Chicago, the Windy City. The backdrop of Upton Sinclair’s “The Jungle”, home of the Michael Jordan and the dominant Bulls, largest city in Illinois but not the capital, and third largest city in America by population, Chicago is one of the greatest cities on Earth by many measures.

There are many neighborhoods in Chicago, and we will not go into depth for all of them. We will highlight some of the best that Chicago has to offer, and a few places to avoid on a visit.

Generally, the southern parts of Chicago can be skipped or avoided when visiting the city. That is not to say that Calumet, Whitehall, Cicero, and the surrounding areas are all terrible, but they offer much less than the middle and northerly neighborhoods to someone visiting for a weekend or even a couple of weeks.

Wicker Park is a happening place filled with color and life. Stores and shops line the main streets interspersed with cafes, bars, and restaurants, and the arteries of this neighborhood are surrounded by residential homes and flats. It is one of the most walkable neighborhoods in Chicago, not least because it is not all that big.

Downtown is where the magic happens, or at least its is where many of the most recognizable and popular destinations are. It is densely packed with fun things to do, some of them free, and you could spend weeks in just this area of the city without running out of activities. Which neighborhoods comprise downtown in its entirety is a matter of debate, and we will not bother ourselves with listing them, but rather with the benefits the area offers.

Starting south and working our way north along the lake is Lakefront Trail, which offers a path to pedestrians and bikers for 18.5 miles along the shore of Lake Michigan, through parks and at the edge of the city. It is a fantastic addition to a traditional American city that is vehicle centric over any great distance, despite buses and local trains.

As you work north, you will reach McCormick Place, a convention center, and Soldier Field, home of the Chicago Bears. Just across the street from Soldier Field you reach the Field Museum and the Museum Campus, which also includes the Adler Planetarium and the Shedd Aquarium. These facilities can take a whole day each to explore, so don’t plan on rushing through them all at once.

Continuing on you find Grant Park, a well kept green space with sports fields and plenty of room for activities. The Art Institute of Chicago is next, with a collection including works from van Gogh, Picasso, Renoit, and Monet, to name only a few. The Art Institute is one of our favorite museums, rivaling the Louvre in France for quality, if not in scale.

Michigan Ave

Old Town is, as the name suggests, one of the older neighborhoods in Chicago. Though there is no organization or governing body known as Old Town, it is an accepted and recognized area of the city. It is said that if you can hear the bells from St. Michaels church, you are still in Old Town. St. Michaels is an interesting building in its own right, having partially survived the Great Fire of 1871.

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