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

As of October 2025, 53 flights take off from Jacksonville and land in Chicago each week. The most common flight departure day for this route is Thu, with 42% of weekly flights taking off on this day.

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

Atlanta (ATL) has the shortest average layover time for this route: 1h 32m.

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

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

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

Philadelphia (PHL) was the most common stop: 67% of momondo users choosing 1-stop flights on this route connected there.

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 44% 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.

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

As of October 2025, there are 7 flights per day flying from Jacksonville to Chicago. The most common time of day flights depart is 4:00PM, with 62% of flights taking off at noon.

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: 4h 21m.

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

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

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 October 2025, 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.

$68 Cheap Flights from Jacksonville to Chicago in 2025/26

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

Prices are currently low for flights on this route. Typical prices usually range from $297 to $473. The lowest price recently found on this route was $222.

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9:48 am - 10:43 pmJAX-MDW

13h 55m2 stops

7:23 pm - 5:40 pmMDW-JAX

21h 17m1 stop

$222Multiple Airlines

Find Deal

Thu, Nov 27 - Thu, Dec 4

6:36 pm - 10:12 pmJAX-MDW

4h 36m1 stop

6:37 pm - 2:25 pmMDW-JAX

18h 48m2 stops

$223Frontier

Find Deal

Fri, Dec 5 - Sun, Dec 7

4:37 pm - 6:30 pmJAX-ORD

2h 53mnonstop

11:20 am - 2:53 pmORD-JAX

2h 33mnonstop

$261United Airlines

Find Deal

Tue, Dec 16 - Wed, Dec 31

11:30 am - 1:15 pmJAX-ORD

2h 45mnonstop

4:00 pm - 11:04 amORD-JAX

18h 04m2 stops

$263United Airlines

Find Deal

Mon, Nov 17 - Mon, Nov 17

5:00 pm - 6:25 pmJAX-MDW

2h 25mnonstop

1:45 pm - 5:00 pmMDW-JAX

2h 15mnonstop

$277Southwest

Find Deal

Thu, Dec 4 - Mon, Dec 8

5:45 pm - 7:35 pmJAX-ORD

2h 50mnonstop

7:00 pm - 10:34 pmORD-JAX

2h 34mnonstop

$278American Airlines

Find Deal

Thu, Dec 4 - Mon, Dec 8

5:35 am - 7:00 amJAX-MDW

2h 25mnonstop

1:45 pm - 5:00 pmMDW-JAX

2h 15mnonstop

$286Southwest

Find Deal

Sat, Dec 6 - Mon, Dec 8

5:39 pm - 10:09 pmJAX-MDW

5h 30m1 stop

6:17 pm - 11:59 pmMDW-JAX

4h 42m1 stop

$291Delta

Find Deal

Sat, Jan 17 - Mon, Jan 19

6:52 am - 8:45 amJAX-ORD

2h 53mnonstop

1:46 pm - 5:15 pmORD-JAX

2h 29mnonstop

$297American Airlines

Find Deal

Tue, Nov 25 - Tue, Dec 2

11:33 am - 2:40 pmJAX-MDW

4h 07m1 stop

5:05 pm - 10:43 pmMDW-JAX

4h 38m1 stop

$297Delta

Find Deal

Thu, Dec 25 - Tue, Dec 30

United Airlines flights from Jacksonville to Chicago

Our best United Airlines deals on Jacksonville to Chicago flight tickets

United Airlines

Dec 16

JAX4:37 pmJacksonville

2h 53m

ORD6:30 pmChicago O'Hare Intl

Dec 31

ORD11:20 amChicago O'Hare Intl

2h 33m

JAX2:53 pmJacksonville

$261

Find similar

United Airlines

Nov 17

JAX11:30 amJacksonville

2h 45m

ORD1:15 pmChicago O'Hare Intl

Nov 17

ORD4:00 pmChicago O'Hare Intl

18h 04m

2 stops

JAX11:04 amJacksonville

$263

Find similar

United Airlines

Nov 27

JAX8:00 amJacksonville

2h 44m

ORD9:44 amChicago O'Hare Intl

Dec 4

ORD11:05 amChicago O'Hare Intl

2h 33m

JAX2:38 pmJacksonville

$271

Find similar

American Airlines flights from Jacksonville to Chicago

Our best American Airlines deals on Jacksonville to Chicago flight tickets

American Airlines

Dec 4

JAX5:45 pmJacksonville

2h 50m

ORD7:35 pmChicago O'Hare Intl

Dec 8

ORD7:00 pmChicago O'Hare Intl

2h 34m

JAX10:34 pmJacksonville

$278

Find similar

American Airlines

Nov 25

JAX6:52 amJacksonville

2h 53m

ORD8:45 amChicago O'Hare Intl

Dec 2

ORD1:46 pmChicago O'Hare Intl

2h 29m

JAX5:15 pmJacksonville

$297

Find similar

American Airlines

Dec 6

JAX6:00 amJacksonville

6h 07m

1 stop

ORD11:07 amChicago O'Hare Intl

Dec 6

ORD7:00 pmChicago O'Hare Intl

2h 35m

JAX10:35 pmJacksonville

$305

Find similar

Fly from

Fly to

Route

Depart

Return

Price

JacksonvilleChicago

JAX - MDW

JAXMDW

Jacksonville

Thu 11/27

9:48 am-10:43 pm

2 stops13h 55m

Chicago Midway

Thu 12/4

7:23 pm-5:40 pm

1 stop21h 17m

$222

JacksonvilleChicago

JAX - MDW

JAXMDW

Jacksonville

Fri 12/5

6:36 pm-10:12 pm

1 stop4h 36m

Chicago Midway

Sun 12/7

6:37 pm-2:25 pm

2 stops18h 48m

$223

JacksonvilleChicago

JAX - ORD

JAXORD

Jacksonville

Tue 12/16

4:37 pm-6:30 pm

Nonstop2h 53m

Chicago O'Hare Intl

Wed 12/31

11:20 am-2:53 pm

Nonstop2h 33m

$261

JacksonvilleChicago

JAX - ORD

JAXORD

Jacksonville

Mon 11/17

11:30 am-1:15 pm

Nonstop2h 45m

Chicago O'Hare Intl

Mon 11/17

4:00 pm-11:04 am

2 stops18h 04m

$263

JacksonvilleChicago

JAX - MDW

JAXMDW

Jacksonville

Thu 12/4

5:00 pm-6:25 pm

Nonstop2h 25m

Chicago Midway

Mon 12/8

1:45 pm-5:00 pm

Nonstop2h 15m

$277

JacksonvilleChicago

JAX - ORD

JAXORD

Jacksonville

Thu 12/4

5:45 pm-7:35 pm

Nonstop2h 50m

Chicago O'Hare Intl

Mon 12/8

7:00 pm-10:34 pm

Nonstop2h 34m

$278

JacksonvilleChicago

JAX - MDW

JAXMDW

Jacksonville

Sat 12/6

5:35 am-7:00 am

Nonstop2h 25m

Chicago Midway

