13 Best Adventurous and Cultural Things to Do in Chicago

View of Chicago's skyline from the river cruise

This is a list of recommended best things to do in Chicago which embraces both adventurous and cultural explorations of the city’s landscapes. From a peaceful stroll along the Riverwalk to a nerve wrecking ride atop the Willis Tower and everything in between, Chicago offers a wide spectrum of exciting things to do and places to visit.

This is a guide that helps you explore Chicago’s rich history and deeply diverse culture and discover some exciting attractions along the way. My recommended list of the best things to do in Chicago is divided into the following categories:

Table of Content

Adventurous Things to Do in Chicago

Architecture Boat Tour

Weather permitting, one of the best things to do in Chicago is to take a river cruise – and especially the architecture cruise, as you will see so much and also learn so much about the architecture, the evolution, the culture, as well as the history of the city. It is a very comprehensive sightseeing tour.

There are a few operators, and I took my cruise with Shoreline Sightseeing and the experience was enjoyable. The guide was very knowledgeable and gave the presentation with a great sense of humor.

They have two locations – the Michigan Avenue Pier and Navy Pier. Both locations are ideal where you can bundle the other activities on your itinerary together with the cruise.

Skydeck atop the Willis Tower

Skydeck Chicago - Willis Tower
Credit: Julien Hautcoeur/Shutterstock

If you have taken the architecture boat tour, your guide would probably have told you about the rich history of the Sears Tower. Yes, it’s now called the Willis Tower, but old-time Chicagoans still call it Sears Tower.

The 103rd floor of the skyscraper offers a panoramic 360-degree view over four states on a clear day. The “Skydeck Experience” also give you a tour of the Windy City’s rich history and culture.

The most adventurous attraction is “The Ledge” – get out if you dare! It is an all-glass balcony that extends over four feet outside the building. This is definitely not for the faint of hearts.

360 – John Hancock Center

360 Chicago - John Hancock Cener
Credit: 360

360 is located at 875 N Michigan Avenue. People still call this building the John Hancock Center (the same way people call the Willis Tower Sears Tower.)

Its Observation Deck offers one of the best panoramic views of the city and its surrounding areas. Breathtaking is an understatement.

The highlight of your visit – if you dare – is the TILT. In a way, it is like the glass balcony (the Ledge) from the Willis Tower but taken one step further. You will be tilted so that your body is facing downward! Yikes! Are you sure you want to do it?

Outdoor Things to Do in Chicago

Chicago Riverwalk

The Riverwalk is one of my favorite places to go in Chicago. You can go there just for a leisurely stroll as well as for waterfront dining. Go here for a map and directions, as well as dining options and special events.

As far as attractions are concerned, there are canoe and kayak rentals available if you are of the adventurous type! It always gets me nervous when I see those tiny kayaks getting in the way of those large river cruise boats.

Or you can just dip your toes in the water and do nothing. Sometimes I’ll just sit there sipping a cocktail while writing my travel blog.

Many drinking and dining options are available. One of my favorites is Chicago Brewhouse. Don’t forget to grab a Chicago dog. And remember: No ketchup allowed!

Cloud Gate

Cloud Gate aka The Bean in Chicago

The shiny, iconic structure that reflects the skyline of Chicago is officially called “Cloud Gate” but is more widely known as “The Bean”. It is the major attraction of Chicago’s Millennium Park.

The kidney-bean shaped sculpture is 33 feet high, 42 feet wide, 66 feet long, and weighs 110 tons (220,000 pounds).

Taking selfies will never be this much fun again. The mirror-like surface of The Bean gives you numerous angles, perspectives, and reflections to create the most interesting and unique pictures.

You can create different views during the day or night, rain or shine, cloudy or snowy. The possibilities are endless.

If you need a drink to calm your nerves after the ride, BAR 94 serves local craft beers and custom cocktails.

Navy Pier in Chicago - entertainment center

Navy Pier is a large waterfront dining and entertainment complex and is also the pier from where several river cruises operate. It is also home to the iconic Centennial Wheel. Navy Pier is one of the favorite attractions in Chicago for both locals and tourists alike.

This place is vibrant, lively, and is always packed with people having fun. During summer, especially on weekends, there are often live music, DJ performances, or other live and exciting events taking place.

In the summer season, there are also firework displays on Wednesday and Saturday nights.

Arts and Museum in Chicago

Art Institute of Chicago

The Art Institute of Chicago is an iconic museum and has the largest collection of Impressionist arts outside of the Louvre. It is also where one of Vincent van Gogh’s Self Portraits is housed. Many masterpieces from renowned Impressionist artists such as Monet and Renoir can also be found.

