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Join Date: Feb 2016
Location: SE Wisconsin
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Bikes: Lemond '01 Maillot Jaune, Lemond '02 Victoire, Lemond '03 Poprad, Lemond '03 Wayzata DB conv(Poprad), '79 AcerMex Windsor Carrera Professional(pur new), '88 GT Tequesta(pur new), '01 Bianchi Grizzly, 1993 Trek 970 DB conv, Trek 8900 DB conv
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I've not dealt with a bike in Chicago/Union Station, but I've taken the Hiawatha (Milw-Chicago commuter) many times. I think 30 minutes is cutting things perhaps optimistically tight. Amtrak (particularly the non-commuter lines) doesn't have a great history with being that on-time..at least in these parts. If you're prepared to start riding from Union Station(you've seen my comments in your Great Lakes Regional thread), then roll the dice and see how it works out.