Chicago (MDW) to London (LON): 3,945 miles (6,349 km) great-circle, about 8h 25m nonstop by our estimate. Cheapest fare observed: $1078 round-trip on Porter Airlines, with 2 stops, departing June 28, 2026.
$1078 round-trip, Porter Airlines PD2388, departing 2026-06-28 at 10:25, returning 2026-07-06. The recorded itinerary left on a Sunday, returning on a Monday 8 nights later; the fare was observed 64 days before departure. "Book this flight" opens Kiwi.com with the same airline and dates.
At $1078, it ranked 22nd of the 30 round-trip fares we recorded from MDW (median $316). That is 27.3 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 Moscow (4,962 mi) at $2003.
Porter Airlines had the cheapest fare on 4 of 30 MDW routes. It is the 10th longest of the 30 routes we track from MDW.
Of 49 departure airports with a fare to London, Chicago (MDW) ranked 43rd at $1078. Lowest: $46 from Dublin (DUB); highest: $1356 from Sydney (SYD); 14 nonstop. Cheapest-fare airlines (routes): Ryanair (7), easyJet (4), Etihad (4), Frontier (4), Air Canada (3) and WestJet (3), plus 19 more.
That depends on your passport and trip, so check the official source for United Kingdom: GOV.UK: check if you need a UK visa. 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/Chicago, Europe/London; flight time is our estimate.