7 Things to Do During a Bold Weekend in Chicago

some of the best things to do in Chicago

Considering a trip to Chicago this summer? If so, make sure it’s a Bold one by soaking up the warm breeze off of Lake Michigan and checking out these Project Bold Life-approved attractions that the “Windy City” has to offer. Yes, there’s great Midwestern food to be eaten, but there’s some cool history, too! So check out this list of the seven best things to do in Chicago.

(Sure, Chicago is fun, but what if you want to visit Antarctica? Project Bold Life has got you covered.)

1. Unveil the Untold Stories of Chicago’s Notorious Mob Era on an Exhilarating Prohibition Tour

A bunch of people chilling in Chicago
As Midwestern cities go, Chicago is pretty cool. But compared to cities around the world… it’s pretty darn cool.

One of the notable parts of Chicagoan history is its heavy ties with the mob. The prohibition tour in Chicago allows tourists to explore and retrace the Chicago Speakeasies. In addition, visitors can experience and learn about the fascinating past of Prohibition in Chicago.

Besides guided buses and walking tours around three or four neighborhood speakeasies, you can also get an insight into the drinks representing the 20s Chicago Prohibition. The prohibition tour provides visitors around River North, West Loop, Wicker Park, and Wrigley Field Speakeasies.

In addition, tourists can also dress the part of a 1920s mobster during the tour for a more immersive experience. The two-hour tour will also stop over ten relevant sites that shaped the era, like the Biograph Theater, the St. Valentine’s Day Massacre, and the Holy Name Cathedral.

Check out Prohibition Tours for a curated experience and see what this whole Al Capone was all about.

2.   Soak Up the Sun and Savor the Thrills at Navy Pier

Another historical landmark filled with tons of activities for locals and tourists is the Navy Pier. Constructed in 1916, the Navy Pier is a part of Daniel Burnham’s 1909 Plan for Chicago. The architect designed the area as the People’s Pier. The pier’s original name was Municipal Pier 32 before but got renamed in honor of the WWI Navy personnel in 1927.

Nowadays, the pier hosts numerous activities for families and friends to enjoy. It also holds restaurants and provides perfect photographic views of Lake Michigan and the Chicago Skyline. Tourists can enjoy attractions like the cruise tours, the Chicago Children’s Museum, and the Navy Pier Beer Garden. In addition, people can also walk around Polk Bros Park, where they can enjoy free events and programs every weekend.

Sign up for a ride on Lake Michigan’s cool waters here.

Apparently, all the cool kids are wearing this backpack now, so you should take it on your Chicago trip and maybe stuff it with… bratwursts? Click the image to check it out.

3.   Observe the Chicago Skyline at the 360 Chicago Observation Deck

Looking at the scenery from different perspectives can help you find something new about them. Although the Chicago skyline is a sight on its own, seeing it from a different angle can make you appreciate its beauty better.

The 360 Chicago Observation Deck does that from its place on the 94th floor of John Hancock Center. Unlike other observation decks, the building gives you a 360-degree view of the Windy City, the lake, and its surrounding areas. The building location also offers viewers a closer look at the Magnificent Mile and Lake Shore Drive. In addition, you can also take a ride on Tilt.

The Tilt gives you over 1000 feet over the Magnificent Mile on Michigan Avenue. The attraction makes it a unique experience for every Chicago tourist, regardless of age.

a bunch of logos repping the best things to do in Chicago
The best things to do in Chicago involve food, water and gangsters. That’s a fact.

4.   Indulge Your Space Interests at Adler Planetarium

Chicago offers its tourists numerous attractions and sights that match their likes, interests, and passions. Astronomy lovers and space enthusiasts would have a blast spending a weekend at Adler Planetarium. The space museum on Northerly Island is historic as it’s the first planetarium built in America.

Adler Planetarium provides its guests with several family-friendly attractions with interactive experiences for everyone to enjoy. It also has theater programs showing daily and year-round educational events for school tours or family holidays.

Some of the museum’s well-known exhibits include Astronomy in Culture and Chicago’s Night Sky. Other museums, like the Field Museum and Shedd Aquarium, are also a few distance away.

Click here for Adler Planetarium tickets and see the stars (as well as other celestial bodies).

5.   Dive into Chicago’s Deep-Dish Pizza Culture at Lou Malnati’s Pizzeria – A Slice of Heaven!

No Chicago weekend getaway is complete without diving into distinct Chicagoan food culture. Of all dishes, deep-dish pizzas are a Chicago staple. Also called Chicago-style pizza, this dish has a thick crust stacked with layers of meaty red sauce, cheese, and toppings.

Tourists looking to taste the classic deep-dish pizza should head to Lou Malnati’s. Being one of the oldest deep-dish pizzerias in Chicago, you couldn’t go wrong in ordering a slice for you and your family after a walk in the city.

Check out Lou Malnati’s Pizzeria’s Instagram for some inspirational pizza pics.

6.   Boating and Urban Kayaking Along the Chicago River

Leisurely take in the beauty of Chicago from the Chicago River by renting electric boats and kayaks during your visit. Boating and kayaking provide a different perspective of the city and a more private way of touring the Windy City.

some people walking in Chicago
Want to have fun in Chicago? Do at least one item on this list.

Urban kayaking is increasing in popularity this year. It’s one of the best ways to shake up your perspective while visiting Chicago. Tourists can rent kayaks and move through the river or Lake Michigan alone, but there are guided tours for those who’d want an organized journey through the waters.

In addition, the night riverboat tours give the best views of the Merchandise Mart, showered in rotating digital art displays.

Get your kayaking fix here.

7.   Find How Nature Meets Art at the Morton Arboretum

Located west of downtown Chicago is the Morton Arboretum. The garden looks like a world away from the metropolis due to its pastoral landscape and seasonal art installations. Some pieces focus on natural sciences, like live tree growth exhibits.

The arboretum also features the work of sculptor Daniel Popper and his largest exhibitions worldwide. In addition, it has a maze garden and 16 miles of hiking trail, perfect for an urban getaway for outdoor-loving folks.

Get your tree-loving groove on here.


Don’t get caught doing something that will get you in trouble–read this Project Bold Life article on the do’s and don’ts of traveling to restrictive countries!

About the Author

Through timely and thoughtful articles, the book Project Bold Life: The Proven Formula to Take on Challenges and Achieve Happiness and Success, and other media, we deliver engaging content that educates, motivates and inspires you to live a Bold Life.
Previous ArticleNext Article

This will close in 0 seconds

This will close in 0 seconds

Send this to a friend