Trip Report: Chicago (part 1) Post Valentine’s Day Getaway, An Introduction


Introduction: Post Valentine’s Day getaway
Amtrak Hiawatha Milwaukee Intermodal Station to Chicago Union Station
Waldorf Astoria Chicago


I decided to take my wife on an overnight trip to Chicago the day after Valentines day.  I tried booking our preferred hotel using points on Valentines day night but it was sold out well in advance.  However the day after Valentines day which happened to be a Sunday and Sunday night stays are typically easier to book using points at most properties.  We figured to take the train down to Chicago and have a nice relaxing ride instead of fighting traffic and paying tolls and parking.

About to board the Hiawatha

We had a relaxing ride down to Chicago’s Union Station.  I transferred points to Amtrak to actually ride this route for free. The Amtrak Hiawatha is the service between Milwaukee and Chicago.

We then had a lovely stay at our favorite city hotel-The Waldorf Astoria Chicago.  We haven’t stayed here since it was the Elysian back in 2010 and we loved our stay so much.  We were finally happy to make it back there and this time we got to redeem points as the property is a Hilton portfolio property.

Waldorf Astoria Chicago lobby

This will be a quick “mini” trip report as it was just an overnight and we didn’t do much in Chicago besides hang out in the hotel, do some clothes shopping for my wife and attend the 2015 Chicago Auto Show. I won’t cover those bits in this report.

2015 Chicago Auto Show

Porsche at the 2015 Chicago Auto Show

Burberry Chicago

Water Tower




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