Know the terms
There are a couple of terms you are sure to hear when you arrive in Chicago that you need to know. Firstly, the downtown central business district of Chicago is known as the Loop, with the river bordering the north and west, and Roosevelt Road in the south. Secondly, if you’re advised to take the “L,” that means the train, so named because it’s short for “elevated,” which some parts of this system still are.
Remember where the lake is
Most of downtown Chicago was rebuilt after the Great Fire of 1871, famously started when Mrs. O’Leary’s cow kicked over a lantern. While not ideal for Chicagoans of the time, city planners were able to modernize, and today, Chicago is an easy city to navigate. Remembering that Lake Michigan is to the east will allow you to keep your sense of direction.
Know the grid system
Chicago has a grid system that can make your visit a lot easier. According to the system, the center of the city is the intersection of State and Madison Streets in the heart of the Loop. All addresses on east-west streets are appropriately prefixed “east” or “west” depending on if they fall east or west of State Street, just as streets are labeled “north” or “south” if you’re north or south of Madison Street. The higher the address number, the farther away from this intersection you are.
Check the weather
With a six-month winter and a short but blazing summer to be expected, it’s important to check the forecast whatever the time of year. Don’t trust a look out of the window, as sunny days are some of the coldest during winter, and overcast days can be surprisingly balmy in spring and autumn. The weather is very changeable throughout the day too, with sudden drops in temperature and downpours not uncommon.
Even if the forecast is favorable, be prepared for the wind, especially if you’re downtown. With the breeze coming off the lake, the city’s famed skyscrapers funnel and suck the wind between them, making the streets of the Loop very gusty. Fashion goes out the window during a harsh Chicago winter, so dress practically with lots of layers. Hold onto your hats, though, as they’re prone to fly off.
Take the L
The L train system, as mentioned above, is the best way to travel between Chicago’s sprawling expanse of neighborhoods. There are eight lines, which all converge in the Loop. Despite its name deriving from the elevated parts of the system, many stations are underground, with entrances clearly signposted at street level. At certain stations in the Loop, you may also be treated to an impromptu musical performance while waiting for the train.
Pick up a Ventra
A Ventra card is the most convenient way of paying for the CTA system. It’s $5 for a card, but that amount will be credited to the card if you register it online. You can buy train tickets at stations, and buses still accept cash, but a card is a lot more convenient than queuing at machines and counting your coins. There are also savings to be made with Ventra on journeys that include multiple legs.
Research the neighborhoods
There are many charming and vibrant neighborhoods to visit, but make sure you do your research before you go. Most of the city’s visitor-friendly neighborhoods are on the north and west side of the Loop, with the exception of Hyde Park on the south side, which can be reached via the Metra or one of many express buses.
Prepare for traffic
If you’re planning to drive around the city or even to take a taxi, leaving adequate time to allow for the inevitable traffic is essential. In a 2015 study, Chicago had five of the 20 most congested stretches of road in the U.S. The harshness of the winter causes disruption half of the year, and that damage to the roads means that roadworks are frequent and necessary in the summer months.
Chicago is a great city for cycling if you want to avoid the traffic and the often busy public transport. The 18-mile (29-kilometer) Lakefront Trail is a particular gem for cyclists, stretching all the way from Hyde Park in the south to Edgewater in the north. It offers beautiful views of the lake on one side and the famed skyline on the other. Chicago’s bike share system is called Divvy, and with hundreds of locations around the city, you can rent a bike for 24 hours for under $10.
Hold the ketchup
A Chicago-style hot dog is a beef frankfurter with some or all of the following: yellow mustard, chopped white onions, sweet pickle relish, a dill pickle spear, tomato slices or wedges, pickled sport peppers, and a dash of celery salt. If you order one, the greatest crime you can commit is asking for ketchup. As such, some hot dog places will not even have ketchup if you ask for it. When in Rome.
Don’t waste time with thin crust
Even the city’s most famous deep dish chains, such as Giordano’s, Pizano’s, and Gino’s East, offer thin crust pizza. And while it’s delicious, the deep dish simply has to be ordered, if only so you can finally understand the term “pizza pie.” A word of warning, though, be careful how much you order as a single slice is practically a meal in itself, and the wait for one can be long (but totally worth it) as a pizza that thick takes a while to cook.
Be wary of Malört
If anyone offers you a “Chicago Handshake,” beware. Consisting of an “old-school” Midwestern beer, typically Old Style, and a shot of Jeppson’s Malört, a Swedish-style schnapps, it’s the second part of this one-two punch that you should fear. Malört was brought to Chicago in the 1930s by Swedish immigrant Carl Jeppson and takes its bitter flavor from the herb wormwood, the same as absinthe. A real Illinois experience, Cook County alone consumes 90% of the Malört produced.
Know your teams
Sports are a big part of Chicago life, so naturally, you need to know how to not upset the locals. Fans of the Chicago Cubs, the “North Siders” and the newly crowned World Series champions, wear blue items with a prominent red C. Don’t get them confused with their south-side rivals, the Chicago White Sox, who wear black and white. Away from baseball, Chicago only has one major team in football, basketball and ice hockey, and their most-hated rivals are teams from nearby places including St. Louis, Detroit, Minnesota, and Cleveland.