My Tips for Planning a Trip to Chicago

There is a massive downside of having family members that live abroad, and that is that you don’t get to see them in person very often. However, with a sister in the states, married to my brother-in-law who is in the military, it means that they move around quite frequently, and I can get to go and explore their new locations and discover lots of new places.

One of the cities that they have lived in, well, just north of, was Chicago. They lived less than an hour’s drive away, so it was a fun place to visit the surrounding area as well as the city itself. It is often nicknamed as the US’ second city after New York, and it is easy to see why! It is one of America’s great cities. It isn’t always a natural choice for someone coming from abroad, but with an incredible skyline, famous local foods, and friendly residents, there are a number of reasons to make a visit over there (not to mention that the Chicago O’Hare airport is a great hub to then travel on to other destinations).

But what are the best things to do and my tips for a visit? Here are some things to make a trip to the Windy City the best that it can be.

one world trade center under cloudy sky during daytime
Photo by Pixabay on

Remember Where Lake Michigan Is

Fun fact for you, a lot of the downtown Chicago area was rebuilt after a huge fire back in the 1800s. The city planners at the time rebuilt and made the city easier to navigate. If you can remember where Lake Michigan is, and if it is to the east of you, it will help you to be able to know where you are and then find your route. That or Google Maps! 😉

Check the Forecast

Although the term ‘Windy City’ is more to do with politics than the weather, you should still check the forecast when planning your trip. For starters, the Chicago area has a six-month winter pretty much, and a short but hot summer season. Some sunny days in winter can be deceiving, as they can actually be ice cold and very bitter (speaking from someone who visited in November once and then March). The weather is very changeable throughout the day too. Not only that, but being quite an exposed city, right on the edge of Lake Michigan (more like an ocean it’s so huge), the winds can be bitterly cold if you go and it is a little breezy.

Chicago Style

If you’re visiting, then some Chicago street food is a must, which will tend to be a hot dog. But going Chicago style means a beef sausage with yellow mustard, chopped onions, sweet pickle relish, a pickle spear, tomato slices, pickled peppers, and a dash of celery salt. You simply can’t ask for ketchup! A lot of places don’t even have ketchup even if you’re offered it, so go Chicago style unless you want to look like an obvious tourist.

person walking on the road
Photo by Ricardo Esquivel on

Top Tourist Attractions

There are a number of Chicago tourist attractions that you need to add to your list when you’re planning a trip. It can vary for whoever is travelling, but some of the top choices are:

  • Millennium Park – this is a green space in the city, with art and sculptures (home to ‘The Bean’ sculpture), as well as ice rinks in winter, and a theatre. It is a popular spot for weddings too! I saw several brides and grooms there having their photos taken.
  • Navy Pier – although it isn’t out to sea, the Navy Pier extends out to Lake Michigan, and has rides, stalls, food, and shops. A proper tourist thing to do, but it’s a lot of fun.
  • Willis Tower – if you’ve seen those videos on Facebook of being at the top of a tower and leaning out on the window to look down, then likely that it was the Willis Tower! For older kids and teens, this would be a fun spot to visit and take in all of the sights.
  • The Art Institute of Chicago – this is a world famous art museum, which explains it all really!
  • Field Museum of Natural History – this showcases the biological and anthropological collections gathered from around the world. The permanent collection features 20 million artifacts and specimens, with displays on Ancient Egypt and North, Central and South America cultures.
  • Wrigley Field – home to the Chicago Cubs, it was built in 1914 and is the second-oldest baseball park in the US. Ballpark tours are conducted in-season, when you can visit the press box and field, as well as dugouts (as long as there is no game that day).

Have fun planning your trip – there are some fun things to see and do, as well as the good food and shopping! Do as the locals do and take public transport to get around, as traffic can be heavy.

*this is a collaborative post.

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