Our trip to Chicago back in September was a sweet surprise. I have to admit that the city was not necessarily on my top 5 of must-see cities – the only lasting impression I had of the city was from scenes from one of my favourite 80s movies, Ferris Bueller’s Day Off. However, when we were invited to a wedding across the Atlantic, I was quite taken with the idea of spending some time exploring the city.
In real life, Chicago was full of splendid views, architectural icons, spectacular sundowns and wide skies, drinks and dinners, old signage, boat cruises, super friendly people, that enormous lake and lots of fun in general.
Here are some highlights to put onto your to-do list, in case you ever happen to find yourself in Chicago.
Go on the Architectural Boat Tour
I probably won’t have to tell you that Chicago is famous for its architecture. The city has often been proclaimed the birthplace of the skyscraper and home to the Chicago School. You can experience many great buildings walking around downtown, but if you want to sit back and relax while getting a great overview of the buildings and the history of Chicago, book one of the Architectural Boat Tours offered by the Chicago Architecture Foundation.
Have a Drink with a View Over Chicago
I am convinced that views should be enjoyed with a drink in your hand. The John Hancock Center has a quite decent bar on its 96th floor called the Signature Room and as the Hancock is located close to the lakefront, it offers great views of both the lake and the city. Be sure to arrive at dusk and to get a table near the window. If you don’t, tip the concierge to give you any window table that becomes available during your stay. As soon as you get settled, order an Old Fashioned and enjoy the view. The drinks are so-so, but the views make up for it, trust me.
Take a Walk around Wicker Park
Wicker Park is a great neighborhood to walk around and get lost between cafés, restaurants, bars and little shops. While you are there, I recommend you get to spend some time browsing the shelves at Myopic Books or have some coffee at Volumes Bookcafé. If you need a snack, you should visit Antique Tacos – their Sweet & Spicy Chicken Tacos are to die for, so is the Guacamole.
Other attractions include The Wormhole, a café that is home to the original Delorean from Back to the Future, or the Revel Room, a beautiful bar we visited on our first night and which surprised us with a live jazz session. All those places are located on Milwaukee Avenue, the lifeline of Wicker Park, but I suggest you take some detours to truly discover the neighborhood.
Pay the Chicago Conservatory a Visit
When it started to rain during one of our walks through the city, we ducked into the Lincoln Park Conservatory. While marveling at an exotic tree with huge bean-shaped fruits, a docent started chatting to us and gave us a private tour around the greenhouse. The sweet old man told us all kinds of stories about the plants, the conservatory itself and about Chicago. The Conservatory seems like one of those places where time seems to have stood still, so this might have even been one of my favorite parts of our vacation.
Explore Frank Lloyd Wright’s Home and Studio in Oak Park
Oak Park offers another peek into the past of Chicago, where one Mister Frank Lloyd Wright started his career. The picturesque village located on the outskirts is home to an abundance of Wright’s early works. There is the home he built for his family and his first studio, as well as quite a few residential buildings he was commissioned to design in the immediate vicinity of his home. The Frank Lloyd Wright Trust offers a guided tour through the premises of 951 Chicago Avenue, where Wright lived and worked from 1889 till 1909. Additionally, you can borrow an audio guide and take a walk along Forest Avenue to take a look at some of the houses he designed.