Are there nonstop flights from Chicago (ORD) to Guadalajara (GDL)?

Yes. Volaris, Viva, Aeroméxico fly this route. Flight time is about 3h 47m.

What is the fastest connection from Chicago (ORD) to Guadalajara (GDL)?

via Monterrey ≈ 4h 17m, via San Antonio ≈ 4h 17m, via Dallas-Fort Worth ≈ 4h 18m (estimated flying time, excluding layovers).

from 15,000 JAL miles, from 15,000 ANA miles (economy, one way, based on the published award charts).

Chicago O'Hare International Airport (ORD) to Guadalajara International Airport (GDL)・2,789 km

Nonstop flights available (3 airlines). Flight time about 3h 47m. Nonstop return flights also operate.

With milesJAL 15,000 miles+ (via DFW)ANA 15,000 miles+ (via IAH)Economy, one way, estimate. Tap a connection for miles by cabin.

33 one-stop options, sorted by estimated flying time. Tap one to see the airlines on each leg and booking links.

Times are estimated from distance. Check schedules, frequency and availability with the airline or a booking site.