$109 Cheap Flights from Jacksonville (JAX) to Chicago (ORD)

View $109 flight on Wed, Jul 8, 2026Opens in a new window

Popular airlines from Jacksonville International Airport (JAX) to Chicago O'Hare Intl. Airport (ORD)

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Cheap Flights from Jacksonville to Chicago (JAX-ORD)

Prices were available within the past 7 days and start at $109 for one-way flights and $209 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

United
Tue, Jul 28 - Wed, Aug 5
JAX
Jacksonville
ORD
Chicago
$209 Roundtrip, found 1 hour ago
$209
Roundtrip
found 1 hour ago
Select United flight, departing Tue, Jul 28 from Jacksonville to Chicago, returning Wed, Aug 5, priced at $209 found 1 hour ago
Frontier Airlines
Fri, Jun 26 - Tue, Jun 30
JAX
Jacksonville
ORD
Chicago
$210 Roundtrip, found 8 hours ago
$210
Roundtrip
found 8 hours ago
Select Frontier Airlines flight, departing Fri, Jun 26 from Jacksonville to Chicago, returning Tue, Jun 30, priced at $210 found 8 hours ago
American Airlines
Tue, Jun 2 - Wed, Jun 3
JAX
Jacksonville
ORD
Chicago
$217 Roundtrip, found 2 hours ago
$217
Roundtrip
found 2 hours ago
Select American Airlines flight, departing Tue, Jun 2 from Jacksonville to Chicago, returning Wed, Jun 3, priced at $217 found 2 hours ago
United
Tue, Jul 28 - Wed, Aug 5
JAX
Jacksonville
ORD
Chicago
$217 Roundtrip, found 1 hour ago
$217
Roundtrip
found 1 hour ago
Select United flight, departing Tue, Jul 28 from Jacksonville to Chicago, returning Wed, Aug 5, priced at $217 found 1 hour ago
Delta
Tue, Jul 28 - Wed, Aug 5
JAX
Jacksonville
ORD
Chicago
$219 Roundtrip, found 1 hour ago
$219
Roundtrip
found 1 hour ago
Select Delta flight, departing Tue, Jul 28 from Jacksonville to Chicago, returning Wed, Aug 5, priced at $219 found 1 hour ago
Frontier Airlines
Fri, Jun 26 - Tue, Jun 30
JAX
Jacksonville
ORD
Chicago
$220 Roundtrip, found 8 hours ago
$220
Roundtrip
found 8 hours ago
Select Frontier Airlines flight, departing Fri, Jun 26 from Jacksonville to Chicago, returning Tue, Jun 30, priced at $220 found 8 hours ago
United
Wed, Aug 5 - Wed, Aug 12
JAX
Jacksonville
ORD
Chicago
$223 Roundtrip, found 2 hours ago
$223
Roundtrip
found 2 hours ago
Select United flight, departing Wed, Aug 5 from Jacksonville to Chicago, returning Wed, Aug 12, priced at $223 found 2 hours ago
United
Wed, Jun 24 - Wed, Jul 1
JAX
Jacksonville
ORD
Chicago
$223 Roundtrip, found 3 hours ago
$223
Roundtrip
found 3 hours ago
Select United flight, departing Wed, Jun 24 from Jacksonville to Chicago, returning Wed, Jul 1, priced at $223 found 3 hours ago
Delta
Wed, Aug 5 - Tue, Aug 11
JAX
Jacksonville
ORD
Chicago
$224 Roundtrip, found 5 hours ago
$224
Roundtrip
found 5 hours ago
Select Delta flight, departing Wed, Aug 5 from Jacksonville to Chicago, returning Tue, Aug 11, priced at $224 found 5 hours ago
Southwest Airlines
Sat, May 30 - Tue, Jun 2
JAX
Jacksonville
ORD
Chicago
$272 Roundtrip, found 1 hour ago
$272
Roundtrip
found 1 hour ago
Select Southwest Airlines flight, departing Sat, May 30 from Jacksonville to Chicago, returning Tue, Jun 2, priced at $272 found 1 hour ago

Alternative airports near Chicago

Prices were available within the past 7 days. Prices and availability are subject to change.

