Flights from Chicago to Jacksonville, Florida

Our cheapest offers for flights from Chicago to Jacksonville, Florida

Here you can compare cheap flights from Chicago (CHI) to Jacksonville, Florida (JAX) for one-way or return trips. The following offers were searched for and found on idealo during the last few days. Or start your own flight search to Jacksonville, Florida. Prices and availability may change at any time.

Outbound Return Airlines Shop Baggage Price
Chicago
Jacksonville, Florida
Outbound
02/13/26
direct
UA2443
02h 27min
Return
02/26/26
1 Stopover (BOS)
B61310, B60811
07h 46min
United Airlines ?
$339
Best option
Chicago
Jacksonville, Florida
Outbound
04/03/26
direct
UA2443
02h 34min
Return
04/16/26
direct
UA1239
02h 51min
United Airlines ?
$373
found 3 days ago
Chicago
Jacksonville, Florida
Outbound
04/03/26
direct
UA2443
02h 34min
Return
04/16/26
direct
UA1733
02h 50min
United Airlines ?
$388
found 3 days ago
Chicago
Jacksonville, Florida
Outbound
02/13/26
direct
UA2443
02h 27min
Return
02/26/26
direct
UA0457
02h 51min
United Airlines ?
$424
Chicago
Jacksonville, Florida
Outbound
04/03/26
direct
AA3350
02h 32min
Return
04/16/26
direct
AA4269
02h 46min
American Airlines ?
$488
found 3 days ago
Chicago
Jacksonville, Florida
Outbound
02/13/26
1 Stopover (PHL)
AA2992, AA4755
08h 10min
Return
02/26/26
1 Stopover (PHL)
AA4392, AA1452
08h 24min
American Airlines ?
$516
Chicago
Jacksonville, Florida
Outbound
02/13/26
direct
AA3350
02h 39min
Return
02/26/26
direct
AA3486
02h 40min
American Airlines ?
$582
Chicago
Jacksonville, Florida
Outbound
02/13/26
1 Stopover (JFK)
B61306, B62377
09h 59min
Return
02/26/26
1 Stopover (BOS)
B61310, B60811
07h 46min
JetBlue Airways ?
$590
Chicago
Jacksonville, Florida
Outbound
04/03/26
direct
AA3350
02h 32min
Return
04/16/26
direct
AA4269
02h 46min
American Airlines ?
$1,008
found 3 days ago
Chicago
Jacksonville, Florida
Outbound
04/03/26
2 Stopovers (LAX, MSP)
F92445, SY0426, SY0325
40h 17min
Return
04/16/26
4 Stopovers (EWR, MUC, KRK, LHR)
LH7730, LH7608, LH1622, AA7046, AA0087
49h 51min
Frontier Airlines, Sun Country Airlines ?
$1,441
found 3 days ago
Prices based on recent searches, subject to last-minute changes
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Tips and tricks to help you find cheap flights from Chicago to Jacksonville, Florida

Favorite airline: United Airlines
United Airlines is the most popular airline for flights from Chicago to Jacksonville, Florida.
United Airlines
44 %
JetBlue Airways
20 %
American Airlines
18 %
Direct flights are more expensive
On this route, direct flights are $ 6.00 more expensive than flights with a stopover.
non stop flight
1 stop
2 stops
02h 34min
05h 44min
14h 14min
$270
$264
$321
The favorite connection is non-stop
55 % of travelers decide to book a direct flight on this route.
Route
bookings
Direct flights
02h 34min, from $270
55 %
1 stopover New York - John F. Kennedy International Airport, NY
06h 09min, from $1,927
14 %
1 stopover Minneapolis - St. Paul International Airport, MN
14h 23min, from $308
12 %

Important flight information

Flight information: Chicago - Jacksonville, Florida

Roundtrip from $338.30
Flight duration min. 02:10 / max. 04:15
Return flight duration min. 02:35/ max. 03:01
Distance 1375 km
Flights per week 57
Departure airport Airport Chicago-IL, all airports (CHI)
Arrival airport Airport Jacksonville, Florida (JAX)
Destination country Flights to United States
Alternative routes to United States
Alternative flights to Jacksonville, Florida
Flight destinations with a similar price
Flight destinations with a similar price