One of the best urban train rides is out from La Salle Street to Joliet. Among other things you will pass some Chicagoland train watching landmarks on the way out. On weekends you can ride Metra for $5 bucks all weekend. You will see trains and railfans at Joliet, if it is slow you can always talk to another fan. One guy told me he leaves his wife at the casino then watches trains.
Train watching in Joliet, Illinois - Trains Magazine
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