Flight Routes from Chicago to San Juan (Puerto Rico)

Trip type

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
Best option
Chicago
San Juan (Puerto Rico)
Outbound
07/26/26
direct
F93346
04h 57min
Return
08/05/26
direct
F93345
05h 15min
Frontier Airlines
$254
Chicago
San Juan (Puerto Rico)
Outbound
07/26/26
1 Stopover (CLT)
AA3280, AA2830
10h 00min
Return
08/05/26
1 Stopover (MIA)
AA0967, AA1211
08h 08min
American Airlines ?
$259
Chicago
San Juan (Puerto Rico)
Outbound
07/26/26
direct
F93346
04h 57min
Return
08/05/26
direct
F93345
05h 15min
Frontier Airlines ?
$263
Chicago
San Juan (Puerto Rico)
Outbound
05/16/26
direct
NK2205
04h 32min
Return
05/29/26
1 Stopover (MIA)
NK3036, NK1712
17h 00min
Spirit Airlines
$270
Chicago
San Juan (Puerto Rico)
Outbound
05/16/26
1 Stopover (MIA)
NK1713, NK3035
29h 46min
Return
05/29/26
1 Stopover (MIA)
NK3036, NK1712
17h 00min
Spirit Airlines
$271
Chicago
San Juan (Puerto Rico)
Outbound
05/16/26
1 Stopover (TPA)
F91252, F92216
24h 49min
Return
05/29/26
1 Stopover (FLL)
NK0572, NK0001
09h 05min
Frontier Airlines ?
$287
Chicago
San Juan (Puerto Rico)
Outbound
07/26/26
direct
NK2205
04h 47min
Return
08/05/26
1 Stopover (MIA)
NK3036, NK1712
16h 35min
Spirit Airlines
$353
Chicago
San Juan (Puerto Rico)
Outbound
05/16/26
1 Stopover (MIA)
F92672, F92284
24h 38min
Return
05/29/26
direct
AA2592
05h 07min
Frontier Airlines ?
$371
Chicago
San Juan (Puerto Rico)
Outbound
06/25/26
1 Stopover (MCO)
F93044, F94726
07h 42min
Return
06/30/26
1 Stopover (PHL)
F91165, F92111
08h 15min
Frontier Airlines
$387
Chicago
San Juan (Puerto Rico)
Outbound
05/16/26
direct
UA0695
04h 56min
Return
05/29/26
direct
UA2089
05h 13min
United Airlines ?
$392
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
$ 196
$ 451
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
39 %
1 stopover Orlando International Airport, FL
07h 00min, from $ 221
18 %
1 stopover Charlotte Douglas International Airport, NC
13h 01min, from $ 338
15 %

Important flight information

Flight information: Chicago - San Juan (Puerto Rico)

Roundtrip from $ 253,97
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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