Book United Chicago to San Juan flight deals from $275

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Search flights from Chicago to San Juan (ORD - SJU)

October

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Sunday 21st

Return Monday 5th
from$ 324*Viewed: 3 hours ago

Monday 22nd

Return Tuesday 6th
from$ 308*Viewed: 3 hours ago

Wednesday 24th

Return Thursday 8th
from$ 275*Viewed: 3 hours ago

November

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Tuesday 6th

Return Wednesday 21st
from$ 401*Viewed: 3 hours ago

Wednesday 14th

Return Thursday 29th
from$ 384*Viewed: 3 hours ago

Monday 19th

Return Tuesday 4th
from$ 368*Viewed: 3 hours ago

December

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Sunday 9th

Return Monday 17th
from$ 368*Viewed: 48 minutes ago

Monday 10th

Return Tuesday 25th
from$ 330*Viewed: 3 hours ago

Tuesday 11th

Return Wednesday 26th
from$ 379*Viewed: 3 hours ago
**Prices have been available for round trips within the last 48 hours and may not be currently available. Fares listed may be Basic Economy, which is our most restrictive fare option and subject to additional restrictions. Additional baggage charges and fees for other optional service may apply. Other terms and conditions may apply..
Two-story homes in orange, green, and blue line the streets of San Juan

Plan ahead for flights from Chicago to San Juan

from
to
Type
Dates
Price*
Chicago (ORD)
to San Juan (SJU)
Roundtrip
Depart Wed 24 Oct 2018
Return Thu 8 Nov 2018
from$ 275*Viewed: 3 hours ago
Chicago (ORD)
to San Juan (SJU)
Roundtrip
Depart Mon 14 Jan 2019
Return Sun 27 Jan 2019
from$ 297*Viewed: 11 hours ago
Chicago (ORD)
to San Juan (SJU)
Roundtrip
Depart Sat 26 Jan 2019
Return Sun 3 Feb 2019
from$ 297*Viewed: 1 day ago
Chicago (ORD)
to San Juan (SJU)
Roundtrip
Depart Sun 3 Feb 2019
Return Mon 11 Feb 2019
from$ 297*Viewed: 1 day ago
Chicago (ORD)
to San Juan (SJU)
Roundtrip
Depart Sat 2 Mar 2019
Return Sun 10 Mar 2019
from$ 297*Viewed: 1 hour ago
Chicago (ORD)
to San Juan (SJU)
Roundtrip
Depart Sat 23 Feb 2019
Return Mon 4 Mar 2019
from$ 302*Viewed: 1 day ago
Chicago (ORD)
to San Juan (SJU)
Roundtrip
Depart Mon 22 Oct 2018
Return Tue 6 Nov 2018
from$ 308*Viewed: 3 hours ago
Chicago (ORD)
to San Juan (SJU)
Roundtrip
Depart Sun 21 Oct 2018
Return Mon 5 Nov 2018
from$ 324*Viewed: 3 hours ago
Chicago (ORD)
to San Juan (SJU)
Roundtrip
Depart Mon 10 Dec 2018
Return Tue 25 Dec 2018
from$ 330*Viewed: 3 hours ago
Chicago (ORD)
to San Juan (SJU)
Roundtrip
Depart Fri 11 Jan 2019
Return Wed 23 Jan 2019
from$ 330*Viewed: 11 hours ago
*Prices have been available for round trips within the last 48 hours and may not be currently available. Fares listed may be Basic Economy, which is our most restrictive fare option and subject to additional restrictions. Additional baggage charges and fees for other optional service may apply. Other terms and conditions may apply.