Flights from Chicago to San Juan (Puerto Rico)

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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.

Chicago
San Juan (Puerto Rico)
05/14/24
direct
NK0129
04h 49min
05/30/24
1 Stopover (MCO)
F93907, F93043
08h 15min
Spirit Airlines
$217
Found several days ago
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Best option
Chicago
San Juan (Puerto Rico)
05/14/24
direct
NK0129
04h 49min
06/06/24
direct
NK0130
05h 18min
Spirit Airlines
$489
Found several days ago
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Chicago
San Juan (Puerto Rico)
Pay attention to transfer at connecting flight
07/24/24
2 Stopovers (MEX, PTY)
AM0683, CM0137, CM0187
34h 02min
08/23/24
2 Stopovers (BOG, MEX)
AV0259, AV0072, Y40934
30h 24min
Aeroméxico, Copa Airlines
$746
Found several days ago
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Chicago
San Juan (Puerto Rico)
05/14/24
direct
NK0129
04h 49min
05/30/24
1 Stopover (MCO)
F93907, F93043
08h 15min
Spirit Airlines
$218
Found several days ago
 Check
Chicago
San Juan (Puerto Rico)
05/14/24
direct
NK0129
04h 49min
05/30/24
1 Stopover (MCO)
NK1908, NK2350
10h 46min
Spirit Airlines
$254
Found several days ago
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Chicago
San Juan (Puerto Rico)
05/14/24
1 Stopover (MCO)
F93044, F93908
07h 05min
05/30/24
1 Stopover (MCO)
NK1908, NK2350
10h 46min
Frontier Airlines ?
$271
Found several days ago
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Chicago
San Juan (Puerto Rico)
05/14/24
1 Stopover (CLT)
AA1924, AA2993
07h 20min
06/06/24
2 Stopovers (MIA, DCA)
AA2421, AA2362, AA2304
18h 12min
American Airlines ?
$349
Found several days ago
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Chicago
San Juan (Puerto Rico)
05/14/24
1 Stopover (CLT)
AA1924, AA2993
07h 20min
05/30/24
1 Stopover (CLT)
AA2150, AA2013
17h 31min
American Airlines ?
$417
Found several days ago
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Chicago
San Juan (Puerto Rico)
05/14/24
1 Stopover (EWR)
UA0407, UA1543
11h 10min
06/06/24
direct
UA2088
05h 11min
United Airlines ?
$443
Found several days ago
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Chicago
San Juan (Puerto Rico)
08/07/24
2 Stopovers (CLT, MIA)
AA0450, AA2751, AA2141
15h 45min
09/06/24
2 Stopovers (CLT, DCA)
AA2150, AA1041, AA2304
18h 21min
American Airlines ?
$451
Found several days ago
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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 %

Flight information: Chicago - San Juan (Puerto Rico)

Roundtrip from $216.79
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 Chicago-IL all Airports (ORD, MDW, RFD) (CHI)
Arrival airport San Juan - Luis Muñoz Marín International Airport (SJU)
Destination country Puerto Rico
Alternative flights to San Juan (Puerto Rico)
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* Prices may vary, please check the travel details given by the online travel agency before booking. Prices include taxes.