OAJ - ORD

$189 Find Cheap Flights from Jacksonville to Chicago

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 3/21. 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
Travelers love KAYAK
41,299,237 searches in the past 7 days on KAYAK

Save 24% or moreCompare multiple travel sites with one search.

Track pricesNot ready to book? Create a price alert for when prices drop.

Bundle and saveSave money when you bundle your flight + hotel.

Filter your dealsChoose cabin class, free Wi-Fi and more.

Everything you should know

Cheapest round-trip
$339
Delta
Wed 3/25Sat 3/28
OAJ - ORD • 1 stop
Cheapest one-way
$189
Delta
Sat 3/21
OAJ - ORD • 1 stop
Top airlines
Delta
Cheapest • from $339 (round-trip)
American Airlines
Best reviews • 7.2 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
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

Wed, Mar 25 - Sat, Mar 28
Delta Logo
11:06 am - 4:39 pmOAJ-ORD
6h 33m1 stop
Delta Logo
2:45 pm - 10:14 pmORD-OAJ
6h 29m1 stop
$339Delta
Find Deal
Wed, Jan 21 - Sun, Jan 25
Delta Logo
5:40 am - 10:08 amOAJ-ORD
5h 28m1 stop
Delta Logo
9:52 am - 5:46 pmORD-OAJ
6h 54m1 stop
$350Delta
Find Deal
Wed, Jan 21 - Sun, Jan 25
American Airlines Logo
1:57 pm - 8:15 pmOAJ-ORD
7h 18m2 stops
American Airlines Logo
6:05 am - 11:11 amORD-OAJ
4h 06m1 stop
$355American Airlines
Find Deal
Wed, Mar 25 - Sat, Mar 28
Delta Logo
6:25 pm - 11:54 pmOAJ-ORD
6h 29m1 stop
Delta Logo
2:45 pm - 10:14 pmORD-OAJ
6h 29m1 stop
$358Delta
Find Deal
Wed, Mar 25 - Sat, Mar 28
Delta Logo
6:25 pm - 9:19 amOAJ-ORD
15h 54m2 stops
Delta Logo
2:45 pm - 10:14 pmORD-OAJ
6h 29m1 stop
$386Delta
Find Deal
Wed, Mar 25 - Sat, Mar 28
Delta Logo
6:25 pm - 9:19 amOAJ-ORD
15h 54m2 stops
Delta Logo
2:45 pm - 10:14 pmORD-OAJ
6h 29m1 stop
$405Delta
Find Deal
Wed, Nov 26 - Mon, Dec 1
American Airlines Logo
10:59 am - 4:05 pmOAJ-ORD
6h 06m1 stop
American Airlines Logo
6:35 pm - 12:11 amORD-OAJ
4h 36m1 stop
$447American Airlines
Find Deal
Wed, Nov 19 - Sun, Nov 23
Delta Logo
11:56 am - 3:26 pmOAJ-ORD
4h 30m1 stop
Delta Logo
6:45 am - 1:46 pmORD-OAJ
6h 01m1 stop
$461Delta
Find Deal
Wed, Jan 21 - Sun, Jan 25
American Airlines Logo
1:57 pm - 8:15 pmOAJ-ORD
7h 18m2 stops
American Airlines Logo
3:48 pm - 10:58 pmORD-OAJ
6h 10m2 stops
$559American Airlines
Find Deal
Wed, Nov 26 - Sun, Nov 30
American Airlines Logo
10:59 am - 4:05 pmOAJ-ORD
6h 06m1 stop
American Airlines Logo
5:00 am - 12:35 pmORD-OAJ
6h 35m1 stop
$695American Airlines
Find Deal
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.

What’s the cheapest day of the week to fly from Jacksonville to Chicago?

The average price of all round-trip flights from Jacksonville to Chicago O'Hare Intl Airport clicked on KAYAK for each day over the last 12 months.

If your flying dates are flexible, you should consider flying to Chicago on a Saturday, as we generally find the cheapest rates on that day for this route. On the other hand, Friday is the most expensive day to fly from Jacksonville to Chicago. For your return ticket, we recommend flying on a Wednesday and avoiding Saturdays for the best deals.

Find deals

Good to know

Low seasonAugust
Cheapest flight$189
Best time to beat the crowds with an average 42% drop in price.
Most popular time to fly and prices are also 29% lower on average.
Flight from Jacksonville to Chicago

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 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 $189 for a one-way ticket and $339 for a round-trip.

  • Do I need a passport to fly between Jacksonville and Chicago?

    No

  • Which aircraft models fly most regularly from Jacksonville to Chicago?

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

  • Which airline alliances offer flights from Jacksonville to Chicago?

    oneworld is the only airline alliance operating flights between Jacksonville and Chicago.

  • How does KAYAK find such low prices on flights from Jacksonville to Chicago?

    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.

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Chicago 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?

    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 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?

    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 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.
7.2
American AirlinesOverall score based on 11042 reviews
6.4Food
7.2Comfort
8.0Crew
6.9Entertainment
7.5Boarding
Airline reviews

I enjoyed the extra leg room compared to other airlines. The first stewards made my daughter’s birthday special by giving her an extra snack. Then the last one coming home from Chicago to Appleton made our night really enjoyable Thanks for making our trip enjoyable

10.0 Excellentchloe, Nov 2025MCO - ORD
Read more American Airlines reviews

I enjoyed the extra leg room compared to other airlines. The first stewards made my daughter’s birthday special by giving her an extra snack. Then the last one coming home from Chicago to Appleton made our night really enjoyable Thanks for making our trip enjoyable

It was good..clean, comfy seat. Friendly warm welcoming crew. Was able to check my cabin luggage at the gate which I was able to pickup in a decent time from baggage claim. The app gave all updates from delays to baggage claim info. Overall smooth flight.

It was a typical flight. We had a delay which seems to be the normality now. And we had no in flight service due to conditions.

After we landed we sat on the tarmac for 1.5 hours waiting to get to our gate. Ridiculous.

Terrible. Flight delayed for more than 8 hours with only a $12 meal voucher provided for the inconvenience. The airplane did not have breaks on arrival yet they still made us go through the motions and board on time knowing we could not take off then sit for 40+ minutes before having to get of the time. A complete waste of my time. I cannot believe they can stay business with these shenanigans. I’ll avoid this company like the plague moving forward as the lack of accountability is disgraceful.

This was the best 2 flights I have had with American out of SGF. Great crew both flights.

Excellent - explanations were clear staff was nice and flight was comfortable

Lost bag and 2 days no word leaving for cruise no clothes or stuff

Any flight to ORD after about 2pm this summer has been challenging. Flight was delayed getting in (coming from ORD) and that led to it not leaving before a ground stop due to lightening before they could fuel the plane, and so forth. They made up some time but we were still late in arriving at ORD, and that led to missed connections.

Food was ok, but not as good as I have had before on AA.

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

Information on your arrival and departure airports

Jacksonville (OAJ)
O'Hare Intl (ORD)