Chicago (MDW) to Mexico City (MEX): 1,681 miles (2,705 km) great-circle, about 3h 50m nonstop by our estimate. Cheapest fare observed: $252 round-trip on Volaris, with 1 stop, departing June 11, 2026.
$252 round-trip, Volaris Y45037, departing 2026-06-11 at 20:49, returning 2026-06-23. The recorded itinerary left on a Thursday, returning on a Tuesday 12 nights later; the fare was observed 47 days before departure. "Book this flight" opens Kiwi.com with the same airline and dates.
At $252, it ranked 13th of the 30 round-trip fares we recorded from MDW (median $316). That is 15.0 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 Seattle (1,729 mi) at $210.
Volaris had the cheapest fare on 2 of 30 MDW routes. It is the 18th longest of the 30 routes we track from MDW.
Of 24 departure airports with a fare to Mexico City, Chicago (MDW) ranked 7th at $252. Lowest: $73 from Guadalajara (GDL); highest: $1375 from Addis Ababa (ADD); 13 nonstop. Cheapest-fare airlines (routes): Volaris (6), Viva Aerobus (5), Aeromexico (4), Arajet (2), Copa (1) and Ethiopian (1), plus 5 more.
The reverse, Mexico City (MEX) to Chicago (CHI), was $274 round-trip on United Airlines, 1 stop, departing May 21, 2026. Mexico City to Chicago flights.
That depends on your passport and trip, so check the official source for Mexico: Instituto Nacional de Migracion (Mexico). 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, America/Mexico_City; flight time is our estimate.