The Tailor-Made Guide to 21 Attractions You Should Visit in Chicago, Part 1
- Barry Pickard
- Jun 9
- 9 min read
**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
Hi, I'm Barry, the owner of Tailor-Made Itineraries and I have been designing bespoke self-guided tours for adventurous and curious travellers since 2015. I am a history graduate with a passion for travel.
I created this blog to show, through my own adventures, how you can have an incredible travel experience as an independent traveller, giving you the information to navigate the world with confidence.
Contents
Have you ever wondered what makes Chicago such a magnetic city for travellers? As you step off the plane and into the bustling streets, the aroma of deep-dish pizza wafts through the air, mingling with the fresh scent of Lake Michigan. The sound of jazz music spills out from a nearby club, blending with the chatter of locals and the hum of the city. Welcome to Chicago, a city that’s as vibrant and diverse as its skyline.
I’ve spent countless hours exploring every nook and cranny of this incredible city. From the iconic Bean in Millennium Park to the hidden gems that only locals know about, I’ve got the inside scoop on the best attractions Chicago has to offer. This guide is tailor-made for independent travellers like you, who crave authentic experiences and off-the-beaten-path adventures.
In this post, I’ll take you on a sensory journey through 21 must-visit attractions in Chicago. Whether you’re a history buff, a foodie, or an art lover, you’ll find something that piques your interest. So, grab a cup of coffee, sit back, and let’s dive into the heart of the Windy City together. You’ve found the right article to get all the insider tips and tricks you need for an unforgettable trip to 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.
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.
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!).
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.
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.
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.
Where to Stay in Chicago
Chicago offers a diverse range of accommodation options, catering to every budget and travel style. Whether you're looking for a luxurious stay in the heart of the city, a boutique hotel with local charm, or a budget-friendly option that keeps costs down, you'll find plenty of choices.
For my trip, I opted for Motel 6 Prospect Heights, a practical and economical choice. Since I had a hire car, staying outside the city centre allowed me to save on accommodation costs while still having easy access to Chicago’s top attractions.
If you prefer to stay in the heart of the action, Cambria Hotel, Staypineapple, and Chicago Marriott Downtown are excellent choices. These hotels place you right in the city centre, within walking distance of iconic landmarks, shopping, and dining.
For those looking to explore the Hyde Park area, home to the Griffin Museum of Science and Industry and the University of Chicago, Sophy Hyde Park and Hyatt Place Chicago-South offer stylish and comfortable stays.
If your itinerary includes a visit to Oak Park, where you can explore the Frank Lloyd Wright properties, consider staying at Carleton of Oak Park, a charming hotel that provides easy access to this historic neighborhood.
No matter where you choose to stay, Chicago’s accommodations ensure a memorable and convenient experience. Click the links to book your ideal stay and make the most of your trip!
Conclusion
I hope you’ve enjoyed this first part of my tailor-made guide to Chicago’s top attractions. From the bustling streets of downtown to the serene shores of Lake Michigan, Chicago is a city that never ceases to amaze. Each attraction has its own unique charm and story, waiting to be discovered by curious travellers like you. As you explore these spots, I hope you find the same joy and excitement that I did.
Stay tuned for Part 2, where I’ll delve into even more of Chicago’s hidden gems and must-see sights. There’s so much more to uncover, and I can’t wait to share it all with you.
Related Blog Posts
If you are interested in finding out more about Chicago, please view the Tailor-Made Itineraries posts below:
If you’ve got any questions or want to share your own Chicago experiences, drop a comment below. I’d love to hear from you!
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
Contact Me: tailoritineraries@gmail.com
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.
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