Chicago
Self-guided

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Our most recommended Chicago Self-guided

Eastside Chicago: City Exploration Game

1. Eastside Chicago: City Exploration Game

Start the adventure at The Art Institute of Chicago. It will take you between 1.5 to 2 hours to complete and you can also explore at your own pace. Pause the game and resume anytime from the location where you paused it. You will finish at the Fountain of the Great Lakes. As you solve challenges, the story unfolds and exact directions on your phone will guide you to the next location. So, are you up for an exciting city game? After your booking, you will receive an email on how to download the game to your phone. You can play on your own, in a large group, or in several smaller groups that compete against each other and meet at the final stop of the game. For larger groups, one person can purchase access for the entire group by selecting the number of people in the group. All group members will be able to download and play the city game on their phones. Alternatively, each person can make their own purchase.

Chicago: Riverwalk Self-Guided Walking Tour

2. Chicago: Riverwalk Self-Guided Walking Tour

Learn about Chicago's history, culture, and architecture on a self-guided tour via an app. Enjoy animated videos allowing you to visualize what you cannot see, such as snapshots from different centuries or interior rooms. Start by downloading the app that will function as your personal guide, audio tour, and map all in one (download instructions received via email after booking). After downloading the app, head to the starting point of the tour at McCormick Bridgehouse & Chicago River Museum. As you being to walk, spot the DuSable Bridge and learn about the iconic terracotta Wrigley Building. From there, head west and pass Wabash Bridge, once voted America’s Most Beautiful Bridge. After that, see the Chicago Vietnam Veterans Memorial, a tribute to the soldiers who lost their lives during the Vietnam War. Next, stop by the 600-foot Marina Towers. Learn how these towers function as a “city within a city.” Head to the Dearborn Street Bridge and hear why an angry mob once gathered here with axes. Listen to the tale of one of the strangest and deadliest shipwrecks in American history. Learn how a devastating shipwreck happened on a river only 20-feet deep. Continue on toward the Merchandise Mart, a gorgeous example of Art Deco architecture. Learn how the Chicago River helped this city go from a small settlement to a bustling hub of culture and commerce. Next, arrive at Wolf Point, where Chicago’s very first hotel stood almost 200 years ago. Dig into the era when this place was little more than a wild frontier, then head back the way you came for the final section of the tour. Stop at the Tribune Tower containing pieces of historic buildings from across the world, including the Notre Dame Cathedral and the Berlin Wall. Next, come face to face with NBC’s Chicago headquarters, modeled after the famous skyscraper at 30 Rockefeller Center. Finally, arrive at the last bridge separating the Chicago River from Lake Michigan, where the tour concludes. Take in the soothing scenery and snap a few photos for your Instagram.

Chicago: Millennium Park Self-Guided Walking Tour

3. Chicago: Millennium Park Self-Guided Walking Tour

On this self-guided walking tour where your phone is your personal guide, explore Millennium Park’s best sights and dive into some of Chicago’s little-known history along the way. This tour has been developed by local guides, creative writers, and professional voice artists. Begin your tour at the park’s north end, by Harris Theater for Music and Dance. From there, simply follow the audio instructions and the route via the app that will be your guide, narrator, and map in one. Head south toward the Pritzker Pavilion while learning some background on how the park came into existence. As an added perk, most stops along the tour have animated videos allowing you to visualize what you cannot see, such as snapshots from different centuries or interior rooms. Once at the impressive pavilion, learn about the vast array of performances held here and the high-tech design which makes it all possible, as well as the man behind it: Jay Pritzker. Get the full story on this precocious kid who went from building model cities out of his grandfather’s scrap wood to designing some of the most famous structures in the country. As you continue, you’ll come to the park’s so-called Secret Garden. Take a stroll along a peaceful boardwalk surrounded by plant life and listen to the little-known symbolism behind the garden’s design. Pause for a fantastic look at Chicago’s skyline before heading past the Art Institute of Chicago and ending up at the astonishing Crown Fountain. Get familiar with the intricately detailed face towers of the fountain, then head north toward Chicago’s most famous sculpture. At last, arrive at Cloud Gate, known by the locals as The Bean. Learn about the artist behind it as well as the technique he used to create such a huge, smooth surface. At the end of your tour, don’t forget to snap some surreal pictures of your reflection.

Frequently asked questions about Chicago Self-guided

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What people are saying about Chicago

My husband and I enjoyed the Chicago River Walk tour. We learned a lot about the City’s architecture and history at our own pace. It’s a great way to get a little exercise while learning at the same time. Looking forward to another tour to learn more about the City.

Millennium Park was really nice! I enjoyed seeing the bean although visitors could not get close because of COVID-19.

Be sure to wear your walking shoes! Long walk but well worth it. Would highly recommend!

Caleb was a very cool, informative, & humorous guide, made the tour fun

Great way to discover Millennium Park and learn something too.