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

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

Walking Tour

60 mins

About the Tour

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!

Tour Producer


Richard Junger

Professor, urban historian and former journalist. Most recent book is "Becoming the Second City: Chicago's Mass News Media, 1833-1898" from University of Illinois Press. I'm the guy who says "guess what happened here?" as I walk around Chicago with friends.

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Major Landmarks

  • Streeterville

  • Navy Pier

  • Jane Addams Park

  • Ohio Street Beach

  • Oak Street Beach

  • John Hancock Center

  • Drake Hotel

  • The Chicago Brewery

  • Gold Coast

  • Hilton Mag Mile

  • Hyat Mag Mile

  • Warwick Allerton Hotel

  • Historic Water Tower

  • Magnificient Mile

  • Omni Chicago

Directions to Starting Point

On foot, the tour starts three blocks north of the river at N. Michigan Avenue and E. Grand Avenue. Look for the men's clothing store and jewelry store on the east side of North Michigan.
CTA "L" lines -- The Red line stops both ways at E. Grand Avenue. Get off and walk east three blocks toward N. Michigan Avenue.
CTA bus -- Most Michigan Avenue buses stop at or near N. Michigan and E. Grand Ave. Check route maps or ask a driver.
Millennium Station -- The CTA Metra Electric lines and the Indiana South Shore Railway stop there. Just go up to street level and walk north seven blocks on North Michigan Avenue
Metra Ogilvie and Union stations are much longer walks. Consider the "L" or a CTA bus
Parking garages -- Available but pricey. It will save to use mass transit. One of the cheaper garages is under Millennium Park at 5 S. Columbus Drive. Walk north along Michigan Avenue to the starting spot. Check the "Magnificent Mile SpotHero Parking Page" online for parking closer to the Magnificent Mile, but it will cost more.

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Places to stop along the way

There are restaurants and bars along most of the route. A few in Streeterville are less expensive, but the many more right along the Mag Mile can be quite pricey. West of Michigan Avenue is less expensive. Jane Addams park is a nice place to sit and rest, maybe even enjoy an ice cream on the right day. Both the Ohio and Oak Street beaches have refreshments and seating, perhaps a bar, during the summer months. And you can always pull up a nice piece of beach sand and rest or sunbath on, or take a break on seating along the picturesque Lakeshore Trail. For an hour or two or all day, this tour is the perfect way to experience the best of Chicago!

Best time of day

Touring is good at any daylight hour when the weather is decent. Surface automotive traffic is worse mornings 7 to 10 and afternoons 4 to 7 local time. Traffic is less of a problem on weekends, but the streets can still be busy. Chicago is the windy city and a chilly Lake Michigan breeze can be uncomfortable without proper clothing, especially in late fall, winter, and early spring. Check the weather forecast those times of the year and dress appropriately. When the lake is exceptionally rough, the city will close the Lakeshore Trail, so be wary of big storms. Icy days may not be the best time for this tour either, given the trail's proximity to the lake. Always walk carefully.


Chicago's big buildings can do strange things to GPS signals, especially along North Michigan Avenue. If the audio stops for an extended period of time, use your smartphone map to get back/stay on the route.

As mentioned in the tour, watch out for right turns on red lights and motorists speeding through red lights. The tour is best during good visibility daylight hours, but downtown Chicago is a safe city. Hours may vary for Mag Mile stores and shops. Call or check online if you are interested in a particular store or stores.


Preview mode limited to first 3 locations.
Chicago walking tour: Streeterville, Lakefront Trail and the Magnificent Mile