Select flight to Midway Intl. MDW. Closest option available. Average driving time to city center is 16 minutes. Flights from $335
MDW
Midway Intl.
Closest
Average driving time to city center16 min
Flights from $335

Frequently asked questions

How much does a flight from Jacksonville, FL (JAX-Jacksonville Intl.) to Chicago, IL (ORD-O'Hare Intl.) cost?
You can find cheap one-way flights from $109 and cheap return flights from $209 Jacksonville, FL (JAX-Jacksonville Intl.) to Chicago, IL (ORD-O'Hare Intl.) with Expedia. One-way flights typically cost between $166 and $680, and return flights often range between $299 and $977. Flight prices vary based on the month and day of the week you want to travel, as well as the airline and how far in advance you book your ticket. Filter your search on Expedia by "Price (lowest to highest)" to see the cheapest fares first, and use the Price Tracking tool to receive alerts when Jacksonville, FL (JAX-Jacksonville Intl.) to Chicago, IL (ORD-O'Hare Intl.) ticket fares go up or down.*Typical price ranges based on flights available on Expedia in the last year. Prices include multi-airline options.
What is the cheapest month to fly from Jacksonville, FL (JAX-Jacksonville Intl.) to Chicago, IL (ORD-O'Hare Intl.)?
September is the cheapest month to fly from Jacksonville to Chicago, with average return fares around $287. This price is about 17% lower than the average for the year, as September often sees a dip in travel after the summer season. Other affordable months to consider are August and October.*Averages based on flights available on Expedia in the last year.
Which airlines fly direct from Jacksonville, FL (JAX-Jacksonville Intl.) to Chicago, IL (ORD-O'Hare Intl.)?
Choose from 2 airlines operating direct flights from JAX to ORD:

  • United operates around 37 direct flights from JAX to ORD every week
  • American Airlines operates around 30 direct flights from JAX to ORD every week

What is the cheapest airline that flies from Jacksonville, FL (JAX-Jacksonville Intl.) to Chicago, IL (ORD-O'Hare Intl.)?
Sun Country Airlines is one of the cheapest airlines offering connecting flights from Jacksonville Intl. (JAX) to O'Hare Intl. (ORD), with round-trip tickets starting from around $208. Use Expedia's search tool to compare the prices and schedules of airlines that fly this route to find the best option for your plans and budget.*Prices based on flights available on Expedia in the last year.
How do I find cheap flights from Jacksonville, FL (JAX-Jacksonville Intl.) to Chicago, IL (ORD-O'Hare Intl.)?
To find a cheap flight from Jacksonville, FL (JAX-Jacksonville Intl.) to Chicago, IL (ORD-O'Hare Intl.), be flexible with your dates. Traveling outside of peak vacation months and booking a mid-week flight can help you save. Early morning and late night flights are often more affordable, too. Expedia allows you to compare flight times, airlines and routes all in one place to find low fares. You can also set up Price Tracking and receive alerts when fares go up or down.
What is the best airline to fly with from Jacksonville, FL (JAX-Jacksonville Intl.) to Chicago, IL (ORD-O'Hare Intl.)?
The best airline to fly with from Jacksonville, FL (JAX) to Chicago, IL (ORD) will differ from traveler to traveler. If you like to fly early, United offers early morning flights. If price is the most important factor, United typically offers the lowest fares. American Airlines offers the most daily flights from Jacksonville to Chicago, which is great if flexibility is what you value most. The best carrier for this journey could also be the one you have a loyalty membership with, as flying with that airline or another airline within the same alliance could help you collect points or enjoy lounge access.
What is the best time to fly from Jacksonville, FL (JAX-Jacksonville Intl.) to Chicago, IL (ORD-O'Hare Intl.)?
For flights from Jacksonville, FL (JAX) to Chicago, IL (ORD), September and August are the best months to consider. September is particularly affordable, with return flights averaging around $287. While August is popular for summer travel, September offers a great balance of lower prices and pleasant weather, making it an excellent choice for your trip.*Prices based on flights available on Expedia in the last year.
How many flights per day from Jacksonville, FL (JAX-Jacksonville Intl.) to Chicago, IL (ORD-O'Hare Intl.)?
On average, there are around 10 nonstop flights per day from Jacksonville Intl. (JAX) to O'Hare Intl. (ORD). For more options, look at flights that include layovers.
What is the earliest flight from Jacksonville, FL (JAX-Jacksonville Intl.) to Chicago, IL (ORD-O'Hare Intl.)?
The earliest flight from Jacksonville International Airport (JAX) to O'Hare International Airport (ORD) typically departs at around 5:00 AM, operated by American Airlines. This early departure allows you to make the most of your day in Chicago. To compare early flights on Expedia, select the "Early Morning" and "Morning" filters in your search.
What are the most popular departure times for flights from Jacksonville, FL (JAX-Jacksonville Intl.) to Chicago, IL (ORD-O'Hare Intl.)?
The most popular departure times for flights from Jacksonville (JAX) to Chicago (ORD) are in the early morning, from 6am to 9am. About 28% of passengers prefer this time window. Many major carriers, including American Airlines and Delta, offer flights during this window. This timing works well because it allows you to arrive in Chicago with a full day ahead of you.
How long does it take to fly from Jacksonville, FL (JAX-Jacksonville Intl.) to Chicago, IL (ORD-O'Hare Intl.)?
Direct flights from JAX to ORD usually take about 2 hours 50 minutes, traveling roughly 865 miles. If you opt for a connecting flight, expect to add around 4 hours to your journey. Keep in mind that actual flight times can vary due to wind patterns, weather, and air traffic.
Can you fly business or first class from Jacksonville, FL (JAX-Jacksonville Intl.) to Chicago, IL (ORD-O'Hare Intl.)?
First class is available on flights from JAX to ORD. First class cabins are available on:

