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The Tailor-Made Guide to 21 Attractions You Should Visit in Chicago, Part 1

Updated: Mar 28


Chicago Attractions You Should Visit

**Disclosure: I collaborated with Choose Chicago and several of the attractions mentioned for my trip to Chicago. Regardless of this, please be advised that all opinions expressed in this blog post are genuine and authentically my own. This post also contains affiliate links.** 

Author: Barry Pickard

Chicago is a city that has something for everyone. It is a city that is rich in history and culture, and it is a great destination for travellers to visit. The city has a long and storied history, dating back to the early 1800s when it was founded as a small trading post on the shores of Lake Michigan. Over the years, Chicago has grown into one of the largest and most vibrant cities in the United States.


Attractions You Should Visit in Chicago
The Chicago Skyline


Chicago is known for its world-class museums, stunning architecture, and beautiful parks. It is also home to some of the best restaurants in the country, serving up everything from deep-dish pizza to hot dogs and Italian beef sandwiches. Whether you are interested in art, history, or just want to experience the energy of a big city, Chicago has something for you. Read on to discover our pick of the attractions that you should have on your itinerary when visiting Chicago.


Chicago Attractions You Should Visit

Don’t forget that Tailor-Made Itineraries delights in creating bespoke self-guided tours. So, if visiting any of these attractions in Chicago appeals to you, reach out to me by email. I would be more than happy to design a self-guided tour around your requirements incorporating the attractions of Chicago.




Chicago Attractions You Should Visit


21. Skydeck Chicago - Willis Tower


The Skydeck Chicago is one of the most popular attractions in Chicago. Located on the 103rd floor of the Willis Tower it offers breath-taking views of the city and Lake Michigan. Formerly known as the Sears Tower, it was once the tallest building in the world.


Attractions You Should Visit in Chicago
Skydeck Chicago - Willis Tower

The Skydeck features a glass ledge that extends out from the building, allowing visitors to stand 1,353 feet above the ground and look straight down at the city below. It is a thrilling experience that is not for the faint of heart. As well as the views, there is also a fun, interactive display showcasing the building’s history and feats of engineering.


Tailor-Made Top Tip: After visiting the Skydeck, take the opportunity to visit the Color Factory Chicago, which is on the basement floor of Willis Tower.




20. Cloud Gate


Perhaps the most iconic sight in Chicago, Cloud Gate, also known as “The Bean,” is a public sculpture by Indian-born British artist Sir Anish Kapoor that is located in Millennium Park. The 110-ton sculpture is made of highly polished stainless-steel plates that reflect Chicago’s famous skyline and the clouds above. It is one of Chicago’s most popular attractions and a must-visit for anyone traveling to the city.


Tailor-Made Top Tip: Get there early to avoid the crowds if you are looking for that perfect selfie-moment.




19. Klairmont Kollections


Klairmont Kollections is a private car collection of museum quality housed in a 100,000 square foot building which is adorned from floor to ceiling with vintage and neon signage and other eclectic collectibles. The prized collection has over 300 award-winning and unique automobiles from 1909 to present day. Klairmont Kollections is a must-see attraction for car enthusiasts and history buffs alike.



The highlights for me were the iconic Batmobiles, the many examples of classic American muscle cars, and the gaudy Swarovski Crystal Rolls Royce (although I’m not sure that I would have the nerve to actually drive it!).


Attractions You Should Visit in Chicago
Klairmont Kollections

Tailor-Made Top Tip: Quite uniquely among Chicago’s attractions, Klairmont Kollections provide free parking, with ample spaces.


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18. Color Factory Chicago


Color Factory Chicago is an interactive art museum located on the lower level of Willis Tower in Chicago. Visitors are invited to experience the joy of color through interactive installations, immersive rooms, and carefully curated moments inspired by the city of Chicago.



A visit to the museum includes surprise giveaways, sweet treats, and plenty of opportunities for all the family to have fun. The giant green ball pit was possibly the highlight for me and is a fun way of recreating the Chicago River on St. Patrick’s Day.



Tailor-Made Top Tip: Look out for the cameras in some of the exhibition spaces, they will help you capture all the fun digitally. Make sure to sign up for your QR code at the start of the experience in order to use the cameras.




17. The Peggy Notebaert Nature Museum


The Peggy Notebaert Nature Museum is a natural history museum and helps visitors experience nature and science up close. The museum offers educational interactive events and programs for families, adults, and groups, as well as many interactive play spaces for all the family to enjoy.


Tailor-Made Top Tip: The highlight of the museum has to be the Butterfly Haven, which lets you get up close to these beautiful creatures.




