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I live in Ottawa, Ontario and want to drive to Chicago on holiday. Advice on scenic routes? How about good places to leave the car and commute into Chicago? I have done that in Poughkeepsie by parking at the rail station and taking the train to Manhattan. I really like to drive the smaller roads, no more than five or six hours per day. What is the best route. I'd prefer to avoid the direct route along the Canadian side of Lake Ontario through Toronto!
Welcome aboard the RoadTrip America Forums!
As I was first reading your request, I was thinking of the basic route, ON-416/ON-401/ON-402/I-69. But then I got to the part about not wanting that, prefering something scenic and relaxing instead. There are a couple of options. If number of days on the road is not a constraint, then you should give serious consideration to going 'over the top' of Lake Huron - using the Trans Canada Highway through Sudbury to Sault Ste. Marie and then down through Wisconsin on US-2/US-41. That's as scenic a route as you're going to find, but would take about four days at your preferred pace. If you don't have that much time, then the other alternative would be to use 'back' roads such as ON-7/ON-9/ON-23/ON-7 and connecting local roads through Ontario to Sarnia, and then either I-69/I-94 through Michigan. There really aren't too many other good options. That second routing would still take three days at your pace.
As far as chicago goes, you should look to stay somewhere near an 'El' station or a commuter rail terminal.
AZBuck
Buck's link to Commuter Rail will take you to Metra, which is the main commuter rail line intro Chicago, however, their routes are only in Illinois (with one stop in Kenosha, just north of the Wisconsin state line). Unless you follow Buck's suggestion to come over the lakes and down through Wisconsin, you'll be better off using the South Shore Line which provides rail service from Chicago into Northwest Indiana, where you could get on the train before dealing with much Chicagoland Traffic.
Another thought would be to locate yourself in the south suburbs of Chicago, where there are some reasonably places to stay and access to the Metra from that area. There's good accommodations in areas around Tinley Park (Rock Island line of Metra) and Matteson (Metra Electric District line of Metra). Usually there's good parking at either of those stations. I've ridden the Electric District line before, out of Richton Park, but it stops up in Matteson, too.
I can't recommend any specific properties there, though. When we travel into that area, we usually stay with family.
Donna
Another option would be to stay out around O'Hare Airport. From there you can ride the CTA Blue Line into the city - it's cheaper and runs more often than Metra. There is a large multi-story parking garage at the Cumberland station right off I-90 just east of the airport, and parking rates are quite reasonable.