72 hours is $308
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

  • 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 $165Free CancellationRating
8.0
4,299 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 4,299 momondo users rating the airline 8.0/10. The cheapest Southwest deal from Chicago Midway Airport to Jacksonville in the last 72 hours was $165 (round-trip), much lower than the average airfare cost of $369 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.

An easier way to manage your Jacksonville trip

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.
Start using Trips
Find my bookings

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.
1 adult
Sat 3/28
Sat 4/4
By creating a price alert you accept our terms of use and privacy policy.

Find better results for your trip to the United States