Mon 12/8

1:45 pm-5:00 pm

Nonstop2h 15m

$286

JacksonvilleChicago

JAX - MDW

JAXMDW

Jacksonville

Sat 1/17

5:39 pm-10:09 pm

1 stop5h 30m

Chicago Midway

Mon 1/19

6:17 pm-11:59 pm

1 stop4h 42m

$291

JacksonvilleChicago

JAX - ORD

JAXORD

Jacksonville

Tue 11/25

6:52 am-8:45 am

Nonstop2h 53m

Chicago O'Hare Intl

Tue 12/2

1:46 pm-5:15 pm

Nonstop2h 29m

$297

JacksonvilleChicago

JAX - MDW

JAXMDW

Jacksonville

Thu 12/25

11:33 am-2:40 pm

1 stop4h 07m

Chicago Midway

Tue 12/30

5:05 pm-10:43 pm

1 stop4h 38m

$297

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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 $289. 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 $293.

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 $414. 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 $723.

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 at noon. Flights from Jacksonville to Chicago during this time can be as low as $381. In contrast, the most expensive time of day to depart to Chicago is in the morning when prices are around $471.

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 $367 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 October 2025, prices for Jacksonville to Chicago flights are approximately 97% more expensive 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	$172
Fastest flight time	2h 25m
Direct flights	Every day
Airports in Chicago	1 airport

The best one-way flight to Chicago from Jacksonville in the past 72 hours is $172. The best round-trip flight deal from Jacksonville to Chicago found on momondo in the last 72 hours is $358.

The fastest flight from Jacksonville to Chicago takes 2h 25m

Direct flights go from Jacksonville to Chicago every day.

There is 1 airport near Chicago: 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 25m.
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 October 2025, 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 Airbus A319, making up 26.87% of the total bookings. Other popular models include Boeing 737-800 with 18.94%, Airbus A320-100/200 with 14.34%, and Boeing 737 MAX 8 with 12.22%.
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 (40% of total bookings). The next most popular airlines are United Airlines (34%), Southwest (21%), 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 7,998 reviews	Search Delta flights
Frontier	PriceFrom $145	Free Cancellation	Rating 5.8 3,122 reviews	Search Frontier flights
American Airlines	PriceFrom $179	Free Cancellation	Rating 7.2 11,035 reviews	Search American Airlines flights
Southwest	PriceFrom $207	Free Cancellation	Rating 8.0 4,243 reviews	Search Southwest flights
United Airlines	PriceFrom $232	Free Cancellation	Rating 7.4 8,998 reviews	Search United Airlines flights

Southwest Flights From Jacksonville to Chicago
Southwest flies from Jacksonville to Chicago around 1 time per week, with 4,243 momondo users rating the airline 8.0/10. The cheapest Southwest deal from Jacksonville to Chicago in the last 72 hours was $207 (round-trip), much lower than the average airfare cost of $394 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, 8,998 ratings). United Airlines flies from Jacksonville to Chicago around 7 times per week, with deals starting from $232 round-trip and rising to an average price of around $394.

Merrillville

New Buffalo

Hammond

Benton Harbor

Saint Joseph

Portage

Lansing

Schererville

Valparaiso

Crown Point

Munster

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 $68

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 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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United Airlines flights from Jacksonville to Chicago

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Our best American Airlines deals on Jacksonville to Chicago flight tickets

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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

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 $289. 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 $293.

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 at noon. Flights from Jacksonville to Chicago during this time can be as low as $381. In contrast, the most expensive time of day to depart to Chicago is in the morning when prices are around $471.

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 October 2025, prices for Jacksonville to Chicago flights are approximately 97% more expensive when compared to flights at the same time last year.

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

Frontier, Sun Country Air, and JetBlue 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: 67% 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 Atlanta (ATL) offer the lowest average round-trip price of $216.

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: 4h 21m.

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

Atlanta (ATL) has the shortest average layover time for this route: 1h 32m.

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

As of October 2025, there are 7 flights per day flying from Jacksonville to Chicago. The most common time of day flights depart is 4:00PM, with 62% of flights taking off at noon.

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

As of October 2025, 53 flights take off from Jacksonville and land in Chicago each week. The most common flight departure day for this route is Thu, with 42% 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.