We spent a couple days exploring Chicago this September. I have been a handful of times visiting friends and passing through on my way back to college. Dennis had never been before though! We were planning on meeting my parents for a Notre Dame Football game and decided to tack on a few days in Chicago before we went to South Bend.
On a last minute but fantastic recommendation of a friend we stayed at The Robey Hotel in Wickerpark. It’s conveniently located right off an L stop and not too far from the downtown Loop area. The neighborhood has a lot of new development and we had fun exploring some of the boutiques and restaurants. The hotel itself has a beautiful rooftop bar with views of downtown. There is also a smaller, lower rooftop with a tiny hot-tub-sized pool!
On our one full day in the city, we started the morning early with a quick breakfast at Dove’s Luncheonette. The food is Tex-Mex inspired and they have an extensive Mezcal collection on display behind the counter! It was probably one of my favorite spots we ate at. After breakfast we headed downtown for an architectural boat tour.
If you’ve ever gone to Chicago and asked for recommendations, someone has probably said, “Do the Architectural Boat Tour!” It really is a special and unique way to see the city. It’s not just for architects! The tours typically depart near the Tribune tower and Apple Store on Michigan Avenue. The tour was over 90 minutes long and we covered a lot of ground (water?) and history! There are a couple of companies that run tours, including: Shoreline Sightseeing and Wendella Sightseeing. The highlight for me was when we turned around in the river to look back at Willis (Sears) Tower. It was a perspective I had never seen before – and it didn’t hurt that we had the most perfect weather! I tried not to over saturate this post too much with boat tour photos! Hopefully they’ll inspire you to visit and do the tour yourself!
After our tour we wandered down Michigan Avenue to Millennium Park. The park is an interesting urban experiment. All of Millennium Park was built over existing railyards and parking garages. Chicago successfully took what is an ugly necessity and hid it below a beautiful, lively park. It’s considered one of the world’s largest rooftop gardens. Highlights in the park include the Cloud Gate sculpture by artist Anish Kapoor, famously nicknamed “The Bean,” the interactive Crown Fountain by Jaume Plensa and the Jay Pritzker Pavilion designed by architect Frank Gehry. At the south end of the park is the Chicago Art Institute. The main entrance on Michigan Avenue is into a classical, Beaux-Arts building from 1893, originally designed for the World’s Columbian Exposition. The Modern Wing of the institute opened in 2009 and was designed by architect, Renzo Piano. We didn’t have time this trip to visit the Institute. I visited before and would high recommend it! We did walk across the BP Pedestrian Bridge on the east side of the park to the shore of Lake Michigan. We realized that we started and ended out summer on the shores of Lake Michigan – but very different sides of it!
We grabbed a late lunch (and a cocktail) at Cindy’s. The restaurant is on the top floor of the Chicago Athletic Association. We had such beautiful weather and got to really appreciate the view of Millennium Park and the marina. Initially, we had thought about staying at the hotel (and might on a future adventure). It was recently renovated in 2007. The designers, Roman + Williams, were careful to keep some of the fun quirky athletic inspired details in the rooms and common spaces.
After lunch, we wandered back north along Michigan Avenue. Keeping with what seemed to become our theme for the trip (roof top bars), we decided to grab a drink at the top of the John Hancock Center. While not as tall as it’s counterpart, the Willis (Sears) Tower, the Hancock Tower still has 100 floors and the bar-restaurant is on the 96th! It’s a bit touristy (as expected) but we were both happy we decided to do it. The views are spectacular. Even the women’s restroom has large windows that look south across the city!
We ended the day grabbing dinner with some good friends and catching up. We’re already planning our next trip back to the city. There is still so much to explore! - Rebecca