Flights from Chicago to San Juan (Puerto Rico)

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Outbound flight: 12/31/20
14:29 CHI
23:09 SJU
Chicago-IL all Airports (ORD, MDW, RFD)
San Juan - Luis Muñoz Marín International Airport
1 Stopover
Spirit Airlines
Return flight: 01/07/21
01:10 SJU
08:56 CHI
San Juan - Luis Muñoz Marín International Airport
Chicago-IL all Airports (ORD, MDW, RFD)
1 Stopover
Spirit Airlines
$211
Check
Outbound flight: 12/31/20
16:50 CHI
01:30 SJU
Chicago-IL all Airports (ORD, MDW, RFD)
San Juan - Luis Muñoz Marín International Airport
1 Stopover
American Airlines
Return flight: 01/07/21
01:10 SJU
08:56 CHI
San Juan - Luis Muñoz Marín International Airport
Chicago-IL all Airports (ORD, MDW, RFD)
1 Stopover
Spirit Airlines
$213
Check
Outbound flight: 12/31/20
16:50 CHI
01:30 SJU
Chicago-IL all Airports (ORD, MDW, RFD)
San Juan - Luis Muñoz Marín International Airport
1 Stopover
American Airlines
Return flight: 01/07/21
01:10 SJU
08:56 CHI
San Juan - Luis Muñoz Marín International Airport
Chicago-IL all Airports (ORD, MDW, RFD)
1 Stopover
Spirit Airlines
$213
Check
Outbound flight: 12/31/20
12:00 CHI
22:14 SJU
Chicago-IL all Airports (ORD, MDW, RFD)
San Juan - Luis Muñoz Marín International Airport
1 Stopover
American Airlines
Return flight: 01/07/21
01:10 SJU
08:56 CHI
San Juan - Luis Muñoz Marín International Airport
Chicago-IL all Airports (ORD, MDW, RFD)
1 Stopover
Spirit Airlines
$213
Check
Outbound flight: 12/31/20
12:00 CHI
22:14 SJU
Chicago-IL all Airports (ORD, MDW, RFD)
San Juan - Luis Muñoz Marín International Airport
1 Stopover
American Airlines
Return flight: 01/07/21
01:10 SJU
08:56 CHI
San Juan - Luis Muñoz Marín International Airport
Chicago-IL all Airports (ORD, MDW, RFD)
1 Stopover
Spirit Airlines
$213
Check
Outbound flight: 12/31/20
12:00 CHI
22:14 SJU
Chicago-IL all Airports (ORD, MDW, RFD)
San Juan - Luis Muñoz Marín International Airport
1 Stopover
American Airlines
Return flight: 01/07/21
01:10 SJU
08:56 CHI
San Juan - Luis Muñoz Marín International Airport
Chicago-IL all Airports (ORD, MDW, RFD)
1 Stopover
Spirit Airlines
$213
Check
Outbound flight: 12/31/20
12:00 CHI
22:14 SJU
Chicago-IL all Airports (ORD, MDW, RFD)
San Juan - Luis Muñoz Marín International Airport
1 Stopover
American Airlines
Return flight: 01/07/21
01:10 SJU
08:56 CHI
San Juan - Luis Muñoz Marín International Airport
Chicago-IL all Airports (ORD, MDW, RFD)
1 Stopover
Spirit Airlines
$213
Check
Outbound flight: 12/31/20
14:29 CHI
23:09 SJU
Chicago-IL all Airports (ORD, MDW, RFD)
San Juan - Luis Muñoz Marín International Airport
1 Stopover
Spirit Airlines
Return flight: 01/07/21
01:10 SJU
08:56 CHI
San Juan - Luis Muñoz Marín International Airport
Chicago-IL all Airports (ORD, MDW, RFD)
1 Stopover
Spirit Airlines
$222
Check
Outbound flight: 12/31/20
14:29 CHI
23:09 SJU
Chicago-IL all Airports (ORD, MDW, RFD)
San Juan - Luis Muñoz Marín International Airport
1 Stopover
Spirit Airlines
Return flight: 01/07/21
01:10 SJU
08:56 CHI
San Juan - Luis Muñoz Marín International Airport
Chicago-IL all Airports (ORD, MDW, RFD)
1 Stopover
Spirit Airlines
$229
Check
Outbound flight: 12/31/20
14:29 CHI
23:09 SJU
Chicago-IL all Airports (ORD, MDW, RFD)
San Juan - Luis Muñoz Marín International Airport
1 Stopover
Spirit Airlines
Return flight: 01/07/21
01:10 SJU
08:56 CHI
San Juan - Luis Muñoz Marín International Airport
Chicago-IL all Airports (ORD, MDW, RFD)
1 Stopover
Spirit Airlines
$229
Check
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: United Airlines
9 % of flights from Chicago to San Juan (Puerto Rico) are booked with United Airlines.
United Airlines
9 %
American Airlines
8 %
Interjet
4 %
Direct flights are more expensive
Flights with a stopover are on average $110.00 cheaper than direct flights.
non stop flight
1 stop
2 stops
04h 53min
06h 56min
13h 25min
$268
$158
$466
The favorite connection is non-stop
31 % of all bookings on the route Chicago to San Juan (Puerto Rico) are for non-stop flights.
Route
bookings
Direct flights
04h 53min, from $268
31 %
1 stopover Fort Lauderdale-Hollywood International Airport, FL
06h 56min, from $158
22 %
1 stopover Orlando International Airport, FL
06h 50min, from $187
13 %
Flight information Chicago - San Juan (Puerto Rico)
Alternative flight routes
Cheap direct flights
Flight details Chicago - San Juan (Puerto Rico)
  • Flight duration: min. 04:30 / max. 07:00
  • Distance: 3318 km
  • Flights per week: 28
  • Return flight duration: min. 05:10 / max. 06:05
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* Prices may vary, please check the travel details given by the online travel agency before booking. Prices include taxes.