The Loop
Walk along the Chicago River - The Chicago River is lined with wide sidewalk promenades and criss-crossed with steel bridges. And best of all, these hulking bridges are raising bridges, so it's totally cool to watch the bridges go up. Bells ring, lights flash, gates go down (like railroad crossings), and streets are closed off. Slowly the bridge sections raise up to let the boats pass through. For a great walk, start on the south side of the river at Michigan Ave., and stroll west along the promenade to Lake St.

Boat rides on the Chicago River - In summer, take a boat ride on the Chicago River. It's fun chugging along the river, passing under all the bridges, looking up at the skyscrapers.

Pick up Shoreline Water Taxi at S. Wacker Dr., one block from the Sears Tower. The boat runs up the river, stops at N. Michigan Ave., and goes out to Navy Pier.

Skydeck - Willis Tower (formerly Sears Tower) - Willis Tower is one of the tallest buildings in North America, and has the highest observation deck. Completed in 1974, it is 1,450 feet high, with a black aluminum surface and 16,000 windows (robotic washing machines wash the windows).
The speedy elevator takes you up to the Skydeck, open 10 - 10 in summer, 10 - 8 in winter. From the observation deck, Chicago is amazing from every angle, and in the distance, if it's a clear day, you can see into three other states. Cars driving on the roads down below "look like ants." Step out onto The Ledge, a glass floor, and look down.
Go late in the day or early evening to avoid crowds, and enjoy the nighttime views of the city.
Tip: Use Chicago CityPass and no waiting in long ticket lines.
Harold Washington Library Center (State St.) - Named after Harold Washington, the first African American mayor of Chicago, the Children's Library on the second floor is amazing, the largest collection of children's books in Chicago. Little kids will enjoy the Storybook Dollhouse, a dollhouse filled with 100 different little storybook characters - Paddington bear, Lyle the crocodile, curious George, the three bears, Corduroy, and more! The Children's Library reading room is a great place to spend time when the weather is crummy.
Ride the "L" elevated train - In the late 19th century, the elevated train was designed to bring people to heart of the downtown. When every train came in, it made a "loop" and then headed out a different direction.
Today, ride the L, for a unique train ride above the streets of Chicago. Wait on wooden platforms that shake when the train comes into the station, ride high above the streets, trains rumbling over the tracks, squealing and groaning as they goes around the corners.
For a short ride in the Loop, get on the Brown line at Quincy station (beautifully restored), ride around the Loop counterclockwise to Clark, then get a pink train going clockwise, and you'll end back up at Quincy (close to the Sears Tower).
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