Guadalajara (GDL) to Chicago (CHI): 1,733 miles (2,789 km) great-circle, about 4h 00m nonstop by our estimate. Cheapest fare observed: $319 round-trip on United Airlines, with 1 stop, departing July 16, 2026.
$319 round-trip, United Airlines UA2141, departing 2026-07-16 at 06:40, returning 2026-07-31. The recorded itinerary left on a Thursday, returning on a Friday 15 nights later; the fare was observed 82 days before departure. "Book this flight" opens Kiwi.com with the same airline and dates.
At $319, it ranked 9th of the 30 round-trip fares we recorded from GDL (median $427). That is 18.4 cents per great-circle mile (round-trip price over one-way distance), below the GDL median of 25.3 cents across 30 round-trip routes.
Routes from GDL of similar length: Charlotte (1,695 mi) at $561 and Sacramento (1,649 mi) at $440.
United Airlines had the cheapest fare on 2 of 30 GDL routes. It is the 13th longest of the 30 routes we track from GDL.
Of 33 departure airports with a fare to Chicago, Guadalajara (GDL) ranked 28th at $319. Lowest: $89 from Atlanta (ATL); highest: $1241 from Nairobi (NBO); 16 nonstop. Cheapest-fare airlines (routes): Frontier (15), Spirit (5), United Airlines (4), American Airlines (2), airline 0O (1) and Alaska Airlines (1), plus 5 more.
That depends on your passport and trip, so check the official source for United States: U.S. Customs and Border Protection: international visitors. 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/Mexico_City, America/Chicago; flight time is our estimate.