Are there nonstop flights from Chicago (ORD) to Hailey (SUN)?

Yes. American Eagle (airline brand), United Express fly this route. Flight time is about 3h 2m.

What is the fastest connection from Chicago (ORD) to Hailey (SUN)?

via Denver ≈ 3h 44m, via Salt Lake City ≈ 3h 47m, via Phoenix ≈ 5h 3m (estimated flying time, excluding layovers).

from 23,000 JAL miles (economy, one way, based on the published award charts).

Chicago O'Hare International Airport (ORD) to Friedman Memorial Airport (SUN)・2,153 km

Nonstop flights available (2 airlines). Flight time about 3h 2m. Nonstop return flights also operate.

With milesJAL 23,000 miles+ (via SEA)Economy, one way, estimate. Tap a connection for miles by cabin.

7 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.