PirateFly ✕ Save Money Savings Hub Best eSIM Get up to €600 Car from €4/Day Airport Transfer Best VPN Tickets & Tours Company About Contact Blog Privacy Policy Cookie Policy Terms of Service Disclaimer ← From Cheap Flights from Chicago to Puerto Rico Chicago → Puerto Rico Any date Find your flight ✕ From ⇄ To When Flexibility ± 30 days Exact date ± 1 day ± 3 days 🌍 Anywhere 🇺🇸 United States €26 🇲🇽 Mexico €79 🇹🇷 Turkey €253 🇪🇸 Spain €153 🇮🇹 Italy €218 🇵🇱 Poland €221 🇬🇧 United Kingdom €210 🇫🇷 France €217 Search flights ← Back Home› Deals› 🇵🇷 Puerto Rico Puerto Rico 1 destinations from Chicago San Juan8 flightsfrom€55
