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Prepare to kick off America's holiday season in style at The Wintrust Magnificent Mile Lights Festival. This mile-long festival has attracted over a million visitors daily for more than 32 years now. The festival's nighttime parade on Michigan Avenue is the largest in the United States, featuring Mickey and Minnie Mouse from The Walt Disney World Resort leading the way. The event boasts an impressive lineup of fantastic floats, giant helium balloons, marching bands, celebrities, musical performances, Santa Claus, fireworks, and more. The parade illuminates over a million lights on 200+ trees along The Avenue, creating a truly awe-inspiring sight.

If you want to experience Greek culture, Chicago's Greektown is a must-visit neighborhood. This vibrant district offers a variety of nightlife spots, restaurants, gift shops, and galleries that celebrate Greek heritage. It's the best place to sample Greek culture outside of Athens and has become the city's go-to destination for Greek food, nightlife, and rich cultural traditions. With many establishments dedicated to preserving old-world traditions, visitors can truly immerse themselves in Greek culture in this neighborhood. Apart from dining and nightlife, visitors can explore The National Hellenic Museum, ride the Greektown Trolley, witness the annual Greek Independence Day parade, and indulge in the Taste of Greece festival. These activities make Greektown the perfect destination for anyone interested in learning more about Greek heritage in Chicago.

Embark on a journey back in time to the days of infamous mobsters like Al Capone, Bugs Moran, and John Dillinger with Untouchable Tours. This unique experience takes patrons to various famous areas in Chicago where notorious gangsters would hang out during the days of Prohibition. During the tour, you'll return to Prohibition-era Chicago and visit the hotspots where Al Capone and his allies and enemies became famous. The guides are actors who adopt the persona of a 1920s gangster and accurately recount the crimes and activities in Chicago during the 1920s and '30s. You'll hear about the exploits of Capone, Moran, Dillinger, and other notorious gangsters. Some sites included are the St. Valentine's Day Massacre, the Biograph Theatre, and Holy Name Cathedral. The tour is educational and highly entertaining, and you even have the chance to win prizes at the end.