Cheap Flights from Jacksonville, FL to Chicago, IL from $81

On Cheapflightsplus.com you will find 6 direct and 280 connecting flights from Jacksonville to Chicago. You can compare airfare deals from 5 airlines and multiple travel sites from $81, 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: $81 (one-way), $139 (round-trip).
Direct flights
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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
08:00 — 09:44
08:00 — 09:44 UA411 United Airlines
Jacksonville — Chicago
2h 44m
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from$141
11:20 — 13:13
11:20 — 13:13 UA5345 United Airlines
Jacksonville — Chicago
2h 53m
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from$141
11:20 — 13:13
11:20 — 13:13 UA3639 United Airlines
Jacksonville — Chicago
2h 53m
Find flight
from$143
11:20 — 13:13
11:20 — 13:13 UA3675 United Airlines
Jacksonville — Chicago
2h 53m
Find flight
from$174
11:30 — 13:14
11:30 — 13:14 UA1239 United Airlines
Jacksonville — Chicago
2h 44m
Find flight
from$143
16:36 — 18:20
16:36 — 18:20 UA457 United Airlines
Jacksonville — Chicago
2h 44m
Find flight
from$141
12:40 — 19:11
12:40 — 14:44 SY326 Sun Country Airlines
Jacksonville — Minneapolis
2h 46m stop
17:30 — 19:11 SY261 Sun Country Airlines
Minneapolis — Chicago
7h 31m
including layover
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from$102
12:50 — 12:28
+1 day
12:42 — 14:54 SY326 Sun Country Airlines
Jacksonville — Minneapolis
19h 56m stop
10:48 — 12:27 SY1629 Sun Country Airlines
Minneapolis — Chicago
24h 38m
including layover
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from$106
14:00 — 18:40
12:55 — 14:48 UA1938 United Airlines
Jacksonville — Washington D.C.
1h 20m stop
17:10 — 18:37 UA2497 United Airlines
Washington D.C. — Chicago
5h 40m
including layover
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from$171
16:33 — 23:51
16:33 — 18:52 F94022 Frontier Airlines
Jacksonville — Philadelphia
3h 46m stop
22:38 — 23:51 F91617 Frontier Airlines
Philadelphia — Chicago
8h 18m
including layover
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from$87
18:54 — 23:15
18:54 — 20:56 UA6209 United Airlines
Jacksonville — Washington D.C.
1h 18m stop
22:18 — 23:30 UA1738 United Airlines
Washington D.C. — Chicago
5h 21m
including layover
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from$145
19:49 — 23:17
19:49 — 21:10 F91549 Frontier Airlines
Jacksonville — Atlanta
1h 5m stop
22:15 — 23:18 F92779 Frontier Airlines
Atlanta — Chicago
4h 28m
including layover
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from$81
19:49 — 00:14
+1 day
19:49 — 21:10 F91549 Frontier Airlines
Jacksonville — Atlanta
1h 48m stop
22:58 — 00:14 F93397 Frontier Airlines
Atlanta — Chicago
5h 25m
including layover
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from$81
07:00 — 20:00
07:00 — 09:19 UA1826 United Airlines
Jacksonville — Newark
3h 6m stop
12:25 — 13:40 UA593 United Airlines
Newark — Boston
4h 23m stop
18:03 — 20:00 UA1015 United Airlines
Boston — Chicago
14h
including layover
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from$189
07:00 — 22:12
07:00 — 09:19 UA1826 United Airlines
Jacksonville — Newark
3h 6m stop
12:25 — 13:40 UA593 United Airlines
Newark — Boston
6h 40m stop
20:20 — 22:12 UA2229 United Airlines
Boston — Chicago
16h 12m
including layover
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from$189
09:44 — 14:41
+1 day
09:44 — 10:19 G41933 Allegiant Air
Jacksonville — Nashville
10h 31m stop
20:50 — 23:59 NK1419 Spirit Airlines
Nashville — Newark
12h 58m stop
12:57 — 14:41 NK1183 Spirit Airlines
Newark — Chicago
29h 57m
including layover
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from$135
09:44 — 15:31
+1 day
09:44 — 10:19 G41942 Allegiant Air
Jacksonville — Nashville
6h 28m stop
16:47 — 18:14 NK1770 Spirit Airlines
Nashville — New Orleans
18h 39m stop
12:53 — 15:31 NK2167 Spirit Airlines
New Orleans — Chicago
30h 47m
including layover
Find flight
from$135
11:47 — 08:55
+1 day
11:47 — 13:46 G43491 Allegiant Air
Jacksonville — Akron
6h 8m stop
19:54 — 22:34 G4530 Allegiant Air
Akron — Miami
8h 6m stop
06:40 — 08:55 NK1986 Spirit Airlines
Miami — Chicago
22h 8m
including layover
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from$121
13:56 — 14:41
+1 day
13:56 — 16:11 G43153 Allegiant Air
Jacksonville — Flint
17h 4m stop
09:15 — 11:05 G41526 Allegiant Air
Flint — Newark
1h 52m stop
12:57 — 14:41 NK1183 Spirit Airlines
Newark — Chicago
25h 45m
including layover
Find flight
from$118
13:56 — 14:41
+1 day
13:56 — 16:11 G41551 Allegiant Air
Jacksonville — Flint
17h 4m stop
09:15 — 11:05 G41533 Allegiant Air
Flint — Newark
1h 52m stop
12:57 — 14:41 NK1183 Spirit Airlines
Newark — Chicago
25h 45m
including layover
Find flight
from$147
15:28 — 18:44
+1 day
16:29 — 18:07 G4629 Allegiant Air
Jacksonville — Norfolk
20h 47m stop
12:13 — 14:16 NK2130 Spirit Airlines
Norfolk — Orlando
40m stop
21:25 — 23:29 NK2190 Spirit Airlines
Orlando — Chicago
28h 16m
including layover
Find flight
from$183
15:28 — 15:31
+1 day
15:28 — 17:04 G4629 Allegiant Air
Jacksonville — Norfolk
12h 51m stop
05:55 — 08:00 NK1262 Spirit Airlines
Norfolk — Orlando
5h 23m stop
13:23 — 15:31 NK1369 Spirit Airlines
Orlando — Chicago
25h 3m
including layover
Find flight
from$186
16:18 — 08:22
+1 day
16:18 — 17:17 G41133 Allegiant Air
Jacksonville — Belleville
3h 45m stop
21:02 — 22:45 G43102 Allegiant Air
Belleville — Fort Walton Beach
7h 15m stop
06:00 — 08:22 G41455 Allegiant Air
Fort Walton Beach — Chicago
17h 4m
including layover
Find flight
from$120
17:29 — 23:43
+1 day
17:29 — 19:50 G43493 Allegiant Air
Jacksonville — Grand Rapids
2h 32m stop
22:22 — 23:33 G455 Allegiant Air
Grand Rapids — Las Vegas
18h 23m stop
17:56 — 23:43 NK184 Spirit Airlines
Las Vegas — Chicago
31h 14m
including layover
Find flight
from$156
17:29 — 14:16
+1 day
17:29 — 19:50 G43493 Allegiant Air
Jacksonville — Grand Rapids
2h 32m stop
22:22 — 23:33 G455 Allegiant Air
Grand Rapids — Las Vegas
8h 59m stop
08:32 — 14:16 NK187 Spirit Airlines
Las Vegas — Chicago
21h 47m
including layover
Find flight
from$176
18:40 — 16:48
+1 day
18:40 — 21:06 MX2503 Mexicana
Jacksonville — Hartford
14h 19m stop
11:25 — 12:55 NK2042 Spirit Airlines
Hartford — Nashville
2h 3m stop
14:58 — 16:48 NK2028 Spirit Airlines
Nashville — Chicago
23h 8m
including layover
Find flight
from$177
20:21 — 20:40
+1 day
20:21 — 21:41 G43059 Allegiant Air
Jacksonville — Knoxville
13h 13m stop
10:54 — 12:58 G4494 Allegiant Air
Knoxville — Miami
5h 22m stop
18:20 — 20:40 NK3 Spirit Airlines
Miami — Chicago
25h 19m
including layover
Find flight
from$122
20:26 — 17:15
+1 day
20:26 — 22:23 G4611 Allegiant Air
Jacksonville — Indianapolis
7h 37m stop
06:00 — 06:46 SY1986 Sun Country Airlines
Indianapolis — Minneapolis
8h 50m stop
15:36 — 17:15 SY259 Sun Country Airlines
Minneapolis — Chicago
21h 49m
including layover
Find flight
from$135
21:42 — 14:41
+1 day
21:42 — 23:34 G42737 Allegiant Air
Jacksonville — Pittsburgh
6h 56m stop
06:30 — 07:55 NK1781 Spirit Airlines
Pittsburgh — Newark
5h 2m stop
12:57 — 14:41 NK1183 Spirit Airlines
Newark — Chicago
17h 59m
including layover
Find flight
from$147
21:42 — 14:41
+1 day
21:42 — 23:34 G42749 Allegiant Air
Jacksonville — Pittsburgh
6h 56m stop
06:30 — 07:55 NK1781 Spirit Airlines
Pittsburgh — Newark
5h 2m stop
12:57 — 14:41 NK1183 Spirit Airlines
Newark — Chicago
17h 59m
including layover
Find flight
from$154
*Departure and arrival times - local. Updated on June 28, 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 07:00 to 21:45 from 4 Jacksonville airports and arrive 07:00 to 21:45 to 7 Chicago airports. Average flight time is 2h 49m.

