Flights from Chicago to San Juan (Puerto Rico)

Our cheapest offers for flights from Chicago to San Juan (Puerto Rico)

Here you can compare cheap flights from Chicago (CHI) to San Juan (Puerto Rico) (SJU) 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 San Juan (Puerto Rico). Prices and availability may change at any time.

Outbound Return Airlines Shop Baggage Price
Chicago
San Juan (Puerto Rico)
Outbound
04/03/26
direct
NK0586
04h 33min
Return
04/16/26
1 Stopover (JFK)
B62104, B62105
08h 10min
Spirit Airlines ?
$353
Best option
Chicago
San Juan (Puerto Rico)
Outbound
02/13/26
direct
NK3020
04h 43min
Return
02/26/26
direct
NK3013
05h 22min
Spirit Airlines
$404
Chicago
San Juan (Puerto Rico)
Outbound
02/13/26
direct
NK3020
04h 43min
Return
02/26/26
1 Stopover (MCO)
F91823, F93043
12h 24min
Spirit Airlines
$381
Chicago
San Juan (Puerto Rico)
Outbound
04/03/26
direct
AA1060
04h 40min
Return
04/16/26
direct
AA2845
05h 30min
American Airlines ?
$480
Chicago
San Juan (Puerto Rico)
Outbound
12/18/25
direct
NK3020
04h 43min
Return
12/30/25
direct
NK3011
05h 15min
Spirit Airlines
$530
Chicago
San Juan (Puerto Rico)
Outbound
12/18/25
direct
NK3020
04h 43min
Return
12/30/25
direct
NK3011
05h 15min
Spirit Airlines
$543
Chicago
San Juan (Puerto Rico)
Outbound
04/03/26
direct
AA1060
04h 40min
Return
04/16/26
direct
AA2845
05h 30min
American Airlines ?
$544
Chicago
San Juan (Puerto Rico)
Outbound
02/13/26
3 Stopovers (MEX, CUN, MEX)
Y40701, Y40104, AM0513, AM0786
34h 32min
Return
02/26/26
1 Stopover (ATL)
F92871, F91441
20h 38min
Volaris, Aeroméxico ?
$596
Chicago
San Juan (Puerto Rico)
Outbound
04/03/26
1 Stopover (CLT)
AA1784, AA2098
11h 45min
Return
04/16/26
1 Stopover (PHL)
AA3298, AA1049
07h 36min
American Airlines ?
$602
Chicago
San Juan (Puerto Rico)
Outbound
02/13/26
direct
AA1758
04h 40min
Return
02/26/26
direct
AA3276
05h 30min
American Airlines ?
$633
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 San Juan (Puerto Rico)

Favorite airline: American Airlines
79 % of flights booked on the route from Chicago to San Juan (Puerto Rico) are booked with American Airlines, Spirit Airlines and United Airlines.
American Airlines
29 %
Spirit Airlines
27 %
United Airlines
23 %
Direct flights are the cheapest connection
On this route, direct flights are $ 2.00 cheaper than flights with a stopover.
non stop flight
1 stop
2 stops
04h 39min
13h 20min
15h 45min
194 USD
196 USD
451 USD
The favorite connection is non-stop
Flights from Chicago to San Juan (Puerto Rico) are most often booked as a direct flight.
Route
bookings
Direct flights
04h 39min, from 194 USD
39 %
1 stopover Orlando International Airport, FL
07h 00min, from 221 USD
18 %
1 stopover Charlotte Douglas International Airport, NC
13h 01min, from 338 USD
15 %

Important flight information

Flight information: Chicago - San Juan (Puerto Rico)

Roundtrip from 352,50 USD
Flight duration min. 04:30 / max. 07:00
Return flight duration min. 05:10/ max. 06:05
Distance 3318 km
Flights per week 28
Departure airport Airport Chicago-IL, all airports (CHI)
Arrival airport Airport San Juan - Luis Muñoz Marín International Airport (SJU)
Destination country Flights to Puerto Rico
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