What is the cheapest airline that flies from Chicago to Jacksonville?

Frontier, JetBlue, and Sun Country Air are the most popular carriers operating from Chicago to Jacksonville

How many flights depart from Chicago to Jacksonville on average per week?

As of August 2025, there are 101 flights per week flying from Chicago to Jacksonville. The most common day of the week flights depart is Mon, with 19% of flights taking off on this day.

Which layover airport offers the lowest fares from Chicago to Jacksonville?

Flights via Atlanta (ATL) offer the lowest average round-trip price of $216.

How many flights depart from Chicago to Jacksonville on average per day?

14 flights are operational daily from Chicago to Jacksonville as of August 2025. The most popular departure time for this route is 6:00PM, with 48% of flights per day taking off in the evening.

What airlines fly to Jacksonville?

American Airlines, United Airlines and Delta are the top three most popular airlines that fly to Jacksonville from Chicago according to our data. American Airlines is the first choice among our users, with 42% of people opting to fly with this airline when traveling to Jacksonville. Keep in mind that there are 6 different airlines that fly to Jacksonville on a routine basis, so you have a few additional options to choose from.

Which airport is the most popular layover for flights between Chicago and Jacksonville?

Charlotte (CLT) was the most common stop: 75% of momondo users choosing 1-stop flights on this route connected there.

Which layover airport has the shortest connection time from Chicago to Jacksonville?

Atlanta (ATL) has the shortest average layover time for this route: 0h 50m.

Which layover airport has the shortest travel time from Chicago to Jacksonville?

Flights connecting via Charlotte (CLT) have the shortest average one-way travel time: 4h 04m.

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

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

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

As of August 2025, there are 6 operators available to choose from for flights from Chicago to Jacksonville Airport.

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

The minimum age for a child to fly alone is five, but airlines offering an unaccompanied minor (UNMR) service may have their age restrictions, such as regulations concerning flight duration, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Chicago to Jacksonville Airport.

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

The travel and health documents you'll need for your trip to Jacksonville Airport may differ based on your itinerary and personal situation. Typically, you should have several documents on hand, such as a national ID card or driver's license and a passport that is valid for six months after your intended arrival at Jacksonville Airport. It is always advisable to seek advice from your airline or a trusted third party, such as IATA.

$71 Cheap Flights from Chicago to Jacksonville in 2025

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Find the cheapest flights from Chicago to Jacksonville

