Chicago (MDW) to Istanbul (IST): 5,463 miles (8,792 km) great-circle, about 11h 25m nonstop by our estimate. Cheapest fare observed: $1164 round-trip on Porter Airlines, with 3 stops, departing June 9, 2026.
$1164 round-trip, Porter Airlines PD2388, departing 2026-06-09 at 10:25, returning 2026-07-10. The recorded itinerary left on a Tuesday, returning on a Friday 31 nights later; the fare was observed 45 days before departure. "Book this flight" opens Kiwi.com with the same airline and dates.
At $1164, it ranked 23rd of the 30 round-trip fares we recorded from MDW (median $316). That is 21.3 cents per great-circle mile (round-trip price over one-way distance), close to the MDW median of 22.1 cents across 30 round-trip routes.
Routes from MDW of similar length: Tbilisi (5,960 mi) at $1502 and Moscow (4,962 mi) at $2003.
Porter Airlines had the cheapest fare on 4 of 30 MDW routes. It is the 7th longest of the 30 routes we track from MDW.
Of 117 departure airports with a fare to Istanbul, Chicago (MDW) ranked 103rd at $1164. Lowest: $60 from Antalya (AYT); highest: $1639 from Wellington (WLG); 29 nonstop. Cheapest-fare airlines (routes): Pegasus Airlines (13), Qatar (7), WestJet (6), Wizz Air (6), Gulf Air (5) and Turkish (5), plus 51 more.
Travelpayouts fares (cheapest per route, observed April 25, 2026); OurAirports coordinates and elevations; IANA zones America/Chicago, Europe/Istanbul; flight time is our estimate.