✈Deal FoundAiFly Score: 34/100Verified 22 Apr 2026 12:14 UTC
Chicago to San Juan with AA from $256.
✓ Verified DealJust published
Tickets from $256 both ways. Checked baggage is not included in the base fare.
📖 Traveler Resources:
✈️ Airport Guides
📍 Chicago Midway (MDW) Airport — Terminals, Transport & Tips
✈️ Airport Guides
📍 Chicago Midway (MDW) Airport — Terminals, Transport & Tips
Available Dates
Select a date to check live prices on Skyscanner.
6 May – 13 May$256✈︎ 7h 20mSkyscanner →
7 May – 14 May$256✈︎ 7h 20mSkyscanner →
8 May – 15 May$256✈︎ 7h 20mSkyscanner →
9 May – 16 May$256✈︎ 7h 20mSkyscanner →
9 Aug – 19 Aug$256✈︎ 7h 20mSkyscanner →
11 Aug – 19 Aug$256✈︎ 7h 20mSkyscanner →
12 Aug – 19 Aug$256✈︎ 7h 20mSkyscanner →
13 Aug – 20 Aug$256✈︎ 7h 20mSkyscanner →
13 Aug – 21 Aug$256✈︎ 7h 20mSkyscanner →
18 Aug – 26 Aug$256✈︎ 7h 20mSkyscanner →
Prices verified at time of publication. Always confirm on Skyscanner before booking.
🌍 About San Juan
Discover San Juan — one of the world's most captivating destinations, offering unforgettable experiences for every type of traveller.