Round-trip

One-way

Last minute

Direct

Cheap round-trip flights

6:20 am - 5:10 pmMDW-JAX

9h 50m1 stop

11:37 am - 11:20 pmJAX-MDW

12h 43m1 stop

$180Frontier

Find Deal

Sun, Oct 12 - Fri, Oct 17

8:25 am - 9:04 pmMDW-JAX

11h 39m1 stop

11:37 am - 11:20 pmJAX-MDW

12h 43m1 stop

$181Frontier

Find Deal

Sun, Oct 12 - Fri, Oct 17

6:15 pm - 9:47 pmORD-JAX

2h 32mnonstop

4:26 pm - 6:10 pmJAX-ORD

2h 44mnonstop

$257United Airlines

Find Deal

Wed, Oct 15 - Tue, Oct 21

10:30 am - 1:45 pmMDW-JAX

2h 15mnonstop

1:20 pm - 2:45 pmJAX-MDW

2h 25mnonstop

$257Southwest

Find Deal

Wed, Sep 24 - Wed, Oct 1

5:50 pm - 9:22 pmORD-JAX

2h 32mnonstop

4:32 pm - 6:25 pmJAX-ORD

2h 53mnonstop

$267United Airlines

Find Deal

Tue, Oct 28 - Fri, Oct 31

3:05 pm - 6:15 pmMDW-JAX

2h 10mnonstop

5:45 am - 7:10 amJAX-MDW

2h 25mnonstop

$267Southwest

Find Deal

Tue, Oct 28 - Fri, Oct 31

6:36 pm - 9:59 pmORD-JAX

2h 23mnonstop

7:22 am - 9:06 amJAX-ORD

2h 44mnonstop

$272American Airlines

Find Deal

Sat, Oct 4 - Tue, Oct 7

9:55 am - 1:24 pmORD-JAX

2h 29mnonstop

7:53 pm - 9:30 pmJAX-ORD

2h 37mnonstop

$285American Airlines

Find Deal

Sat, Sep 20 - Mon, Sep 22

5:34 pm - 12:06 amMDW-JAX

5h 32m1 stop

3:45 pm - 9:44 pmJAX-MDW

6h 59m1 stop

$287Delta

Find Deal

Mon, Nov 24 - Tue, Dec 2

6:30 pm - 11:55 pmMDW-JAX

4h 25m1 stop

5:01 pm - 9:36 pmJAX-MDW

5h 35m1 stop

$292Delta

Find Deal

Tue, Sep 16 - Mon, Sep 22

Delta flights from Chicago to Jacksonville

Our best Delta deals on Chicago to Jacksonville flight tickets

Delta

Nov 24

MDW5:34 pmChicago Midway

5h 32m

1 stop

JAX12:06 amJacksonville

Dec 2

JAX3:45 pmJacksonville

6h 59m

1 stop

MDW9:44 pmChicago Midway

$287

Find similar

Delta

Sep 16

MDW6:30 pmChicago Midway

4h 25m

1 stop

JAX11:55 pmJacksonville

Sep 22

JAX5:01 pmJacksonville

5h 35m

1 stop

MDW9:36 pmChicago Midway

$292

Find similar

Delta

Sep 5

MDW6:00 amChicago Midway

4h 33m

1 stop

JAX11:33 amJacksonville

Sep 6

JAX6:20 amJacksonville

4h 16m

1 stop

MDW9:36 amChicago Midway

$297

Find similar

Frontier flights from Chicago to Jacksonville

Our best Frontier deals on Chicago to Jacksonville flight tickets

Frontier

Oct 12

MDW6:20 amChicago Midway

9h 50m

1 stop

JAX5:10 pmJacksonville

Oct 17

JAX11:37 amJacksonville

12h 43m

1 stop

MDW11:20 pmChicago Midway

$180

Find similar

Frontier

Oct 12

MDW8:25 amChicago Midway

11h 39m

1 stop

JAX9:04 pmJacksonville

Oct 17

JAX11:37 amJacksonville

12h 43m

1 stop

MDW11:20 pmChicago Midway

$181

Find similar

Frontier

Oct 9

ORD5:05 amChicago O'Hare Intl

11h 03m

1 stop

JAX5:08 pmJacksonville

Oct 12

JAX6:05 pmJacksonville

6h 34m

1 stop

ORD11:39 pmChicago O'Hare Intl

$188

Find similar

Fly from

Fly to

Route

Depart

Return

Price

ChicagoJacksonville

MDW - JAX

MDWJAX

Chicago Midway

Sun 10/12

6:20 am-5:10 pm

1 stop9h 50m

Jacksonville

Fri 10/17

11:37 am-11:20 pm

1 stop12h 43m

$180

ChicagoJacksonville

MDW - JAX

MDWJAX

Chicago Midway

Sun 10/12

8:25 am-9:04 pm

1 stop11h 39m

Jacksonville

Fri 10/17

11:37 am-11:20 pm

1 stop12h 43m

$181

ChicagoJacksonville

ORD - JAX

ORDJAX

Chicago O'Hare Intl

Wed 10/15

6:15 pm-9:47 pm

Nonstop2h 32m

Jacksonville

Tue 10/21

4:26 pm-6:10 pm

Nonstop2h 44m

$257

ChicagoJacksonville

MDW - JAX

MDWJAX

Chicago Midway

Wed 9/24

10:30 am-1:45 pm

Nonstop2h 15m

Jacksonville

Wed 10/1

1:20 pm-2:45 pm

Nonstop2h 25m

$257

ChicagoJacksonville

ORD - JAX

ORDJAX

Chicago O'Hare Intl

Tue 10/28

5:50 pm-9:22 pm

Nonstop2h 32m

Jacksonville

Fri 10/31

4:32 pm-6:25 pm

Nonstop2h 53m

$267

ChicagoJacksonville

MDW - JAX

MDWJAX

Chicago Midway

Tue 10/28

3:05 pm-6:15 pm

Nonstop2h 10m

Jacksonville

Fri 10/31

5:45 am-7:10 am

Nonstop2h 25m

$267

ChicagoJacksonville

ORD - JAX

ORDJAX

Chicago O'Hare Intl

Sat 10/4

6:36 pm-9:59 pm

Nonstop2h 23m

Jacksonville

Tue 10/7

7:22 am-9:06 am

Nonstop2h 44m

$272

ChicagoJacksonville

ORD - JAX

ORDJAX

Chicago O'Hare Intl

Sat 9/20

9:55 am-1:24 pm

Nonstop2h 29m

Jacksonville

Mon 9/22

7:53 pm-9:30 pm

Nonstop2h 37m

$285

ChicagoJacksonville

MDW - JAX

MDWJAX

Chicago Midway

Mon 11/24

5:34 pm-12:06 am

1 stop5h 32m

Jacksonville

Tue 12/2

3:45 pm-9:44 pm

1 stop6h 59m

$287

ChicagoJacksonville

MDW - JAX

MDWJAX

Chicago Midway

Tue 9/16

6:30 pm-11:55 pm

1 stop4h 25m

Jacksonville

Mon 9/22

5:01 pm-9:36 pm

1 stop5h 35m

$292

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How to get the cheapest flight ticket from Chicago 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

