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
Best option
Chicago
San Juan (Puerto Rico)
Outbound
10/18/25
direct
NK1530
04h 47min
Return
10/24/25
direct
NK1531
04h 58min
Spirit Airlines
$240
Chicago
San Juan (Puerto Rico)
Outbound
10/18/25
direct
NK1530
04h 47min
Return
10/24/25
direct
NK1531
04h 58min
Spirit Airlines
$243
Chicago
San Juan (Puerto Rico)
Outbound
10/18/25
direct
NK1530
04h 47min
Return
10/24/25
direct
NK1531
04h 58min
Spirit Airlines
$252
Chicago
San Juan (Puerto Rico)
Outbound
10/18/25
direct
NK1530
04h 47min
Return
10/24/25
direct
NK1531
04h 58min
Spirit Airlines
$255
Chicago
San Juan (Puerto Rico)
Outbound
09/23/25
1 Stopover (BOS)
B61012, B60861
16h 34min
Return
09/30/25
1 Stopover (BOS)
B60562, B60311
13h 54min
JetBlue Airways ?
$257
Chicago
San Juan (Puerto Rico)
Outbound
09/19/25
direct
NK1530
04h 47min
Return
09/29/25
direct
NK1531
04h 58min
Spirit Airlines
$258
Chicago
San Juan (Puerto Rico)
Outbound
09/23/25
1 Stopover (MCO)
NK0507, NK3159
13h 17min
Return
09/30/25
1 Stopover (MCO)
NK3160, NK0506
08h 52min
Spirit Airlines
$258
Chicago
San Juan (Puerto Rico)
Outbound
09/23/25
1 Stopover (MCO)
NK3200, NK3166
16h 56min
Return
09/30/25
1 Stopover (MCO)
NK3160, NK0506
08h 52min
Spirit Airlines
$261
Chicago
San Juan (Puerto Rico)
Outbound
06/07/25
1 Stopover (MCO)
NK2189, NK1989
07h 19min
Return
06/23/25
direct
NK2534
05h 16min
Spirit Airlines
$269
Chicago
San Juan (Puerto Rico)
Outbound
09/23/25
1 Stopover (MCO)
NK0507, NK3159
13h 17min
Return
09/30/25
1 Stopover (MCO)
NK3160, NK1109
10h 07min
Spirit Airlines
$271
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 $239.23
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 (ORD, MDW, RFD) (CHI)
Arrival airport Airport San Juan - Luis Muñoz Marín International Airport (SJU)
Destination country Flights to Puerto Rico
Alternative flights to San Juan (Puerto Rico)
Flight destinations with a similar price