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10 Shocks to Expect When You Vacation in Chicago

Posted on July 16, 2022July 11, 2022 by Mark Wolters

Hey there, fellow travelers! Today, we’re talking about visiting Chicago. Chicago is a vibrant city in the heart of the Midwest and a cultural hub for the surrounding states. As with any travel destination, there are many surprises in store for Chicago visitors. If you’re thinking about planning a vacation in Chicago, don’t be surprised at these “shocks.”

The windy city has some incredible beaches in the summer time.

Chicago Drivers

Driving in Chicago can be nerve-wracking, especially when the car next to you decides to cross four lanes at once! You have to be on high alert if you’re going to drive in Chicago because they drive fast and aggressively. Luckily, if you’re staying in the city, you won’t need to drive too much as it’s really easy to get around Chicago without a car.

What NOT To Do in Chicago

Parking in Chicago

Once you’ve braved the traffic and made it to Chicago, you’re in for another shock, which is the price of parking in Chicago. Parking is hard to find and expensive. Don’t expect to find free parking anywhere in Chicago, and if you do, make sure you read all the signs around you to make sure it’s really free. Some Chicago hotels charge as much as $100 per night to park your car, so make sure you factor this in when choosing your hotel or if you’re deciding whether or not to rent a car! If you do need parking, Spot Hero is a great app to use.

Chicagoans

Chicago natives are an interesting bunch. They are a mixture of big-city attitudes and Midwest nice, and they can be intimidating, but they love to show off their city. They will tell you where to get the best Chicago pizza and how to get to the ballgame, as long as you’re going to the correct side of town. Don’t be shocked if they have different names for places than what you expect. Likewise, Comiskey Park was demolished in 1991, but true Chicagoans will still tell you that the White Sox play at Comiskey.

Want to stay on the good side of Chicago residents? Avoid these Chicago mistakes:

  • Sears Tower will always be Sears Tower, even though it was renamed Willis Tower in 2009.
  • The ‘85 Bears are the greatest football team of all time; don’t even try to insinuate otherwise
  • Don’t say you’re from Chicago unless you’re FROM CHICAGO. You will be quizzed and questioned if you say you’re from Chicago, so be prepared to back up that answer with a specific neighborhood, high school, and baseball team.
  • Don’t dawdle. Chicagoans are always in a hurry so whether you are walking or driving, speed up or get out of the way!
  • If you’re parking on the street in a snowstorm, you better dig out your own car. Chicago has this thing called “dibs” which rules that you own the spot you shoveled out. It’s an unwritten rule, but if you take someone’s spot, be prepared to pay the price.

Wrigley Field

After Boston’s Fenway Park, Chicago’s Wrigley Field is the 2nd oldest baseball stadium in the country. It’s a historic institution and well worth a visit. If you can get seats in the bleachers, you’ll have a great time in the sun. If you can’t get game tickets, the neighborhood surrounding the ballpark is full of fun bars and restaurants. There are 81 home games each season, and many of them are during the day, so it’s a fun thing to do when you visit Chicago. Of course, the prices inside the stadium are shocking.

It may be spelled “Willis” but it is always pronounced “Sears”

Chicago Pizza

If there’s one thing Chicago visitors should eat in Chicago, it’s Chicago-style pizza. There’s a pretty strong rivalry between New York-style and Chicago-style, but Chicago is all about the deep dish. Every Chicagoan has their favorite, and then there are places that cater to tourists. If you want to try Chicago pizza, here are a few suggestions:

  • Lou Malnati’s
  • Gino’s East
  • Giordano’s
  • Pizzeria Uno
  • Pequod’s

Just keep in mind how filling deep dish pizza is; you won’t be able to polish off more than a few slices! And beware, these pizzas take longer to cook, so plan ahead when going out to eat!

What to Eat in Chicago

And yes, you can put ketchup on your hot dog! It won’t be “Chicago-style” but you won’t catch too much grief over it!

The Taste of Malort

If a Chicagoan offers to buy you a shot, don’t do it! Malort is a local legend in Chicago and it is terrible! Shockingly terrible! Made from wormwood, Malort is a distant relative of absinthe, and we think Chicagoans just pretend to like it so they can serve it to unsuspecting tourists.

Food Diversity

Chicago is a big city, but it’s made up of individual neighborhoods, each with its own culture and cuisine. It’s more than just pizza and hot dogs! A few Chicago neighborhoods where you can have amazing food include:

  • Greektown
  • Chinatown
  • Pilsen for Mexican food
  • Italian Village
  • Little India

Chicago is often called the largest Polish city outside of Poland, as there are nearly two million Polish people in Chicago, so you can definitely find some amazing Polish food in Chicago!

Chicago Museums

Chicago is an amazing cultural destination. They have world-class museums and theater productions, and pretty much any kind of culture you could want. A Chicago family vacation is easy with so many educational attractions. Some of Chicago’s best attractions include:

  • The Shedd Aquarium
  • The Field Museum
  • The Museum of Science & Industry
  • The Art Institute of Chicago
  • Museum of Contemporary Art Chicago

Chicago Weather

Although Chicago is known as the Windy City because of the long-winded politicians back in the day, it actually is a pretty windy town. If you’re in the Loop where most of the tall buildings are, the skyscrapers funnel the wind down the streets and it can blow you over! In fact, Chicago winters will have two temperatures: the actual temperature and the wind chill temperature. Winter in Chicago can be horribly cold, but it’s also a beautiful city when decorated for the holidays.

Of course, Chicago summers are a huge celebration of the warm weather. Everyone goes outside to enjoy the warmth, and you’ll find tons of beer gardens and neighborhood festivals where you can take advantage of the summer weather in Chicago.

Grab Some Wolters World Travel Gear!

Don’t let these “shocks” keep you from planning a vacation in Chicago. It’s really a fun city with lots of museums, great food, and pretty good sports teams. If you’re ready to start planning your vacation in Chicago, Choose Chicago has everything you need to plan your trip!

Want more of our Midwest travel tips? Check out some of our other blog posts:

  • Five Things You Will Love & Hate About Chicago
  • Five Things You Will Love & Hate About Midwest Travel
  • The Best Stops on Route 66
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