Explore Chicago on Foot: Tips and Fun Facts

BlogHer Original Post

This is a four-week series to help attendees explore Chicago. Please also visit Walking Tour One, Walking Tour Two and Walking Tour Three.

If you haven't checked out the Chicago Walking Tours yet, and are looking forward to getting to know Chicago a bit, we suggest you look into them now. They're chock-full of history, architectural facts, hidden Chicago gems and some of the greatest shopping in the city. BlogHer community member Cynthia Clampitt created three tours, plus put together these tips and fun facts, and we couldn’t wait to share them with you. Read on for a great city guide about the city’s architectural history, expansive public parks, tips for keeping your bearings, and what to do near the Sheraton Chicago Hotel and Towers.


While New York is considered a great world city, Chicago is often said to be the great American city. It is where the high-rise was born and American architecture got its start (try to think of any famous American architect who isn’t associated with Chicago—we’ve had Louis Sullivan, Frank Lloyd Wright, Mies van der Rohe, and Helmut Jahn, to name a few).

Chicago owes its remarkable architectural history to the Great Chicago Fire, which destroyed a huge swathe of the city, including all of downtown, in 1871. In the late 1800s, a booming city that needed an entire new downtown seemed like the best place to start experimenting with new ideas in architecture. Armed with affordable steel, Elisha Graves Otis’s new elevators, big dreams, and ambition, architects came from all over the world, ready to rebuild Chicago. And thus was born, not only American architecture, but also the “skyscraper,” as the tall buildings would be called.

The first skyscraper, the Home Insurance Building, was built in Chicago in 1885. At ten stories tall, it was the tallest building in the country. With the success of this building, skyscrapers began to appear all over Chicago, and soon in other cities, getting taller and taller as people became more confident.

Chicago has a lot more to offer than tall buildings, however. The city’s motto is Urbs in Horto—City in a Garden—and this is not wishful thinking; the city has more than 7,300 acres of parkland, 552 parks, 33 beaches, 16 historic lagoons, and 10 bird and wildlife gardens. Among the best known of Chicago’s parks is Grant Park, which parallels South Michigan Avenue for most of its length.

Partly because of this great architectural history, but also because of the fabulous stores, monumental artwork, and gorgeous lakefront, Chicago is a wonderful place for a walking tour. Taking a bus or taxi is always an option, but there are a lot of things worth looking at up close.

Chicago offers a tremendous array of sights and activities—one could spend weeks trying to see and do everything—but a lot of the city’s history and beauty can be taken in within a relatively short distance of the Sheraton Chicago Hotel and Towers, where BlogHer ’09 is taking place. The walking tours below can be broken up or combined, depending on your timeframe, interests, and stamina. The two Michigan Avenue tours are about a mile each. The Loop is a little less than one half mile square, though you may cover more ground than that, depending on which bits you choose to see.

Tips to help you keep your bearings

  • The lake is east. If you can see the lake, or have a sense of where the lake is, you can always figure out the direction you’re going.
  • The baseline for north/south numbering is Madison Street and for east/west numbering is State Street.
  • Each full block is assigned a series of 100 numbers. For example, the Hilton Chicago is at 720 S. Michigan Avenue, which means it’s in the 700 block, or the seventh block south of Madison Street. The Sheraton Chicago Hotel & Towers is at 301 East North Water Street, so it is in the third block east of State Street.
  • Address numbers are even on the north and west sides of the streets. (If you like mnemonics, just remember “new”: north-even-west.) Addresses are odd on the south and east sides. Therefore, you can tell just by looking at the Hilton Chicago’s address that it is on the west side of Michigan Ave.

Near the Sheraton Chicago Hotel and Towers

  • While the walking tours below will offer a feast of architecture, history, and shopping opportunities, you don’t have to go too far from the hotel to have a good time. One block north, at 401 E. Illinois St., you can visit Fox & Obel, Chicago’s answer to New York’s Dean & Deluca. You can shop for ultra-goodies, or just stop in the café for some of the great truffle fries or perhaps a decadent dessert.
  • Just a few blocks east of Fox & Obel, and you’ve reached Navy Pier. This Chicago landmark, which extends more than half a mile into the waters of Lake Michigan, offers the glitter and glamour of a really wonderful fairground. The huge Ferris wheel, impressive in daytime but magic at night, when it’s outlined with hundreds of lights, will be one of the first things to catch your eye, but that’s just the beginning of delights. Inside, there are gardens, shopping arcades, and fun rides. Shops and carts offer Indian jewelry, Russian dolls, cinnamon almonds, cooking gear, books, clothes, and Chicago memorabilia. Chicago Shakespeare Theater, one of the world’s great Shakespeare companies, has its impressive theater here. There is a food court and numerous restaurants, including Riva, which offers some of the city’s best seafood.
  • One of the pier’s real surprises is the Smith Museum of Stained Glass Windows—the only museum of its kind in the United States. A gorgeous stroll among vivid colors takes you through the history of stained glass. (Chicago has long been the world’s center of stained glass window manufacturing, and this is where Tiffany had his workshops.) If you make it out to the end of the pier, take a peak at the old Grand Ballroom, which hints at the pier’s long history. The pier also offers a great view of the city, so take your camera.

We hope that you take advantage of being in this great city, whether through walking tours, taking part in the photo promenade through Chicago, or just shopping along the Magnificent Mile. 

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Cynthia Clampitt is a freelance writer who specializes in food, history, and travel, and is the author of Waltzing Australia. She has lived near Chicago for most of her life, and no matter where she wanders in the world, she is always glad that this remarkable place is home.


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