Flights 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
Chicago
San Juan (Puerto Rico)
Outbound
05/16/26
1 Stopover (MIA)
AA1694, AA3115
13h 13min
Return
05/29/26
1 Stopover (DFW)
AA2742, AA2740
18h 25min
American Airlines ?
$259
Best option
Chicago
San Juan (Puerto Rico)
Outbound
05/16/26
direct
UA0695
04h 56min
Return
05/29/26
direct
UA2089
05h 13min
United Airlines ?
$392
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
03/28/26
2 Stopovers (EWR, ATL)
NK0107, NK0352, NK3830
24h 34min
Return
04/25/26
direct
NK2208
05h 15min
Spirit Airlines
$275
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
03/28/26
direct
NK0586
04h 33min
Return
04/25/26
1 Stopover (MIA)
F92383, F92671
16h 18min
Spirit Airlines ?
$321
Chicago
San Juan (Puerto Rico)
Outbound
03/28/26
1 Stopover (IAH)
UA2426, UA1497
08h 01min
Return
04/25/26
1 Stopover (BOS)
B60662, B60311
10h 31min
United Airlines ?
$369
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
03/28/26
1 Stopover (JFK)
B61206, B60703
09h 31min
Return
04/25/26
1 Stopover (BOS)
B60662, B60311
10h 31min
JetBlue Airways ?
$400
Prices based on recent searches, subject to last-minute changes
Page 1 / 2

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 $ 258,80
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
Flight destinations with a similar price