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.

Bike Tours

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.

Bus Tours

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.

Boat Tours

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.

Architecture Tours

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!

Walking Tours

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.

What comes to mind first when you think of the great city of Chicago? Wind? Pizza? Lake Michigan? The Art Institute? Michael Jordan? Wrigley Field? You get the point: all of the above—and yet still many, many more possibilities—would be quite acceptable answers, because Chicago has a lot going for it.

In the mix here, though, would also have to be: architecture. Chicago’s architecture is legendary the world over for its daring designs, visionary buildings, and soaring skyscrapers. But don’t take my word for it. Head out asap on one of the following architecture tours. Each one of these architecture tours offers access to a special side of Chicago’s multi-faceted architectural splendors. And best of all, each one of these architecture tours is part of a Go City Chicago attraction pass that might prove useful to you as you plan your next architecture-themed outing to the Windy City!

Shoreline Architecture River Cruise

Year in and year out, the Shoreline Architecture River Cruise is one of the most popular activities for visitors to Chicago from all over the world. You can board the Shoreline Architecture River Cruise at your choice of two convenient locations: at either Navy Pier or on Michigan Avenue near The Wrigley Building (speaking of great architecture!). The cruise typically lasts about 75 minutes, and along the way you’ll learn all about the history of Chicago’s storied skyline.

An especially neat detail about the Shoreline Architecture River Cruise is that it takes you down all three branches of the Chicago River (Main, North, and South). This ensures that you’ll have plenty of opportunities to snap that perfect photograph of your favorite building from just the right angle!

Frank Lloyd Wright Home and Studio

One of the 20^th Century’s most famous architects, Frank Lloyd Wright, had deep ties to the Midwest, and in particular, the city of Chicago. Chicago is where, for many years, he lived and worked, developing his inimitable style, completing early commissions, and building a reputation as an innovative, visionary artist whose design influence still resonates today.

Frank Lloyd Wright is responsible for many fine buildings and homes throughout the Chicagoland area, and if you so desire, there are tours you can take while in the Windy City that will enable you to explore several of them. However, if you have time for only one Frank Lloyd Wright-focused outing, then make a point to visit his home and studio. Located in Oak Park, just west of downtown Chicago, the Frank Lloyd Wright Home and Studio is where he and his family resided for some 20 years as Wright toiled away on hundreds of architectural plans. For anyone with even a passing interest in architecture, it’s a tour not to be missed.

Robie House

But who wants to experience just one Frank Lloyd Wright-focused outing? The Robie House, located in Hyde Park on the campus of the University of Chicago, is considered by some experts to be one of the most significant structures in the history of American architecture. Completed in 1910, this single-family home stands today as a fine example of Wright’s so-called “Prairie Style.” It was named a National Historic Landmark in 1963, and added to the National Register of Historic Places in 1966.

If that’s not enough, the Robie House is also a UNESCO World Heritage Site, and you can visit it without even needing to remove your wallet. As the Robie House is part of both the All-Inclusive Pass and the Explorer Pass produced by Go City Chicago, you can simply have your attraction pass scanned at the gate and join a tour of this extraordinary building just like that.

Chicago History Museum

The Chicago History Museum’s focus isn’t strictly exclusively on architecture—its terrific exhibits cover all manner of historical Chicago, of course—but architecture buffs will discover in short order that all the same it’s well worth a visit. The Chicago History Museum occupies a prominent location near the southwest entrance to Lincoln Park, at the lively intersection of Clark Street and North Avenue. If you have the time, energy, and inclination, consider approaching the museum on foot from the south, with a walk along North Astor Street. This quiet block is the heart of Chicago’s opulent Gold Coast neighborhood, and you’ll see some striking architecture and beautiful homes in the wild as you make your way to the museum.

When you arrive at the Chicago History Museum, whip out your attraction pass, enter hassle-free, and enjoy! Popular permanent galleries here include “City on Fire: Chicago 1871,” which demonstrates how the Great Chicago Fire forever altered Chicago’s architecture, and “Chicago: Crossroads of America,” which houses noteworthy artifacts gathered from all throughout Chicago.