  • The fastest flight 2h 44m
  • Average flight time 2h 49m
  • The earliest flight 07:00
  • The latest flight 21:45
  • Distance 854 ml

The cheapest months to travel to Chicago are june (from 109 $), july (from 113 $), august (from 116 $).

The most expensive months are february (from 268 $), january (from 268 $), september (from 214 $).

What is the lowest airfare Jacksonville to Chicago?

The cheapest plane ticket found by our users is $81. This airfare is for economy class on one-way F91549 flight by Frontier Airlines for June 29, 2025 which leaves Jacksonville in Jacksonville at 19:49 am and arrives at Chicago Midway at 23:17.

Economy class
$81
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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 5 regular airlines and 3 low-cost airlines. Most of the flights on this route are operated by Frontier Airlines - 3 departures per week at the price of from $ 81 . And the most expensive tickets are offered by United Airlines airline - from $ 442.

Direct flights

There are 6 nonstop flights on the route. The fastest direct flight is UA411 by United Airlines takes 2h 44m and the cheapest is F91549 by Frontier Airlines for $141.

  • UA - United Airlines
    from $141
    Find
See more direct flights

Connecting Flights

There are 280 flights with layovers on the route. The fastest connecting flight is F91549 by Frontier Airlines takes 4h 28m and the cheapest is F91549 by Frontier Airlines for $81.

  • F9 - Frontier Airlines
    from $81
    Find
  • SY - Sun Country Airlines
    from $102
    Find
  • MX - Mexicana
    from $177
    Find
  • UA - United Airlines
    from $145
    Find
  • G4 - Allegiant Air
    from $118
    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 $81
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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

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.

    To find a plane ticket, please select dates.

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