OAJ - CHI

$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

 
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
$339
Delta
Tue 3/24Sat 3/28
OAJ - MDW • 1 stop
Cheapest one-way
$189
Delta
Sat 3/21
OAJ - ORD • 1 stop
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We hope you love your trip to Chicago!
Flight Deals
Booking Insights
Flight Deals

Cheap Flights from Jacksonville to Chicago (OAJ-CHI)

 
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, Mar 24 - Sat, Mar 28
Delta Logo
5:40 am - 9:56 amOAJ-MDW
5h 16m1 stop
Delta Logo
4:30 pm - 10:14 pmMDW-OAJ
4h 44m1 stop
$339Delta
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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
$358Delta
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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
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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
$415Delta
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Tue, Mar 24 - Sat, Mar 28
Delta Logo
2:25 pm - 8:50 amOAJ-MDW
19h 25m2 stops
Delta Logo
4:30 pm - 10:14 pmMDW-OAJ
4h 44m1 stop
$456Delta
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Thu, Nov 13 - Mon, Nov 17
Delta Logo
5:30 am - 10:19 amOAJ-ORD
5h 49m1 stop
Delta Logo
6:45 am - 1:46 pmORD-OAJ
6h 01m1 stop
$487Delta
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Thu, Nov 13 - Mon, Nov 17
Delta Logo
5:30 am - 11:52 amOAJ-MDW
7h 22m1 stop
Delta Logo
6:00 am - 11:16 amMDW-OAJ
4h 16m1 stop
$487Delta
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Thu, Nov 13 - Mon, Nov 17
American Airlines Logo
5:00 am - 10:58 amOAJ-ORD
6h 58m2 stops
American Airlines Logo
3:44 pm - 11:02 pmORD-OAJ
6h 18m1 stop
$530American Airlines
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Thu, Nov 13 - Mon, Nov 17
American Airlines Logo
5:00 am - 10:58 amOAJ-ORD
6h 58m2 stops
American Airlines Logo
10:15 am - 6:31 pmORD-OAJ
7h 16m2 stops
$535American Airlines
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Sat, Dec 20 - Sat, Jan 3
American Airlines Logo
7:55 pm - 11:59 pmOAJ-ORD
5h 04m1 stop
American Airlines Logo
6:38 pm - 11:59 pmORD-OAJ
4h 21m1 stop
$564American Airlines
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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 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

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

  • 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 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.

  • 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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