Prices

Airlines

Layovers

Other information

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 during the month September is also very affordable. Most momondo users find prices during this month for around $313.

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. The lowest ticket price found for a Wednesday departure recently was $375. 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 because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $432.

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

Flying to Jacksonville from Chicago at noon is the least expensive time of day to depart. momondo users have found prices as low as $338 when looking at flights departing at noon. Flights to Jacksonville are more costly in the evening, with an average ticket price of $415. 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 to Jacksonville flight route?

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

How far in advance should I book a flight to Jacksonville?

You are more likely to see cheaper flights to Jacksonville from Chicago when booking weeks ahead of your departure date. In general, you can expect to find flights to Jacksonville for around $377 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Jacksonville from Chicago for as low as $329 on momondo.

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

There are 4 cabin classes available to choose from on Chicago to Jacksonville flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

How have Chicago to Jacksonville flight prices changed over time?

As of August 2025, prices for Chicago to Jacksonville flights are approximately 28% cheaper when compared to flights at the same time last year.

When to book flights from Chicago to Jacksonville

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

Estimated round-trip price

Cheap Chicago to Jacksonville (CHI to JAX) flight deals and tips

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

Best Price Found	$89
Fastest flight time	2h 10m
Direct flights	Every day
Airports in Jacksonville	1 airport

The best one-way flight to Jacksonville from Chicago in the past 72 hours is $89. The best round-trip flight deal from Chicago to Jacksonville found on momondo in the last 72 hours is $203.

The fastest flight from Chicago to Jacksonville takes 2h 10m

Direct flights go from Chicago to Jacksonville every day.

There is 1 airport near Jacksonville: Jacksonville (JAX)

Search flight deals

How far is Chicago to Jacksonville by plane?
The straight-line distance from Chicago to Jacksonville is 863.3 mi. By plane, this route typically takes 2h 10m.
When did momondo last update prices for flights from Chicago to Jacksonville Airport?
Prices for flights from Chicago to Jacksonville Airport are updated daily.
How many operators does momondo search for flights from Chicago to Jacksonville Airport?
As of August 2025, there are 6 operators available to choose from for flights from Chicago to Jacksonville Airport.
How old do you have to be to fly from Chicago to Jacksonville Airport?
The minimum age for a child to fly alone is five, but airlines offering an unaccompanied minor (UNMR) service may have their age restrictions, such as regulations concerning flight duration, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Chicago to Jacksonville Airport.
What documentation or ID do you need to fly to Jacksonville Airport?
The travel and health documents you'll need for your trip to Jacksonville Airport may differ based on your itinerary and personal situation. Typically, you should have several documents on hand, such as a national ID card or driver's license and a passport that is valid for six months after your intended arrival at Jacksonville Airport. It is always advisable to seek advice from your airline or a trusted third party, such as IATA.
What is the most popular plane model from Chicago to Jacksonville?
Based on momondo bookings for this flight route, the most popular plane model on flight routes from Chicago to Jacksonville is Boeing 737-800 (27.51% of total bookings). The next most popular plane models are Airbus A319 (24.22%), Boeing 737-700 (11.41%), and Embraer 175 (Enhanced Winglets) (9.30%).
What is the most popular airline from Chicago to Jacksonville?
momondo data reveals that the most frequently booked airline on the route from Chicago to Jacksonville is United Airlines, representing 45% of all bookings. The subsequent popular airlines are American Airlines at 30%, Southwest at 20%, and Frontier at 2%.

