5 Questions You Need to Ask Yourself Before Moving to Chicago

Zara Hanawalt
May 21, 2018
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Deciding to move to a new city can feel daunting – and the truth is, it is a life-altering choice. There’s a lot to consider before you uproot your whole life, and even if a city seems perfect, you really need to weigh your options before committing to a move. Believe it or not, this holds true even if you’re looking to move to a city as beloved as Chicago.

There are a lot of attractive reasons to move to Chicago: the amazing restaurant scene, the passionate sports culture, the stunning lakefront, the renowned comedy scene…the list could go on and on for a while. But while Chicago is certainly an amazing city, it isn’t necessarily the right city for every single person.

If you’re contemplating a move to the Windy City, it’s important to really think about what it means to live in Chicago. Here are five questions you should ask yourself before making the move.

1. How important is good weather?

As we mentioned above, Chicago has a lot of great things going for it…but weather is not one of those things. If you’re someone who loves being outside as often as possible, thrives in warm weather, is prone to seasonal depression, or has never really been exposed to the cold….well, Chicago may not the place for you.

The truth is, Chicago winters can be both long and brutal. While the summers are glorious, they’re fleeting – and both fall and spring can feel downright winter-y as well. For Chicago locals, this is just something we’ve just learned to live with – but for prospective transplants, it’s worth considering. If weather isn’t that important to you, proceed. If you can’t imagine swapping your shorts for a winter coat more often than not…well, might we suggest a long summer vacation in the Windy City in lieu of a permanent move?

2. Do I like the idea of living in the Midwest?

Though Chicago is a huge, cosmopolitan city, it does retain many cultural elements of the Midwest – and while most Chicagoans love that all-American feel, it can be an adjustment for people who are used to living in other regions of the country or world. If you relocate to Chicago, be prepared to hear a few phrases that may sound unfamiliar and pick up subtle cultural elements that feel distinctly Midwestern.

The good news? That Midwestern feel may mean better work-life balance and greater family values than you might find in other large cities. The bad news? Chicago is notoriously segregated, and you may find the homogeneity of many local neighborhoods jarring… especially if you’re expecting the diverse feel of many large coastal cities.

3. Am I comfortable spending a lot of money?

Chicago living doesn’t come cheap. Between high taxes and pricey rent, things can get expensive quickly – and that’s before you factor in the costs of enjoying the city. Of course, if you’re moving from New York or San Francisco, you won’t be as prone to sticker shock upon hearing how much living in Chicago can cost. If you’re from a less expensive area, though? Well, you’ll have to get comfortable spending more money. It’s also worth noting that proximity to all the amazing restaurants, shows and shopping can make sticking to a budget that much harder.

4. What kind of neighborhood would I prefer?

Chicago is very much a city of neighborhoods, and this offers its residents great variety. If you prefer a more urban atmosphere with high-rise buildings and busy streets, a downtown area like Streeterville or River North may be more your speed. On the other hand, there are several other neighborhoods that provide a more residential feel.

The neighborhoods all have something great to offer: Some are family-friendly, some have tons of amazing shopping, some are diverse, some are foodie paradises, some just give you great bang for your buck. It’s all about what kind of ‘hood works best for your lifestyle. The best advice we can give you? Make a trip before committing to a place. Make sure you get a feel for as many neighborhoods as possible, as they are all quite different.

5. Do I really need a car?

Unless you have a family, plan to take frequent road trips, or work in the suburbs, the answer is probably no. Chicago has an easy-to-navigate public transportation system that can get you pretty much anywhere you need to go. The city also has a constant stream of taxis, and Uber or Lyft rides are incredibly easy to secure.

Of course, the walkability is also a huge reason to leave your ride behind – the city is very easy to navigate on foot. Doing so really helps you familiarize yourself with your surroundings, appreciate the beauty of Chicago’s neighborhoods and architecture, and even work off some of the pizza you’ll inevitably be eating should you make the move.

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