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
04/03/26
direct
AA1060
04h 40min
Return
04/16/26
direct
AA2845
05h 30min
American Airlines ?
$480
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
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
04/03/26
1 Stopover (CLT)
AA1784, AA2098
11h 45min
Return
04/16/26
1 Stopover (PHL)
AA3298, AA1049
07h 36min
American Airlines ?
$603
Chicago
San Juan (Puerto Rico)
Outbound
04/03/26
3 Stopovers (MEX, CUN, PUJ)
Y40701, Y40104, DM7007, DM1058
34h 28min
Return
04/16/26
3 Stopovers (IAH, FLL, MIA, MSP)
UA1644, UA1982, SY0416, SY0261
36h 27min
Volaris, AraJet ?
$646
Chicago
San Juan (Puerto Rico)
Outbound
04/03/26
direct
AA1060
04h 40min
Return
04/16/26
direct
AA2845
05h 30min
American Airlines ?
$1,041
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 US$
196 US$
451 US$
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 US$
39 %
1 stopover Orlando International Airport, FL
07h 00min, from 221 US$
18 %
1 stopover Charlotte Douglas International Airport, NC
13h 01min, from 338 US$
15 %

Important flight information

Flight information: Chicago - San Juan (Puerto Rico)

Roundtrip from 352,50 US$
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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