Cheap Flights from Jacksonville, FL to Chicago, IL from $398

Return flight: Chicago – Jacksonville
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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 $398, 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.

Find One-Way and Round-Trip Jacksonville to Chicago Flight Deals

To find the cheapest one way airline ticket select the date with the lowest price on the calendar below and click «Find Flights». To search for round-trip flight deals click on the link «Check prices for return flights» and select the date of the return flight. Cheapest flights in November: $398 (one-way), $683 (round-trip).
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Best Flights from Jacksonville to Chicago Today

Take a look at the list of non stop flights and flights with layovers from Jacksonville to Chicago with the lowest price of $398. Take a look at the list of flights with layovers from Jacksonville to Chicago from $398. There’re no direct flights. The fastest connecting flight – 13h 38m.
Price Departure Arrival Flight Duration Airline Flight
from $610
Find flight
18:56
Jacksonville
Jacksonville
 08:33+1 день
Chicago
O'Hare International
 14h 37m
layover
9h 31m - Newark
 United Airlines
UA3578
UA2050
from $398
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21:45
Jacksonville
Jacksonville
 17:17+1 день
Chicago
O'Hare International
 20h 32m
layover
7h 52m - Covington
6h 52m - Myrtle Beach
 Allegiant Air
G42009
G41988
NK1637
from $411
Find flight
21:01
Jacksonville
Jacksonville
 23:44+1 день
Chicago
O'Hare International
 27h 43m
layover
7h 58m - East Providence
10h 35m - Fort Myers
 Mexicana
MX707
MX712
NK1872
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*Departure and arrival times - local. Prices indicated for one-way flights. Information updated on August 29, 2025
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 Arrival Flight Details Flight Duration Price
18:56 — 08:33
+1 day
18:56 — 21:29 UA3578 United Airlines
Jacksonville — Newark
9h 31m stop
07:00 — 08:33 UA2050 United Airlines
Newark — Chicago
14h 37m
including layover
Find flight
from$610
18:56 — 07:38
+1 day
18:56 — 21:29 UA3578 United Airlines
Jacksonville — Newark
8h 31m stop
06:00 — 07:38 UA2164 United Airlines
Newark — Chicago
13h 42m
including layover
Find flight
from$733
18:56 — 07:34
+1 day
18:56 — 21:29 UA3578 United Airlines
Jacksonville — Newark
1h 1m stop
22:30 — 00:07 UA3484 United Airlines
Newark — Rochester
6h 17m stop
06:24 — 07:34 UA2483 United Airlines
Rochester — Chicago
13h 38m
including layover
Find flight
from$670
21:01 — 23:44
+1 day
21:01 — 23:32 MX707 Mexicana
Jacksonville — East Providence
7h 58m stop
14:07 — 17:38 MX712 Mexicana
East Providence — Fort Myers
10h 35m stop
21:57 — 00:07 NK1872 Spirit Airlines
Fort Myers — Chicago
27h 43m
including layover
Find flight
from$411
21:01 — 17:17
+1 day
21:01 — 23:32 MX707 Mexicana
Jacksonville — East Providence
9h 53m stop
09:25 — 11:33 MX730 Mexicana
East Providence — Myrtle Beach
4h 19m stop
15:52 — 17:17 NK1637 Spirit Airlines
Myrtle Beach — Chicago
21h 16m
including layover
Find flight
from$688
21:45 — 17:17
+1 day
21:45 — 23:38 G42009 Allegiant Air
Jacksonville — Covington
7h 52m stop
07:30 — 09:00 G41988 Allegiant Air
Covington — Myrtle Beach
6h 52m stop
15:52 — 17:17 NK1637 Spirit Airlines
Myrtle Beach — Chicago
20h 32m
including layover
Find flight
from$398
*Departure and arrival times - local. Updated on August 29, 2025

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 398 $).

What is the lowest airfare Jacksonville to Chicago?

The cheapest plane ticket found by our users is $398. 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
$398
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Business class
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First class
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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 $ 411 . And the most expensive tickets are offered by United Airlines airline - from $ 733.

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 $398.

  • MX - Mexicana
    from $411
    Find
  • UA - United Airlines
    from $610
    Find
  • G4 - Allegiant Air
    from $398
    Find
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 $398
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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
    Find

Airplanes

There are flights to Chicago from Jacksonville by 3 airlines that use 0 aircraft brands. They range from huge modern airplanes to small-sized.

Top Domestic Destinations from Jacksonville

You may also consider searching for discounted plane tickets to some other popular places from Jacksonville within United States.

Top International Destinations from Jacksonville

Our state-of-the art metasearch will definitely provide you with the best airfare on international flights. We’re proud to partner with many reliable travel suppliers located outside the US what gives us an opportunity to offer the most competitive prices on far destinations.

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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