Chicago has long been a bucket list favorite with stories of jazz, booze and gossip to go around. The Windy City, as it is fondly known, remains a top destination for everyone on the music scene with jazz bars and blue melodies pouring into the night air. This is a city that thrives on entertainment and opens its door to anyone with soul.

So, if you are planning a summer vacation, Chicago should be added to the list! Here are a few things you should add to your holiday bucket list.

Following the Blues Brothers

The Blues Brothers of Chicago, Illinois might have started as a band performing on Saturday Night Live, but they are best remembered for the chaos they caused on the big screen. Ploughing their way around Chicago in a knock-off police car, the brothers did their best to show off some of Chicago’s main attractions including Wrigley Field and The Daley Centre.

To follow in their footsteps, you can easily hire a car or a motorbike and drive around the city yourself. However, do be careful as Illinois and Chicago in particular have a high rate of motoring accidents, often made much worse by motorcyclists not wearing a helmet (learn about it here). So no drawbridge jumps for you!

Finding the Music Scene

Chicago is all about the music and there are plenty of summer festivals as well as restaurants and bars with live music to keep you going throughout the rest of the year. Lollapalooza is held in Grant Park every year, celebrating all kinds of rock music as well as comedy. There are also lots of street festivals that take over throughout the summer. In fact, throughout the summer months, all you need to do is pack your bag and head towards a park or beach and you are guaranteed to find something going on!

If you are looking for Blues, Buddy Guy’s Legends plays host to local talent as well as well-known names and has hosted David Bowie, Eric Clapton and everyone in between in the past. But it’s not just jazz and blues here, there is also a big hip hop scene and the Beauty Bar is the place to be for Timbuck2uesdays when artists from around the world are celebrated with local talent.

What Else is There?

There is so much to do in Chicago that you will most likely have to make multiple trips to pack everything in. However, it is possible to do a whistle-stop tour that takes in a fair bit. Try the Chicago Riverwalk to take in as much of the fabulous architecture here as possible from the water’s edge. Here, you can enjoy lazing around in restaurants before ambling along again or hit the water via a water taxi or boat cruise to take you to the next stop.

But of course, this is not the end you could also visit any of the museums in town like the Field Museum or Museum of Contemporary Art or pop into the Lincoln Park Zoo to say hi to the polar bears (for free!).


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