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

As of January 2026, there are 16 flights per day flying from Jacksonville to Chicago. The most common time of day flights depart is 12:00PM, with 61% of flights taking off in the afternoon.

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

Flights connecting via Atlanta (ATL) have the shortest average one-way travel time: 5h 38m.

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

Frontier, Southwest, and United Airlines are the most popular carriers operating from Jacksonville to Chicago

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

Philadelphia (PHL) has the shortest average layover time for this route: 1h 57m.

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

Philadelphia (PHL) 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 Jacksonville to Chicago?

Flights via Philadelphia (PHL) offer the lowest average round-trip price of $275.

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

As of January 2026, 113 flights take off from Jacksonville and land in Chicago each week. The most common flight departure day for this route is Mon, with 19% of weekly flights taking off on this day.

What airlines fly to Chicago?

American Airlines, United Airlines and Southwest are the top three most popular airlines that fly to Chicago from Jacksonville according to our data. American Airlines is the first choice among our users, with 47% of people opting to fly with this airline when traveling to Chicago. Keep in mind that there are 5 different airlines that fly to Chicago on a routine basis, so you have a few additional options to choose from.

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

Prices for flights from Jacksonville Airport to Chicago refresh daily.

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

As of January 2026, there are 5 operators available to choose from for flights from Jacksonville Airport to Chicago.

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

Although the minimum age for a child to fly alone is five, airlines that offer an unaccompanied minor (UMNR) service may have their own age limits, which could be impacted by factors such as flight length, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Jacksonville Airport to Chicago.

What documentation or ID do you need to fly to Chicago?

The required travel and health documents for your Chicago trip may vary depending on your itinerary and personal circumstances. As a general rule, you should carry multiple documents, including a national ID card or driver's license and a passport valid for six months after your intended arrival at Chicago. We recommend that you seek guidance from your airline or a reliable third party such as IATA.

$64 Cheap Flights from Jacksonville to Chicago in 2026

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Find the cheapest flights from Jacksonville to Chicago

Round-trip

One-way

Last minute

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Cheap round-trip flights

Enter your travel dates to find the best prices.

