$108 Cheap flight deals from Jacksonville (OAJ) to Chicago (CHI)

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Airfares from $108 One Way, $308 Round Trip from Jacksonville to Chicago

Prices starting at $308 for return flights and $108 for one-way flights to Chicago were the cheapest prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.

Wed, Jul 24 - Tue, Jul 30
OAJ
Jacksonville
ORD
Chicago
$308 Roundtrip, found 20 hours ago
$308
Roundtrip
found 20 hours ago
Select Delta flight, departing Wed, Jul 24 from Jacksonville to Chicago, returning Tue, Jul 30, priced at $308 found 20 hours ago
Wed, Jul 24 - Tue, Jul 30
EWN
New Bern
ORD
Chicago
$323 Roundtrip, found 3 days ago
$323
Roundtrip
found 3 days ago
Select American Airlines flight, departing Wed, Jul 24 from New Bern to Chicago, returning Tue, Jul 30, priced at $323 found 3 days ago
Wed, Jul 24 - Tue, Jul 30
OAJ
Jacksonville
ORD
Chicago
$337 Roundtrip, found 20 hours ago
$337
Roundtrip
found 20 hours ago
Select American Airlines flight, departing Wed, Jul 24 from Jacksonville to Chicago, returning Tue, Jul 30, priced at $337 found 20 hours ago
Wed, Jul 24 - Tue, Jul 30
OAJ
Jacksonville
ORD
Chicago
$343 Roundtrip, found 20 hours ago
$343
Roundtrip
found 20 hours ago
Select Delta flight, departing Wed, Jul 24 from Jacksonville to Chicago, returning Tue, Jul 30, priced at $343 found 20 hours ago
Wed, Jul 24 - Tue, Jul 30
OAJ
Jacksonville
ORD
Chicago
$348 Roundtrip, found 20 hours ago
$348
Roundtrip
found 20 hours ago
Select Delta flight, departing Wed, Jul 24 from Jacksonville to Chicago, returning Tue, Jul 30, priced at $348 found 20 hours ago

More About Flying To Chicago from Jacksonville

Route Information for Flights from Jacksonville to Chicago

Origin Airport IATA Code
OAJ
Destination Airport IATA Code
CHI
Distance
Direct Flight Airlines
Earliest Flight Arrival
Latest Flight Arrival

Jacksonville to Chicago

It has never been easier to find cheap Jacksonville to Chicago flights. Orbitz has some of the best deals around to save you more money on your flight, hotel, and vacation package for the trip you have been waiting for.

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Get the Best Deals on Jacksonville to Chicago Flights

Finding great deals on flights from Jacksonville to Chicago is a snap with Orbitz. With our guaranteed low prices, you don’t have to worry if you are getting the best prices on air tickets, hotels, and cruises. And with all that money you saved, you can enjoy your Chicago vacation even more.

Pile Up Miles With Discount Air Tickets

Not only can you find great bargains on Jacksonville to Chicago flights, but you can rack up frequent flyer miles on the flights too. Enter your frequent flyer number on qualified flights when booking for Orbitz to see the miles pile up in your account.

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Stay on top of the latest updates for flights from Jacksonville to Chicago. We send you free email and mobile alerts to keep you informed about delays to Jacksonville to Chicago flights.

Frequently asked questions

Are there non-stop flights from Jacksonville to Chicago?
The awesome news is, there are. United Airlines and American Airlines are two carriers that will take you directly from Wilmington Intl. Airport (ILM) to Chicago, IL (ORD-O’Hare Intl.).
What is the shortest flight from Jacksonville to Chicago?
Jetting from ILM to Chicago, IL (ORD-O’Hare Intl.) takes at least 3 hours and 4 minutes. Treat yourself to a wine and read a few magazines — it’s the perfect opportunity to sit back and unwind.
What airlines fly from Jacksonville to Chicago most frequently?
United Airlines (UA) operates 30 flights each month between Wilmington, NC (ILM-Wilmington Intl.) to O’Hare Intl. Airport (ORD). Your next grand adventure is just a few clicks away. Also research the deals available with American Airlines (AA). Offering 26 monthly flights between Jacksonville and Chicago, they’ll make sure your journey is just as enjoyable as the destination.
What is the cheapest day of the week to fly?
Consider flying out early in the week to save on your airfare. Orbitz data from 2021 shows that Monday is the cheapest day to depart, followed by Tuesday. Saturday showed the highest average ticket prices likely because many travelers prefer to start their vacation on a weekend.
What is the cheapest month to fly?
We won’t keep you guessing, according to Orbitz data from 2021, the cheapest month to fly is February. Perfect for those who need a weekend getaway, or just a break from it all in the shortest month of the year. Be aware that the most expensive time to fly is during the height of summer in July, and in the holiday month of December.*According to flight demand on Orbitz.com from January to December 2021. Savings are subject to change based on departure location, date and destination.

Fare, taxes & fees: Fares include all taxes and fees, except baggage fees. Rates shown reflect fares found by other Orbitz users over the past 7 days. Due to rapidly changing airline prices & seat availability, these fares may no longer be available.

Refunds/changes/cancellations: Itinerary changes, if permitted for the fare, will have a $30 service fee charged by Orbitz. Additional airline charges may apply.

Other conditions: Schedules, fares and rules are subject to change without notice. Seats are limited and may not be available on all flights/dates or in all markets. Lower fares may be available. Fares will not be honored retroactively or in exchange for any wholly/partially unused ticket. Tickets are non-transferable and non-refundable. Fare rules are provided for the selected itinerary before booking.