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
04/12/25
1 Stopover (MCO)
F93044, F91746
14h 58min
Return
04/27/25
direct
NK0264
05h 23min
Frontier Airlines ?
$195
found 2 days ago
Best option
Chicago
San Juan (Puerto Rico)
Outbound
06/20/25
direct
AA2852
04h 45min
Return
07/19/25
direct
AA1184
05h 10min
American Airlines ?
$465
Chicago
San Juan (Puerto Rico)
Outbound
04/21/25
2 Stopovers (ATL, MCO)
F91596, F94556, F94726
39h 29min
Return
05/19/25
2 Stopovers (BWI, ATL)
F92265, F92509, F91595
35h 43min
Frontier Airlines ?
$197
Chicago
San Juan (Puerto Rico)
Outbound
04/12/25
1 Stopover (MCO)
F93044, F91746
14h 58min
Return
04/27/25
direct
NK0264
05h 23min
Frontier Airlines
$201
found 2 days ago
Chicago
San Juan (Puerto Rico)
Outbound
04/12/25
1 Stopover (MCO)
F93044, F94726
17h 30min
Return
04/27/25
1 Stopover (MCO)
F92249, F92791
18h 39min
Frontier Airlines ?
$214
found 2 days ago
Chicago
San Juan (Puerto Rico)
Outbound
04/21/25
1 Stopover (MCO)
NK1506, NK0980
08h 57min
Return
05/19/25
1 Stopover (ATL)
F92871, F93397
13h 25min
Spirit Airlines
$239
Chicago
San Juan (Puerto Rico)
Outbound
04/21/25
1 Stopover (MCO)
NK1506, NK0980
08h 57min
Return
05/19/25
direct
NK0492
04h 59min
Spirit Airlines
$272
Chicago
San Juan (Puerto Rico)
Outbound
04/21/25
1 Stopover (MCO)
F92792, F94726
16h 10min
Return
05/19/25
1 Stopover (ATL)
F92871, F93397
13h 25min
Frontier Airlines ?
$304
Chicago
San Juan (Puerto Rico)
Outbound
06/20/25
direct
AA2852
04h 45min
Return
07/19/25
direct
AA1184
05h 10min
American Airlines ?
$496
Chicago
San Juan (Puerto Rico)
Outbound
06/20/25
direct
UA0695
04h 51min
Return
07/19/25
direct
UA2089
05h 10min
United Airlines ?
$543
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 $194.89
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