It was a cloudy Sunday morning when I boarded the black bus just off Michigan Avenue with about 30 other passengers. As the tour guide checked our names off a list, he handed us a brochure for the Crime and Mob Tour we were about to take, complete with pictures of some of the most notorious Chicago mobsters. He then wasted no time delving into Chicago’s storied past, starting back in 1840, when the city was already known as a hotbed of crime.
Breakfast at the Skydeck on the 103th floor of Chicago’s Willis Tower was one of my most luxurious VIP experiences in over three years of non-stop travel. And that’s saying a lot. But there was a catch – a very early start to the morning.
I was nervous as I made my way to the kayak shop on the North Branch of the Chicago River. More than 10 years had passed since the last time I kayaked and I wasn’t sure what to expect from my Chicago River Kayak Tour. The shop was located in the old Montgomery Ward’s building right on the river and away from the crowds of the newly opened river walk downtown. While I hoped I might pair up with another solo traveler to share paddling duties, the guides asked me to go solo due to a lack of double kayaks.
While I’ve explored a lot of Chicago in the past by foot, boat or bus tour, I had never pedaled around the city on two wheels. So the Chicago Southside Neighborhoods Bicycle Tour seemed the perfect way to spend a sunny Saturday morning. The tour promised to not only take me through South Side neighborhoods like Bridgeport and Chinatown, but past former gangster hangouts and through the old red light district. I would be learning about a whole different side of Chicago.
Fall is considered one of the best times to visit Chicago, as the weather is pleasant (about 63-75°F during the day), festivals and activities abound, and hotel and flight rates aren’t sky high. To help you plan an autumn trip to the Windy City, here are 40 suggestions for fall experiences in Chicago.
Big adventures don’t have to mean going far from home. Check out the Chicago Local Challenge list below for more ideas on amazing adventures and things to do in your own city. Download the list here! 1. Admire the city from another angle on an architecture river cruise 2. Stand on a glass-bottomed ledge at the Willis Tower […]