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City Culture Shock Series: Moving to Chicago

July 2, 2020

Welcome to Chicago

Is your upcoming long-distance move landing you in the heart of Chicago, Illinois? If you are considering moving to Chicago, we’ve put together all the info you need to absorb the culture shock of this incredibly historic and exciting city.

Yes, It Will Be Cold

Ah, Chicago. The Second City. The Windy City. Home. Home of various sports teams, museums, the Magnificent Mile, the Skydeck, and the Chicago Theatre. Also, Al Capone and Prohibition-era gangster activity. And most notably, the cold weather.

No way of getting around this: it’s cold in Chicago during the winter. Between the lake-effect snow and low-pressure systems coming in from Canada, winter here can be cold and biting. Never mind the snow; the wind can be downright freezing.

Best way to handle this? Don’t go outside. Second-best way to handle this? Get a good winter coat and a sturdy pair of boots and you’re good to go. Third best way to handle this? Travel during the winter months.

And we don’t necessarily mean “travel out of the state.” If the best defense against the cold is to keep moving, the area has plenty of eye candy for everyone to experience, from tourist hotspots like The Bean to multicultural neighborhoods where Chinese blends into Polish before turning a street and meeting Italian.

Da Food

Oh, the food. Polish sausages, Chicago style hot dogs (all-beef dogs on a poppy seed bun and called Red Hots), and the Chicago-style pizza.

The question of Chicago-style versus New York-style pizza has been debated for decades, and while both sides have claimed victory as the preferred pizza style, it ultimately comes down to the consumer’s preference. Chicago-style pizza resembles a lasagna with a crust around it, encouraging the eater to use a knife and fork as one would a steak pie. This style of pizza arguably encourages a more relaxed dining experience; because the pizza is so thick, eating a slice on the run can be a logistical challenge compared to the “fold it and go” approach offered by New York-style pizzas.

It could also be argued the Chicago pizza is purposefully made thicker so as to provide some personal insulation against the winter winds. If you believe that, let us tell you about the argument that eating more pizza can turn you into a supermodel.

Also, regarding the hot dogs, you may be shocked to discover that locals like to put lots of different toppings on their hot dogs, but not ketchup. This may seem odd, as ketchup enjoys the de facto role of being the preferred condiment of choice in other parts of the country. Our advice? Just roll with it and try. Who knows? An all-beef dog might just taste better covered in onions, relish, peppers, mustard, cheese curds, birdseed, tofu, malt balls, and weed killer.

Was that a joke? Probably. Just don’t be surprised if some of that stuff gets offered at a hot dog stand. Asking for ketchup at a restaurant will earn you a dirty look, as opposed to asking for a soda, which will earn you a knowing grin and the follow-up of, “Oh, you mean a pop.”

This has been stated before on this blog and will probably be stated again, but soda does not go “pop” when it gets opened. It goes “whoosh.” We realize calling a soda “whoosh” is a ridiculous impossibility, but the pop/soda thing will always be a cultural hang-up.

Car? What Car?

Chicago is big. The city alone takes up about 237 square miles, which would suggest that personal transportation would be a necessity for living here.

That would be like saying that living in Florida requires owning a boat. This is not so; it requires that you only KNOW a person that owns a boat.

But never mind the boats. The public transit options in Chicago, including buses and elevated trains, make it fairly simple to get from Point A to Point B without relying on a car. True, owning a car comes in handy when you’ve got to move furniture or haul an appliance back home, but like the boat example, all you need is one friend with a truck and you’re on East Street.

Here is the scoop on Public Transportation in Chicago.

  • Stroll through the Pedway. This system of underground tunnels and overhead bridges links 40 blocks of the Central Business District. You’ll find this especially convenient in the winter and was designed as a quick and safe way to get around on foot in Chicago.
  • Hop on the L. This convenient system of elevated trains and buses are utilized by Chicagoans with the simple tap of a Ventra card. Trains cost $2.50 while buses are $2.25.
  • You can still hail a cab like the movies. Taxi’s in Chicago are still very much a thing. But if the weather is miserable, you don’t have to wait outside to find one. Download the Hailo app and chill in your cozy spot until they arrive.
  • Share a ride. The increasing popular ride-sharing apps continue to get Chicagoans around the city and can be helpful especially if you need to go to visit someone in the suburbs, or where public transportation doesn’t connect.

There’s always the biking option, too. The city alone offers 200-plus miles of protected bicycle lanes, and since Chicago lacks the traffic congestion of New York, getting around on a bike can also be an effective means of getting from place to place.

Quick note: if you’re going to bike around the area, go buy your own. Borrowing a friend’s bike all the time isn’t really borrowing. And it’s inconsiderate. Shame shame.

It’s Cubs or Sox

Every sports-loving region of the United States sports some kind of local rivalry, be it Florida/Florida State or Michigan/Michigan State. In Chicago, that rivalry would be between the Chicago Cubs and the Chicago White Sox.

The history behind this rivalry dates back for generations. It’s been theorized the rivalry has lasted so long was due to the fact that, for most of their respective histories, neither team provided their fans with much to get excited over. The White Sox went 88 years between World Series titles, slightly better than the 108 years for the Cubs. Taken from an outsider’s perspective, that seems like two skunks arguing over who smells worse.

Like most good rivalries, these fans tend to take their respective differences with each other much more seriously than the players do, which tends to be most of the fun anyway. Should you decide to take sides, be prepared to verbally defend yourself from opposing fans.

And speaking of sports, it wouldn’t be Chicago if we didn’t discuss…

Da Bears

Yes, the Chicago Bears, the storied sports franchise that gave the world such legendary players as Walter Payton, William “Refrigerator” Perry, Gale Sayers, and Red Grange. If moving to Chicago means having to pick between the Cubs and the Sox, it will also offer the new arrival an opportunity to join the Church of Da Bears, where Mike Ditka is a patron saint.

Fun fact about football season in Chicago: Because the season takes place in the fall and winter, sooner or later the factor of cold weather will be discussed as an advantage to the home team. Da Bears are not the only team to play in cold temperatures (see Bay, Green, and England, New), but fans will nevertheless get excited about the prospect of playing a home game in freezing conditions. These are probably the same fans that plan to attend that game with no shirt on. Let them have their fun.

Things to Experience in Chicago

Willis Tower: the second tallest building in the Western Hemisphere AKA the Sears Tower. On a clear day, you can locate four states from the Skydeck: Indiana, Illinois, Wisconsin, and Michigan.

The Taste of Chicago: The city of Chicago’s largest outdoor food festival, lasts for five days and includes music performances by local artists and celebrities. Look for it each July and enjoy the sweet taste and sound of summer.

Navy Pier: located in the neighborhood of the Near North Side community. this stunning area includes over 50 acres of parks, restaurants, family attractions, gardens, shops, and exhibition facilities. No wonder it drawing nearly two million visitors annually.


Moving in Winter: How to Prepare