The Most Unique Things to Do in Chicago (You'll Only Find Them Here!)

Planning Your Trip to Chicago

As a full-time professional travel blogger, I meticulously plan all of my adventures, whether it's a local town or a trip abroad.

Visiting Chicago as part of a lengthier road trip of the United States? These road trip tips will allow you to start your trip off on the right foot.

Getting Around the City

Chicago has a fabulous public transportation system and I had no issues taking it in the past. However, on my most recent trip, I was only in the city for a short amount of time and needed to make the most of it.

Surprisingly, I found taking Uber in Chicago to be incredibly expensive. Even a short trip was costly and these expenses added up quickly.

For this reason, I suggest that you find a rental car well in advance of your trip and reserve it online.

If you're on a limited budget, take the public transit. If you're short on time and need to get around the city quickly and at your own pace, renting a car is a safe bet.

Where to Stay in Chicago

To elevate your stay, why not stay in a unique accommodation in Chicago? There are many fabulous boutique hotels in Chicago.

Choose a sophisticated lodging experience like one you'd find at The Langham. Stay at a historic hotel like The Drake.

By choosing the right hotel, you'll be treated to vibrant city views, stylish suites and unmatched service. After long days of exploring the city, a boutique hotel in Chicago will help you unwind in style.

Unique Things to Do in Chicago

The Windy City is full of so many hidden gems and unique attractions to discover. I've compiled a list of my favorite places in Chicago that belong on any itinerary.

If you're staying in the city for a couple of days or a week, try to fit as many of these attractions onto your list. These unique things to do in Chicago will help you create the best travel memories.

Cloud Gate / The Bean

Cloud Gate is one of the most unique places to visit in Chicago. You'll only find "The Bean" here! Venture over to Millennium Park in downtown Chicago to marvel as this incredible work of art.

Designed by British artist Anish Kapoor, Cloud Gate is an interactive sculpture. Walk around and beneath The Bean to witness how the surroundings are perfectly reflected. Its stainless steel surface reflects the Chicago city landscape, the sky, and...you!

This is one of the most distinctive and popular monuments in the USA. For this reason, it gets quite busy here. To escape the crowds, I suggest going on a weekday morning. That way, you'll capture photos with less people in them.

360 Chicago

360 Chicago, also known as the John Hancock Observatory, delivers incredible 360-degree panoramic views of the city. A quick elevator ride takes you 1,030 feet above street level, where you can soak in some of Chicago's most breathtaking scenery.

Going at sunset is my top travel tip for this unique attraction, but the observatory is spectacular at any time of day. If you can, consider going twice (once during daylight and again at night) for two completely different and equally memorable views.

For an extra adrenaline boost, try the TILT experience. This is one of the most unique things to do in Chicago that I haven't seen anywhere else. Stand in a glass enclosure, grip the handlebars, and slowly tilt outward over the city. It's a thrilling, one-of-a-kind perspective overlooking the streets below.

Garfield Park Conservatory

Garfield Park Conservatory is a bit outside the downtown core, but it's absolutely worth the detour. If you love botanical gardens or have a soft spot for plants, this spot should be on your Chicago itinerary.

It's one of the largest botanical conservatories in the United States. Inside, you'll find eight stunning display gardens filled with plant life from around the world. Outside, the grounds span over 10 acres, complete with beautifully landscaped areas and a serene water lily pond.

It's an especially magical place in winter. The conservatory's tropical climate offers a welcome escape from the cold. I visited in June and loved wandering through both the lush indoor greenhouses and the peaceful outdoor gardens.

The 606

Extending up above the city, The 606 is an abandoned stretch of rail line that's been transformed into a public trail and park. It's a hidden gem in Chicago for visitors and beloved by locals.

While other cities in the USA and Canada have repurposed old rail lines into walking trails, the one in Chicago is quite lengthy at 2.7 miles. The High Line in NYC, while amazing, is only 1.45 miles long.

There's also a colorful collection of public art and murals to admire as you walk or cycle on The 606. Moreover, this is a public space that everyone can enjoy for free any time of the day or season.

National Museum of Mexican Art

The National Museum of Mexican Art showcases an impressive collection that celebrates Mexican art and culture. From ancient works to contemporary pieces, the museum offers a rich and diverse look at Mexico's artistic heritage.

Outside of Mexico, it's rare to find a museum devoted entirely to Mexican art and culture. It's certainly a hidden gem in Chicago. Plus, admission is always free (donations are welcome!) and there are several galleries to explore.

Founded by 1982, this museum represents the Mexican community in the United States. It's home to one of the country's largest Mexican art collections, including over 22,000 pieces.

River Boat Architecture Cruise

One of the most unique things to do in Chicago is an architecture boat tour aboard First Lady. This is often the most recommended tour or attraction to experience in the city by those who have visited, myself included.

First Lady cruises put architecture first and they are the only cruise that partners with the Chicago Architecture Center. The tours are about 90 minutes long, so it'll only take up a small portion of your afternoon.

Drift past buildings like the Willis Tower, the Wrigley Building, and Marina City. I'd admired the unique corn cob architecture of Marina City on the cover of Wilco's Yankee Hotel Foxtrot years before I got to finally see them in person.

Chicago Magic Lounge

Looking for something unique to do in Chicago at night? The Chicago Magic Lounge offers an enchanting and interactive experience.

Located inside an Art Deco style theater behind the facade of a vintage laundromat, the Chicago Magic Lounge combines a magic show with an intimate speakeasy.

World class magicians perform perform classic Chicago-style bar magic as you sip craft cocktails and taste light bites. Then, enjoy an atmospheric performance in the cabaret theater by some of the best musicians from across the globe.

Adler Planetarium

Did you know that the Adler Planetarium is the first planetarium in the United States? It doesn't matter whether you're young or old, prepare to be dazzled by the Adler Planetarium.

The Adler Planetarium makes learning about science and space travel fun for everyone. Their domed theaters illustrate the cosmos beautifully through their captivating shows about the history of the universe, black holes and more.

The Adler Planetarium's Doane Observatory is home to one of the largest telescopes available to the public in the country. In fact, you can see celestial objects that are trillions of miles away! Try to plan your visit for an Adler at Night event, which happen on Wednesdays (weather permitting).