OAJ - ORD

$209 Find Cheap Flights from Jacksonville to Chicago O'Hare Airport

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Jacksonville to Chicago departing on 7/2. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
1 adult, Economy, 0 bags

KAYAK searches hundreds of travel sites at once for deals on flights to Chicago O'Hare Intl Airport

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Jacksonville to Chicago, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Jacksonville to Chicago, as well as popular online travel agencies
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Everything you should know

Cheapest round-trip
$317
Delta
Tue 6/2Tue 6/9
OAJ - ORD • 1 stop
Cheapest one-way
$209
Delta
Thu 7/2
OAJ - ORD • 1 stop
Top airlines
Cheapest • from $317 (round-trip)
Best reviews • 7.1 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
Nonstop flights
Not available
There are currently no direct flights between Jacksonville and Chicago. You'll need at least 1 connection.
Insights
Insights
Insights
Insights
Top layover airports
Cheapest • Avg $524 (round-trip)
Shortest trip • 4h 55m (one-way)
Insights
Insights
Insights
Insights
Start a new search
KAYAK searches 100s of sites at once to find you the best travel deals.
We hope you love your trip to Chicago!
Flight Deals
Booking Insights
Flight Deals

Cheap Flights from Jacksonville to Chicago (OAJ-ORD)

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Jacksonville to Chicago that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Jacksonville to Chicago

Tue, Jun 2 - Tue, Jun 9
Delta Logo
6:47 pm - 10:27 pm
OAJ
-
ORD
4h 40m
1 stop
Delta Logo
5:30 am - 11:21 am
ORD
-
OAJ
4h 51m
1 stop
$317Delta
Mon, Jun 1 - Sat, Jun 6
Delta Logo
6:00 am - 10:16 am
OAJ
-
ORD
5h 16m
1 stop
Delta Logo
3:00 pm - 10:04 pm
ORD
-
OAJ
6h 04m
1 stop
$345Delta
Thu, Jun 11 - Tue, Jun 16
Delta Logo
12:06 pm - 5:04 pm
OAJ
-
ORD
5h 58m
1 stop
Delta Logo
5:30 am - 11:21 am
ORD
-
OAJ
4h 51m
1 stop
$398Delta
Sun, Jul 5 - Wed, Jul 8
American Airlines Logo
1:14 pm - 4:46 pm
OAJ
-
ORD
4h 32m
1 stop
American Airlines Logo
6:30 am - 2:32 pm
ORD
-
OAJ
7h 02m
1 stop
$407American Airlines
Mon, Jul 20 - Fri, Jul 24
Delta Logo
6:44 pm - 11:53 pm
OAJ
-
ORD
6h 09m
1 stop
Delta Logo
5:30 am - 11:19 am
ORD
-
OAJ
4h 49m
1 stop
$417Delta
Wed, May 20 - Sun, May 24
Delta Logo
4:07 pm - 8:26 pm
OAJ
-
ORD
5h 19m
1 stop
Delta Logo
5:30 am - 11:06 am
ORD
-
OAJ
4h 36m
1 stop
$443Delta
Thu, Jun 11 - Tue, Jun 16
Delta Logo
12:06 pm - 5:04 pm
OAJ
-
ORD
5h 58m
1 stop
Delta Logo
5:30 am - 11:21 am
ORD
-
OAJ
4h 51m
1 stop
$449Delta
Fri, Jun 5 - Sun, Jun 7
American Airlines Logo
6:11 pm - 11:58 pm
OAJ
-
ORD
6h 47m
1 stop
American Airlines Logo
6:29 am - 2:35 pm
ORD
-
OAJ
7h 06m
1 stop
$475American Airlines
Thu, Jun 11 - Tue, Jun 16
American Airlines Logo
1:14 pm - 5:42 pm
OAJ
-
ORD
5h 28m
1 stop
American Airlines Logo
10:00 am - 5:46 pm
ORD
-
OAJ
6h 46m
2 stops
$759American Airlines
Sun, Jul 5 - Tue, Jul 21
American Airlines Logo
1:14 pm - 4:46 pm
OAJ
-
ORD
4h 32m
1 stop
American Airlines Logo
9:59 am - 5:45 pm
ORD
-
OAJ
6h 46m
2 stops
$760American Airlines
Booking Insights

KAYAK's insights & trends for Jacksonville to Chicago flights

Get data-powered insights and trends into flights from Jacksonville to Chicago to help you find the cheapest flights, the best time to fly and much more.

