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Chicago in 2 Days

Guest post by slichty

Map tips: each color represents a different day. Click a marker to learn more about the spot, and click the star in the map header to save the entire map under Your Places in Google Maps.

Day 1

We left Cleveland around 8 AM and arrived in Chicago, Illinois at about 3 PM. Though we weren’t in rush hour, technically, there was still a lot of traffic. We checked in to the Hampton Inn, conveniently located near Michigan Avenue. The hotel offers free breakfast and a rooftop pool. The pool itself is small, but the view of Lake Michigan is top notch. Once the kids got over their excitement of staying in a hotel in Chicago (!!), we headed to the American Girl Doll, Lego, and Disney stores, and came back with more toys we didn’t need. But…when in Rome, I guess.

We had deep dish pizza for dinner at Giordano’s. The service was slow, but the food was delicious.

Day 2

  • Shedd Aquarium
  • Navy Pier
  • Dylan’s Candy Bar
  • Shake Shack

We purchased discount tickets for the Shedd Aquarium in advance of our trip from https://www.365ticketsusa.com/shedd-aquarium. We took a cab from our hotel to Shedd (a first for the kids!), and arrived about an hour before the aquarium opened. There’s a walking path along the lake and gardens outside the aquarium to explore. Having purchased our tickets in advance helped us avoid a very long line, which actually left people waiting to get in until others left due to capacity. We got our tickets to the dolphin show immediately when we entered because the shows are only every 1.5 and fill up quickly. We enjoyed Shedd’s a lot, and the dolphin show was a highlight.

From Shedd’s, we took a water taxi to Navy Pier. It was an unusually chilly day in Chicago for July, so the ride was a little cold and “wobbly” as the kids said, but it provided a beautiful view of the city and convenient access to Navy Pier. We enjoyed lunch at a Mexican restaurant on the second floor of Navy Pier.

We then headed back to the hotel to swim (even though it was barely 70 degrees), and then went back out to check out Dylan’s Candy Bar on Michigan Avenue (now closed, sadly). This place was so cool–two floors of every kind of candy you could imagine. The kids each got a small bucket to fill with candy of their choice for $17.95 each.

And if that wasn’t enough sugar, we topped off a fun and busy day with milkshakes and fries at the Shake Shack.

This was our kids’ first trip to a “big city” and they absolutely loved it. It’s a few months later and they’re still talking about our time in Chicago.

Traveled in July 2018

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