Chicago to San Juan, Puerto Rico for only $231 roundtrip

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Cheap flights from Chicago to San Juan, Puerto Rico for only $231 roundtrip with United Airlines.

The example dates listed below range between $231 and $269 roundtrip.

DEPART:
Chicago, USA

ARRIVE:
San Juan, Puerto Rico

RETURN:
Chicago, USA

DATES:
Availability from January to November 2025 (excluding summer)

Example dates:
26th Jan – 2nd Feb
28th Jan – 4th Feb
29th Jan – 5th Feb
30th Jan – 6th Feb
31st Jan – 7th Feb
1st-8th Feb
3rd-10th Feb
4th-11th Feb
5th-12th Feb
21st-28th Feb
26th Feb – 5th Mar
27th Feb – 6th Mar
28th Feb – 7th Mar
4th-11th Mar
5th-12th Mar
12th-19th Mar
18th-25th Mar
10th-17th Apr
25th Apr – 2nd May
29th Apr – 6th May
30th Apr – 7th May
2nd-9th May
7th-14th May
9th-16th Sep
10th-17th Sep
16th-23rd Sep
17th-24th Sep
23rd-30th Sep
24th Sep – 1st Oct
1st-8th Oct
26th Oct – 2nd Nov
28th Oct – 4th Nov

and more…

STOPS:
New York (outgoing only)

AIRLINES:
United Airlines