So I am flying to New York, via Los Angeles in about 5 hours time. I will be going to New York, Chicago and Detroit. What are some places which are very easy to spot? I know it is winter so it might be difficult, but I would like to get at least one spot over there. I am going to the Ford Museum in Detroit as well as the Gilmore Car Museum in Michigan.

Detroit is not a nice area. Chicago, NY and Detroit are probably all snowed in right now.

Michigan Avenue in Chicago, IL.

Detroit will have nowhere that is easy to spot. I go there yearly and the most I ever see is a Bentley downtown. The Henry Ford Museum is a brilliant museum and has lots of interesting stuff.

The only place I know to go in Chicago is Bentley Gold Coast. There are definitely others, I haven't been there in a while so I have no idea what else.

Forget NY. NOBODY is driving their exotics anytime soon unless they're filming snow drifting videos, which in NYC, they aren't. Don't waste your time looking for cars, enjoy NY doing other things.

You won't find much in Detroit, Th most I've seen there is a Bentley.
In Chicago, if you go into the downtown area, the are bound to see some exotics :)
When I was there, I saw: FF, SLR, Bentleys, Rolls etc.

P.S
Near the outskirts of Detroit, there is a museum called the Stahl Museum---it is sort of hard to get to, but It pays off!
They have everything from REO's to Kaiser Darrins's to A Tucker!
A worker there let me sit in the Tucker!

Mannhattan Motorcars is good to go to as well

In Detroit I saw a Tesla and a Viper… so don't expect much