If you really want to get around Chicago and see what makes the city shine, don’t get on a Segway; you’ll only get laughed at. Instead, you’ll want to book an architectural boat tour along the Chicago River. There are a number of operators — like Wendella and Shoreline Sightseeing — and most of them launch from the Riverwalk just below from Michigan Avenue and Wacker Drive or at Navy Pier.
They all offer a guided tour with well-informed docents, but one of our favorites is done through the Chicago Architecture Foundation on Chicago’s First Lady cruises. Considering you’re going to get schooled on some of the city’s most important buildings, don’t you think having an expert from that organization makes sense?
Tours usually last about 90 minutes and cost about $40 for non-CAF members and they’re worth every penny. During the tour, your guide will entertain you with stories about how Chicago grew to be one of the most important city’s in the world while discussing upwards of 50 buildings, including the Wrigley Building, Tribune Tower, Marina City, River City, the Sears (now Willis) Tower, Navy Pier, Merchandise Mart, Montgomery Ward building and more. And it’s pretty cool going under all those bridges!
Don’t worry if you booked and it rains. All the boats have indoor space and you can also get snacks or drinks from the bar. Tours tend to be very popular so get tickets in advance here, and arrive about 30 minutes before you’re set to depart to grab a good seat.