✓Good DealAiFly Score: 41/100Verified 4 May 2026 05:43 UTC
Chicago to San Juan with American Airlines from $256.
✓ Verified Deal
Tickets from $256 both ways. Checked baggage is not included in the base fare.
✈️ American Airlines — AFR 53/100 (premium-light-strict)
In this fare:
- Checked baggage: Not included — paid checked baggage extra
- Onboard meal: Snack
- WiFi: Paid wifi
- Cabin: 30″ pitch on 737-800
📖 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.
7 May – 14 May$256Skyscanner →
8 May – 15 May$256Skyscanner →
9 May – 16 May$256Skyscanner →
9 Aug – 19 Aug$256Skyscanner →
11 Aug – 19 Aug$256Skyscanner →
12 Aug – 19 Aug$256Skyscanner →
13 Aug – 20 Aug$256Skyscanner →
13 Aug – 21 Aug$256Skyscanner →
18 Aug – 26 Aug$256Skyscanner →
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.
