1.) Sample some of the city’s local food specialties
Chicago is known for its garden dogs and its own pizza style and one would be foolish to not try either while there. Chicago-style pizza is a deep-dish pizza that has a buttery crust and is up to three inches tall at the edge, making it even slightly higher than the copious amounts of cheese and chunky tomato sauce, thus acting as a large bowl; it is the antithesis of the thin crust style pizza. Some famous Chicago-style pizza institutions are Giordano’s, Lou Malnati’s, and the most known of them all (outside of Chicago that is), Pizzeria Uno and its offspring, Pizzeria Due, which is a block away.
The Chicago-style dog (or garden dog as it is also known due to the many toppings found on it) is a steamed, all-beef frankfurter on a poppy seed bun topped with yellow mustard, chopped white onions, sweet pickle relish, a dill pickle spear, tomato slices or wedges, pickled sports peppers, and a dash of celery salt. I sampled a Chicago dog on my most recent trip there and while it was extremely messy to eat with most of the toppings falling off, it truly was a distinctive take on the traditional wiener. D and I got ours from Portillos but other beloved spots include Superdawg and Gold Coast Dogs.
2.) Take public transportation everywhere
The Chicago Transit Authority operates an extensive network of buses and a rapid transit elevated and subway system known as the “L” (for “elevated”) both within the city and a few adjacent suburbs. You’ll have a less stressful visit and save considerable money if you forgo renting a car, skip taxis and instead opt for one of the fast and efficient buses or L lines. The L’s Blue Line also offers service between O’Hare International Airport and the Loop, the historic and commercial center of the city’s downtown, making it by far the cheapest ground transportation option. For most visitors, the CTA will get you to just about anywhere.
3.) Stay in either the Magnificent Mile or River North areas
Although hundreds of hotels abound across Chicago, for tourists, a good central location is the Magnificent Mile, home to the city’s largest shopping district as well as famous buildings such as the Wrigley Building and the John Hancock Center. You’ll be able to walk to countless things but also be in close proximity to various public transportation stops and stations. The River North (it hosts the largest concentration of art galleries in the United States outside of Manhattan) is a couple of blocks west of the Magnificent Mile area but equally convenient and attractive in terms of its location to restaurants and sites. Although other hotel options exist along the Lake Shore Drive and in the Loop, I feel their slight removal from the tourist’s Chicago make them not as all around pleasing to stay at.
4.) Look when Chicago museums are offering free days
Museums like the Art Institute of Chicago and the Field Museum offer free days/hours each month throughout the year. It’s worth investigating this prior to your trip, as it could potentially mean saving you money. Information will generally be posted on the museums’ websites directly or other Chicago tourism websites.
5.) Try to take in a professional sporting event
Home to five professional sports teams (hockey, football, basketball, and two baseball), Chicagoans take their sports very seriously and have staunch loyalties to those teams. Attending a game is a great way to get immersed in the local culture.