My Favorite Guided Tours of Chicago

One of the best ways to see the best of what Chicago has to offer is on a guided tour. This is especially true if you’re a first-time visitor looking for ideas on top things to do. Yet by the same token, these public tours can be quite informative for repeat visitors like me. In …

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This Tiffany glass dome is said to be the world's largest of its kind on a Chicago guided tour

One of the best ways to see the best of what Chicago has to offer is on a guided tour. This is especially true if you’re a first-time visitor looking for ideas on top things to do. Yet by the same token, these public tours can be quite informative for repeat visitors like me. In fact, I just experienced each of these following attractions, whether it was a guided tour or of the self-guided variety. As much as there are others to consider during your visit, the following are my favorite and most recent tours of Chicago.

American Writer’s Museum

180 N. Michigan Ave.
Chicago, IL  60601
(312) 374-8790

If you love American literature, you might want to put the American Writer’s Museum (AWM) on your itinerary. Just a short walk from Millennium Park, AWM isn’t a large museum, covering 11,000 square feet on a single floor. However, AWM is the first of its kind in the U.S., full of interactive displays and family friendly. At this time, public tours are not available on a regular basis. Nevertheless, you won’t have any trouble going on a solo tour, while admiring the permanent and temporary exhibits. Better yet, each of the exhibits are included with your paid admission. Among the highlights you can enjoy are the Nation of Writers Gallery, chronicling American writers across over 400 years. In addition, you may also like the Wintrust Chicago Gallery, featuring leading Chicago writers like Roger Ebert, Ann Landers, Carl Sandburg and Richard Wright.

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Art Institute of Chicago

111 S. Michigan Ave.
Chicago, IL  60603
(312) 443-3600

If you’re an art lover, you must absolutely visit the Art Institute of Chicago. After all, it’s one of the world’s finest art museums, as well as one of the oldest and largest. Moreover, you probably already have it on your itinerary. Although you can certainly go on a self-guided tour, with or without using the museum’s free app, you can also take a tour. For example, the most practical tour to consider is the Visitor Welcome tour. These tours last just 30 minutes and will cover artwork you shouldn’t miss, like the large collection of Monet paintings and Grant Wood’s “American Gothic”. However, you shouldn’t miss other notable pieces of art, like Andy Warhol’s “Elizabeth Taylor” and Edward Hopper’s “Nighthawks”. That’s also not to mention Marc Chagall’s stunning “American Windows”. In this case, you may have to ask for assistance to find Chagall’s beautiful stained glass windows as its location can be tricky to find.

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Staff member serving Chicago style deep dish pizza at Lou Malnati's pizzeria on a guided foodie tour
Chicago-Style Deep Dish Pizza (credit: Randy Yagi)

Bobby’s Bike Hike Chicago

540 N. Lake Shore Drive
Chicago, IL  60611
(312) 245-9300

Are you interested in a foodie tour? Bobby’s Bike Hike Chicago has it. What about a scenic bike tour of famous Chicago landmarks? Yes, Bobby’s has that and walking tours too, not to mention kayak tours. In other words, Bobby’s Bike Hike Chicago has a wide variety of affordable tours, with options for adults only, families with children and more. Although you can choose any tour, a Chicago Favorites Walking & Food Tour is quite popular. In this case, you get to try out some of Chicago’s most famous food items, like Lou Malnati’s deep-dish pizza and Chicago-style hot dog. Similarly, your tour guide will lead you to famous landmarks like the Wrigley Building and the River Walk. If that’s not enough, you also get to savor an Italian beef sandwich from Bongiorno’s and a brownie at the historic Palmer House hotel. Incidentally, the Palmer House was the first to create a brownie for guests attending the 1893 Chicago World’s Fair. Among the best in the nation, Bobby’s is led by Jeremy Lewno, who named the thriving small business after his father Bob.

Chicago’s First Lady Architectural River Cruise

112 E. Wacker Drive
Chicago, IL  60601
(847) 358-1330

Of all the many Chicago tours and attractions, the top recommendation might be a Chicago architectural river cruise. Although you have a few tour operators to choose from, I was fortunate to connect with Chicago’s First Lady Cruises. Even though any tour operator can offer you a splendid experience, First Lady Cruises definitely stood out. That’s because of its association with the prestigious Chicago Architecture Center, which also happens to be nearby. Another key point is that First Lady is listed among TripAdvisor’s Top Ten Tours in America. Furthermore, Chicago’s First Lady is also USA Today’s No. 1 boat tour in North America. The 90-minute Architectural River Cruise will take you across all three sections of the Chicago River. During this time, your tour guide will point out famous architectural landmarks like Willis Tower, Tribune Tower, Marina City and the historic Montgomery Ward Complex.

