Metro Chicago and Southern Wisconsin Vacation Ideas Metro Chicago and Southern Wisconsin - Road Trip Planner
 

Guided Tours in Chicago, Illinois, Milwaukee, Wisconsin Dells, Madison

Things to do / Travel Guide

Metro Chicago and southern Wisconsin is a quirky region, filled with great architecture, rich history, and great food and pastimes; therefore, it's only natural that the region offers excellent tours.

Chicago Walking, Biking, and Bus Tours

Many aspects of Chicago are best covered by foot, so walking tours are available in abundance. Many of the 77 different Chicago communities are self-sufficient and of unique individual character, so taking a walking tour can show you things a car can't. To really explore the opulence of a neighborhood like the Astor Street homes in Gold Coast, you need to do it by foot. Other interesting options by foot are tours of Chicago's best chocolate shops, and a Chicago theater tour.

Sometimes two-wheeling it during the warmer months is an attractive option, and bike tours are easy to find when you have many bike stations through out the city. You can bike past Chicago's finest architecture like the historic skyscrapers or even the homes in the Gold Coast. Neighborhood tours are also popular by bike, including the area around Second City in Lincoln Park, where you might run into some of former Second City cast members like Rachel Dratch or Horatio Sanz - they still frequent the area.

Oftentimes the four-wheel excursion is the most convenient choice. Bus tours are available for viewing everything from the shops and buildings along Michigan Avenue to the grand architecture from yesteryear.

Chicago Specialty Tours

“Duck” tours are always available during the summer and show great views of the Chicago skyline from Lake Michigan and the Chicago River. Ride from Navy Pier on Lake Michigan, inland via the Chicago River to view the Michigan Avenue Bridge, the Centennial Fountain, and the famed House of Blues. Further up Lake Michigan there are great views from the water! With the Sears Tower standing from the distance and Shedd Aquarium almost popping out into the water- there is plenty to see from the water.


The Chicago Architecture Foundation offers many tours of the best and most popular of Chicago's architectural wonders. Many of these are walking, biking, or bus tours, but they also offer a river cruise focusing on the city's beloved buildings. Every one of Chicago's manifold building styles, every interesting building, is commented on in these tours. There are also neighborhood tours and happy hour tours. The source of these tours is the ArchiCenter, located on South Michigan Avenue and West Adams Street.

Another Chicago favorite is the gangster tour, epitomized by Untouchable Tours, which departs from Near North Side on Clark and Ohio. It's a “live action” tour, so you get the skinny on such colorful personalities as Al Capone and John Dillinger, and infamous events like the Valentine's Day Massacre - in real time right before your eyes. The bus tour paints a dramatized though informative picture of the city's not-so-clean historic underbelly.

If offbeat tours sound interesting, try one of Chicago's ghost tours which take place all around the Windy City's spooky joints, such as the Rosehill Cemetery in Andersonville. Some of these tours come complete with special sensors and detectors of the supernatural. Also on the unique side are tours featuring the Segway mode of transportation. Whether you're going down Lake Shore Drive on the edge of Lake Michigan to look at Buckingham Fountain in Grant Park or visiting the sites in the Loop, the “segway” is an interesting option for touring.

Chicago and Southern Wisconsin - Frank Lloyd Wright Tours

Frank Lloyd Wright has so many tours dedicated to his famous homes and buildings that he deserves his own sub-section. All throughout the Midwest, Frank Lloyd Wright designed some of the most influential buildings and homes to date. There are tours of Hyde Parks' Robie House in southern Chicago, and of the prolific amount of houses he built in his ten year stay in Oak Park, Illinois.

Many great designs of Frank Lloyd Wright's are in southern Wisconsin, in Racine, Milwaukee, and Madison. Some of the featured homes in Milwaukee are the American System-Built homes starting in 1916, and Wright-inspired Schulenberg House, built in 1954. Highlights in Madison include the Lamp House built in 1903, the Unitarian Meeting House constructed in 1947, and the Frank Lloyd Wright-inspired Monona Terrace overlooking Lake Monona. With so many homes built, it's impossible to list them all. Be assured that everywhere there is even a small cluster of Frank Lloyd Wright homes or other buildings, there will be tours in or around them. Tours are available by foot or bus.

Southern Wisconsin

Not to be outdone by Chicago, southern Wisconsin has some very unique tours available. Aquatic “duck” tours are a popular choice for Lake Geneva, where tours are offered six times daily from mid-June until early September, and twice a day in the spring and fall. Tours can last between one and three hours, depending on your availability, and they showcase the glorious mansions surrounding the lake.

The Wisconsin Dells are another great place for boat tours, where you can enjoy the majestic scenery for the Upper Dell waters. Shore landing breaks allow you to stretch your fins and walk to Witches Gulch and Stand Rock. The season opens during April and closes come October. Oh, and there are more duck tours at the Dells, too.

Milwaukee boasts some classic water cruises. Tours are available in the Riverwalk downtown area of the local breweries along the Milwaukee River, in which you can taste the finest brews available from Beer City. River tours are also available for the history buffs who are interested in the history of Milwaukee and its architecture. These latter tours usually last four hours and are only available during the spring and summer months.