Chicago (MDW) to New York (NYC): 730 miles (1,174 km) great-circle, about 2h 00m nonstop by our estimate. Cheapest fare observed: $211 round-trip on Southwest, nonstop, departing July 24, 2026.
$211 round-trip, Southwest WN4120, departing 2026-07-24 at 19:45, returning 2026-07-26. The recorded itinerary left on a Friday, returning on a Sunday 2 nights later; the fare was observed 90 days before departure. "Book this flight" opens Kiwi.com with the same airline and dates.
At $211, it ranked 9th of the 30 round-trip fares we recorded from MDW (median $316). That is 28.9 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: Philadelphia (667 mi) at $141 and New Orleans (827 mi) at $282.
Southwest had the cheapest fare on 12 of 30 MDW routes. It is the 27th longest of the 30 routes we track from MDW.
Of 50 departure airports with a fare to New York, Chicago (MDW) ranked 13th at $211. Lowest: $95 from Miami (MIA); highest: $1609 from Auckland (AKL); 18 nonstop. Cheapest-fare airlines (routes): Spirit (8), Frontier (7), Alaska Airlines (3), JetBlue (3), Southwest (3) and Air Canada (2), plus 20 more.
Travelpayouts fares (cheapest per route, observed April 25, 2026); OurAirports coordinates and elevations; IANA zones America/Chicago, America/New_York; flight time is our estimate.