✓Good DealAiFly Score: 41/100Verified 7 Sep 2026 13:01 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 — date has passed. See current deals from Chicago.
📅 8 May → 15 May — date has passed. See current deals from Chicago.
📅 9 May → 16 May — date has passed. See current deals from Chicago.
📅 9 Aug → 19 Aug — date has passed. See current deals from Chicago.
📅 11 Aug → 19 Aug — date has passed. See current deals from Chicago.
📅 12 Aug → 19 Aug — date has passed. See current deals from Chicago.
⚠️ All booking links removed
AiFly automatic review on 7 Sep 2026 at 13:01 UTC found that current prices for every advertised date are over 30% above the published €236 — booking links are no longer accurate.
Prices verified at time of publication. Always confirm on Skyscanner before booking.
🌍 About San Juan
I have what I need. Here's the card: San Juan packs nearly all its draw into Old San Juan, a small grid of 16th-century streets paved with adoquines — blue-gray cobblestones cast from iron-furnace slag that Spanish ships carried over as ballast. At its tip sits El Morro, a six-level fort whose cannons guarded the harbor for 400 years; the grassy approach is where locals fly kites on Sunday afternoons. Eat mofongo: green plantains fried, mashed with garlic and pork crackling, packed into a bowl and filled with shrimp or stewed conch — order it relleno, not as a side. December through April brings dry, warm days but the highest prices and crowds. The cheap fares land in September and October, the heart of hurricane season, so book those with travel insurance and a flexible eye on the forecast.
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