Best way to travel from Chicago to Boston and New York?|126134

I_m from Brazil, but I_m going to take a training session at Chicago (St. Charles actually) and 1 week vacation right after it.
I really would like to go to Boston (Red Sox fan) and them to New York. I need some advice for what are the best way to go from one place to another in 1 week, and them return to Chicago so I can get my flight back to Brazil.
Plus, any suggestion for best places to visit or things to do in each city would be highly appreciated. Another point, I_ll be going with my girlfriend!

Thanks!

Here_s the right way to do this
Get your Red Sox tickets first
Then fly ORD_BOS as a round trip bc airlines will charge you ridiculous amounts of money for one -way flights
Once in Boston you can get public transportation that will easily take you into the city and of course Fenway
From Boston to NYC take Amtrak as round trip

http://ticketsamtrak.com

Returning to South Station Boston from NYC assume you_ll be 30 minutes late and coordinate connecting flight schedules accordingly
In Amtrak code NYC is NYP _New York Penn and South Station Boston is BOS
The secret to doing NYC is to take advantage of the fact that it wakes up very early and goes to bed very late.Your basic strategy therefore is to do the things that can only be done before 5:00PM before 5:00 PM return to your hotel sleep for a couple of hours and then go out and find dinner and explore the city until midnight or thereabouts
I_ll finish this in a day or so
Btw Just so you know cars are more of a hassle than they_re worth in both NYC and Boston but especially NYC .Both cities can be easily and most efficiently navigated using public transportation

First response is reasonable. Driving time from Chicago to either is about 19 hours; it_s about 1000 miles.

Airplane to Boston and take the train from Boston to NY or vice versa.