Montego Bay (MBJ) to Chicago (CHI): 1,725 miles (2,776 km) great-circle, about 3h 55m nonstop by our estimate. Cheapest fare observed: $284 round-trip on United Airlines, nonstop, departing April 25, 2026.
$284 round-trip, United Airlines UA1160, departing 2026-04-25 at 13:52, returning 2026-05-02. The recorded itinerary left on a Saturday, returning on a Saturday 7 nights later; the fare was observed 0 days before departure. "Book this flight" opens Kiwi.com with the same airline and dates.
At $284, it ranked 2nd of the 11 round-trip fares we recorded from MBJ (median $436). That is 16.5 cents per great-circle mile (round-trip price over one-way distance), below the MBJ median of 50.2 cents across 11 round-trip routes.
Routes from MBJ of similar length: Boston (1,698 mi) at $485 and Atlanta (1,120 mi) at $248.
United Airlines had the cheapest fare on 2 of 11 MBJ routes. It is the 3rd longest of the 11 routes we track from MBJ.
Of 33 departure airports with a fare to Chicago, Montego Bay (MBJ) ranked 27th at $284. Lowest: $89 from Atlanta (ATL); highest: $1241 from Nairobi (NBO); 16 nonstop. Cheapest-fare airlines (routes): Frontier (15), Spirit (5), United Airlines (4), American Airlines (2), airline 0O (1) and Alaska Airlines (1), plus 5 more.
That depends on your passport and trip, so check the official source for United States: U.S. Customs and Border Protection: international visitors. Connecting elsewhere? Check that country's transit rules too.
Travelpayouts fares (cheapest per route, observed April 25, 2026); OurAirports coordinates and elevations; IANA zones America/Jamaica, America/Chicago; flight time is our estimate.