Observation Decks

So, let’s be clear and acknowledge straight off the top that an observation deck is not, strictly speaking, an “architecture tour.” With that out of the way, let’s get real: you’re going to spend all this time, effort, and energy exploring the many architectural wonders of Chicago, and then decide not to see said architectural wonders from perhaps their most amazing vantagepoints? Come on, now.

Chicago has two observation decks worth knowing about, both of which provide breathtaking and unique views of the city and its distinct charms. Skydeck Chicago occupies the 103^rd floor of the iconic Willis Tower (it’ll always be the Sears Tower to us locals!) and lets you peer out across the city from an all-glass enclosed box known as The Ledge—you’ll either love it or hate it. 360 Chicago is found on the 94^th floor of the 875 Michigan Avenue building (you will encounter literally no one who calls it this—it’s known to real breathing human beings from Chicago as the John Hancock Center). You can’t go wrong seeing the city’s architecture from either landmark, and regardless of which one you go with, your admission will be free at the point of access when you use your Chicago CityPASS.

BONUS: Chicago Architecture Center

A disclaimer: Unlike the attractions detailed above, nothing associated with the fabulous Chicago Architecture Center is found on any sort of local attraction pass (like the Go City Chicago Explorer Pass). However, did you see how I just described the Chicago Architecture Center as “fabulous”? That’s because it is, and I would be remiss if I didn’t conclude this article on architecture tours in Chicago by at least mentioning this outstanding resource.

Located on Wacker Drive, one block east of Michigan Avenue and one block south of the Chicago Riverwalk, the Chicago Architecture Center is your home for all things, well, Chicago architecture! Here you’ll find exhibits on the city’s architectural history, as well as galleries dedicated to envisioning what a Chicago “of the future” might look like, but the standout feature would have to be a model Chicago that contains over 4,000 buildings. The Chicago Architecture Center also runs some several dozen different architectural tours, including its acclaimed River Cruise. This 90-minute excursion is a real gem, and I would highly recommend it.

When traveling for business, chances are you’re going to end up in Chicago at some point. The modern metropolis in the Midwest always ranks as one of the top destinations for business meetings and events, for good reason with its two airports, O’Hare and Midway, a major convention center, top-notch accommodations, restaurants for entertaining and interesting options for group outings. Have a look at the business bets.

Matter of Conventions

As the largest and most flexible use convention center in North America with 2.6 million square feet of event space, McCormick Place just so happens to be the choice venue for large scale trade and consumer events from the Chicago Auto Show to world congresses. Minutes from downtown, the center is on the lakefront and offers views of the iconic city skyline. Travelers who come to town to attend a convention or conference at McCormick are within a short distance of hotels, restaurants and attractions.

The Destination for Dining

Finding a place for a business lunch or dinner will never be a problem because Chicago is home to more than 7,300 restaurants including AAA Diamond Five Diamond establishments: Acadia, Alinea and Oriole, and more casual eateries. One way to get a taste is to come out for Chicago Restaurant Week, the annual dining event that takes place every winter (January 24-February 9 this year). More than 400 restaurants around town offer pre-fixe multi-course menus of sumptuous cuisine from Contemporary American to Asian Fusion, Italian, Mediterranean and so much more. 

Entertaining Around the Loop

When entertaining clients or colleagues is on the agenda, a night out taking in a Broadway-caliber production at one of the Chicago theaters in the Loop area downtown is always a good idea. Try to snag one of the best seats in the house at the James M. Nederlander Theatre which has the Donna Summer Musical on the playbill in February 2020 or the Cadillac Palace Theatre for My Fair Lady in March, and the  CIBC Theatre to see upcoming award-winning productions, Waitress and Dear Evan Hansen.

Seeing the Sights and Teambuilding: Group Outings

Meeting planners or anyone looking to organize an outing for a group in town might consider the Big Bus Chicago Hop-On and Hop-Off Tour. People can explore at their leisure and see iconic Chicago sites, such as the Magnificent Mile, the Field Museum and the Adler Planetarium. For those who want to experience the local flavor, Chicago Pizza Tours serves up a delightful experience and explores the classic pizzerias nestled in the different neighborhoods.

As for fun activities that work well for teambuilding, head to WhirlyBall Chicago for bumper cars, laser tag and games, or 10Pin Lanes to break the ice over pizza, pool and bowling.