12:00 pm - 5:43 pm

JAX

ORD

6h 43m

1 stop

9:40 am - 6:10 pm

ORD

JAX

7h 30m

1 stop

$235JetBlue

Tue, Feb 3 - Tue, Feb 10

11:37 am - 9:03 pm

JAX

ORD

34h 26m

2 stops

6:03 am - 4:23 pm

ORD

JAX

9h 20m

1 stop

$236Multiple Airlines

Tue, Feb 3 - Sat, Feb 7

3:50 pm - 2:26 pm

JAX

MDW

23h 36m

2 stops

6:00 am - 6:39 pm

MDW

JAX

11h 39m

1 stop

$237Multiple Airlines

Thu, Feb 19 - Mon, Feb 23

8:56 pm - 12:05 pm

JAX

MDW

16h 09m

2 stops

6:20 am - 6:23 pm

MDW

JAX

11h 03m

1 stop

$238Frontier

Mon, Feb 2 - Fri, Feb 6

8:00 am - 9:46 am

JAX

ORD

2h 46mnonstop

6:06 pm - 9:44 pm

ORD

JAX

2h 38mnonstop

$239United Airlines

Sat, Feb 7 - Sat, Feb 7

8:12 am - 5:12 pm

JAX

ORD

10h 00m

1 stop

11:39 am - 7:12 am

ORD

JAX

18h 33m

1 stop

$241Frontier

Fri, Apr 10 - Sun, Apr 12

8:12 am - 11:42 pm

JAX

MDW

16h 30m

1 stop

12:33 pm - 7:12 am

MDW

JAX

17h 39m

1 stop

$241Frontier

Fri, Apr 10 - Sun, Apr 12

4:23 pm - 6:19 pm

JAX

ORD

2h 56mnonstop

1:00 pm - 8:10 pm

ORD

JAX

6h 10m

1 stop

$249United Airlines

Wed, Feb 4 - Tue, Feb 10

5:00 am - 11:45 am

JAX

MDW

7h 45m

1 stop

2:40 pm - 7:30 pm

MDW

JAX

3h 50m

1 stop

$259Southwest

Sat, Feb 7 - Sat, Feb 7

5:45 pm - 7:15 pm

JAX

MDW

2h 30mnonstop

1:35 pm - 4:50 pm

MDW

JAX

2h 15mnonstop

$269Southwest

Sat, Feb 21 - Tue, Feb 24

American Airlines flights from Jacksonville to Chicago

Our best American Airlines deals on Jacksonville to Chicago flight tickets

American Airlines

Feb 4

JAX6:00 amJacksonville

6h 06m

1 stop

ORD11:06 amChicago O'Hare Intl

Feb 4

ORD3:21 pmChicago O'Hare Intl

5h 48m

1 stop

JAX10:09 pmJacksonville

$259

American Airlines

Feb 14

JAX5:02 pmJacksonville

7h 34m

1 stop

ORD11:36 pmChicago O'Hare Intl

Feb 16

ORD6:08 amChicago O'Hare Intl

6h 41m

1 stop

JAX1:49 pmJacksonville

$288

American Airlines

Feb 14

JAX12:03 pmJacksonville

2h 51m

ORD1:54 pmChicago O'Hare Intl

Feb 16

ORD7:34 pmChicago O'Hare Intl

2h 24m

JAX10:58 pmJacksonville

$290

JetBlue flights from Jacksonville to Chicago

Our best JetBlue deals on Jacksonville to Chicago flight tickets

JetBlue

Feb 3

JAX12:00 pmJacksonville

6h 43m

1 stop

ORD5:43 pmChicago O'Hare Intl

Feb 10

ORD9:40 amChicago O'Hare Intl

7h 30m

1 stop

JAX6:10 pmJacksonville

$235

JetBlue

Jan 27

JAX12:00 pmJacksonville

6h 43m

1 stop

ORD5:43 pmChicago O'Hare Intl

Jan 31

ORD9:40 amChicago O'Hare Intl

7h 35m

1 stop

JAX6:15 pmJacksonville

$245

JetBlue

Feb 6

JAX12:00 pmJacksonville

6h 43m

1 stop

ORD5:43 pmChicago O'Hare Intl

Feb 8

ORD9:15 amChicago O'Hare Intl

7h 55m

1 stop

JAX6:10 pmJacksonville

$251

Fly from

Fly to

Route

Depart

Return

Price

JacksonvilleChicago

JAX - ORD

JAXORD

Jacksonville

Tue 2/3

12:00 pm-5:43 pm

1 stop6h 43m

Chicago O'Hare Intl

Tue 2/10

9:40 am-6:10 pm

1 stop7h 30m

$235

JacksonvilleChicago

JAX - ORD

JAXORD

Jacksonville

Tue 2/3

11:37 am-9:03 pm

2 stops34h 26m

Chicago O'Hare Intl

Sat 2/7

6:03 am-4:23 pm

1 stop9h 20m

$236

JacksonvilleChicago

JAX - MDW

JAXMDW

Jacksonville

Thu 2/19

3:50 pm-2:26 pm

2 stops23h 36m

Chicago Midway

Mon 2/23

6:00 am-6:39 pm

1 stop11h 39m

$237

JacksonvilleChicago

JAX - MDW

JAXMDW

Jacksonville

Mon 2/2

8:56 pm-12:05 pm

2 stops16h 09m

Chicago Midway

Fri 2/6

6:20 am-6:23 pm

1 stop11h 03m

$238

JacksonvilleChicago

JAX - ORD

JAXORD

Jacksonville

Sat 2/7

8:00 am-9:46 am

Nonstop2h 46m

Chicago O'Hare Intl

Sat 2/7

6:06 pm-9:44 pm

Nonstop2h 38m

$239

JacksonvilleChicago

JAX - ORD

JAXORD

Jacksonville

Fri 4/10

8:12 am-5:12 pm

1 stop10h 00m

Chicago O'Hare Intl

Sun 4/12

11:39 am-7:12 am

1 stop18h 33m

$241

JacksonvilleChicago

JAX - MDW

JAXMDW

Jacksonville

Fri 4/10

8:12 am-11:42 pm

1 stop16h 30m

Chicago Midway

Sun 4/12

12:33 pm-7:12 am

1 stop17h 39m

$241

JacksonvilleChicago

JAX - ORD

JAXORD

Jacksonville

Wed 2/4

4:23 pm-6:19 pm

Nonstop2h 56m

Chicago O'Hare Intl

Tue 2/10

1:00 pm-8:10 pm

1 stop6h 10m

$249

JacksonvilleChicago

JAX - MDW

JAXMDW

Jacksonville

Sat 2/7

5:00 am-11:45 am

1 stop7h 45m

Chicago Midway

Sat 2/7

2:40 pm-7:30 pm

1 stop3h 50m

$259

JacksonvilleChicago

JAX - MDW

JAXMDW

Jacksonville

Sat 2/21

5:45 pm-7:15 pm

Nonstop2h 30m

Chicago Midway

Tue 2/24

1:35 pm-4:50 pm

Nonstop2h 15m

$269

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first

How to get the cheapest flight ticket from Jacksonville to Chicago

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

What is the cheapest month to fly to Chicago?

