Chicago (MDW) to Los Angeles (LAX): 1,747 miles (2,812 km) great-circle, about 4h 00m nonstop by our estimate. Cheapest fare observed: $203 round-trip on Southwest, nonstop, departing June 6, 2026.
$203 round-trip, Southwest WN3364, departing 2026-06-06 at 20:35, returning 2026-06-13. The recorded itinerary left on a Saturday, returning on a Saturday 7 nights later; the fare was observed 42 days before departure. "Book this flight" opens Kiwi.com with the same airline and dates.
At $203, it ranked 7th of the 30 round-trip fares we recorded from MDW (median $316). That is 11.6 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: Portland (1,747 mi) at $372 and Seattle (1,729 mi) at $210.
Southwest had the cheapest fare on 12 of 30 MDW routes. It is the 14th longest of the 30 routes we track from MDW.
Of 40 departure airports with a fare to Los Angeles, Chicago (MDW) ranked 13th at $203. Lowest: $77 from Seattle (SEA); highest: $1224 from Sapporo (CTS); 11 nonstop. Cheapest-fare airlines (routes): Frontier (18), Spirit (5), Southwest (3), EVA Air (2), Fiji Airways (2) and WestJet (2), plus 8 more.
The reverse, Los Angeles (LAX) to Chicago (CHI), was $126 round-trip on Frontier, 1 stop, departing June 2, 2026. Los Angeles 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.