Making the most of a trip to Chicago: top things to see and do in the Windy City

Finally planning a visit to Chicago? As the third largest city in America, the Windy City has much to offer visitors. From world-class museums to restaurants that serve up rich and flavorful cuisine, there’s more than enough to keep you busy for an entire week or longer. I teamed up with to bring you my tips for making the most of your Chicago trip. Check out Expedia’s list of great vacation rentals to keep you well rested for your packed week in the Windy City!

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Let’s get into the highlights so you can properly plan your inaugural trip to this essential American metropolis.

Tour its world-class museums

Many laud Chicago’s skyline, but in truth, its collection of museums is the best thing about this dynamic city. Start your museum crawl at the Art Institute of Chicago, where you’ll find over 300,000 pieces sourced from all over the world.

Hosting 1.5 million visitors every year, it is one of America’s most prestigious art museums. With galleries covering everything from American artists like Edward Hopper and Mary Cassatt, European masters like Claude Monet, and Asian pieces dating back to early days of Chinese civilization, culture hounds could spend all day here. Other spots worth visiting include the Field Museum of Natural History, the Chicago Cultural Center, and the Richard H. Driehaus Museum, but this is just a short list. If you are heavily into these attractions, you could spend an entire week going from one museum to the next.

Go on a culinary tour

When it comes to cuisine, North America as a whole lags behind the older parts of the world. However, a dynamic food culture has emerged in several centers, with Chicago leading the way. From Chicago deep dish pizza to Italian beef sandwiches, the fare may be casual compared to the elegance of European dishes, but it is certainly unique and worth experiencing.

Rather than attempting to hunt down the best of Chicago on your own, we suggest signing up for a food tour soon after arriving in Chicago. Led by passionate foodies, these culinary enthusiasts have dedicated their lives to finding the restaurants which best represent Chicago’s most famous dishes.

Get a selfie with the Cloud Gate

Also known as ‘The Bean’, Cloud Gate is a chrome-plated art installation that can be found in Millennium Park. Made from stainless steel plates that were shaped like a bean and welded together, it is remarkable not just for its reflectivity, but the lack of any visible seams on its exterior.

Immensely popular among locals and tourists alike, it is besieged with photo takers during the summer months and on weekends – take both these facts into account when planning your visit to this astounding work of art.

Take in the view from Willis Tower

Previously known as the Sears Tower, the Willis Tower towers over the rest of downtown Chicago, as it stands at a height of 1,450 feet above the asphalt and concrete below. At one time, it was the tallest building in the world (from 1973 to 1998) and was the tallest in America until the New World Trade Center in NYC passed it in 2014.

Despite relinquishing its title, it is still a popular viewpoint for those looking to get a view over Lake Michigan and the rest of Chicago. Walk on the glass floor (if you dare) – it won’t let go…

Shop until you drop on the Magnificent Mile

Have a taste for luxury goods? If so, you’ve come to the right city – the Magnificent Mile is a street lined with some of the best-known brands in the world. Referring to North Michigan Avenue, you’ll have an opportunity to shop at places like Coach, Chanel, UNIQLO, and many more leading retailers.

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