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
10/24/25
direct
NK2080
04h 45min
Return
10/26/25
1 Stopover (MCO)
F91745, F93043
10h 51min
Spirit Airlines
$234
Best option
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
10/24/25
direct
NK2080
04h 45min
Return
10/26/25
1 Stopover (MCO)
F91745, F93043
10h 51min
Spirit Airlines
$250
Chicago
San Juan (Puerto Rico)
Outbound
10/24/25
1 Stopover (PHL)
F92112, F91016
23h 25min
Return
10/26/25
1 Stopover (MCO)
F91745, F93043
10h 51min
Frontier Airlines ?
$297
Chicago
San Juan (Puerto Rico)
Outbound
10/24/25
direct
NK2080
04h 45min
Return
10/26/25
1 Stopover (MCO)
F91745, F93043
10h 51min
Spirit Airlines ?
$332
Chicago
San Juan (Puerto Rico)
Outbound
10/24/25
2 Stopovers (PHL, CLT)
AA0471, AA3012, AA2199
12h 25min
Return
10/26/25
2 Stopovers (CLT, LGA)
AA0783, AA2031, AA0462
16h 46min
American Airlines ?
$501
Chicago
San Juan (Puerto Rico)
Outbound
10/24/25
1 Stopover (MIA)
AA0534, AA0967
08h 54min
Return
10/26/25
1 Stopover (PHL)
AA1147, AA1854
07h 34min
American Airlines ?
$520
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
12/18/25
1 Stopover (MIA)
AA1277, AA3250
11h 01min
Return
12/30/25
1 Stopover (PHL)
AA0419, AA1937
14h 07min
American Airlines ?
$644
Chicago
San Juan (Puerto Rico)
Outbound
10/24/25
1 Stopover (MIA)
AA0534, AA0967
08h 54min
Return
10/26/25
1 Stopover (PHL)
AA1147, AA1854
07h 34min
American Airlines ?
$661
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 $ 233,97
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
Alternative flights to San Juan (Puerto Rico)
Flight destinations with a similar price
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