Walk at the right time. While Chicago is great to walk in, it's not always great to walk in. The winters are incredibly cold, and will refuse to allow you to enjoy the outdoors. The summers can also be intensely hot and make you equally as uncomfortable. Plan according to your preference.
Get out to the lake. Chicago is unique in that a majority of the city-especially the most beautiful parts-sit on the multi-mile lakefront. One of the best places to walk is along this stretch of Lake Michigan.Whether it's a sunny, summer day or a brisk, autumn morning, you will find any number of people using the lakefront. Everyone from walkers, runners, bicyclers, chess players and performers use it as their main stomping grounds, and so should you.Do yourself a favor when you visit Chicago: plan to spend an afternoon (or early morning, if that's for you) walking the Lake. Start downtown at Oak Street and head North, up to the giant ship-restaurant at North Avenue, or go South and walk all the way to Navy Pier-one of Chicago's main tourist attractions. Whichever way you decide you want to go, you'll be fine and the sights will be even better.
Stroll through one of the city's historic neighborhoods. The city is full of great, residential neighborhoods that are really nice to walk through and can make a perfectly pleasant day. In all honesty, there are any number of areas where you can walk around and see the beautiful architecture, but some of the best neighborhoods are Wrigleyville (where Wrigley Field is), the Gold Coast, Lincoln Park, Lakeview and River North. These areas are known to be very safe and user-friendly. They are lined with trees, some shops and lots of people. They are great places to spend some time and a perfect opportunity to get to know the city from the inside out.
Go to The Magnificent Mile. As any woman could tell you, Michigan Avenue (aka The Mag Mile) is the main shopping district of Chicago. It's begins at Oak Street (right next to the beach) and ends... well, it seems to never end. The main shopping district goes from Oak to the Chicago River. It a plethora of stores, and something for everyone. Visit men’s stores, women’s stores, toy stores, candy shops, a gourmet popcorn store, and souvenir shops. It's a great stretch of road to walk down. There are usually street performers on nice days and people all moving along. There are great sights and images and old buildings to look at. It really is just amazing mile-long walkway. Though the real "Mag Mile" ends at the Chicago River, Michigan Avenue continues through downtown and into Grant Park. But before you get all the way to Grant Park, you'll hit Chicago's newest and one of the best attractions: Millennium Park. The Millennium area is a great place to walk around. It's a huge park with some newer landmarks (like the Bean) and some great little eateries and other attractions. And though it's right downtown, it's a nice area.
Head to South Beach-Chicago's version of South Beach. You can sit outside at a table, have some dinner or a drink, and just people watch. Where Rush intersects with State Street is a totally transformed area of Chicago. It features some of the city's best restaurants and on a hot, summer night the whole place will be packed full of people. It's best to just sit and relax and enjoy the show. You'll see all kinds of people, dressed up for dinner, for one of the many bars or clubs in the area. It's bursting with nightlife and music, and really just gives off an ultra-cool vibe. Enjoy the show.
