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Bike and Roll Chicago offers several locations to rent bicycles or Segways to explore the city. They provide five different tour options, such as The Amazing Lakefront, Friendly Neighbors, Chicago River & Parks, The Presidential Tour, and Bikes @ Nite, so you can pick the one that best suits your interests. Join one of their award-winning bike tours and see all the top attractions in Chicago. Glide along the stunning lakefront on a Segway. Please wear appropriate walking shoes as you embark on a magical adventure through downtown Chicago, lit with beautiful illuminations.

If you want to have a good laugh and witness some of the best comedic talents in the show business, you should visit The Second City Theater. This theater has been the breeding ground for many famous comedians like John Belushi, John Candy, Bill Murray, Dan Aykroyd, Gilda Radner, Mike Myers, Chris Farley, Steve Carell, Stephen Colbert, and Tina Fey. The Second City is an improvisational comedy company that started in Chicago. The company has stages in Toronto and Los Angeles, 11 touring ensembles, and training centers and programs in other cities. The performances are semi-improvised and feature scripted material with new content added after the second act, often based on audience suggestions

The Christkindlmarket Chicago is a traditional holiday market that offers a unique shopping experience, family-friendly events, and intercultural activities. It is considered the most authentic of its kind outside of Europe. The market combines beloved German and European traditions with local charm and international flair. It draws inspiration from the 16th-century Christkindlesmarkt in Nuremberg, Germany, which was one of the first outdoor markets of its kind. The Christkindlmarket is well-known for its high-quality gifts and food, holiday cheer, and ability to create lasting family memories. The German-style outdoor market has become so popular that it has expanded to several locations in Illinois and Wisconsin. The Christkindlmarket offers a one-of-a-kind shopping experience, lively entertainment, and a variety of original food and beverages, such as imported mulled wine from Germany called Glühwein. In 2022, it was ranked number three worldwide and number one outside of Europe by Big 7 Travel, and it has been recognized as one of the best Christmas markets. The Chicago Tribune, Choose Chicago, and Chicago Magazine have all mentioned the Christkindlmarket as a popular and preferred destination.

If you plan a trip to Chicago, take advantage of the chance to visit the Chicago Cultural Center. This iconic landmark offers a wide range of daily shows, lectures, films, and art exhibits, all free of charge. While you are there, be sure to take some time to explore the unique features of the building, including guided tours that can teach you more about its history and architecture. With over 1,000 programs and exhibitions annually, the Chicago Cultural Center is a hub for performing, visual, and literary arts. If you are interested in learning more about the building's history and architecture, guided tours are available. During your visit, you can marvel at the world's largest Tiffany stained-glass dome, beautiful mosaics, intricate marble and molding work, and coffered ceilings - all of which have made this building a true Chicago landmark.