Best airlines flying from Chicago to Jacksonville

Compare and see reviews for airlines that fly from Chicago to Jacksonville with momondo

Airline	Rating	Free Cancellation	Price
Frontier	PriceFrom $112	Free Cancellation	Rating 5.8 3,200 reviews	Search Frontier flights
Delta	PriceFrom $131	Free Cancellation	Rating 7.9 7,979 reviews	Search Delta flights
American Airlines	PriceFrom $174	Free Cancellation	Rating 7.2 10,000 reviews	Search American Airlines flights
Southwest	PriceFrom $190	Free Cancellation	Rating 8.0 4,242 reviews	Search Southwest flights
JetBlue	PriceFrom $233	Free Cancellation	Rating 7.2 2,918 reviews	Search JetBlue flights
United Airlines	PriceFrom $237	Free Cancellation	Rating 7.4 8,943 reviews	Search United Airlines flights

Southwest Flights From Chicago to Jacksonville
Southwest flies from Chicago to Jacksonville around 5 times per week, with 4,243 momondo users rating the airline 8.0/10. The cheapest Southwest deal from Chicago to Jacksonville in the last 72 hours was $190 (round-trip), much lower than the average airfare cost of $466 for Southwest flights on this route.
United Airlines Flights From Chicago to Jacksonville
The best United Airlines deal for Chicago to Jacksonville flight tickets found on momondo in the last 72 hours was $237, round-trip. It should be noted that an average United Airlines flight deal for this route in this time was higher, at $426 round-trip. United Airlines operates 15 flights out of Chicago into Jacksonville in an average week, so prices vary by time and availability. 8,943 United Airlines reviews by users on momondo have scored the airline at 7.4/10.

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?

Yes. momondo enables you to select and highlight flights to Jacksonville from Chicago with this policy.

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

momondo helps you find the best flight between Chicago and Jacksonville by providing filters to narrow your choice of flights to those matching your criteria. You can select flights based on numerous factors such as price, departure and landing times, airport and airline.

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

Yes momondo offers price alerts on flights to Jacksonville from Chicago. After performing a search on this page you should be able to see the price alert set up feature. Simply provide a valid email address and momondo will instantly alert you when prices change.

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.

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Cheap flights from Chicago to Jacksonville from $71

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 to Jacksonville departing on 11/17. 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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Delta flights from Chicago to Jacksonville

Our best Delta deals on Chicago to Jacksonville flight tickets

Frontier flights from Chicago to Jacksonville

Our best Frontier deals on Chicago to Jacksonville flight tickets

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How to get the cheapest flight ticket from Chicago 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 during the month September is also very affordable. Most momondo users find prices during this month for around $313.

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

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

What is the cheapest Chicago to Jacksonville flight route?

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

How far in advance should I book a flight to Jacksonville?

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

There are 4 cabin classes available to choose from on Chicago to Jacksonville flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

How have Chicago to Jacksonville flight prices changed over time?

As of August 2025, prices for Chicago to Jacksonville flights are approximately 28% cheaper when compared to flights at the same time last year.

What is the cheapest airline that flies from Chicago to Jacksonville?

Frontier, JetBlue, and Sun Country Air are the most popular carriers operating from Chicago to Jacksonville

What airlines fly to Jacksonville?

Which airport is the most popular layover for flights between Chicago and Jacksonville?

Charlotte (CLT) was the most common stop: 75% of momondo users choosing 1-stop flights on this route connected there.

Which layover airport offers the lowest fares from Chicago to Jacksonville?

Flights via Atlanta (ATL) offer the lowest average round-trip price of $216.

Which layover airport has the shortest travel time from Chicago to Jacksonville?

Flights connecting via Charlotte (CLT) have the shortest average one-way travel time: 4h 04m.

Which layover airport has the shortest connection time from Chicago to Jacksonville?

Atlanta (ATL) has the shortest average layover time for this route: 0h 50m.

How many flights depart from Chicago to Jacksonville on average per day?

14 flights are operational daily from Chicago to Jacksonville as of August 2025. The most popular departure time for this route is 6:00PM, with 48% of flights per day taking off in the evening.

How many flights depart from Chicago to Jacksonville on average per week?

As of August 2025, there are 101 flights per week flying from Chicago to Jacksonville. The most common day of the week flights depart is Mon, with 19% of flights taking off on this day.

When to book flights from Chicago to Jacksonville

Cheap Chicago to Jacksonville (CHI to JAX) flight deals and tips

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

Best Price Found

Fastest flight time

Direct flights

Airports in Jacksonville

How far is Chicago to Jacksonville by plane?

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

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

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

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

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

What is the most popular airline from Chicago to Jacksonville?

Best airlines flying from Chicago to Jacksonville

Compare and see reviews for airlines that fly from Chicago to Jacksonville with momondo

Southwest Flights From Chicago to Jacksonville

United Airlines Flights From Chicago to Jacksonville

Traveling to a place near Jacksonville?

Why use momondo?

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

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

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

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

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.

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.

Find better results for your trip to the United States

Airports servicing Florida