Chicago walking tour: Streeterville, Lakefront Trail and the Magnificent Mile

With more tourist destinations per square mile than any other city in the region, Chicago’s list of attractions is unbeatable. On this walking tour, I’ll show you a number of the places that led to the city being called “the jewel of the American Midwest.” I’ll show you the once-independent “Deestrict of Michigan” – otherwise known as Streeterville – Ohio and Oak Street Beaches, the historic Water Tower, and the North Michigan Avenue shopping district, better known as the Magnificent Mile. Along the way, you'll have the opportunity to pause the tour and enjoy some of the many attractions the city has to offer. As you stroll along the Lakefront Trail, you’ll discover the real reason Chicago’s called ”the Windy City” and “the Air-conditioned City.” Enjoy the delicious breeze that the lake provides even on the hottest days of summer while hearing stories of famous shipwrecks and storms around what was once the fourth busiest port in the world. On this tour, you can also look forward to: • Hearing the story of George Streeter, the would-be dictator of his own sand bar and saloon, and his ”Battle of the Lake Michigan District” • Seeing the Gold Coast up close, one of the U.S’ wealthiest neighborhoods • Promenading past the creme de la creme of American retail, and malls like the more moderately-priced Water Tower Place • Learning why Chicago is a favorite among beer lovers • Finding out about the Gold Coast’s ”Mansion of Woe” and the home with its own running Champaign faucet • Watching the street musicians perform around the famous Water Tower • Learning the origins behind Navy Pier’s name • Walking in the shadow of the 105th tallest building in the world, the John Hancock Center • Discovering what Abraham Lincoln had to do with Chicago, and hearing about the city’s two Nobel Peace Prize winners • Listening to the story of Chicago’s Mickey Spillane and finding out what happened to a couple of Al Capone’s enemies The tour starts and ends at the same North Michigan Avenue location, right in the heart of the downtown hotel and tourist district. By the end of your walk, you’ll be able to show everyone on Instagram or TikTok that you saw the very best Chicago has to offer!

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