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 45% 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.

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.

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.

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

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

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

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

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

As of December 2025, 99 flights take off from Jacksonville and land in Chicago each week. The most common flight departure day for this route is Wed, with 19% of weekly flights taking off on this day.

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

As of December 2025, there are 14 flights per day flying from Jacksonville to Chicago. The most common time of day flights depart is 11:00AM, with 73% of flights taking off at noon.

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 December 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.

$64 Cheap Flights from Jacksonville to Chicago in 2025/26

1 adult

0 bags

Discover deals from 900+ travel sites with momondo.

Save money when you book flights with momondo

Big names and deals

Search 100s of travel sites to compare prices.

Filter for what you want

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

Trusted and free

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

Price Alerts

Not ready to book? to track prices.

Search flight deals

Find the cheapest flights from Jacksonville to Chicago

Round-trip

One-way

Last minute

Direct

Cheap round-trip flights

Enter your travel dates to find the best prices.

5:23 pm - 10:24 pm

JAX

ORD

6h 01m1 stop

6:00 am - 4:27 pm

ORD

JAX

9h 27m1 stop

$242Frontier

Mon, Dec 29 - Mon, Jan 5

5:23 pm - 10:12 pm

JAX

MDW

5h 49m1 stop

8:15 am - 4:27 pm

MDW

JAX

7h 12m1 stop

$242Frontier

Mon, Dec 29 - Mon, Jan 5

2:40 pm - 4:27 pm

JAX

ORD

2h 47mnonstop

6:06 pm - 9:44 pm

ORD

JAX

2h 38mnonstop

$245United Airlines

Thu, Feb 5 - Wed, Feb 11

6:50 pm - 11:44 pm

JAX

ORD

5h 54m1 stop

11:15 am - 8:10 pm

ORD

JAX

7h 55m1 stop

$246United Airlines

Wed, Dec 31 - Wed, Jan 7

5:20 pm - 6:50 pm

JAX

MDW

2h 30mnonstop

5:55 am - 12:55 pm

MDW

JAX

6h 00m1 stop

$247Southwest

Fri, Feb 13 - Sun, Feb 15

12:05 pm - 10:35 am

JAX

ORD

23h 30m2 stops

6:00 pm - 6:30 pm

ORD

JAX

23h 30m1 stop

$247Multiple Airlines

Thu, Feb 5 - Sun, Feb 15

6:30 am - 10:32 am

JAX

MDW

5h 02m1 stop

6:45 am - 2:20 pm

MDW

JAX

6h 35m1 stop

$248Delta

Sat, Jan 10 - Thu, Jan 15

8:46 pm - 9:27 pm

JAX

ORD

25h 41m1 stop

5:32 pm - 5:08 pm

ORD

JAX

22h 36m2 stops

$253Multiple Airlines

Sun, Feb 8 - Wed, Feb 11

6:00 pm - 7:30 pm

JAX

MDW

2h 30mnonstop

9:50 am - 4:55 pm

MDW

JAX

6h 05m1 stop

$254Southwest

Thu, Jan 15 - Sat, Jan 17

6:30 am - 10:06 am

JAX

MDW

4h 36m1 stop

6:40 pm - 12:01 am

MDW

JAX

4h 21m1 stop

$258Delta

Sat, Feb 14 - Mon, Feb 16

Frontier flights from Jacksonville to Chicago

Our best Frontier deals on Jacksonville to Chicago flight tickets

Frontier

Dec 29

JAX5:23 pmJacksonville

6h 01m

1 stop

ORD10:24 pmChicago O'Hare Intl

Jan 5

ORD6:00 amChicago O'Hare Intl

9h 27m

1 stop

JAX4:27 pmJacksonville

$242

Find similar

Frontier

Dec 29

JAX5:23 pmJacksonville

6h 01m

1 stop

ORD10:24 pmChicago O'Hare Intl

Jan 2

ORD6:00 amChicago O'Hare Intl

9h 27m

1 stop

JAX4:27 pmJacksonville

$243

Find similar

Frontier

Feb 19

JAX9:23 pmJacksonville

16h 28m

2 stops

ORD12:51 pmChicago O'Hare Intl

Feb 22

ORD6:00 pmChicago O'Hare Intl

23h 30m

1 stop

JAX6:30 pmJacksonville

$244

Find similar

United Airlines flights from Jacksonville to Chicago

Our best United Airlines deals on Jacksonville to Chicago flight tickets

United Airlines

Feb 5

JAX2:40 pmJacksonville

2h 47m

ORD4:27 pmChicago O'Hare Intl

Feb 11

ORD6:06 pmChicago O'Hare Intl

2h 38m

JAX9:44 pmJacksonville

$245

Find similar

United Airlines

Dec 31

JAX6:50 pmJacksonville

5h 54m

1 stop

ORD11:44 pmChicago O'Hare Intl

Jan 7

ORD11:15 amChicago O'Hare Intl

7h 55m

1 stop

JAX8:10 pmJacksonville

$246

Find similar

United Airlines

Feb 5

JAX4:38 pmJacksonville

2h 47m

ORD6:25 pmChicago O'Hare Intl

Feb 15

ORD6:22 pmChicago O'Hare Intl

2h 27m

JAX9:49 pmJacksonville

$248

Find similar

Fly from

Fly to

Route

Depart

Return

Price

JacksonvilleChicago

JAX - ORD

JAXORD

Jacksonville

Mon 12/29

5:23 pm-10:24 pm

1 stop6h 01m

Chicago O'Hare Intl

Mon 1/5

6:00 am-4:27 pm

1 stop9h 27m

$242

JacksonvilleChicago

JAX - MDW

JAXMDW

Jacksonville

Mon 12/29

5:23 pm-10:12 pm

1 stop5h 49m

Chicago Midway

Mon 1/5

8:15 am-4:27 pm

1 stop7h 12m

$242

JacksonvilleChicago

JAX - ORD

JAXORD

Jacksonville

Thu 2/5

2:40 pm-4:27 pm

Nonstop2h 47m

Chicago O'Hare Intl

Wed 2/11

6:06 pm-9:44 pm

Nonstop2h 38m

$245

JacksonvilleChicago

JAX - ORD

JAXORD

Jacksonville

Wed 12/31

6:50 pm-11:44 pm

1 stop5h 54m

Chicago O'Hare Intl

Wed 1/7

11:15 am-8:10 pm

1 stop7h 55m

$246

JacksonvilleChicago

JAX - MDW

JAXMDW

Jacksonville

Fri 2/13

5:20 pm-6:50 pm

Nonstop2h 30m

Chicago Midway

Sun 2/15

5:55 am-12:55 pm

1 stop6h 00m

$247

JacksonvilleChicago

JAX - ORD

JAXORD

Jacksonville

Thu 2/5

12:05 pm-10:35 am

2 stops23h 30m

Chicago O'Hare Intl

Sun 2/15

6:00 pm-6:30 pm

1 stop23h 30m

