San Juan
Puerto Rico
CHI SJU
Lowest fare we found€89per adult
- Depart
- Wed 13 Jan · 22:21
- Return
- One-way
- Duration
- 4h 42m
- Stops
- Direct
Airline not specifiedBaggage not specified by providervia Aviasales Recently checked (found 4 hours ago)
View deal Caribbean
Cheap flights to Caribbean
Caribbean. Explore the places we cover in Caribbean.
Recently found fares
From cached departure cities: Chicago
San Juan
Puerto Rico
CHI SJU
Lowest fare we found€199per adult
- Depart
- Tue 8 Dec · 05:35
- Return
- Sun 13 Dec · 03:43
- Duration
- 14h 22m
- Stops
- 1 stop
Airline not specifiedBaggage not specified by providervia Aviasales Recently checked (found 6 days ago)
View deal San Juan
Puerto Rico
CHI SJU
Lowest fare we found€205per adult
- Depart
- Thu 10 Dec · 05:35
- Return
- Mon 14 Dec · 03:43
- Duration
- Not specified
- Stops
- 1 stop
F9Baggage not specified by providervia Aviasales Recently checked (fetched 14 Nov, 21:02)
View deal 
San Juan
Puerto Rico
CHI SJU
Lowest fare we found€227per adult
- Depart
- Thu 3 Dec · 15:36
- Return
- Tue 8 Dec · 05:01
- Duration
- 17h 7m
- Stops
- 1 stop
Airline not specifiedBaggage not specified by providervia Aviasales Recently checked (found 3 days ago)
View deal San Juan
Puerto Rico
CHI SJU
Lowest fare we found€243per adult
- Depart
- Mon 16 Nov · 10:19
- Return
- Tue 24 Nov · 05:19
- Duration
- 21h 42m
- Stops
- 1 stop
Airline not specifiedBaggage not specified by providervia Aviasales Recently checked (found 1 hour ago)
View deal San Juan
Puerto Rico
ORD SJU
Lowest fare we found€243per adult
- Depart
- Mon 16 Nov · 10:19
- Return
- Tue 24 Nov · 05:19
- Duration
- 5h 50m
- Stops
- 1 stop
F9Baggage not specified by providervia Aviasales Recently checked (fetched 14 Nov, 21:02)
View deal San Juan
Puerto Rico
CHI SJU
Lowest fare we found€250per adult
- Depart
- Wed 20 Jan · 15:39
- Return
- Wed 27 Jan · 07:15
- Duration
- 40h 41m
- Stops
- 1 stop
Airline not specifiedBaggage not specified by providervia Aviasales Recently checked (found 2 days ago)
View deal San Juan
Puerto Rico
ORD SJU
Lowest fare we found€251per adult
- Depart
- Wed 25 Nov · 23:53
- Return
- Wed 2 Dec · 16:07
- Duration
- 4h 39m
- Stops
- Direct
F9Baggage not specified by providervia Aviasales Recently checked (fetched 14 Nov, 21:02)
View deal San Juan
Puerto Rico
CHI SJU
Lowest fare we found€251per adult
- Depart
- Wed 25 Nov · 23:53
- Return
- Wed 2 Dec · 16:07
- Duration
- 15h 31m
- Stops
- 1 stop
Airline not specifiedBaggage not specified by providervia Aviasales Recently checked (found 3 days ago)
View deal San Juan
Puerto Rico
CHI SJU
Lowest fare we found€254per adult
- Depart
- Sat 16 Jan · 11:10
- Return
- Sun 24 Jan · 17:02
- Duration
- 29h 53m
- Stops
- 1 stop
Airline not specifiedBaggage not specified by providervia Aviasales Recently checked (found 5 days ago)
View deal Cheapest months in our cache
Chicago
- January 2027 · €89 Recently checked (found 4 hours ago)
- December 2026 · €199 Recently checked (found 6 days ago)
- November 2026 · €243 Recently checked (found 1 hour ago)
- March 2027 · €307 Recently checked (found 6 days ago)
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Key facts
- Cached fares
- 24
- Direct fares in our cache
- 2/24 (8%)
- Cached duration range (minimum–median)
- 4h 39m – 5h 50m
Countries in this region
Departure cities with recently found fares
Questions answered by our data
When is it cheapest to fly to Caribbean from Chicago?
January 2027 — €89. Try flexible dates and nearby airports. Cached fares are not a guarantee of availability.
Do you hold direct fares from Chicago?
We currently hold 2 direct fares among 24 fares with reported stops. This does not describe every flight on the route.
Try flexible dates and nearby airports. Cached fares are not a guarantee of availability.