16. Frank Lloyd Wright Home & Studio


This historic house and studio was designed and owned by architect Frank Lloyd Wright. Located in Oak Park, a suburb of Chicago, the building was the first over which Wright exerted complete artistic control. Designed as a home for his family, the Oak Park residence was a site of experimentation for the young architect during the twenty-year period he lived there.


Attractions You Should Visit in Chicago
Frank Lloyd Wright Home & Studio

Wright revised the design of the building multiple times, continually refining ideas that would shape his work for decades to come. The Home and Studio was the birthplace of Wright’s vision for a new American architecture. Wright designed over 150 projects in his Oak Park Studio, establishing his legacy as a great and visionary architect. Today, you can book on to one of the many daily public tours of this historic house.



Tailor-Made Top Tip: Combine a tour of the house with a self-guided audio tour of several Frank Lloyd Wright designed homes along Forest Avenue, just yards from his house. The audio tour can be booked at the same time you buy your tickets for the house & studio tour.



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15. Adler Planetarium


This museum is one of the oldest and largest planetariums in the world and strives to inspire people of all ages to explore and understand the universe. There are a variety of exhibits and shows that explore the solar system, the stars, and the galaxies. There is also the Skywatch Theater, an impressive 75-foot-diameter screen that projects images of the night sky.


Tailor-Made Top Tip: Make a day of it and combine a trip with to the Adler with a visit to the Field Museum or Shedd Aquarium, with both of these attractions being just minutes’ walk from the planetarium.




14. Chicago Riverwalk


This 1.25-mile-long pedestrian and bicycle path that runs along the Chicago River has been a highly popular attraction with visitors and locals alike since it was created in 2001. The Riverwalk is a great way to admire the stunning views of the city skyline, and there are many amenities along the way, with cafes, bars, ice-cream stands, as well as public conveniences.


Tailor-Made Top Tip: The Riverwalk is especially beautiful in the spring and summer but be sure to bring a hat and sunscreen if visiting at that time.




13 Museum of Science and Industry


The MSI is one of the largest science museums in the world and has something for everyone, from kids to adults. The museum is home to over 400 exhibits, including a coal mine, a U-boat, a full-sized Boeing 727, and a working tornado simulator. There are also a variety of educational programs and activities, such as live demonstrations, planetarium shows, and hands-on workshops.


Tailor-Made Top Tip: Plan to spend at least half a day in this vast and interesting museum.


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12. Chicago Crime Tours


To truly understand and appreciate Chicago’s violent history of gangsters, including the antics of the infamous Al Capone and John Dillinger, book onto one of the highly informative and entertaining Chicago Crime Tours bus tours. Hear the stories of the city’s notorious gangsters and visit the site of St. Valentine’s Day Massacre and the alley where Dillinger was gunned down by the FBI, as well as other landmarks of note.


Tailor-Made Top Tip: There are tours available during the day and also at night.




11. Frank Lloyd Wright's Robie House


The Robie House is a Prairie School house designed by Frank Lloyd Wright and built in 1909. It is one of Wright's most famous works and is considered a masterpiece of American architecture. The Robie House is a large, L-shaped house with a strong horizontal emphasis. The interior of the Robie House is just as impressive as the exterior. The house is filled with natural light and has large, open spaces. The furniture and fixtures were designed by Wright to complement the architecture.


 - Attractions You Should Visit in Chicago
Frank Lloyd Wright's Robie House

The Robie House is a National Historic Landmark and is open to the public for tours. It is a must-see for anyone interested in Frank Lloyd Wright or American architecture.


Tailor-Made Top Tip: The Robie House is located within the University of Chicago campus, which is a delightful area to spend time walking around.




Conclusion


Overall, Chicago is a city that should be on every traveller’s bucket list. With its rich history, vibrant culture, and endless attractions, it is truly one of the most exciting cities in the world.


Related Blog Posts

If you are interested in finding out more about Chicago, please view the Tailor-Made Itineraries posts below:


Comment below and let us know what your favourite place was to visit in Chicago.


Don’t forget that Tailor-Made Itineraries delights in creating bespoke self-guided tours. So, if visiting any of these attractions in Chicago appeals to you, reach out to me by email. I would be more than happy to design a self-guided tour around your requirements incorporating the attractions of Chicago.


Join me next time on my adventures when I continue my list of attractions that you should visit in Chicago. Tailor-Made Itineraries posts every two weeks, and you can subscribe to the latest blog and newsletter here. Until then, happy reading and safe travels.

Barry

Tailor-Made Itineraries creates one-of-a-kind bespoke self-guided travel itineraries for adventurous and curious travellers.

These self-guided tours deliver a personalised and exciting holiday experience that takes the effort out of trip planning.

Chicago Attractions You Should Visit
Chicago Attractions You Should Visit

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