Which airlines provide the cheapest flights from Jacksonville to Chicago O'Hare Airport?

The cheapest round-trip price for the route for each airline clicked by KAYAK users in the last 72 hours.

In the past 3 days, the cheapest round-trip tickets from Jacksonville to Chicago O'Hare Airport were found on Delta ($317) and American Airlines ($407).

Good to know

Cheapest flight$209
Flight from Jacksonville to Chicago O'Hare Airport

When to book flights from Jacksonville to Chicago

Are your dates flexible? Find out the best times to travel from Jacksonville to Chicago based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated round-trip price
KAYAK looks at all historical flight data for each date to provide a predicted price for one-way trips or round-trips with a duration up to 40 days. While we try to provide actual minimum prices for each date, some prices are predictions and actual prices may differ.

FAQs for booking Jacksonville to Chicago O'Hare Airport flights

  • What is the cheapest flight from Jacksonville to Chicago O'Hare Intl Airport?

    In the last 3 days, the lowest price for a flight from Jacksonville to Chicago O'Hare Intl Airport was $209 for a one-way ticket and $317 for a round-trip.

  • Do I need a passport to fly between Jacksonville and Chicago O'Hare Airport?

    No

  • Which aircraft models fly most regularly from Jacksonville to Chicago O'Hare Airport?

    We unfortunately don’t have that data for this specific route.

  • Which airline alliances offer flights from Jacksonville to Chicago O'Hare Airport?

    oneworld is the only airline alliance operating flights between Jacksonville and Chicago O'Hare Airport.

  • How does KAYAK find such low prices on flights from Jacksonville to Chicago O'Hare Airport?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Jacksonville to Chicago O'Hare Airport.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Jacksonville to Chicago O'Hare Airport?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Chicago O'Hare Airport from Jacksonville is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Jacksonville to Chicago O'Hare Airport?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Chicago O'Hare Airport with an airline and back to Jacksonville with another airline. Booking your flights between Jacksonville and ORD can sometimes prove cheaper using this method.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Jacksonville to Chicago O'Hare Airport?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Chicago O'Hare Airport from Jacksonville up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

Reviews of the top airline flying from Jacksonville to Chicago

 
See real verified KAYAK customer reviews for airlines flying from Jacksonville to Chicago. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with from Jacksonville to Chicago? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
7.1
American AirlinesOverall score based on 11666 reviews
6.9Entertainment
7.9Crew
7.2Comfort
6.4Food
7.5Boarding
Airline reviews

It was good, the staff was great, and the food, was as usual, tea and biscuit. Bathroom was clean, and the plane was clean as well.

10.0 ExcellentDeepa, Apr 2026
DFW - ORD
Read more American Airlines reviews

It was good, the staff was great, and the food, was as usual, tea and biscuit. Bathroom was clean, and the plane was clean as well.

Very good I can’t complain one bit. Thank you American Airlines for making my flight enjoyable and safe!

The staff and service on American Airlines were truly outstanding. I had requested wheelchair assistance for my mother due to her knee issues, and the team went above and beyond every step of the way—from boarding in Boston to our arrival in Chicago. Their care, professionalism, and attentiveness made the entire experience smooth and stress-free. I’m very grateful for the support they provided.

The new planes (American Eagle) are beautiful and especially comfortable. The flight attendants are consistently professional and courteous. And, while it may seem inconsequential, the new liquid tube of coffee creamer—in contrast to the powdered coffee creamer—makes all the difference in a cup of coffee.

I'm not sure American is capable of on-time arrivals and departures. When you land at ORD, you almost always get held on the tarmac because your gate is still occupied. I may have missed my connection, but that ended up up being significantly delayed as well. Once again, I finally got home well after midnight.

Crew at the gate was very crabby and not at all polite. The plane was very hot the entire flight. And the seat cushion was very worn out.

The staff are very, very professional. It's what flying should feel like.

Flight was delayed half hour before boarding, but when I checked flight aware the plane that would Pick us up had a delay of more than an hour. AA should let us know in advance to avoid waiting several hours in the airport

Delays with no explanation. It could have been handled better.

Jill was the flight attendant in first class she was fabulous!! Best flight attendant I have had in years.!! And I fly every other week. Other can learn from her!!

Everything you need to know for your flight from Jacksonville to Chicago

Information on your arrival and departure airports