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Stops
- Up to 1 stop$950
Airlines
- American Airlines$950
Cabin Class
- First$950
- Business$993
Departure Airports
- Luis Munoz Marin International Airport$950
Arrival Airports
- Chicago O Hare Airport$950
Layover Airports
- Charlotte Douglas International Airport$993
- Miami International Airport$950
- Philadelphia International Airport$1100
Best Price. GUARANTEED.
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05/29/25
SJU
10h 55m
MIA
05/29/25
ORD
06/05/25
ORD
11h 5m
MIA
06/05/25
SJU
$950
Free cancellation within 83 hours of booking
05/29/25
SJU
7h 26m
MIA
05/29/25
ORD
06/05/25
ORD
11h 5m
MIA
06/05/25
SJU
$984
Free cancellation within 83 hours of booking
05/29/25
SJU
10h 55m
MIA
05/29/25
ORD
06/05/25
ORD
12h 5m
MIA
06/05/25
SJU
$993
Free cancellation within 83 hours of booking
05/29/25
SJU
10h 55m
MIA
05/29/25
ORD
06/05/25
ORD
10h 20m
CLT
06/06/25
SJU
$993
Free cancellation within 83 hours of booking
05/29/25
SJU
7h 26m
MIA
05/29/25
ORD
06/05/25
ORD
10h 20m
CLT
06/06/25
SJU
$1027
Free cancellation within 83 hours of booking
05/29/25
SJU
7h 26m
MIA
05/29/25
ORD
06/05/25
ORD
12h 5m
MIA
06/05/25
SJU
$1027
Free cancellation within 83 hours of booking
05/29/25
SJU
6h 53m
CLT
05/29/25
ORD
06/05/25
ORD
11h 5m
MIA
06/05/25
SJU
$1064
Free cancellation within 83 hours of booking
05/29/25
SJU
5h 20m
Direct
05/29/25
ORD
06/05/25
ORD
11h 5m
MIA
06/05/25
SJU
$1090
Free cancellation within 83 hours of booking
05/29/25
SJU
10h 55m
MIA
05/29/25
ORD
06/05/25
ORD
13h 9m
PHL
06/05/25
SJU
$1100
Free cancellation within 83 hours of booking
05/29/25
SJU
10h 55m
MIA
05/29/25
ORD
06/05/25
ORD
13h 46m
CLT
06/06/25
SJU
$1100
Free cancellation within 83 hours of booking
05/29/25
SJU
6h 53m
CLT
05/29/25
ORD
06/05/25
ORD
10h 20m
CLT
06/06/25
SJU
$1107
Free cancellation within 83 hours of booking
05/29/25
SJU
6h 53m
CLT
05/29/25
ORD
06/05/25
ORD
12h 5m
MIA
06/05/25
SJU
$1107
Free cancellation within 83 hours of booking
05/29/25
SJU
5h 20m
Direct
05/29/25
ORD
06/05/25
ORD
12h 5m
MIA
06/05/25
SJU
$1133
Free cancellation within 83 hours of booking
05/29/25
SJU
5h 20m
Direct
05/29/25
ORD
06/05/25
ORD
10h 20m
CLT
06/06/25
SJU
$1133
Free cancellation within 83 hours of booking
05/29/25
SJU
7h 26m
MIA
05/29/25
ORD
06/05/25
ORD
13h 46m
CLT
06/06/25
SJU
$1134
Free cancellation within 83 hours of booking
05/29/25
SJU
7h 26m
MIA
05/29/25
ORD
06/05/25
ORD
13h 9m
PHL
06/05/25
SJU
$1134
Free cancellation within 83 hours of booking
05/29/25
SJU
10h 55m
MIA
05/29/25
ORD
06/05/25
ORD
6h 50m
CLT
06/05/25
SJU
$1167
Free cancellation within 83 hours of booking
05/29/25
SJU
10h 55m
MIA
05/29/25
ORD
06/05/25
ORD
8h 31m
CLT
06/05/25
SJU
$1167
Free cancellation within 83 hours of booking
05/29/25
SJU
10h 55m
MIA
05/29/25
ORD
06/05/25
ORD
6h 23m
CLT
06/06/25
SJU
$1167
