$114 Cheap Flights from Jacksonville (JAX) to Chicago (ORD)

View $114 flight on Mon, Jun 9, 2025Opens in a new window

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

  • Plan, book, fly with confidence

  • trending down icon
    Be in the know
    Get alerts if flight prices drop or rise*
  • bex rewards loyalty icon
    Book smarter
    Save up to 30% on select hotels after you book a flight*
  • one key icon
    Earn twice
    Earn your airline miles on top of our OneKeyCash
    Learn about One Key
Find available prices by choosing your travel dates.

Cheap Flights from Jacksonville to Chicago (JAX-ORD)

Prices were available within the past 7 days and start at $114 for one-way flights and $223 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

JetBlue Airways
Tue, Jun 17 - Wed, Jun 25
JAX
Jacksonville
ORD
Chicago
$223 Roundtrip, found 5 hours ago
$223
Roundtrip
found 5 hours ago
Select JetBlue Airways flight, departing Tue, Jun 17 from Jacksonville to Chicago, returning Wed, Jun 25, priced at $223 found 5 hours ago
Frontier Airlines
Mon, Jun 9 - Tue, Jun 10
JAX
Jacksonville
ORD
Chicago
$248 Roundtrip, found 20 hours ago
$248
Roundtrip
found 20 hours ago
Select Frontier Airlines flight, departing Mon, Jun 9 from Jacksonville to Chicago, returning Tue, Jun 10, priced at $248 found 20 hours ago
Frontier Airlines
Mon, May 5 - Mon, Jun 9
JAX
Jacksonville
ORD
Chicago
$248 Roundtrip, found 6 hours ago
$248
Roundtrip
found 6 hours ago
Select Frontier Airlines flight, departing Mon, May 5 from Jacksonville to Chicago, returning Mon, Jun 9, priced at $248 found 6 hours ago
Frontier Airlines
Fri, Jun 6 - Sat, Jun 14
JAX
Jacksonville
ORD
Chicago
$249 Roundtrip, found 5 hours ago
$249
Roundtrip
found 5 hours ago
Select Frontier Airlines flight, departing Fri, Jun 6 from Jacksonville to Chicago, returning Sat, Jun 14, priced at $249 found 5 hours ago
Frontier Airlines
Mon, Jun 9 - Mon, Jun 16
JAX
Jacksonville
ORD
Chicago
$253 Roundtrip, found 6 hours ago
$253
Roundtrip
found 6 hours ago
Select Frontier Airlines flight, departing Mon, Jun 9 from Jacksonville to Chicago, returning Mon, Jun 16, priced at $253 found 6 hours ago
JetBlue Airways
Tue, Aug 26 - Tue, Sep 2
JAX
Jacksonville
ORD
Chicago
$255 Roundtrip, found 1 day ago
$255
Roundtrip
found 1 day ago
Select JetBlue Airways flight, departing Tue, Aug 26 from Jacksonville to Chicago, returning Tue, Sep 2, priced at $255 found 1 day ago
Delta
Wed, May 28 - Mon, Jun 2
JAX
Jacksonville
ORD
Chicago
$258 Roundtrip, found 12 hours ago
$258
Roundtrip
found 12 hours ago
Select Delta flight, departing Wed, May 28 from Jacksonville to Chicago, returning Mon, Jun 2, priced at $258 found 12 hours ago
Frontier Airlines
Mon, Jun 2 - Wed, Jun 11
JAX
Jacksonville
ORD
Chicago
$259 Roundtrip, found 3 hours ago
$259
Roundtrip
found 3 hours ago
Select Frontier Airlines flight, departing Mon, Jun 2 from Jacksonville to Chicago, returning Wed, Jun 11, priced at $259 found 3 hours ago
American Airlines
Sat, Sep 13 - Tue, Sep 16
JAX
Jacksonville
ORD
Chicago
$260 Roundtrip, found 1 hour ago
$260
Roundtrip
found 1 hour ago
Select American Airlines flight, departing Sat, Sep 13 from Jacksonville to Chicago, returning Tue, Sep 16, priced at $260 found 1 hour ago
United
Wed, Jun 4 - Sat, Jun 14
JAX
Jacksonville
ORD
Chicago
$265 Roundtrip, found 1 hour ago
$265
Roundtrip
found 1 hour ago
Select United flight, departing Wed, Jun 4 from Jacksonville to Chicago, returning Sat, Jun 14, priced at $265 found 1 hour ago
Flights from Jacksonville (JAX) to Chicago (ORD)
Origin airport
Jacksonville Intl.
Destination airport
O'Hare Intl.
Airlines serving
American Airlines, Delta, Frontier Airlines, JetBlue Airways, Southwest Airlines, United
Roundtrip price
$222
Distance
865 mi

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 June. 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 2025. You can also book with separate airlines for your outbound and return journeys, from $114 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.

