Chicago (ORD) to San Juan (SJU): 2,074 miles (3,338 km) great-circle, about 4h 40m nonstop by our estimate. Cheapest fare observed: $197 round-trip on Spirit, nonstop, departing April 26, 2026.
$197 round-trip, Spirit NK2205, departing 2026-04-26 at 10:00, returning 2026-05-03. The recorded itinerary left on a Sunday, returning on a Sunday 7 nights later; the fare was observed 1 day before departure. "Book this flight" opens Kiwi.com with the same airline and dates.
At $197, it ranked 12th of the 30 round-trip fares we recorded from ORD (median $221). That is 9.5 cents per great-circle mile (round-trip price over one-way distance), below the ORD median of 16.6 cents across 30 round-trip routes.
Routes from ORD of similar length: Guatemala City (1,899 mi) at $242 and San Francisco (1,842 mi) at $268.
Spirit had the cheapest fare on 4 of 30 ORD routes. It is the 12th longest of the 30 routes we track from ORD.
Of 20 departure airports with a fare to San Juan, Chicago (ORD) ranked 8th at $197. Lowest: $127 from Orlando (MCO); highest: $632 from Washington DC (IAD); 7 nonstop. Cheapest-fare airlines (routes): Frontier (9), Spirit (4), American Airlines (2), JetBlue (2), Southwest (1) and United Airlines (1), plus 1 more.
Travelpayouts fares (cheapest per route, observed April 25, 2026); OurAirports coordinates and elevations; IANA zones America/Chicago, America/Puerto_Rico; flight time is our estimate.