If you're riding the bus to this area, get off around LaSalle and Lakeshore. There's a pedestrian underpass that will take you under Lakeshore Drive, and out to the lakefront. This Google satellite picture will help you spot it.
North of Oak Street Beach, there's a long concrete seawall that's probably at least 50 feet wide. It separates the lake from US 41 (Lakeshore Drive), and provides a great place for pedestrians. A lot of Chicagoans emerge from their apartments on sunny days with a beach blanket, and lay out on the concrete, as if it was a soft, sandy beach. I instead decided to walk from here down to Oak Street Beach (perhaps 1/2 mile).
On a sunny spring day, it's a gorgeous place, that's alive and energetic. There will be plenty of people out exercising and playing on the concrete and nearby sidewalks, and even a few swimming in the water (yes, the picture says "no swimming", but it is allowed further down from here).
Oak Street Beach is just a tiny patch of sand, bordered on one side by that concrete wall, and on the other by the northern end of Michigan Avenue, and of course, Oak Street. The water looks clean and refreshing (and surprisingly blue-green!) but it remains cold throughout much of the year.
The view north shows the line of high-rent apartment and condo buildings that line the waterfront, providing lucky residents with a great view of the lake.
Looking south, you see the big buildings at the northern end of Michigan Avenue, the Magnificent Mile. I don't think there are many other places in the country that combine skyscrapers and sand, quite like this.
If you watched Late Night with Conan O'Brien during his visit to Chicago in 2005, you enjoyed a great aerial view of the lakefront and beaches, as "the bear" arrived in town. Click here for the PG-13 rated clip.
The Magnificent Mile runs along Michigan Avenue, from Oak Street Beach to the Chicago River. At it's northern end, one of Chicago's boldest structures stands guard: the John Hancock Center (known to locals as Big John).
The John Hancock Center is Chicago's second tallest building (if you count the antenna towers at the top--third tallest if you don't). It was the tallest building in Chicago, or anywhere else outside of New York City, between 1969 and 1973, according to Emporis. And, unlike the Sears Tower, if you visit the observatory atop Big John, you can step outside, and feel the wind rushing past. Oh, and the admission tickets are also $2 cheaper than the tower's taller neighbor.
Michigan Avenue is known worldwide for an incredible number of high-fashion, high-price stores. In addition to stand-alone shops, you'll find several high-rise malls, that are just like the ones you'd find in the 'burbs, except these spread up instead of out.
Since I can't afford any of Chicago's expensive stores, I stayed out on the street, and enjoyed the spring colors. In May, there are tulips everywhere!
There is one historical structure you should appreciate, as you walk down Michigan Avenue. It looks like a castle, but it's actually the old Water Tower. (There's also an old pumping station across the street, built with a similar gothic design.)
The water tower was constructed in 1869. Inside the center column, there used to be a 138 foot tall standpipe, used to equalize the pressure from the nearby pumping station. It became obsolete in the early 20th century and was removed.
The Old Water Tower and Pumping Station were the only public buildings in the area to survive the Great Chicago Fire of 1871.
Nowadays, the old water tower serves as a small photography gallery for the city of Chicago. Local artists are presented on a rotating schedule. The museum is free, and will probably only occupy about 10 minutes of your time, unless you have a specific interest in the featured photographer. While inside, you can also peer into the tower's center column (but unfortunately, you're not allowed to climb to the top).
At least a dozen bus lines run up and down Michigan Avenue, so consult your CTA map to make sure you know where you're going when you step aboard. The nearest train line is three blocks to the west--the red line, underneath State Street.
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