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Shy, Strange, Manic

A Travel, London and Theatre blog, always on the hunt for the next adventure!

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Three things to see and do in Chicago

November 15, 2023

There are lots of reasons why Chicago often lands on the radar of international tourists. The beautiful skyline, the sporting heritage and the deep-dish pizzas are never far from a visitor’s itinerary. If you’re looking to explore this beautiful city for yourself, here are three of the best ways to spend your time. 

Get in the party mood 

festival crowd

The city of Chicago is a cultural hub for music, and this love is brought into focus throughout the calendar year with various festivals and events that celebrate the very best of what the city has to offer. If you time it right, you can tie in your trip to the Windy City with one of the famous festivals hosted here that are sure to live long in your memory. Generally speaking, summer is the perfect time to visit the city if you’re looking to experience a local music event.

Lollapalooza is one of the city’s most famous festivals, and celebrates music from a range of genres including hip hop, heavy metal and electronic dance; the star-studded lineups attract over 100,000 movers and shakers every year. Or, for a true taste of Chicago, head to the Windy City Smokeout – a festival that serves up barbecue from local pitmasters, beer from brewing aficionados and great music in equal measure.

See the city from above

chicago skyline

There is plenty to love about Chicago at ground level, but admiring its beauty from above allows you to see it in an entirely different light. And what better way to get a bird’s eye view of the metropolitan hustle and bustle than by scaling the city’s tallest building? Head to the 103rd floor of the Willis Tower where you’ll be treated to panoramic views of the city; on a clear day, you’ll be able to see for 50 miles and spot four different surrounding states. If you’re feeling brave, step out onto the glass floor balcony for a stomach-turning yet unforgettable vista. 

You can also find 360º views from 94 stories up in the air at the John Hancock Centre. The aptly named 360 CHICAGO showcases views of Lake Michigan and the world-famous Chicago skyline. You can even get a downward view of the city on the TILT ride.

Head to a ball game

chicago cubs sign

Back on more comfortable footing, any trip to Chicago wouldn’t be complete without taking in a local sporting event. Football, baseball, basketball and plenty more sports besides are all big business in this part of the world, and savouring a game is a great way to immerse yourself in the local culture. In fact, Chicago is one of just a handful of US cities that has a team competing in each of the five major professional sports leagues in the country.

Even if you can’t get tickets to a game, visiting one of the city’s sporting venues is a must. Wrigley Field, home to the Chicago Cubs, is one of the oldest MLB stadiums still in use, playing host to over 100 years’ worth of sporting history. Just a 15-minute drive along the banks of Lake Michigan will see you arrive at Soldier Field. With a capacity of over 61,000, Soldier Field is Chicago’s biggest sporting venue; both the Chicago Bears (NFL) and Chicago Fire (MLS) call this place home. And that’s not the only place where size matters. The United Center, home to the NBA’s Chicago Bulls, is the biggest arena in America’s premier basketball league with over 20,000 seats. 

Where will you start?

With endless possibilities and so many places to explore, make sure you carefully plan your trip to get the most out of your time in Chicago. Add these three things to your to-do list and you’re bound to enjoy a trip you won’t soon forget.

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Kariss
Hey, I'm Kariss, welcome to my corner or the internet. Expect to find adventure and amusement with a touch of eccentricity as I cover all things Travel, London and Theatre related! Find out more here or why not drop me an email at shystrangemanic@gmail.com

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