Nairobi (NBO) to Chicago (CHI): 8,022 miles (12,910 km) great-circle, about 16h 35m nonstop by our estimate. Cheapest fare observed: $1241 round-trip on Brussels Airlines, with 1 stop, departing April 25, 2026.
$1241 round-trip, Brussels Airlines SN4529, departing 2026-04-25 at 22:20, 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 $1241, it ranked 26th of the 30 round-trip fares we recorded from NBO (median $615). That is 15.5 cents per great-circle mile (round-trip price over one-way distance), below the NBO median of 26.4 cents across 30 round-trip routes.
Routes from NBO of similar length: Atlanta (8,048 mi) at $1436 and New York (7,355 mi) at $1142.
Brussels Airlines had the cheapest fare on 2 of 30 NBO routes. It is the 3rd longest of the 30 routes we track from NBO.
Of 33 departure airports with a fare to Chicago, Nairobi (NBO) ranked 33rd at $1241. 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 Africa/Nairobi, America/Chicago; flight time is our estimate.