Free cancellation within 83 hours of booking
05/29/25
SJU
8h 16m
PHL
05/29/25
ORD
06/05/25
ORD
11h 5m
MIA
06/05/25
SJU
$1174
Free cancellation within 83 hours of booking
05/29/25
SJU
7h 26m
MIA
05/29/25
ORD
06/05/25
ORD
6h 50m
CLT
06/05/25
SJU
$1201
Free cancellation within 83 hours of booking
05/29/25
SJU
7h 26m
MIA
05/29/25
ORD
06/05/25
ORD
6h 23m
CLT
06/06/25
SJU
$1201
Free cancellation within 83 hours of booking
05/29/25
SJU
6h 53m
CLT
05/29/25
ORD
06/05/25
ORD
13h 9m
PHL
06/05/25
SJU
$1214
Free cancellation within 83 hours of booking
05/29/25
SJU
8h 16m
PHL
05/29/25
ORD
06/05/25
ORD
10h 20m
CLT
06/06/25
SJU
$1217
Free cancellation within 83 hours of booking
05/29/25
SJU
8h 16m
PHL
05/29/25
ORD
06/05/25
ORD
12h 5m
MIA
06/05/25
SJU
$1217
Free cancellation within 83 hours of booking
05/29/25
SJU
5h 20m
Direct
05/29/25
ORD
06/05/25
ORD
13h 9m
PHL
06/05/25
SJU
$1239
Free cancellation within 83 hours of booking
05/29/25
SJU
8h 16m
PHL
05/29/25
ORD
06/05/25
ORD
13h 46m
CLT
06/06/25
SJU
$1324
Free cancellation within 83 hours of booking
05/29/25
SJU
8h 16m
PHL
05/29/25
ORD
06/05/25
ORD
13h 9m
PHL
06/05/25
SJU
$1324
Free cancellation within 83 hours of booking
05/29/25
SJU
8h 16m
PHL
05/29/25
ORD
06/05/25
ORD
6h 50m
CLT
06/05/25
SJU
$1391
Free cancellation within 83 hours of booking
05/29/25
SJU
8h 16m
PHL
05/29/25
ORD
06/05/25
ORD
8h 31m
CLT
06/05/25
SJU
$1391
Free cancellation within 83 hours of booking
Top Deals on flights Business Class from San Juan to Chicago O Hare Airport
San Juan, PR (SJU) - Chicago, US (CHI)
May 29
SJU
9h 21m
CLT
May 30
ORD
as low as
$448
San Juan, PR (SJU) - Chicago, US (CHI)
May 29
SJU
8h 13m
MIA
May 29
ORD
as low as
$448
San Juan, PR (SJU) - Chicago, US (CHI)
May 29
SJU
13h 1m
MIA
May 29
ORD
as low as
$448
San Juan, PR (SJU) - Chicago, US (CHI)
May 29
SJU
10h 55m
MIA
May 29
ORD
as low as
$448
San Juan, PR (SJU) - Chicago, US (CHI)
May 29
SJU
10h 41m
CLT
May 30
ORD
as low as
$448
San Juan, PR (SJU) - Chicago, US (CHI)
May 29
SJU
12h 1m
CLT
May 30
ORD
as low as
$448
San Juan, PR (SJU) - Chicago, US (CHI)
May 29
SJU
13h 4m
PHL
May 29
ORD
as low as
$521
San Juan, PR (SJU) - Chicago, US (CHI)
May 29
SJU
5h 20m
Direct
May 29
ORD
as low as
$588
San Juan, PR (SJU) - Chicago, US (CHI)
May 29
SJU
8h 56m
JFK
May 29
ORD
as low as
$588
San Juan, PR (SJU) - Chicago, US (CHI)
May 29
SJU
9h 27m
PHL
May 29
ORD
as low as
$672
San Juan, PR (SJU) - Chicago, US (CHI)
May 29
SJU
8h 16m
PHL
May 29
ORD
as low as
$672
San Juan, PR (SJU) - Chicago, US (CHI)
May 29
SJU
9h 49m
DFW
May 29
ORD
as low as
$797
Flights to Chicago
Browse origins
- Flights
- Caribbean
- Puerto Rico
- San Juan
Browse destinations
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- North America
- United States
- Illinois
- Chicago
- Chicago O Hare Airport
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