Hey there, fellow travelers! Today, we visit Chicago! Chicago is one of the best cities in the United States, whether you want culture, architecture, food, or sports. As you know, here at Wolters World, we like to prepare travelers with the good, and the bad, of visiting a new travel destination. So these are the five things you’ll love, and the five things you’ll hate when you visit Chicago.
Hate #1: Chicago Winter Weather
Chicago winters are no joke. Chicago is known as the Windy City and in the winter, the wind whips cold air off of Lake Michigan and it is not pleasant to be out walking around, or whatever you call walking at an angle so as not to get blown over. The wind chill can make winter temperatures dangerous. If you decide to visit Chicago in the winter, make sure you are prepared with a warm coat, lots of layers and waterproof shoes. Also, make sure you don’t walk where it says don’t walk. Sometimes ice falls off of those skyscrapers.
Love #1: Chicago Architecture
Chicago is world-renowned for innovative architecture. For years, the Sears Tower (now Willis Tower) was the tallest building in the world. Chicago is the home of the skyscraper, but it’s also known for historic architecture in buildings like the Tribune Tower and the Wrigley building. One of the best things to do in Chicago is the Architecture Tour on the Chicago River. Each October, the Chicago Architecture Foundation hosts Open House Chicago, with free access to over 250 Chicago buildings.
Hate #2: Chicago Panhandlers
If you take the train to Chicago and arrive at Union Station, or spend any time in tourist areas, you’ll see a lot of panhandlers in Chicago and they can be kind of aggressive. After the first few people, you will start to get tired of it. Just be firm and keep walking.
Love #2: Chicago People
Chicago is the third-largest city in the US, so you might not expect the people to be very friendly. But the people of Chicago are super friendly and super helpful. (Unless you are holding up traffic!) They are always happy to stop and help you with directions or recommendations. Chicago has a small-town feel in a big city. If you’re interested, the Chicago Office of Tourism has a Chicago Greeter service that will match you up with a local for a free tour!
Hate #3: Chicago Parking
I highly recommend not having a car in Chicago, which is the opposite of the advice I give for the rest of the country. Parking in Chicago is outrageous. Chicago hotels charge as much as $100 per night just to park your car! So, before you jump on a cheap hotel rate, make sure you factor in the cost of parking as well. If you must drive to Chicago, park it and leave it, don’t use it to get around the city, as it’s more hassle than it’s worth. Most locals in Chicago use the SpotHero app to find the best rates on Chicago parking.
Love #3: Chicago Food
Chicago food is amazing! There are tons of diverse neighborhoods serving up ethnic foods, from Greektown, Chinatown, Little Italy, Mexican, Polish and Indian restaurants to the popular restaurants downtown. Chicago-style pizza is world-famous, and Portillo’s Italian Beef and hotdogs are another must-eats while in Chicago. If you see a line of people outside a popcorn shop, that’s Garrett’s, where they sell the delicious “Chicago Mix” popcorn tins.
Hate #4: Driving in Chicago
Another reason to not have a car in Chicago is the driving. The streets are congested and there is no rush hour anymore, it’s all day, every day. The Loop downtown Chicago has lots of one-way streets and underground streets, so it’s very confusing if you don’t know where you are going.
Love #4: Clean Streets of Chicago
Chicago is one of the cleanest big cities I’ve seen in the US. The city spends a lot of money to keep everything clean and looking nice. If you walk along Michigan Avenue, you’ll notice the planters lining the street are changed out frequently with the seasons, and it’s so nice to be in a big city that’s so clean. Of course, that could just be because the wind blows everything away, but let’s go with the city is doing a good job of keeping the city looking beautiful.
Hate #5: Price of Chicago Attractions
There are a ton of really great Chicago attractions, but they are expensive! It’s about $20 to access each museum, like the Shedd Aquarium or the Field Museum, so if you bring the whole family, it can really add up quickly. There are free days offered at several Chicago museums, but they can be pretty crowded, so it’s a choice of paying more or dealing with crowds. You can also consider one of the CityPass options that bundle several attractions together at a discount.
Love #5: Getting Around Chicago
Chicago is super easy to get around. As I mentioned already, you don’t need a car when you visit Chicago. The public transportation system, called the “L” is super easy to use and very affordable. Additionally, the streets are on a grid and everything is numbered in a way that makes sense, so it’s pretty easy to find your way around, especially with the lake bordering one whole side of the city. It’s a super walkable city, so make sure you wear comfortable shoes and enjoy strolling the streets of the Second City.
Chicago is one of the best cities in the US, so I recommend including it in your USA vacation itinerary. The “hates” are really just things to have a heads up on rather than a reason not to visit Chicago. Want more tips for planning a US vacation? Check out these other blog posts: