The Tailor-Made Guide to 21 Attractions You Should Visit in Chicago, Part 2

Barry Pickard
Jun 10
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.

Have you ever found yourself wondering what else Chicago has to offer beyond its famous landmarks? Imagine strolling through the vibrant neighbourhoods, where the scent of freshly brewed coffee mingles with the aroma of street food, and the sounds of live music fill the air. Welcome to Chicago, a city that never runs out of surprises.

This post will be your guide to uncovering the hidden gems of this incredible city. In Part 1, we explored some of the must-visit attractions, and now, I’m excited to share even more of my favourite spots with you. As an avid traveller and Chicago enthusiast, I’ve spent many days discovering the best places that this city has to offer. This guide is perfect for independent travellers like you, who are eager to dive deeper into the local culture and experience Chicago like a true insider.

In this post, we’ll continue our journey through 21 attractions you should visit in Chicago. From quirky museums to charming parks, there’s something for everyone. So, grab your walking shoes and let’s explore the lesser-known wonders of the Windy City together. You’ve come to the right place for all the insider tips and tricks you need for an unforgettable adventure 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.

About Chicago

Chicago is a city that has something for everyone. From its world-famous architecture to its vibrant nightlife, there's no shortage of things to see and do in the Windy City. Chicago was founded in 1833 and quickly grew into a major commercial center. Chicago's rapid growth was fuelled by its location on the Great Lakes, which made it a major transportation hub. The city was also home to a number of major industries, including steel, meatpacking, and railroads.

In the early 20th century, Chicago experienced a period of great change. The city's population exploded, and its skyline was transformed by the construction of a number of iconic skyscrapers. Chicago also became a major center for art, culture, and education. Today, Chicago is a thriving metropolis with a population of over 2.7 million people.

10. WNDR Museum

The WNDR Museum is an immersive art and technology experience, featuring over 20 exhibits that are designed to ignite your curiosity and spark your imagination. From interactive installations to thought-provoking exhibits, there’s something for all ages, with the installations being regularly updated to provide new and exciting experiences.

I particularly enjoyed Yayoi Kusama’s installation ‘Let’s Survive Forever’ during my visit. The infinity mirror room was full of reflective spheres and was a mind-blowing experience. It also reminded me of the 80’s horror classic ‘Phantasm’ – bit of an obscure reference, but you know if you know! Unfortunately, this exhibit has since ended, but you can have as much fun at the Flip Disc, WNDR Light Floor and Colorwave exhibits, as well as the eye-catching artwork of Keith Haring, and Lauren Asta’s ‘Lost in Da Stardust.

Tailor-Made Top Tip: Book your tickets in advance to avoid disappointment and schedule at least an hour for your visit.

9. Chicago History Museum

The Chicago History Museum is the perfect place to learn about the city’s fascinating story. The museum has a variety of exhibits that cover everything from its early days as a fur trading post to its current status as a global metropolis.

The exhibits we enjoyed the most in this family orientated museum were the ‘Great Chicago Fire’ and the full-size tram car and train. The museum also has a good café and a well-stocked gift shock.

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Tailor-Made Top Tip: There is ample parking at the corner of Clark Street and La Salle Drive. Parking here also has the advantage that you can easily explore the rest of Lincoln Park, including the zoo.

8. Unity Temple

Unity Temple is a Unitarian church in the Chicago suburb of Oak Park and was designed by the American architect Frank Lloyd Wright and built between 1905 and 1908. Unity Temple is considered to be one of his most important structures. Because of its consolidation of aesthetic intent and structure through use of a single material, reinforced concrete, Unity Temple is considered by many architects to be the first modern building in the world.

The building is a simple, unadorned cube of concrete, but despite looking a little austere and gloomy, the rooms are actually filled with light from skylights, making this a truly beautiful and inspiring building.

Tailor-Made Top Tip: Unity Temple is still a working house of worship, but you can book onto one of their regular tours in order to explore this iconic building.

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7. International Museum of Surgical Science

The International Museum of Surgical Science (IMSS) is a medical museum founded in 1954 by Dr. Max Thorek, a world-renowned surgeon and educator. The museum’s mission is to ‘collect, preserve, and exhibit the history of surgery and the healing arts.’

IMSS has a collection of over 25,000 artefacts, including surgical instruments, medical equipment, and medical artwork. The museum’s collection is one of the largest and most comprehensive in the world. The museum is a great place to learn about the history of surgical science, with its exhibits being engaging and informative.

Tailor-Made Top Tip: Check out the museum website to see what temporary exhibitions are on display. ‘Embroidered Morphologies’ by artist Deborah Simon was on during my visit and I found it visually stunning.

6. Lincoln Park Zoo

The Lincoln Park Zoo is a 35-acre zoo, home to over 1,100 animals from over 200 species. Some of the zoo’s most popular animals include polar bears, penguins, giraffes, lions, tigers, and red pandas. The zoo also has a variety of educational exhibits and programmes that teach visitors about animals and conservation.

Tailor-Made Top Tip: The zoo is free to enter, which is always a great reason for a visit.

5. The Art Institute of Chicago

The Art Institute of Chicago is one of the most popular tourist destinations in the city, and for good reason. With a world-renowned collection of art spanning over 5,000 years, there’s something for everyone to enjoy.

Whether you’re a fan of impressionist paintings, ancient Egyptian artifacts, or modern photography, you’re sure to find something to love at the Art Institute. Some of the museum’s most famous works include Edward Hopper’s ‘Nighthawks,’ and Grant Wood’s ‘American Gothic.’ There are also significant works of van Gogh, Georgia o’ Keeffe, and Auguste Rodin.

Tailor-Made Top Tip: One of the most significant works of art at the Institute, the American Windows, by Marc Chagall, is quite isolated and hidden. You can be find it in Gallery 144 in the east wing.

4. Crown Fountain

The Crown Fountain is a unique and interactive work of public art located in Millennium Park. It was created by Spanish artist Jaume Plensa and opened in 2004. The fountain consists of two 50-foot-tall glass towers that project video images of Chicago residents onto their faces. When visitors approach the fountain, the water jets from the mouths of the faces, creating a playful and refreshing experience.

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In addition to its beauty and interactivity, the Crown Fountain also has a deeper meaning. The faces projected on the towers represent the diversity of Chicago's population. The fountain is a celebration of the city's people and its spirit of community.

Tailor-Made Top Tip: The fountain is a short walk from Cloud Gate, so it is ideal to combine a visit to both.

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3. Charnley-Persky House

The Charnley-Persky House is a historic house museum located in the Gold Coast neighbourhood. It was nominally designed by renowned architect Louis Sullivan and built in 1892, however, Frank Lloyd Wright, who worked for Sullivan when in his twenties, later stated that it was himself who designed the house. Whoever designed the house, you can see the start of the progression from Sullivan’s style and architectural thought to the revolutionary designs of Lloyd Wright. The house is arguably the first example of the Prairie School style, which is characterized by its use of horizontal lines, natural materials, and open floor plans.

The Charnley-Persky House is open to the public for tours. Visitors can learn about the history of the house, its architecture, and its role in Chicago's architectural development. The house is also a great place to see some beautiful original furniture and decorative details.

Tailor-Made Top Tip: Tours can be booked online for Wednesdays, Fridays and Saturdays. Try and book the mid-week slot to take advantage of a free tour. Tickets for the other two days cost $10.

2. Field Museum

The Field Museum is one of the largest and most comprehensive natural history museums in the world. Located on the shores of Lake Michigan, the museum was founded in 1893, and it houses over 24 million specimens of plants, animals, fossils, artifacts, and cultural objects.

The Field Museum has something to offer everyone, from families with young children to adults with a lifelong interest in the natural world. My favourite exhibits included Sue, the largest and most complete T-Rex skeleton ever found; the Halls of the Pacific, which has fascinating displays of Pacific Island culture; and the eye-catching, colourful Hall of Gems.

Tailor-Made Top Tip: The Field Museum is opposite the Shedd Aquarium and a short walk from the Adler Planetarium, so a full day can easily be enjoyed on the campus.

1. Navy Pier

Navy Pier is located on the shores of Lake Michigan and offers stunning views of the city skyline. Navy Pier is home to a variety of attractions, including a 15-story Ferris wheel, an IMAX theatre, the Children’s Museum, as well as a variety of restaurants and shops.

Tailor-Made Top Tip: Bring a jacket, since even on a nice day, it can get quite windy at the pier.

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 second part of my tailor-made guide to Chicago’s top attractions. From the eclectic neighbourhoods to the serene green spaces, Chicago is a city that constantly surprises and delights. Each attraction we’ve explored has its own unique story and charm, waiting to be discovered by curious travellers like you. As you continue your journey, I hope you find the same sense of wonder and excitement that I did.

Stay tuned for more travel tips and guides to help you make the most of your adventures. There’s always something new to discover, and I can’t wait to share it all with you.