Chicago (MDW) to Seattle (SEA): 1,729 miles (2,782 km) great-circle, about 3h 55m nonstop by our estimate. Cheapest fare observed: $210 round-trip on Southwest, nonstop, departing June 6, 2026.
$210 round-trip, Southwest WN4061, departing 2026-06-06 at 16:35, returning 2026-06-21. The recorded itinerary left on a Saturday, returning on a Sunday 15 nights later; the fare was observed 42 days before departure. "Book this flight" opens Kiwi.com with the same airline and dates.
At $210, it ranked 8th of the 30 round-trip fares we recorded from MDW (median $316). That is 12.1 cents per great-circle mile (round-trip price over one-way distance), below the MDW median of 22.1 cents across 30 round-trip routes.
Routes from MDW of similar length: Guadalajara (1,727 mi) at $394 and Portland (1,747 mi) at $372.
Southwest had the cheapest fare on 12 of 30 MDW routes. It is the 16th longest of the 30 routes we track from MDW.
Of 18 departure airports with a fare to Seattle, Chicago (MDW) ranked 6th at $210. Lowest: $122 from Houston (IAH); highest: $690 from Punta Cana (PUJ); 5 nonstop. Cheapest-fare airlines (routes): Frontier (13), Alaska Airlines (2), Air Canada (1), Southwest (1) and United Airlines (1).
The reverse, Seattle (SEA) to Chicago (CHI), was $735 round-trip on American Airlines, nonstop, departing April 26, 2026. Seattle to Chicago flights.
Travelpayouts fares (cheapest per route, observed April 25, 2026); OurAirports coordinates and elevations; IANA zones America/Chicago, America/Los_Angeles; flight time is our estimate.