Chicago is full of diversity, from the people that live there, to the people it attracts. There’s so much to see and do in the Windy City – famous architecture, historic landmarks, and of course, plenty of pizzerias to stuff your guts. Since Chicago attracts travelers with such varied agendas, of course many of the tours in Chicago are extremely different too. Tourists can choose to walk the city, hop on a bus or even eat their way through Chi-town.
Of course there are the bus tours, filled with families, singles, the elderly, toddlers and everyone else. It’s pretty much come one, come all. These buses drive around to all the hot spots as you snap pictures for your scrapbook.
But for all the active travelers who don’t want to just hop on a bus and peer out the windows, walking and biking tours are one of the most popular tours in the city. Chicago is one of the most bikable cities in America, so even families can safely enjoy these tours together. My personal favorite form of walking/biking tour kills two birds with one stone (or five if the birds are pizza joints in this analogy). Chicago’s food tours visit the best pizza joints, cupcake shops, fine-dining restaurants or even specific foodie neighborhoods. You don’t feel quite as guilty having a slice of pie at 5 different pizza places in 3 hours when you’re walking (or biking) from place to place to get there.
If walking/food tour combos are not for you, there are plenty of other walking tours that specialize in sightseeing walking (both by day and night), the mob-themed tours, walking tours about Chicago’s music scene, etc. Chicago’s tourism industry knows how to combine sightseeing with everyone’s favorite hobbies.
From my experience though, walking tours are only the second best way to see the city. Boat tours are the way to go when you want to have fun and soak in the city skyline and architecture. Assuming you’re not one to get seasick, boat tours and sightseeing cruises are the ones that are most worth spending money on. Walking tours and bus tours show and teach you all about the city, but you can also find (most of) that stuff out for free on the internet and they don’t charge to walk around Chi-town on your own either. You can’t get the boat experience on your own, and you can’t get this view of the city from the streets.
The boat tours are a big tourist attraction, but locals love it when out-of-towners come to visit and they can all ride together. When I went to visit a friend, she was thrilled that she finally had an “excuse” to do one of the touristy boat tours, but we both had a blast, and our tour guide really entertaining. I can honestly say Vince Vaughn’s charisma very accurately portrayed the Chicago boat tour guide we encountered. You’re trapped on a boat with them for over an hour, so I guess they learn they have to entertain you the whole time, and they certainly do. These tours are made even better by weekend brunches with bottomless mimosas.
Chicago is one of the best cities for touring. Of course to some, the idea of a tour doesn’t sound all that fun. Being in a group with a bunch of people you don’t know, having to listen to a guide ramble on, telling stories that may or may not be good may not sound like vacation, but for me, the walking food tours and boat tours turned a afternoon I would have been spending doing about the same thing into a much more fun experience than I could have imagined. I was a nay-sayer at first, but Chi-town changed my mind on the world of guided tours. This doesn’t mean that I’m willing to take a tour just anywhere now though, or even every time I go to Chicago, but I definitely got extra bang for my buck with these.