Don’t let the spectacular skyline fool you. Don’t get hung up on all the steel and concrete. Forget about the traffic, and disregard the everyday sounds of the hustle and bustle. For all that it is one of the world’s major cities, Chicago is also very much a city of the great outdoors. Here you can luxuriate in lush green parks, bask in scenic trails, and enjoy the many delights of a lovely lakefront—all remaining in the midst of a gleaming metropolis.
But where to begin when it comes to planning your next Chicago outdoor adventure? A great place to start is with a tour of Chicago that gets you out and about into the heart of everything. Keep reading for a list of tour types to consider as you plan your Chicago trip.
Chicago is a bike-friendly city, and thus a great way to set about exploring Chicago’s outdoor scene is by hopping on a bicycle and pedaling away until your heart’s content. Plus, it’s an affordable, eco-friendly option! If you think you might be interested in seeing the city this way, you’ll have some choices at your disposal. When in doubt, you can always rent a bike from a well-regarded company like Bike and Roll Chicago and venture forth on your own schedule. In fact, a four-hour bike rental from Bike and Roll Chicago is included on both the All-Inclusive and Explorer versions of the Go City Chicago Pass. You’ll save money and time going on a bike tour covered by this type of attraction pass.
If you’re in the market for something a bit more structured, you’re in business, because there are a number of guided bike tours of Chicago available, too. The most popular guided bike tour of Chicago is probably the Lincoln Park Bike Adventure, which departs from Navy Pier and takes you along Lake Michigan past such famous attractions like the North Avenue Beach and Lincoln Park Zoo.
A classic means for experiencing Chicago, especially for the first time, is by taking a guided bus tour of the city. Now, don’t read the words “bus tour” and think: What in the world does riding on a bus have to do with the great outdoors? A bus tour of Chicago is a terrific method for moving from outdoor location to outdoor location conveniently, affordably, and while learning more about the ins and outs of the city from your knowledgeable tour guide’s narration.
Depending on what you’re most interested in, there are numerous bus tours to pick from in Chicago. One quality option, again covered by a handy attraction pass like the Go City Chicago Pass, is the Hop-On, Hop-Off Big Bus Chicago 1-Day Classic tour. This Big Bus Chicago tour makes roughly a dozen different stops, including outdoor favorites like Millennium Park, Navy Pier, the Chicago Riverwalk, and more. However, Chicago is also home to bus tours that cover subjects as diverse as the local food and drink scene, Chicago’s mob history, specific neighborhoods, and Chicago’s skyline at night, just to name a few.
Water is at the heart of much of what makes Chicago such a memorable city to visit and a wonderful place to live. To that end, as you plan your dream trip to Chicago, you’ll want to strongly consider taking some sort of tour of the city that gets you out on to Lake Michigan and takes you along the Chicago River. Which means, of course, a boat tour! And there’s no dearth of possibilities on this front either. One of the most popular options is the Tall Ship Windy. The folks behind Tall Ship Windy run several different types of tours, but regardless of which one you go with, you’ll be seeing the sights of Chicago’s shoreline from a 150-foot traditional topsail schooner. It’s a leisurely ride perfect for the whole family.
Another popular boat tour in Chicago is the Shoreline Skyline Lake Tour, which if you go on this tour with your Go City Chicago attraction pass in hand, won’t require you to pay anything out of pocket when boarding. It’s a breezy 40-minute jaunt that provides amazing views of Chicago’s unbeatable skyline from gorgeous Lake Michigan.
A hallmark of Chicago’s greatness is the splendor of its buildings: not only does Chicago possess a striking, remarkable skyline, but its skyline is particularly valued for its architectural importance. As a result, one of the top things to do while out and about in the city is to take an architecture tour of Chicago. Me, personally, if I could pick only one tour to recommend going on, out of all the superb tours profiled here, it would be an architecture tour. You’ll encounter a variety of architecture tours in Chicago, but when in doubt, seek out the Chicago Architecture Center for guidance. They offer scores and scores of well-regarded architecture-centric tours of all stripes.
There’s a sub-category of water-based tour that’s so good we had to save it for its own section, and that’s the architecture tour of Chicago conducted via boat. You’ve got a couple prominent options for architecture boat tours. One is the Shoreline Sightseeing Architecture River Cruise (available on the Go City Chicago pass), which takes you down all three branches of the Chicago River, thus providing you access to rare photo opportunities. The other would be the aforementioned Chicago Architecture Center’s signature River Cruise. It lasts 90 minutes, and is difficult to beat for information, entertainment, and all-around enjoyability!
Last but not least, what better way to have an outdoor adventure in Chicago than by going for a walk? No matter what you want to focus on, you’ll find plenty of guided walking tours here. There are guided walking tours that analyze Chicago’s many architectural wonders, there are guided walking tours that get you up close and personal with some of the city’s most historic sites, and there are guided walking tours that highlight specific neighborhoods or particular cuisines. You name it, it probably exists in one form or another.
And while we’re at it, let’s not forget about Segways! Guided Segway tours can be a fun, charming way to see some of the city’s most popular attractions, too.