Chicago (MDW) to Moscow (MOW): 4,962 miles (7,985 km) great-circle, about 10h 25m nonstop by our estimate. Cheapest fare observed: $2003 round-trip on Southwest, with 2 stops, departing June 18, 2026.
$2003 round-trip, Southwest WN2464, departing 2026-06-18 at 08:00, returning 2026-07-02. The recorded itinerary left on a Thursday, returning on a Thursday 14 nights later; the fare was observed 54 days before departure. "Book this flight" opens Kiwi.com with the same airline and dates.
At $2003, it ranked 29th of the 30 round-trip fares we recorded from MDW (median $316). That is 40.4 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: Warsaw (4,678 mi) at $973 and Istanbul (5,463 mi) at $1164.
Southwest had the cheapest fare on 12 of 30 MDW routes. It is the 8th longest of the 30 routes we track from MDW.
Of 130 departure airports with a fare to Moscow, Chicago (MDW) ranked 126th at $2003. Lowest: $213 from Delhi (DEL); highest: $2476 from Havana (HAV); 3 nonstop. Cheapest-fare airlines (routes): Pegasus Airlines (11), Etihad (8), Qatar (6), Icelandair (5), Wizz Air (5) and Air China (4), plus 53 more.
Travelpayouts fares (cheapest per route, observed April 25, 2026); OurAirports coordinates and elevations; IANA zones America/Chicago, Europe/Moscow; flight time is our estimate.