As you wander around the museum you may come across a striking and huge glass window on display. It is called the Tiffany Window which is located above the Woman’s Board Grand Staircase. It is composed of 48 panels of different types of vibrantly colored glass and is 26 feet tall and 18 feet wide. This is one of my most favorite photo spots.

A wide spectrum of arts from numerous countries and cultures across the World are also on display. The place is enormous, and to really be able to appreciate and understand everything that you are seeing, I recommend allocating at least one full day to the museum.

Chicago History Museum

The Chicago History Museum is a smaller and lesser-known museum, but this is actually my personal favorite because it tells you the story of the city – its history and its culture, the challenges that it faced and the resilience of its people, and everything that comes along with it. If you really want to know the city, make sure that a visit to the museum in on top of your list of things to do in Chicago.

  • Some of my most favorite collections are:
  • Sun-Times Photo Collection
  • City on Fire
  • Lincoln’s Chicago
  • Crossroads of America
  • Remembering Dr. King

Field Museum

Field Museum in Chicago
Credit: Jim Lambert/Shutterstock

One of the most popular museums and attractions in Chicago is the Field Museum. It is located right next to the Soldier Field and is best known for its documentaries of natural history. Educational displays document advancements from distant ancient cultures to the scientific and technological breakthroughs to today.

The main theme of the museum is “discovery across time”. It takes the visitor to explore the cultures from across the World from past to present.

It also offers plenty of interactive and immersive activities and is great for kids of all ages.

Cultural Things to Do in Chicago

Visit a Jazz Club

Dining room of the jazz club Andy's.
Credit: Andy’s Jazz Club and Restaurant

Chicago is home to one of the richest jazz scenes in the country and is also the birthplace of many legendary jazz musicians. Jazz is embedded deep into the culture of the city. Your trip to the Windy city will be incomplete without a visit to a jazz club.

Just a short walk from the Magnificent Mile is Andy’s Jazz Club and Restaurant. It is an ideal place for dinner with jazz or for a date night. Andy’s is conveniently located within walking distance from many hotels in the area. Reservations are required and there is a $15 cover charge which is good for one show only.

Located uptown at Lawrence and Broadway is the Green Mill which was a speakeasy run by the mobsters during the days of Prohibition. It was a favorite hangout of Al Capone who had a particular booth reserved for him. Today, it is one of the liveliest jazz clubs in the city with live music playing nightly. Reservations are not accepted. Cash only. No credit cards.


Chicago Chinatown - entrance

The Chinatown here is one of the smaller ones in the US. It is definitely less vibrant and less extensive when compared to its counterparts in San Francisco or NYC. Nevertheless, there are some very nice dim sum restaurants as well as authentic Hong Kong style cafes and teahouses.

My Favorite dim sum restaurant is Ming Hin Cuisine. For a bowl of authentic Hong Kong style “cart noodles”, go to Ken Kee.

One of the cultural experiences to explore is the Chinatown Square Zodiacs. It captures twelve bronze sculptures of animals of the Chinese zodiac on individual pedestals.

Get A Deep-Dish Pizza

Chicago's famous deep-dish pizza
A cross-section showing Giordano’s layers

Your visit to Chicago is not complete without having a feast of deep-dish pizzas. And even better, have two!

While there are literally numerous places in the city to grab one of their World-famous deep-dish pizzas, the two most famous rivalries are Giordano’s and Lou Malnati’s. And I am listing them here strictly in alphabetical order to avoid any controversy which name should go first.

My personal palate will tell you that Giordano’s pizzas have better layers, but Lou’s have a fresher and more robust tomato sauce. But I’ll let you be the judge.

Get A Chicago Dog

Chicago dog comes with onions, tomatoes, peppers, and pickles and are seasoned with mustard, relish, and celery salt.
Credit: Portillo’s

Getting a Chicago dog is certainly on the top of most visitor’s list of things to do in Chicago and there is no shortage of amazing hot dogs throughout the city. In the Riverwalk area, there are several pubs and restaurants where washing down a hot dog with a beer is one of the most favorite orders.

Other local favorites include The Wiener Circle, Chicago’s Doghouse, and Portillo’s.

My personal favorite is Portillo’s where their hot dog with everything on it is nicknamed “drag the dog through the garden”. It is served on a steamed poppy seed bun and is topped with onions, tomatoes, peppers, pickles, mustard, relish, and celery salt. And remember, no ketchup, please!

You may also like...