A Guide to Moving to Chicago

A Guide to Moving to Chicago


by Kara Masteller, intern writer for (the former) Executive Auto Shippers

The third-largest city in the United States is housed just around the middle of the country. Surrounded by the kindness of Midwesterners, but deeply rooted in an urban lifestyle, Chicago will give you the city vibe you crave and you’ll meet some wonderful people who crave the same. Located in Illinois, there are plenty of career opportunities in a wide variety of markets. The workforce of Chicago is not dominated by one particular industry, but rather a mixed business landscape. The diverse economy echoes the diverse population which has contributed to the rich history of the city. If you’re the adventurous type you will feel right at home, as there is no shortage of places to explore within the city.

Moving to Chicago

Careful! While it may be tempting to commit to the first apartment or living space you look at, make sure you’re considering a few things before signing that lease. Consider whether renting or buying will benefit you the most. Like many cities, Chicago life is heavily influenced by the neighborhood you’re a part of. Renting and buying benefits can vary from place to place, so whichever neighborhood you end up in may influence your decision on what will be best for you (and your family, should that apply).
Also, make sure you’re considering how you plan to get to and from work. The third-largest city in the U.S. doesn’t come without its transportation challenges. If you’re living on one side of the city and working on the other, it’ll feel like half of your time will be spent getting from here to there. While the windy city boasts a robust mass transit system (CTA), consisting of buses, Amtrack, and of course the famous “L” train, these routes do not all connect. Ensuring that you live and work on the same transportation line can save you some sanity in your new commute life. If you have a car, remember that parking will be a nightmare, no matter how many parking passes you purchase. And if the parking is not enough of an expense, most of the major interstates around the city are Toll Roads, although you can trim this expense slightly by utilizing the I-PASS system.
Keeping expenses like these in mind. Chicago is still a great option for those who want to live in a big city without the crazy price tag, but it’s not without cost. There are plenty of online resources to help you learn how to get started in the city while saving as much as you can. Additionally, sites like Forbes and SmartAsset have great tips on how to navigate the city you’re about to call home.

Safety and Education

Moving the whole family to the Windy City? Chicago can have an intimidating reputation, but there are many resources out there making downtown Chicago a safe place to live and learn. There are plenty of family-friendly neighborhoods the locals recommend. There are also many family-friendly suburbs within a short commute to downtown. The Chicago Police Department also put out a great list of safety tips, so you can read about their recommendations for specific events/places. Additionally, the city is very conducive to walking, which can help cut transportation costs.
As for children’s education, the Chicago Public Schools (CPS) district is the primary option. Students will be assigned to a school based on their place of residence, though there are a number of charter schools and schools with a selective enrollment that branch beyond geographic location. If you haven’t settled on a place to live yet, Chicago Magazine has an article about which schools they consider the best, and parents who have already navigated the system also have some helpful insight. However, keep an open mind when looking at schools: what didn’t work for one family may work well for another.


Once you’ve passed all the stressful checkpoints of moving, it’s time to enjoy the new city you call home! If you want to start out as a tourist in your own city, Navy Pier is a great place to start! Located on Lake Michigan, this pier offers much more than just a beautiful view. It’s packed full of attractions: parks, rides, restaurants, shops, and more. It appeals to all ages and all sorts of interests. After you’ve conquered Navy Pier (though it may take a few days to see it all), you may consider visiting Willis Tower (formerly Sears Tower) for a gorgeous view of the city. For a more educational experience, plan a day trip (although it’ll probably take several day trips to experience it all) to the Museum Campus. This area contains many of Chicago’s biggest attractions, all in one convenient area. Another fascinating thing to do (even for the locals) is to go on an architectural boat ride. It may not have the most “fun” sounding name, but don’t count it out just yet. You can learn a lot not only about architecture but the history of the city you live in and how they interact. This boat ride is a great way to spend an afternoon outdoors, and it could really open your eyes to the deep roots that Chicago holds. Once you’ve learned and appreciated the city’s rich history, no worries about a more active source of entertainment: Chicago is home to 6 professional sports teams. So if you’re a football, baseball, basketball, soccer, or hockey fan, you’re in luck. The Chicago Bears represent the city in the NFL, the Chicago Fire and Chicago Red Stars are respectively the city’s men’s and women’s soccer teams, the Chicago White Sox and Chicago Cubs are both in the MLB, and the Chicago Bulls play in the NBA. So if athletics is your thing, you’ll have entertainment nearly every night, year round.

Food & Drink

When you think Chicago food, you probably think Chicago pizza. While thin-crust pizza has its time and place, that place is not Chi-Town. Chicago is known for its hearty, deep-dish pizza. It’s not like a traditional crust, sauce, then toppings kind of pizza. Chicago style starts with a deep-dish crust, is filled to the brim with cheese and whatever other toppings, and then topped with a thick layer of tomato sauce. It’s a staple, and it’s close to being considered a crime if you haven’t tried it. Pizzeria Uno is said to have introduced this style, so it’s definitely worth a stop. Though Pequod’s is a local favorite with a delicious caramelized crust, as mentioned in this article.

The Chicago-style hot dog should also be on your list. Chicago takes their hot dogs seriously. But while it can be loaded with any topping you can think of from sauerkraut to potato chips, a true Chicago-style dog will not have ketchup. Many establishments don’t even have it available.
If you have some time to plan, check out Girl & The Goat. Though reservations are often needed a month in advance, the legendary “Pig Face” (not as gross as it sounds) is a Chicago favorite. Check out Al’s Italian Beef for another city favorite…Italian beef. For a late night bite, find The Tamale Guy. And if you’re craving Asian cuisine, Argyle is your go-to place for Phu, and it’s rumored that the banh mi from Ba Le is the best in the city.
So whether it’s a big family move or a solo adventure into the city, Chicago will make you and all you’re with smile. It’s filled with great food, people, and places to explore. There are gardens and parks for your pets, amusement parks for your kids, and history embedded throughout the city. The midwestern winters will hardly matter when considering the warmth and enjoyment you’ll get from the city (and the people) of Chicago.

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