A Chicago To Do List: A City Guide for Tourists Visiting for the First Time

With its unparalleled skyline, vibrant culture, and plethora of attractions, it is no wonder why Chicago is one of the most visited cities in the world. From iconic sites like the Willis Tower and Cloud Gate to the Art Institute of Chicago and Navy Pier, a trip to the Windy City is sure to be full of fun. Whether you are planning your first trip to Chicago, or are a returning visitor eager to explore new attractions, this city guide will provide you with all the information you need to make your Chicago adventure one to remember.

Getting Around Chicago

As with any large metropolitan area, it can be difficult to navigate Chicago without a plan. Fortunately, the city offers many convenient transportation options such as the Metra and CTA public transportation networks, Uber and Lyft rideshare services, and even bike share programs like Divvy.

If you plan to stay in the city for more than a few days, consider purchasing a Ventra pass. This plastic card can be used to travel on the CTA trains and buses throughout the city, as well as on Metra regional trains that serve the Chicago metropolitan area.

What to See in Chicago

Chicago is home to many iconic sites and attractions. A trip to this vibrant city wouldn’t be complete without visiting some of these iconic spots:

Willis Tower

Nicknamed “The Big Willie” by locals, the Willis Tower is the second-tallest building in the United States and one of Chicago’s most recognizable landmarks. Visitors can take a thrilling 103-floor elevator ride to the Skydeck at the top of the building, where they can observe stunning views of the city from 1,353 feet up.

Cloud Gate

Cloud Gate, better known as “The Bean” to locals, is an iconic sculpture located in Millennium Park. This 110-ton stainless steel structure is an excellent photo opportunity for visitors of all ages.

Art Institute of Chicago

The Art Institute of Chicago is one of the largest and oldest art museums in the United States. This iconic museum houses an extensive collection of Impressionist, Post-Impressionist, and American art.

Navy Pier

Navy Pier is a popular tourist destination located on Lake Michigan. Here visitors can take a romantic ride on an old-fashioned carousel or take a scenic walk down the pier. Navy Pier also hosts various festivals throughout the year such as the Chicago Flower & Garden Show and the Chicago Air and Water Show.

Popular Activities in Chicago

Chicago is known for its many activities that are perfect for visitors of all ages. Here are just a few fun things you can do while in town:

Take a Boat Tour

A boat tour is one of the best ways to experience all that Chicago has to offer. From architectural cruises down the Chicago River to sightseeing tours along Lake Michigan, visitors can catch glimpses of some of the city’s most iconic landmarks from a unique perspective. Visitors can book a boat tour on Viator here.

Eat at a Local Restaurant

Chicago is home to a variety of delicious restaurants serving up everything from deep dish pizza to classic American cuisine. Be sure to try out one of these local eateries for a truly authentic experience.

Visit a Museum

The city is home to dozens of fascinating museums such as The Field Museum of Natural History, The Museum of Science and Industry, and The Art Institute of Chicago. Many of these museums offer free admission on certain days, so be sure to check out their websites before making plans.

Shop on The Magnificent Mile

The Magnificent Mile is a must-see for any visitor looking for some retail therapy. This shopping district features some of the city’s most upscale stores and boutiques as well as delicious dining options.

Unique Tours in Chicago

Chicago offers many unique tours tailored towards different types of travelers. From architectural tours to food tours, there is something for everyone in this vibrant city. Here are two popular tours in Chicago that you don’t want to miss:

Architectural Boat Tour

The architectural boat tour is a great way to explore some of Chicago’s most iconic buildings from a unique perspective. This tour takes visitors down the river past such architectural delights as the Willis Tower, Navy Pier, and many more. Visitors can book an architectural boat tour on GetYourGuide here.

Chicago Food Tour

Nothing quite beats sampling delicious local cuisine while exploring a new city. The Chicago Food Tour takes visitors on a culinary journey through some of Chicago’s best restaurants and eateries. Enjoy samples of everything from deep dish pizza to hot dogs while learning about the city’s rich culinary history from knowledgeable guides. Visitors can book a food tour on GetYourGuide here.

Conclusion

Whether you are planning your first trip to Chicago or are returning for another visit, there is no shortage of things to do in this vibrant city. From iconic sites like Willis Tower and Cloud Gate to popular activities such as taking a boat tour or visiting museums, there is something for everyone in The Windy City. With so much to see and do, you will certainly never be bored in Chicago!