Activities Aplenty Await in Illinois

Itinerary at a Glance

Illinois is many things to many people. It’s Chicago, one of the largest cities in the U.S., with its stunning skyscrapers, lakefront lifestyle and culture to spare. It’s an old prison which may or may not be haunted, plus the days-gone-by charm of nearby small towns. But Illinois also proudly wears the nickname of the Prairie State and has plenty of farms, forests and rolling hills to prove it. In other words: What are you waiting for?

6 Great Experiences for Architecture Lovers:

  • Chicago River architectural boat tours
  • Edith Farnsworth House
  • Ellwood House Museum
  • Willis Tower
  • Broadway in Chicago tour
  • Hegeler Carus Mansion

Details and Tips

Region: Midwest

Length: 3 nights

Best time of year: Spring, summer or fall

Suitable for: Adults who have a passion for history, architecture, shopping, theater and outdoor adventures

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Day-To-Day Itinerary

Day 1: Exploring Things to Do in Chicago, Illinois


One day isn’t enough to properly explore the City of Big Shoulders, so consider this a preview for your next trip. Start where it all began in Chicago’s Loop. Admire the historic buildings on State Street, including Macy’s, formerly Marshall Field’s, as you make your way to the Art Institute of Chicago and its world-renowned collection of masterpieces. Afterwards, head to nearby Millennium Park, where you’ll find “The Bean,” as locals call Cloud Gate, and other Instagram-worthy sites.


Hungry? We thought so. Stroll the short distance to the Riverwalk, where you’ll be rewarded with plenty of outdoor cafes as well as stunning views of the bustling Chicago River. For more breathtaking views, visit the Willis Tower or Michigan Avenue’s John Hancock Center, the latter of which neighbors shopping galore. Or consider one of the many Chicago River architectural boat tours, a great group activity. Chicago’s theaters are famous around the world for the high-caliber performances they feature as well as their historic architecture. Get an up-close view of the vintage décor of three of them with a Saturday afternoon tour with Broadway in Chicago.


For dinner, get a dose of history as well as delicious locally brewed craft beers and American heartland food with a visit to Chicago Southland’s Flossmoor Station. Housed in a turn-of-the-century building that was formerly a train station, this award-winning brewery attracts locals and visitors alike.

If handcrafted spirits are more to your liking, head to Thornton Distilling, located in the in the oldest standing brewery in Illinois and the home of Drop Dead Spirits. Book a tour to see their on-site artesian well and modern distillery production floor while you learn about the rich history of the building and, yes, taste some of their stellar craft spirits.

If you want to stay in the big city, enjoy a Broadway-style show in Chicago at a variety of theaters including the Cadillac Palace Theatre, which has been entertaining audiences since 1926, and the James M. Nederlander Theatre (which also opened in 1926), which offers a variety of entertaining theater shows.

Day 2: Experiencing Chicago and More of Illinois


For an up-close view of an iconic home created by one of the world’s most influential architects, head 58 miles southwest of Chicago where you’ll find the Edith Farnsworth House in Plano. Designed by Mies van der Rohe, the home represents the fullest expression of modernist ideals that had begun in Europe but was finished in Plano. Another great option is to travel northwest to the Anderson Japanese Gardens in Rockford, one of the top Japanese gardens in North America. This 12-acre oasis features two gardens, a pond-strolling garden and a contemporary Garden of Reflection. Another excellent outdoor option is the Little Red Schoolhouse Nature Center in Willow Springs. This interpretive center features sustainable design, a sensory garden, live native animals, exhibits about local natural history, a nature play area and an accessible trail. Over 3 1/2 miles of walking trails are available.


Check some gifts off your list with a visit to More Polish Pottery in Aurora. At this family-run business, you’ll find an extensive selection of pottery stoneware and handmade products imported directly from Poland.

Add more Illinois architecture knowledge to your experience with a visit to the Ellwood House Museum. Located on 10 acres of parkland in the heart of DeKalb, the museum campus includes seven historic structures, including the 1879 Ellwood Mansion and 1899 Elwood-Nehring House, four gardens and 6,000 square feet of exhibit space.

For a look into the everyday life of a sailor, head to the National Museum of the American Sailor. Horse-lovers won’t want to miss the Tempel Lipizzans. The history of these brilliant horses spans more than six decades while the story of the Lipizzan and classical riding spans more than five centuries. Each performance is set to music and is a study in classical horsemanship and impressive athleticism.

Groups looking for a shopping outing can visit Aurora’s Chicago Premium Outlets, an outdoor center that sports more than 170 stores including Adidas, Coach, Nike, Kate Spade and more. Another nearby shopping destination is Woodfield Mall in Schaumburg. One of the largest shopping destinations in the country, Woodfield Mall houses more than 2 million square feet of shops including Aveda, Coach, H&M, Macy’s and more.


Enjoy a show at the Coronado Performing Arts Center in Rockford. This iconic venue has hosted artists, shows and concerts since 1927. Another great theater option is the historic Paramount Theatre in Aurora. Opened in 1931, the theater presents Broadway shows, concerts, comedy and more in a classic setting. Another historic place to savor a night out is the historic Genesee Theatre in Waukegan. This legendary theater that opened in 1927, hosts concerts, shows and events and has seating for 2,403.

Day 3: More Things to Do in Illinois


Do some time-traveling with a visit to LaSalle where you’ll board the Volunteer, a mule-pulled 1840s replica of the canal boats that once traveled along the I&M Canal. Each hour-long tour begins with Mule Tending 101 presentation before it gently coasts up and down the Illinois and Michigan Canal. History lessons continues with a tour of the Hegeler Carus Mansion in La Salle. Designed by a noted architect and completed in 1897, the mansion, which has seven levels, 57 rooms and some 16,000 square feet of interior space, offers five different tours, including ones for groups.


Thirty-five miles southwest of Chicago, Joliet is a city steeped in history, including the Old Joliet Prison, which once housed famous criminals and now offers tours of its castle-guard towers. Groups can visit the Joliet Historical Society to learn about the prison’s history. Looking for something less spooky? Head to Sue Regis Glass Art, where you can get a hands-on experience of the centuries-old craft. Another option is to travel 25 miles west of Chicago to the city of Lisle, home to the Morton Arboretum. This 1,700-acre public garden and outdoor museum protects more than 100 rare and endangered tree species and the grounds include more than 4,100 different plant species.


Those seeking to savor quality entertainment in a fabulous locale can visit the Rialto Square Theatre in Joliet. Opened in 1926 and listed on the National Register of Historic Places, the beautiful theater offers behind-the-scenes tours in addition to hosting big-name performers.

Day 4: A Beautiful Last Day in Illinois


Tap into the greener side of Illinois with a visit to Starved Rock State Park, located on the Illinois River near Utica. One of Illinois’ most-visited state parks, it features 13 miles of hiking trails, canyons and waterfalls. Groups can also fish, boat and even relax and picnic while savoring extraordinary views. Consider a stay in the Starved Rock Lodge, constructed in the 1930s, should Mother Nature beckon even more.