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Color Factory

233 S. Wacker Drive
Chicago, IL  60606
(347) 378-4071

As far as Chicago attractions go, the top thing to do at Willis Tower is walking onto the Edge at Skydeck Chicago. Indeed, what can be more thrilling than walking onto a small glass platform on the second tallest building in North America? Be that as it may, Skydeck isn’t the only thing you can do at Willis Tower. Indeed, there is the new Catalog, a 300,000 square foot addition featuring dining and attractions like Color Factory Chicago. The latter is a family friendly, interactive art museum that’s quite popular amongst Instagram and TikTok social media influencers. Indeed, Color Factory Chicago features several art installations across multiple rooms with eye catching imagery. In detail, you may find one mirror maze room while another room features an enormous green ball pit that’s perfect for your selfie. In all, it will take you about a half hour to an hour to see everything.

The beautiful Tiffany Glass dome inside the Chicago Cultural Center as seen on a guided tour
Tiffany Glass Dome (credit: Randy Yagi)

Inside Chicago Walking Tours

Chicago, IL 60605
(312) 799-0164

Chicago’s river tours are outstanding, with boats taking you to see several famous buildings representing multiple architectural styles. However, you just see the exterior of these landmark structures, thus missing the oftimes dazzling interior design. In this case, Inside Chicago Walking Tours is the small business I recommend. Not only did I receive a personal invite from owner Hillary Marzec, but the tours itself are phenomenal. Of the public walking tours available, I was fortunate to be part of The two-hour World Within (1) tour. In detail, a tour guide takes you to see some of the most stunning interiors within the Chicago Loop area. For instance, you get to see the lobby of the Rookery, noted for its Frank Lloyd Wright redesign. In addition, you’ll make stops inside the historic Chicago Board of Trade building, Marquette building and the Palmer House. Your tour concludes inside the Chicago Cultural Center, formerly the Chicago Public Library. It is here that you can see what may be the world’s largest dome made of Tiffany glass.

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Rock Bottom Brewery Tour

1 W. Grand Ave.
Chicago, IL  60610
(312) 755-9339

Chicago is home to several outstanding breweries offering tours of its brewing facilities. However, most of these are not in the heart of Chicago, e.g the Loop and Magnificent Mile. Indeed, for you to visit a brewery like Lagunitas, you would have to travel about four miles from the city center. Some other popular brewery tours are even further away. Fortunately, you can visit Rock Bottom Brewery, which happens to be in the vibrant Magnificent Mile section. What’s more, there is easy subway access, since the Grand subway station on CTA’s Red Line is right across the street. The brewery tour itself is just $20 and will be led by either head brewmaster Ray Gonzalez or his capable assistant Zuriel. Afterwards, you can try out their award-winning beers, like Stadtstrasse Kolsch, El Soltero, Mob Boos and Barrel Aged Naughty Scot. Of course you can also dine at Rock bottom, with a menu that features pizza, handhelds, salads, bowls and affordable main courses.

Wrigley Field Chicago Tours

1060 W. Addison St.
Chicago, IL  60613
(773) 388-8270

Taking a tour of Wrigley Field is the the next best thing to going to a Chicago Cubs ballgame. After all, you’re inside this historic stadium, second oldest in Major League Baseball. What’s more, your tour guides will take you around the entire ballpark while talking about its storied history. You even get to see but not touch, the famous Wrigley Field ivy covering the outfield walls. In addition, your tour guides will lead you through the visiting team’s locker room, the press box and other select seats. Your tour concludes right at the Cubs dugout, where you can have your picture taken.

Famous Visiting Ballplayers

Although the visitor locker room is much smaller than the Cubs, can you imagine the people who have been here? For instance, Babe Ruth, Ty Cobb and even Michael Jordan when he was with the cross-town White Sox. In fact, Wrigley was the setting for Babe Ruth’s called HR shot during the 1932 World Series. That’s not to mention baseball icons like Willie Mays, Hank Aaron and inter-league rivals like Stan Musial and Ken Griffey Jr.

About The Author

Randy Yagi is an award-winning freelance writer who served as the National Travel Writer for CBS from 2012-2019. More than 900 of his stories still appear in syndication across 23 CBS websites, including New York, Los Angeles, Chicago and San Francisco. During his peak years with CBS, Randy had a reported digital audience reach of 489 million and 5.5 million monthly visitors. Additionally, his stories have appeared in the Daily Meal, CBS News, CBS Radio, Engadget,, and He earned a Media Fellowship from Stanford University in 2012.