How to Visit Chicago the Right Way

Chicago attracts millions of visitors every year with some of our largest events, attractions, shows, and sightseeing activities. There’s almost an endless amount of things to do, so how do you figure it all out? What’s the key to a good time in Chicago? Here are all the things you’ll need to consider to visit Chicago the right way. 

Millennium Park is a Must


And all of Grant Park isn’t very far behind. This is a fairly touristy area, but unlike Navy Pier, native Chicagoans often go here to hang out and pass the time. There are always events going on at the park, and it’s large enough that you can find a place to escape from the hustle and bustle of the big city if you so choose. Of course you’ll want to see Cloud Gate or, “the Bean,” as we call it. Buckingham Fountain isn’t too far to the south either. The fountain produces a major water display for 20 minutes every hour on the hour, and they add a light show element at night. 

This next one is fairly obvious but…


Come Here in the Summer

Don’t get me wrong, there’s still plenty to do in the winter: checking out Macy’s decorated windows, ice skating at Millennium Park, Zoolights at Lincoln Park Zoo, the Christkindlmarket & the huge Christmas tree in Daley Plaza. But it’s cold. And I’m not talking chilly, I mean bitter, glacial, subzero, I wish I was covered in fur cold. As Chicagoans, we’ve come to embrace it, but if you’re used to a milder climate, you’re going to want to avoid it. Besides, there’s a lot more going on here in the summer anyway.


Find the Hotel that Best Suits You

Is it location? Do you need a pool? Best Rates? Biggest Rooms? With Chicago’s hundreds of choices, there’s bound to be a hotel that fits your needs. Don’t just accept the first one that comes along. There are some phenomenal, iconic hotels in the city that have recently undergone renovations. Some newer hotels pamper you in a more contemporary setting. Other smaller boutique hotels offer a more intimate experience. Here are some guides by area to help make the decision a bit easier: the Loop, River North, and Magnificent Mile.


Speaking of the Magnificent Mile…

Do You Like Shopping?


Not everyone vacations to go shopping, so if you’re not interested go ahead and skip this part. Chicago has some phenomenal retail options, but be prepared to spend some dough if you’re buying things in the city. The highlights include the Shops at North Bridge, Water Tower Place, and the one-million plus square foot Merchandise Mart. Of course, these are all easily dwarfed by the Mag Mile though.

Visit the Skydeck


The Willis Tower’s Skydeck is the highest point in the city, and it’s obviously a huge draw since it’s the biggest skyscraper in the U.S. You can see four surrounding states from this bad boy, and if nothing else, you might be able to spot something you’d like to check out. The views here are truly breathtaking though, so trust me when I saw you won’t be disappointed. To make the most of the experience, show up about an hour before sundown. This way you can see the daytime view of the city, the sunset, and the gleaming nightscape afterwards. Here’s a guide with all the info you’ll need.

Go to at Least One Museum


Chicago’s museums are second to none. While they’re all worth a visit, you should make time to hit at least one that piques your interest. An easy pick might be the Art Institute, which was recently rated the top museum in the entire world by TripAdvisor. Let that one sink in for a moment…

Moving on, the Shedd Aquarium is always a great choice, and the Adler Planetarium is often overlooked, yet underrated. The Field Museum is another big hit, and you can see “Sue,” the most complete T-Rex skeleton ever pieced together. If you’re looking for a cheaper option, Lincoln Park Zoo is free 365 days out of the year.


Let us know if you have any other suggestions by commenting or emailing us at