Chicago (MDW) to Guatemala City (GUA): 1,887 miles (3,037 km) great-circle, about 4h 15m nonstop by our estimate. Cheapest fare observed: $796 round-trip on Frontier, with 2 stops, departing May 16, 2026.
$796 round-trip, Frontier F91887, departing 2026-05-16 at 15:07, returning 2026-05-30. The recorded itinerary left on a Saturday, returning on a Saturday 14 nights later; the fare was observed 21 days before departure. "Book this flight" opens Kiwi.com with the same airline and dates.
At $796, it ranked 20th of the 30 round-trip fares we recorded from MDW (median $316). That is 42.2 cents per great-circle mile (round-trip price over one-way distance), above the MDW median of 22.1 cents across 30 round-trip routes.
Routes from MDW of similar length: San Francisco (1,850 mi) at $424 and Los Angeles (1,747 mi) at $203.
Frontier had the cheapest fare on 11 of 30 MDW routes. It is the 12th longest of the 30 routes we track from MDW.
Of 13 departure airports with a fare to Guatemala City, Chicago (MDW) ranked 13th at $796. Lowest: $225 from Cancun (CUN); highest: $796 from Chicago (MDW); 3 nonstop. Cheapest-fare airlines (routes): United Airlines (3), Copa (2), Frontier (2), Alaska Airlines (1), American Airlines (1) and Avianca (1), plus 3 more.
Travelpayouts fares (cheapest per route, observed April 25, 2026); OurAirports coordinates and elevations; IANA zones America/Chicago, America/Guatemala; flight time is our estimate.