The journey from Monterey to Chicago spans 3,400 kilometers. Flying from Monterey Regional Airport (MRY) to O'Hare (ORD) is the most practical method, taking about 7 hours with a connection. Driving is not recommended due to the 35-hour duration. This route takes you from the Pacific coast to the Midwest.
Total Distance: 3,400 km driving, 3,000 km air distance.
Book at least 3 weeks in advance.
Summer for the best weather in Chicago.