Frequently asked questions

How much does a flight from Jacksonville Intl. Airport (JAX) to O'Hare Intl. Airport (ORD) cost?
Cheap return fares from Jacksonville Intl. Airport (JAX) to O’Hare Intl. Airport (ORD) start from $277. This information is based on the cheapest price found on Expedia for this return journey departing within the next three months. This airfare is for a United flight leaving JAX on April 26 2025 and touching down at ORD. The price was last updated on April 23 2025 and has not changed since.
What is the cheapest month to fly from JAX to ORD?
The cheapest flights from JAX to ORD are usually during off-peak season, when demand is lower. To save money, avoid flying during public holidays, school breaks and major local events.
Which airlines fly direct from Jacksonville Intl. Airport (JAX) to O'Hare Intl. Airport (ORD)?
Hop on a nonstop flight with United Airlines and travel straight from Jacksonville Intl. Airport (JAX) to O’Hare Intl. Airport (ORD).
What is the cheapest airline that flies from JAX to ORD?
With prices starting from $139 for a one-way flight from JAX to ORD, United is currently the cheapest airline on this route. This fare is based on the lowest price found on Expedia departing within the next three months. The flight takes off from JAX on July 4 2025. Prices were last updated on April 23 2025 and have not changed since.
How many flights per day from Jacksonville Intl. Airport (JAX) to O'Hare Intl. Airport (ORD)?
With, on average, 3 direct flights departing from Jacksonville Intl. Airport (JAX) to O’Hare Intl. Airport (ORD) every day, you’ll be up in the air in no time.
What are the most popular departure times for flights from Jacksonville Intl. Airport (JAX) to O'Hare Intl. Airport (ORD)?
The 9 AM departures from JAX to ORD are the busiest. They can also be more expensive. If you want to save money, choose a less crowded time to fly.
What day of the week has the most flights from JAX to ORD?
If you fly on a Friday, you’ll get the greatest range of options for flights from Jacksonville Intl. Airport (JAX) to O’Hare Intl. Airport (ORD).
What is the earliest flight from Jacksonville Intl. Airport (JAX) to O'Hare Intl. Airport (ORD)?
Catch the earliest flight at around 8:12AM UTC-5, heading out of Jacksonville Intl. Airport (JAX). You’ll be flying for approximately 2h 43m, arriving at O’Hare Intl. Airport (ORD) at approximately 9:55AM UTC-6.
How long does it take to fly from Jacksonville Intl. Airport (JAX) to O'Hare Intl. Airport (ORD)?
Flights from JAX to ORD have an average travel time of 2 hours and 45 minutes. The distance between the two airports is 870 mi.
What airline has the least delays from JAX to ORD?
With 100% of flights usually arriving on schedule, Alaska Airlines has the best on-time performance for direct flights from Jacksonville Intl. Airport (JAX) to O’Hare Intl. Airport (ORD). To monitor your flight status and get notifications about any changes, use the Expedia App.
What is the best time to fly from Jacksonville Intl. Airport (JAX) to O'Hare Intl. Airport (ORD)?
To avoid potential delays on the Jacksonville Intl. Airport (JAX) to O’Hare Intl. Airport (ORD) route, aim to fly before 3 PM. Later flights are 22% more likely to be canceled.**Most reliable time of the day and month to travel recommendation is based on January through August 2024 flight status data sourced from OAG’s global flight data platform.
What airports do you fly into for Chicago from Jacksonville Intl. Airport (JAX)?
Take a direct flight from Jacksonville Intl. Airport (JAX) to Chicago and land at O’Hare Intl. Airport (ORD). Another convenient arrival point to this destination is Midway Intl. Airport (MDW).
Is it cheaper to buy a plane ticket from Jacksonville Intl. Airport (JAX) to O'Hare Intl. Airport (ORD) last-minute?
Waiting until just before your departure to book a flight from JAX to ORD often results in higher prices. Although you may find some last-minute deals, they aren’t always guaranteed. Keep your travel plans flexible to maximize your chances of snagging a bargain.
Is it cheaper to book a JAX to ORD flight and hotel package?
Compared with arranging hotels and flights separately, booking a JAX to ORD flight and hotel package with Expedia could result in significant savings. Better yet, having everything in one convenient place takes the hassle out of travel planning. Just pick your flights and select from our wide range of stays, then tailor your trip with other add-ons like tours and car rentals.
Can I cancel or change the date of my flight from Jacksonville Intl. Airport (JAX) to O'Hare Intl. Airport (ORD)?
It’s generally possible to cancel or reschedule your JAX to ORD flight. However, if the booking was made more than 24 hours ago, additional fees may apply. Check your airline’s policies in your itinerary to see what changes are allowed and if any costs are involved. You’ll also find further details on our Customer Service portal.

Explore a world of travel with Expedia

*Available to One Key members.