OAJ - CHI

$377 Find Cheap Flights from Jacksonville to Chicago

This is the cheapest round-trip flight price found by a KAYAK user in the last 72 hours by searching for a flight from Jacksonville to Chicago departing on 6/21. 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.
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KAYAK searches hundreds of travel sites at once for deals on flights to Chicago

 
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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Flights Deals

Cheap Flights from Jacksonville to Chicago

 
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.

Recent round-trip flight deals from Jacksonville to Chicago

KAYAK's recommended round-trip deals from the most popular airlines that fly from Jacksonville to Chicago.
Discover the best prices for you by selecting your travel dates on KAYAK.
American Airlines Logo
1:18 pm - 5:35 pmOAJ-ORD
5h 17m1 stop
American Airlines Logo
7:05 am - 2:18 pmORD-OAJ
6h 13m1 stop
$377American Airlines
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Sat, Jun 21 - Mon, Jun 30
Delta Logo
3:17 pm - 6:59 pmOAJ-ORD
4h 42m1 stop
Delta Logo
7:05 am - 2:37 pmORD-OAJ
6h 32m1 stop
$387Delta
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Fri, May 23 - Tue, May 27
Delta Logo
3:26 pm - 9:24 pmOAJ-ORD
6h 58m1 stop
Delta Logo
7:00 am - 2:46 pmORD-OAJ
6h 46m1 stop
$415Delta
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Thu, Jun 19 - Sun, Jun 22
Delta Logo
5:55 am - 12:20 pmOAJ-ORD
7h 25m1 stop
Delta Logo
7:05 am - 2:37 pmORD-OAJ
6h 32m1 stop
$440Delta
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Sat, May 17 - Mon, May 19
American Airlines Logo
5:00 am - 10:43 amOAJ-ORD
6h 43m2 stops
American Airlines Logo
1:34 pm - 9:53 pmORD-OAJ
7h 19m1 stop
$471American Airlines
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Sat, May 17 - Mon, May 19
Delta Logo
7:12 pm - 11:58 pmOAJ-ORD
5h 46m1 stop
Delta Logo
3:57 pm - 10:10 pmORD-OAJ
5h 13m1 stop
$485Delta
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Thu, May 15 - Mon, May 19
Delta Logo
3:26 pm - 9:45 pmOAJ-MDW
7h 19m1 stop
Delta Logo
6:00 am - 11:14 amMDW-OAJ
4h 14m1 stop
$489Delta
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Thu, Jun 19 - Sun, Jun 22
American Airlines Logo
5:10 am - 10:45 amOAJ-ORD
6h 35m1 stop
American Airlines Logo
5:10 pm - 11:58 pmORD-OAJ
5h 48m2 stops
$620American Airlines
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Sat, Jun 21 - Mon, Jun 30
American Airlines Logo
1:18 pm - 7:13 pmOAJ-ORD
6h 55m1 stop
American Airlines Logo
7:36 am - 2:18 pmORD-OAJ
5h 42m2 stops
$638American Airlines
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Thu, Jun 19 - Sun, Jun 22
American Airlines Logo
2:44 pm - 7:50 pmOAJ-ORD
6h 06m2 stops
American Airlines Logo
5:29 am - 12:51 pmORD-OAJ
6h 22m1 stop
$658American Airlines
Find Deal
Thu, Jun 19 - Mon, Jun 23
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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 clicked on KAYAK for each day over the last 12 months.

When flying from Jacksonville to Chicago, you should consider leaving on a Saturday and avoid Fridays if you are looking for the best rates. For your return to Jacksonville, you’ll find the best rates on Wednesdays and the most expensive ones on Saturdays.

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Good to know

Low seasonSeptember
High seasonJuly
Cheapest flight$377
Best time to beat the crowds with an average 34% drop in price.
Most popular time to fly with an average 6% increase in price.
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 flights from Jacksonville to Chicago

  • What is the cheapest flight from Jacksonville to Chicago?

    In the last 3 days, the lowest price for a flight from Jacksonville to Chicago was $377 for a round-trip ticket.

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

    A passport is not required to fly from Jacksonville to Chicago.

  • Which airports will I be using when flying from Jacksonville to Chicago?

    On your way to Chicago, you’ll fly out from Jacksonville Albert J Ellis. You’ll be landing in one of Chicago’s 2 airports: Chicago Midway or Chicago O'Hare Intl.

  • 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, and SkyTeam are the airline alliances operating flights between Jacksonville and Chicago, with SkyTeam being the most commonly used for this route.

  • 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.

  • 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.

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

Information on your arrival and departure airports

Jacksonville (OAJ)

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