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I can't comment with any real authority on how reliable #8 is (though I did get to experience a 12 hour late #8 last summer that resulted in a nice bus ride), but have you thought of just driving to Milwaukee instead of Chicago? From there, one can catch the very reliable Hiawatha service to Chicago (~90% OTP per Amtrak's website). I'm not sure what the parking situation near MKE is as compared to CHI, though.
 
There's plenty of parking at the Milwaukee Airport station. I'm not sure of the cost in comparison to downtown Milwaukee station, but both are probably a lot cheaper than parking in downtown Chicago.
 
I would check the departure time from St. Paul. If its within 2 or 3 hours leaving MSP, you should be fine. If not drive to Milwaukee and park at the airport station. The cost is $5 per day. You should also go by the CBS station to see what the plan is as well. Sometimes they might run a substitute bus to Chicago. Driving to the Madison South Park & Ride is also an option. There are multiple buses to Chicago, and I believe the parking is free!
 
Thank you all, I will keep an eye on the train and if it seems like it wont make it we will probably run down to the MKE airport Station. Will we need to buy new tickets or can we just get our regular tickets issued at the Airport Station without a problem?
 
Buy your tickets from the kiosk in Milwaukee. The price is always the same as the Hiawatha is an unreserved train. Your tickets are good for any train. Plus youll get a refund for the unused Empire Builder tickets, should you need to do so.
 
Rebook BEFORE you go to the airport station kiosk. If it's after your scheduled departure time (regardless of how late the train is), the QuikTrak kiosk may not be able to retrieve your reservation, and there is no agent at the station to dig it up for you. If you're close enough to the CBS station anyway, you can go in there and have the agent handle it.

Overall, it's good to get into the habit of booking for the train you plan to take, before your scheduled trip, because once eticketing launches system-wide, a lot of stuff people are used to doing and getting away with won't work anymore.

People are already having some issues on the Downeaster because they skip their train without rebooking, and the system cancels their reservation and the print-at-home boarding pass isn't valid on a different train (which is different from how some people might work out a deal with the conductor to board a train other than the one for which they are ticketed).

Bottom line: Book properly before you travel. If you're not going to travel on the original itinerary, change your booking before you would have traveled.
 
Amtrak also opeates a Thruway Bus ( essentially Van Galder coaches from Madison and Janesville to Union Station) There is a park and ride at Dutch Mill ( Rt 18 And 51)

I believe that parkng ride lot is free.

Check Amtrak's Hiawatha schedule for times. There are at least 8 bus departures daily.
 
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