Along the Magnificent Mile is a one-day and night sightseeing tour of Chicago.
- This article is an itinerary.
Most of Chicago lives in apartments, bungalows, condos, and houses on the North Side or the South Side, but this is where they all come together: to work amid the skyscrapers of the Loop, to relax in the parks and beaches along the lake, and to blow their hard-earned cash in the department stores on the Magnificent Mile. In this itinerary, you’ll follow Michigan Avenue as it evolves from shopping district to recreation space, and then you’ll take a turn into the canyons of the commerce-oriented Loop before heading off for a terrific dinner.
You’re walking for most of this itinerary, so wear comfortable shoes, and dress for the climate. If it’s a warm day in the spring, summer, or early fall, bring a small towel for splashing in the fountains at Millennium Park. This route starts in the Near North, proceeds to the Loop, veers off to the Near West Side, and returns to the Near North. Although the route is very straightforward and easy to follow, you may wish to print out the articles for those districts, if only for a few alternate recommendations and further illustration of what you’ll see along the way.
If you skip the shopping and stick with your feet, the day won’t cost very much. Only dinner, the Art Institute, and the Hancock/Sears Tower will put any kind of crimp in your wallet. To cut out the taxi fares, get the exact addresses from the Near North, Loop, and Near West Side guides, and plot public transit routes using the CTA Trip Planner.
Start early! On your way out of the hotel, ask the concierge whether the water is flowing at Buckingham Fountain yet; this will be important later. Grab a quick pastry and cup of coffee or juice to tide you over for the next couple of hours.
If you’re starting on the CTA, take the Red Line subway to the Chicago stop, and walk three blocks east, toward the lake. Skip a couple paragraphs ahead and begin there, as you’ll be walking right by the Water Tower.
Otherwise, take a taxi from your hotel to the Hancock Center. This is only the third-tallest building in Chicago (fifth-tallest in the United States), but it’s better-liked and better-looking than the other two, and it definitely has the best view. Take an elevator up to the Observatory on the 94th floor. Admission is $15 adult, $10 child. Survey the city and the lake, and be sure to look south, for there lies the day’s conquest. There’s a bar with expensive drinks one floor up. Don’t booze it up now, but you might come back for drinks later on.
One block south, at Michigan and Chicago, have a look at the old Water Tower. This is a Chicago icon, and the most famous survivor of the 1871 Chicago Fire, along with the less-celebrated Pumping Station on the other side of Michigan Avenue. Street performers may be in the small square behind the Water Tower. (Don’t bother tours of the interior, though — it’s been scrubbed of any historical traces, and is occasionally used as a gallery space now.) Behind the pumping station on Chicago Ave is a turn-of-the-century firehouse; not quite as old as the other two, but it’s still in use, and you’ll see members of the Chicago Fire Department (human and canine) relaxing out front if they’re not away on a call.
Now, you have two options. If you’re in the mood for sand, head east down Chicago Avenue. You might check to see if the Museum of Contemporary Art has any interesting public art outside its building at Mies van der Rohe Way. When you’ve reach the end of Chicago Avenue, turn left and walk a few blocks north. Use the pedestrian tunnel to cross under Lake Shore Drive. You are at Oak Street Beach. You should have a nice view of Lincoln Park and the North Side. When you’re done, walk back the way you came, or take a taxi directly to the Tribune Tower — back-tracking will make it kind of a long walk.
Alternatively, skip the beach and stroll down Michigan Avenue. This is the heart of the Magnificent Mile, with block after block of fashionable department stores. Pop into as many as you like, but this is expensive territory — and remember, you’ll be carrying whatever you buy for the rest of the day. (That said, if cost is not a concern, stores will be more than happy to have packages wrapped and sent to your hotel while you carry on.) You’ll want to backtrack to 900 N Michigan and Water Tower Place, and then keep heading south on Michigan.
When you’ve almost reached the river, stop. On your left is the Tribune Tower. Walk along its north and south walls; embedded in them are stones from famous sites across the country and around the world. Bore your family with your knowledge of history.
Now, cross over to the west side of the street and look for a curious opening in the sidewalk. There might even be a placard advertising a restaurant down there. Descend to lower Michigan Ave. At this point, your heart will be racing and you will fear for family’s safety. Perhaps a scene from Adventures in Babysitting will play in your mind. Fight these feelings; there is nothing to fear.
Walk to the corner, towards the river, and you will see the Billy Goat Tavern. This legendary haunt for Chicago newspapermen was made famous by John Belushi’s “cheeseburger-cheeseburger-not-Coke-Pepsi” sketch on Saturday Night Live. Go in and have a quick, cheap lunch.