  • American Airlines
  • United Airlines
  • Delta Air Lines

How much is a business class flight from Jacksonville, FL (JAX-Jacksonville Intl.) to Chicago, IL (ORD-O'Hare Intl.)?
A direct, return business class ticket from Jacksonville (JAX) to Chicago (ORD) typically costs between $1,077 - $1,408. A non-stop, one-way business class flight is usually around $438 - $708. Prices often fluctuate based on seasonality and how early you book. You may also be able to find a cheaper business class journey between Jacksonville, FL (JAX-Jacksonville Intl.) to Chicago, IL (ORD-O'Hare Intl.) if you opt for a connecting flight.*Prices based on flights available on Expedia in the last year.
How do I earn miles on a Jacksonville, FL (JAX-Jacksonville Intl.) to Chicago, IL (ORD-O'Hare Intl.) flight with Expedia?
It's easy to earn miles on a Jacksonville, FL (JAX-Jacksonville Intl.) to Chicago, IL (ORD-O'Hare Intl.) flight when you book with Expedia. Before you confirm your booking, simply select your frequent flyer program and enter your program number. As a member of One Key™, you can also earn OneKeyCash™* on top of your airline miles when you book with Expedia.*Excludes taxes and fees. OneKeyCash is not redeemable for cash and can only be used on Expedia and other participating brands.
What airports do you fly into for Chicago from Jacksonville Intl. (JAX)?
From Jacksonville Intl. (JAX), you can fly into O'Hare Intl. (ORD) and Midway Intl. (MDW) in Chicago. Some flights may connect through major hubs like Charlotte-Douglas Intl. (CLT), Ronald Reagan Washington National (DCA), Hartsfield-Jackson Atlanta Intl. (ATL) before reaching Chicago. Compare routes and airports on Expedia to find the best flight options for your travel plans.
Is it cheaper to buy a plane ticket from Jacksonville, FL (JAX-Jacksonville Intl.) to Chicago, IL (ORD-O'Hare Intl.) at the last minute?
Typically, booking a last minute flight from Jacksonville, FL (JAX-Jacksonville Intl.) to Chicago, IL (ORD-O'Hare Intl.) will be more expensive than booking in advance. As the departure date approaches, there are usually fewer seats available which can drive up the cost. However, if there's some wiggle room with your travel dates and times, you could bag a cheap last-minute fare.
Is it cheaper to book a Jacksonville, FL (JAX-Jacksonville Intl.) to Chicago, IL (ORD-O'Hare Intl.) flight and hotel package?
Securing a Jacksonville, FL (JAX-Jacksonville Intl.) to Chicago, IL (ORD-O'Hare Intl.) Chicago Vacation Packages is usually cheaper than booking separately. With Expedia, you can enjoy the ease of organizing your travels all in one place. Select from our extensive range of stays and then add flights, activities and car rentals to your booking. Bundle everything together, and you could save hundreds of dollars.
Can I cancel or change the date of my flight from Jacksonville, FL (JAX-Jacksonville Intl.) to Chicago, IL (ORD-O'Hare Intl.)?
If you booked your Jacksonville, FL (JAX-Jacksonville Intl.) to Chicago, IL (ORD-O'Hare Intl.) flight within the last 24 hours, you may be able to modify or cancel it without any fees. Depending on the airline and the type of ticket you have, additional charges may apply for changes beyond this timeframe. Airline policies and contact information can be found in your itinerary or confirmation email. Or, head to our Customer Service portal if you'd like more information.

