Milwaukee - Chicago 2015

Visiting family and seeing favorite city places

August 2015

14 Days

1 Country

2 Destinations

A Labor Day 2015 trip combining Milwaukee and Chicago, with city sightseeing, local landmarks, food, and time with family. In Milwaukee, highlights included Harley-Davidson Night, the Bronze Fonz, historic City Hall, the Quadracci Pavilion at the Milwaukee Art Museum, a Milwaukee River boat ride, and a visit to the famous SafeHouse. We stayed downtown in a hotel created from the former Gimbels department store before boarding Amtrak for the trip south to Chicago.

In Chicago, we met up with family and stayed downtown along the Chicago River. We explored the city by foot and on the “L,” including a trip to Wrigley Field. Other highlights included drinks high above the city at the John Hancock Center, views from the top of Willis Tower, walking the Magnificent Mile, visiting Millennium Park and the Bean, exploring the Art Institute of Chicago, and enjoying classic Chicago food including deep-dish pizza and a meal at Ditka’s Restaurant. It was a memorable Labor Day getaway linking two great Midwestern cities by train.

Milwaukee - Chicago 2015 Trip Map

Marker numbers show the day of the trip when dates are available. Select a destination for details.

Trip Timeline

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Trip Highlight

Milwaukee Wisconsin

Milwaukee, Wisconsin, United States

I grew up in Wisconsin and lived in Milwaukee for two years, so I wanted to share my Milwaukee with Richard. We stayed downtown in a hotel that was once the iconic Gimbels department store—now beautifully converted, with a view overlooking the river, Wisconsin Avenue, and the Milwaukee Art Museum on the lakefront. From our room, we could see the museum’s stunning “wings” open and close, a graceful dance of...

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Trip Highlight

Chicago, Illinois

Chicago, Illinois, United States

Labor Day Weekend in Chicago – 2015 For Labor Day weekend in 2015, we took the Amtrak train from Milwaukee to Chicago for a family get-together and a few days of enjoying the city. Arriving by train made the trip especially easy, putting us right in the middle of downtown without having to worry about driving or parking. We stayed at a hotel along the Chicago River, a perfect location for exploring downtown on...

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