Cheap Flights from Jacksonville, FL to Chicago, IL from $389

On Cheapflightsplus.com you will find 6 connecting flights from Jacksonville to Chicago. You can compare airfare deals from 3 airlines and multiple travel sites from $389, book and save on cheap plane tickets and last minute offers. Also check out JAX-CHI flight schedule to find best flight time, convenient departure and arrival airports.

Flight Information

Below we will explain in detail what the flights cost on the destination from Jacksonville to Chicago depends on and how to choose the most interesting flight option for you.

Distance between Jacksonville and Chicago is 1373 miles. Time difference between the cities is 1h. Airplanes depart 18:56 to 21:45 from 4 Jacksonville airports and arrive 18:56 to 21:45 to 7 Chicago airports. Average flight time is 17h 35m.

  • The fastest flight 13h 38m
  • Average flight time 17h 35m
  • The earliest flight 18:56
  • The latest flight 21:45
  • Distance 854 ml

The cheapest months to travel to Chicago are july (from 389 $).

What is the lowest airfare Jacksonville to Chicago?

The cheapest plane ticket found by our users is $389. This airfare is for economy class on one-way G42009 flight by Allegiant Air for July 25, 2025 which leaves Jacksonville in Jacksonville at 21:45 am and arrives at Chicago O'Hare International at 17:17.

Economy class
$389
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Business class
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First class
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Flight Schedule Jacksonville (Florida) to Chicago (Illinois)

18:56 — 08:33+1day
14h 37m flight time
Find flight
from$597
18:56 — 21:29 Jacksonville — Newark
UA3578 United Airlines
9h 31m stop
07:00 — 08:33 Newark — Chicago
UA2050 United Airlines
18:56 — 07:34+1day
13h 38m flight time
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from$655
18:56 — 21:29 Jacksonville — Newark
UA3578 United Airlines
1h 1m stop
22:30 — 00:07 Newark — Rochester
UA3484 United Airlines
6h 17m stop
06:24 — 07:34 Rochester — Chicago
UA2483 United Airlines
18:56 — 07:38+1day
13h 42m flight time
Find flight
from$717
18:56 — 21:29 Jacksonville — Newark
UA3578 United Airlines
8h 31m stop
06:00 — 07:38 Newark — Chicago
UA2164 United Airlines
21:01 — 23:44+1day
27h 43m flight time
Find flight
from$402
21:01 — 23:32 Jacksonville — East Providence
MX707 Mexicana
7h 58m stop
14:07 — 17:38 East Providence — Fort Myers
MX712 Mexicana
10h 35m stop
21:57 — 00:07 Fort Myers — Chicago
NK1872 Spirit Airlines
21:01 — 17:17+1day
21h 16m flight time
Find flight
from$673
21:01 — 23:32 Jacksonville — East Providence
MX707 Mexicana
9h 53m stop
09:25 — 11:33 East Providence — Myrtle Beach
MX730 Mexicana
4h 19m stop
15:52 — 17:17 Myrtle Beach — Chicago
NK1637 Spirit Airlines
21:45 — 17:17+1day
20h 32m flight time
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from$389
21:45 — 23:38 Jacksonville — Covington
G42009 Allegiant Air
7h 52m stop
07:30 — 09:00 Covington — Myrtle Beach
G41988 Allegiant Air
6h 52m stop
15:52 — 17:17 Myrtle Beach — Chicago
NK1637 Spirit Airlines
Full flight schedule will help you in detecting at what time planes fly from Jacksonville to Chicago. You can also specify the concrete flights and airlines on the route and how long the flight actually is. Use the calendar for today, tomorrow or other specific date as some flights are available only on certain days of the week.
*Departure and arrival times - local. Updated on October 14, 2025.

Popular Airlines on the Route

The flight Jacksonville — Chicago is served by 3 regular airlines and 1 low-cost airline. Most of the flights on this route are operated by Mexicana - 2 departures per week at the price of from $ 402 . And the most expensive tickets are offered by United Airlines airline - from $ 717.

Direct flights

There’re no direct flights on this route. Try flights with stops.

Connecting Flights

There are 6 flights with layovers on the route. The fastest connecting flight is UA3578 by United Airlines takes 13h 38m and the cheapest is G42009 by Allegiant Air for $389.

  • MX - Mexicana
    from $402
    Find
  • UA - United Airlines
    from $597
    Find
  • G4 - Allegiant Air
    from $389
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See more connecting flights

Airports

You can fly from Jacksonville to Chicago from 4 airports (Jacksonville, Craig Municipal, Jacksonville NAS, Cecil Field).

Jacksonville airports

  • Jacksonville-JAX
    from $389
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  • Craig Municipal-CRG
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  • Jacksonville NAS-NIP
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  • Cecil Field-VQQ
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Chicago airports

  • O'Hare International-ORD
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  • Midway-MDW
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  • Dupage County-DPA
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  • Chicago FSS-CHI
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  • Merrill C Meigs (closed)-CGX
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  • Pal-Waukee-PWK
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  • Chicago NAS-NOH
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How to book a plane ticket yourself?

How to book an air ticket yourself?
  • Fill in the search parameters — cities of departure and destination, departure and return dates and click «Find flights»
  • Select the best flight that you like. Please, check the airports of departure and arrival. Select the best fare, but pay attention to the following flight details - airports of departure and arrival, flight duration and layovers. Please use filters and sort to find the best flight.
  • Click «Buy» when you are ready — our system will redirect you to the site that sells the selected flight ticket.
  • Fill in all passenger and payment information — passport and contact information, please double check all passengers’ names and make a payment for your itinerary.
  • That's it — you will receive an email with your e-ticket usually within 10 minutes after your flight is confirmed. Please, print the e-ticket and have it with you at the airport. You would need to have only a passport and/or a required form of ID to travel. Please, check your Visa requirements if you travel outside of the United States or Canada.

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