The month of September is, on average, the cheapest month to fly to Chicago from Jacksonville, with most prices found around $287. If you’re not able to fly to Chicago in September, then August is your next best option. Flight prices from Jacksonville to Chicago during August average around $291.

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

The cheapest day to depart on your flight to Chicago is on a Friday when prices can be found for as low as $410. This is often the case because there is less demand to fly during this day of the week. When flying out on a Sunday, the most expensive travel day of the week, you can expect to see flight prices from Jacksonville to Chicago for around $677.

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

Our most recent data shows that the best time of day to fly to Chicago is in the evening. Flights from Jacksonville to Chicago during this time can be as low as $406. In contrast, the most expensive time of day to depart to Chicago is in the afternoon when prices are around $464.

What is the cheapest Jacksonville to Chicago flight route?

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

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

You are more likely to see cheaper flights to Chicago from Jacksonville when booking weeks ahead of your departure date. In general, you can expect to find flights to Chicago for around $359 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago from Jacksonville for as low as $281 on momondo.

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

There are 4 cabin classes available to choose from on Jacksonville to Chicago 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 Jacksonville to Chicago flights?

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

How have Jacksonville to Chicago flight prices changed over time?

As of January 2026, prices for Jacksonville to Chicago flights are approximately 42% cheaper when compared to flights at the same time last year.

When to book flights from Jacksonville to Chicago

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

Estimated round-trip price

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

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

Best Price Found	$258
Fastest flight time	2h 20m
Direct flights	Every day
Airports in Chicago	3 airports

The best one-way flight to Chicago from Jacksonville in the past 72 hours is $258. The best round-trip flight deal from Jacksonville to Chicago found on momondo in the last 72 hours is $323.

The fastest flight from Jacksonville to Chicago takes 2h 20m

Direct flights go from Jacksonville to Chicago every day.

There are 3 airports in Chicago. From Jacksonville there are direct flights to Chicago O'Hare Intl (ORD), Chicago Midway (MDW).

Search flight deals

How far is Jacksonville to Chicago by plane?
The straight-line distance from Jacksonville to Chicago is 863.3 mi. In terms of flight time, this usually takes a little over 2h 20m.
When did momondo last update prices for flights from Jacksonville Airport to Chicago?
Prices for flights from Jacksonville Airport to Chicago refresh daily.
How many operators does momondo search for flights from Jacksonville Airport to Chicago?
As of January 2026, there are 5 operators available to choose from for flights from Jacksonville Airport to Chicago.
How old do you have to be to fly from Jacksonville Airport to Chicago?
Although the minimum age for a child to fly alone is five, airlines that offer an unaccompanied minor (UMNR) service may have their own age limits, which could be impacted by factors such as flight length, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Jacksonville Airport to Chicago.
What documentation or ID do you need to fly to Chicago?
The required travel and health documents for your Chicago trip may vary depending on your itinerary and personal circumstances. As a general rule, you should carry multiple documents, including a national ID card or driver's license and a passport valid for six months after your intended arrival at Chicago. We recommend that you seek guidance from your airline or a reliable third party such as IATA.
What is the most popular plane model from Jacksonville to Chicago?
Based on momondo bookings for flights between Jacksonville and Chicago, the leading plane model is Embraer 175, making up 17.78% of the total bookings. Other popular models include Boeing 737 MAX 8 with 17.24%, Airbus A319 with 13.98%, and Airbus A320-100/200 with 13.82%.
What is the most popular airline from Jacksonville to Chicago?
Based on momondo bookings for this flight route, the most popular airline on flight routes from Jacksonville to Chicago is American Airlines (42% of total bookings). The next most popular airlines are United Airlines (34%), Southwest (17%), and Frontier (3%).

