Chicago (MDW) to Guadalajara (GDL): 1,727 miles (2,779 km) great-circle, about 3h 55m nonstop by our estimate. Cheapest fare observed: $394 round-trip on Volaris, nonstop, departing May 1, 2026.
$394 round-trip, Volaris Y41841, departing 2026-05-01 at 20:23, returning 2026-05-08. The recorded itinerary left on a Friday, returning on a Friday 7 nights later; the fare was observed 6 days before departure. "Book this flight" opens Kiwi.com with the same airline and dates.
At $394, it ranked 18th of the 30 round-trip fares we recorded from MDW (median $316). That is 22.8 cents per great-circle mile (round-trip price over one-way distance), close to the MDW median of 22.1 cents across 30 round-trip routes.
Routes from MDW of similar length: Seattle (1,729 mi) at $210 and Portland (1,747 mi) at $372.
Volaris had the cheapest fare on 2 of 30 MDW routes. It is the 17th longest of the 30 routes we track from MDW.
Of 15 departure airports with a fare to Guadalajara, Chicago (MDW) ranked 12th at $394. Lowest: $64 from Mexico City (MEX); highest: $601 from Punta Cana (PUJ); 7 nonstop. Cheapest-fare airlines (routes): Volaris (9), Frontier (3), Aeromexico (1), Arajet (1) and Viva Aerobus (1).
The reverse, Guadalajara (GDL) to Chicago (CHI), was $319 round-trip on United Airlines, 1 stop, departing July 16, 2026. Guadalajara 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.