Off to the “Windy City“: Tips for a successful city trip to Chicago

A city for all senses: from skyscrapers and modern architecture to jazz and deep-dish pizza. As “second city” in the USA, Chicago is often underestimated, but can undoubtedly compete with the classic megacities such as New York and Los Angeles.


Our colleague Jutta raves about the city like others do about New York and London. She has been flying across the pond to Chicago for 25 years now. “Of course, a lot has changed over time, but the fascination with the city stayed the same.” Now she reveals her insider tips for her favorite city Chicago.

The Most Beautiful Sights in Chicago

With its suburbs, Chicago lies on the southwestern shore of Lake Michigan , one of the five major lakes in North America . Comparable to a sea, Lake Michigan spreads out before the stunning silhouette of the third-largest city in the USA.

Chicago is considered to be the birthplace of skyscrapers , as the very first high-rise was built here in 1884.  And these shape the cityscape up until today. Chicago has ever since been a trendsetter when it comes to skyscrapers and has essentially been more innovative than New York City for example. A tour through the city center is thus also a journey through history.

Architecture fans will have their best time in Chicago. A variety of architects with different styles have lived it up here, which makes Chicago one of the most beautiful cities in North America. In order to experience these unique buildings and sights, a ride with the Architectural River Cruise is highly recommended. Simply lean back and let experienced guides teach you all about the city’s wonderful panorama from the Chicago River while passing by the buildings.

Reise Tipps Chicago

The Millennium Park is a great meeting point for locals and tourists alike. During the summer months, there are free Yoga and Pilates sessions in the mornings. The open-air-stage is venue for movie nights during “Movies in the Park” and the host of rock, pop and classical concerts as well as festivals. Here you can find the complete event calendar of the Millennium Parks .

The central work of art in Chicago is the Cloud Gate , a sculpture by the British artist Anish Kapoor. It looks like an oversized bean made of mercury and is therefore also known as “The Bean.” The mirroring surface reflects the skyline of Chicago in a distorted yet intriguing image, making the sculpture to one of the most popular photo subjects in the city.

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Chicago’s Museums

Chicago presents a wide variety of museums, offering something for every taste. The Art Institute , the Field Museum and the Adler-Planetarium , are located in the immediate vicinity of each other and are definitely worth a visit. Since the summer of 2017, book lovers are also getting their money’s worth at the American Writers Museum , which is dedicated to American authors.

Chicago from Above

Taking a view from the top is a must in Chicago. The classics are Willis Tower (formerly Sears Tower) and the John Hancock Tower . In the 103 rd floor of the Willis Tower is a visitor’s platform called the Skydeck. On clear days, the view extends 80 kilometers over Lake Michigan. If you are lucky, you can see the four surrounding states Illinois, Indiana, Wisconsin and Michigan from the observation deck. Especially in the summer months, it is recommended to buy the tickets online .

One insider tip at the Hancock Tower: the ladies’ room on the floor of the restaurant. From there you have the best views of Lake Michigan and Downtown Chicago.

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Shopping in Chicago

Good shopping facilities can be found at the Michigan Avenue , better known as the Magnificent Mile. The State Street is also a tip for extensive shopping tours. The Broadway Antique Market invites to browse where you can snatch one or two bargains. The Armitage Avenue at Lincoln Park is home to upscale boutiques and nice restaurants and pubs. The area around the Lincoln Park captivates with an incomparable flair.

The Best Restaurants and Bars in Chicago

There are many good restaurants and bars in Chicago. Many of them are a bit pricy, but are definitely worth a visit:

Chicago Reisen

Thank you, dear Jutta! You definitely made us want to travel to Chicago. Here you can find the right flight connections from Vienna to Chicago:

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(up to 11 years)

(without seat up to 24 months)

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