$247

JacksonvilleChicago

JAX - MDW

JAXMDW

Jacksonville

Sat 1/10

6:30 am-10:32 am

1 stop5h 02m

Chicago Midway

Thu 1/15

6:45 am-2:20 pm

1 stop6h 35m

$248

JacksonvilleChicago

JAX - ORD

JAXORD

Jacksonville

Sun 2/8

8:46 pm-9:27 pm

1 stop25h 41m

Chicago O'Hare Intl

Wed 2/11

5:32 pm-5:08 pm

2 stops22h 36m

$253

JacksonvilleChicago

JAX - MDW

JAXMDW

Jacksonville

Thu 1/15

6:00 pm-7:30 pm

Nonstop2h 30m

Chicago Midway

Sat 1/17

9:50 am-4:55 pm

1 stop6h 05m

$254

JacksonvilleChicago

JAX - MDW

JAXMDW

Jacksonville

Sat 2/14

6:30 am-10:06 am

1 stop4h 36m

Chicago Midway

Mon 2/16

6:40 pm-12:01 am

1 stop4h 21m

$258

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 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 $408. 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 $701.

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 $401. In contrast, the most expensive time of day to depart to Chicago is in the morning when prices are around $467.

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 $366 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 December 2025, prices for Jacksonville to Chicago flights are approximately 22% 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	$219
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 $219. The best round-trip flight deal from Jacksonville to Chicago found on momondo in the last 72 hours is $381.

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 December 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 20.80% of the total bookings. Other popular models include Airbus A320-100/200 with 18.52%, Boeing 737 MAX 8 with 16.88%, and Boeing 737-800 with 10.91%.
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 (43% of total bookings). The next most popular airlines are United Airlines (33%), Southwest (19%), 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 8,011 reviews	Search Delta flights
Frontier	PriceFrom $145	Free Cancellation	Rating 5.8 3,091 reviews	Search Frontier flights
American Airlines	PriceFrom $179	Free Cancellation	Rating 7.2 11,047 reviews	Search American Airlines flights
Southwest	PriceFrom $203	Free Cancellation	Rating 8.0 4,250 reviews	Search Southwest flights
United Airlines	PriceFrom $221	Free Cancellation	Rating 7.4 9,066 reviews	Search United Airlines flights

Southwest Flights From Jacksonville to Chicago
Southwest flies from Jacksonville to Chicago around 10 times per week, with 4,250 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 $383 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, 9,066 ratings). United Airlines flies from Jacksonville to Chicago around 11 times per week, with deals starting from $221 round-trip and rising to an average price of around $389.

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.

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.

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 1/3

Sat 1/10

Email me momondo's favorite deals

By creating a price alert you accept our terms of use and privacy policy.

Find better results for your trip to the United States

Fly into one of these airports located in Chicago

Chicago Midway Airport

Chicago O'Hare Intl Airport

Chicago Greater Rockford Airport

Popular cities in the United States

Flights to New Yorkfrom $48

Flights to Los Angelesfrom $40

Flights to Miamifrom $47

Flights to Orlandofrom $41

Flights to San Franciscofrom $49

Flights to Las Vegasfrom $40

Flights to Washington, D.C.from $41

Flights to Bostonfrom $57

Flights to Atlantafrom $49

Flights to Dallasfrom $51

Flights to Seattlefrom $56

Flights to Denverfrom $48

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 2/27. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.

Big names and deals

Big names and deals

Filter for what you want

Filter for what you want

Trusted and free

Trusted and free

Price Alerts

Price Alerts

Find the cheapest flights from Jacksonville to Chicago

Cheap round-trip flights

Cheap one-way flights

Cheap last minute flights

Cheap direct flights

Frontier flights from Jacksonville to Chicago

Our best Frontier deals on Jacksonville to Chicago flight tickets

United Airlines flights from Jacksonville to Chicago

Our best United Airlines deals on Jacksonville to Chicago flight tickets

momondo Fare Finder

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

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 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 $401. In contrast, the most expensive time of day to depart to Chicago is in the morning when prices are around $467.

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 December 2025, prices for Jacksonville to Chicago flights are approximately 22% cheaper when compared to flights at the same time last year.

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

United Airlines, American Airlines, and Southwest 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 December 2025, there are 14 flights per day flying from Jacksonville to Chicago. The most common time of day flights depart is 11:00AM, with 73% of flights taking off at noon.

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

As of December 2025, 99 flights take off from Jacksonville and land in Chicago each week. The most common flight departure day for this route is Wed, 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