Travel information

Origin airport
Jacksonville Intl.
Destination airport
O'Hare Intl.
Airlines serving
American Airlines, Delta, Frontier Airlines, JetBlue Airways, Southwest Airlines, United
Roundtrip price
$209
Distance
865 mi
Average flight time
1 hour 56 mins

Book with confidence

Jacksonville to Chicago Flights

The cheapest times to fly from Jacksonville to Chicago

On average, Thursday can be the cheapest time to fly, according to data from the Airlines Reporting Corporation (ARC), one of the world's biggest databases for global airline sales. The data reveals that you could save up to 16% by flying on a Thursday—the cheapest day to travel on average—instead of a Sunday—the most expensive. Some of the most affordable flights from Jacksonville to Chicago are during the month of July. You can find some of the cheapest flights from Jacksonville to Chicago with Expedia's search tool and vast selection of airlines.

 

The best time to book a flight from Jacksonville to Chicago

Sunday is one of the best days to book for cheap flights from Jacksonville to Chicago: Tickets reserved on a Sunday cost between 6% and 13% less than those reserved on a Friday, according to ARC data. The data also suggests booking early can also lead to cheaper airfares. You could save 24% by buying your tickets for domestic flights at least a month in advance and 10% by booking international flights 2 months in advance.

 

How to find cheap round-trip tickets from Jacksonville to Chicago

Being flexible with your dates and using Expedia's Price Drop Protection and Price Tracking features are some of the best ways of finding a cheap ticket from Jacksonville to Chicago in 2026. You can also book with separate airlines for your outbound and return journeys, from $109 one-way. Expedia also offers Price Drop Protection, so if the cost of your airfare goes down after booking, you'll receive a credit for the difference*. This is available for a small fee, and is free to One Key Gold and Platinum tier members.

 

Expedia's Price Tracking feature means you can stay on top of airfares without manually checking every day. It sends you automated price alerts for cheap Jacksonville to Chicago flights and uses historical data to indicate when the best time to book is. Download Expedia's free app to activate this handy tool in a few easy taps.

 

You could also save big by booking one of Expedia's vacation packages. Bundling together your Jacksonville to Chicago airfare with your accommodations and car rental is often cheaper than booking everything separately. There’s also One Key, Expedia's generous rewards program. Join for free and you could earn One Key cash on most bookings to save on future adventures.

 

*Terms apply.

 

Disclaimer: ARC The statistics are based on average round-trip ticket prices between January and August 2023. The percentages you see are averages.

 

Jacksonville to Chicago Flights

*Flight schedules are subject to change.

*Available to One Key members.

 

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