Where to Have Fun in the Windy City

Chicago is one of the best places to visit any time of year. Whether you travel during the winter, spring, summer or fall, there is always a food and wine festival, arts event, cultural fair or various attractions that are celebrating something new and different. As Chicago is so eclectic, it’s important to hit all of the attractions and find some new local favorites to see as well.

First Stop: Get Some Grub

Even with a packed schedule of sights to see, you have to eat and get some energy. There are a few fantastic places that are renowned for their Chicago style and chef expertise. If you are travelling by yourself or with the whole family, a good place to start is the South Water Kitchen located in the Loop. With food for all kinds of eaters, you’ll recognize the Chicago style of the chef right away. The kitchen serves breakfast, lunch and dinner starting at 6 AM and has a variety of American and fusion fare. It’s also fairly priced for being in the city.

Second Stop: Let’s Walk the Bridge

One thing you can’t miss if you’re visiting Chicago is the bascule bridge known as the Michigan Avenue Bridge. This bridge takes you across the Chicago River in downtown. It’s one of the designated landmarks for the Windy City, and it’s full of fun sights to see like famous sculptures and markers. It’s also just a jump away from Bucktown and Wicker Park, where you’ll find some boutiques and designer stores perfect for an afternoon of shopping.

Third Stop: Appreciate the Arts

Chicago has a variety of different museums. Millennium Park is a great place to start for photo opportunities and exploration. It has tons of unique architecture, landscape design and local art to appreciate. You’ll also find Museum Campus here and plenty of other art to behold. If that doesn’t satisfy you, there’s always the City Gallery at the Historic Water Tower, which has work from local photographers and artists spanning all types of genres.

Fourth Stop: After a Long Day in the Windy City

There are a few historic and modern four and five star hotels to choose from in Chicago. When you are looking for the ultimate luxury and views of the skyline, you should check out The Peninsula. It’s the best place to go for history and relaxation. It also has one of the best spas to help you wind down and some gourmet cuisine that you can eat in The Terrace overlooking the city.

Chicago has more personality to offer than you could ever imagine. Just by walking the city streets and exploring for yourself, you’ll find incredible boutiques, historical homes, art on every corner and plenty of places to find gourmet and five-star cuisine restaurants as well as local bars and clubs to satisfy your night life needs.

Kendra Thornton

Published by

Michelle Glynn

Traded globe-trotting for motherhood. Side hustling as a freelance writer since 2001.

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