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Join Date: Aug 2010
Location: Madison, WI
Posts: 11,214
Bikes: 1961 Ideor, 1966 Perfekt 3 Speed AB Hub, 1994 Bridgestone MB-6, 2006 Airnimal Joey, 2009 Thorn Sherpa, 2013 Thorn Nomad MkII, 2015 VO Pass Hunter, 2017 Lynskey Backroad, 2017 Raleigh Gran Prix, 1980s Bianchi Mixte on a trainer. Others are now gone.
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Another option, I think that if you get on the train at a luggage stop, and transfer in Chicago to Milwaukee, I assume Milwaukee is also a luggage stop, you could box your bike and check it as one of your pieces of luggage. Then Amtrak transfers your bike from train to train for you. I do not know if you would have to pay the bike fee once or twice in that case.
I did that in 2013, but that was before they put bike racks in luggage cars, so policies have changed since Amtrak took care of moving my bike from train to train for me, so things may have changed since then..