Best airlines flying from Jacksonville to Chicago

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

Airline	Rating	Free Cancellation	Price
Delta	PriceFrom $108	Free Cancellation	Rating 7.9 8,040 reviews	Search Delta flights
Frontier	PriceFrom $136	Free Cancellation	Rating 5.7 3,056 reviews	Search Frontier flights
American Airlines	PriceFrom $179	Free Cancellation	Rating 7.2 11,118 reviews	Search American Airlines flights
Southwest	PriceFrom $203	Free Cancellation	Rating 8.0 4,257 reviews	Search Southwest flights
United Airlines	PriceFrom $222	Free Cancellation	Rating 7.4 9,156 reviews	Search United Airlines flights

Southwest Flights From Jacksonville to Chicago
Southwest flies from Jacksonville to Chicago around 4 times per week, with 4,257 momondo users rating the airline 8.0/10. The cheapest Southwest deal from Jacksonville to Chicago in the last 72 hours was $203 (round-trip), much lower than the average airfare cost of $379 for Southwest flights on this route.
United Airlines Flights From Jacksonville to Chicago
Another popular option for Jacksonville to Chicago flights is United Airlines (7.4/10, 9,156 ratings). United Airlines flies from Jacksonville to Chicago around 13 times per week, with deals starting from $222 round-trip and rising to an average price of around $385.

Merrillville

New Buffalo

Hammond

Benton Harbor

Saint Joseph

Portage

Lansing

Schererville

Valparaiso

Munster

Crown Point

Chesterton

Monticello

Porter

Griffith

Saint John

Why use momondo?

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

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

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

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

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

Once you have performed a search for Jacksonville to Chicago flights, momondo helps you find the right one by offering useful filters to narrow down your flight selection. Flights can be filtered by multiple factors such as airline, airport and price; but also by other criteria like aircraft type and payment method.

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

If you are not ready to book a flight from Jacksonville to Chicago now, use our insights above to find helpful tips or alternatively set up a price alert, where momondo will track prices on flights to Chicago and let you know when they change.

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Cheap flights from Jacksonville to Chicago from $64

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Jacksonville to Chicago departing on 2/7. 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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American Airlines flights from Jacksonville to Chicago

Our best American Airlines deals on Jacksonville to Chicago flight tickets

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Our best JetBlue deals on Jacksonville to Chicago flight tickets

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Use the filters below to find and compare flights from Jacksonville to Chicago that are best for you.

See travel insights to Chicago from

How to get the cheapest flight ticket from Jacksonville to Chicago

What is the typical price of a round-trip flight between Jacksonville and Chicago?

What is the cheapest month to fly to Chicago?

The month of September is, on average, the cheapest month to fly to Chicago from Jacksonville, with most prices found around $287. If you’re not able to fly to Chicago in September, then August is your next best option. Flight prices from Jacksonville to Chicago during August average around $291.

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

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

Our most recent data shows that the best time of day to fly to Chicago is in the evening. Flights from Jacksonville to Chicago during this time can be as low as $406. In contrast, the most expensive time of day to depart to Chicago is in the afternoon when prices are around $464.

What is the cheapest Jacksonville to Chicago flight route?

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

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

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

There are 4 cabin classes available to choose from on Jacksonville to Chicago 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 Jacksonville to Chicago flights?

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

How have Jacksonville to Chicago flight prices changed over time?

As of January 2026, prices for Jacksonville to Chicago flights are approximately 42% cheaper when compared to flights at the same time last year.

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

Frontier, Southwest, and United Airlines are the most popular carriers operating from Jacksonville to Chicago

What airlines fly to Chicago?

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

Philadelphia (PHL) 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 Jacksonville to Chicago?

Flights via Philadelphia (PHL) offer the lowest average round-trip price of $275.

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

Flights connecting via Atlanta (ATL) have the shortest average one-way travel time: 5h 38m.

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

Philadelphia (PHL) has the shortest average layover time for this route: 1h 57m.

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

As of January 2026, there are 16 flights per day flying from Jacksonville to Chicago. The most common time of day flights depart is 12:00PM, with 61% of flights taking off in the afternoon.

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

As of January 2026, 113 flights take off from Jacksonville and land in Chicago each week. The most common flight departure day for this route is Mon, with 19% of weekly flights taking off on this day.

When to book flights from Jacksonville to Chicago

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

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

Best Price Found

Fastest flight time

Direct flights

Airports in Chicago

How far is Jacksonville to Chicago by plane?

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

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

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

What documentation or ID do you need to fly to Chicago?

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

What is the most popular airline from Jacksonville to Chicago?

Best airlines flying from Jacksonville to Chicago

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

Southwest Flights From Jacksonville to Chicago

United Airlines Flights From Jacksonville to Chicago

Traveling to a place near Chicago?

Why use momondo?

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

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

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

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

An easier way to manage your Chicago 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