Chicago Travel Guide: Top 10 Things to Do in Chicago

Written by Susan Lanier-Graham

November 15, 2021
Home >> Travel >> Chicago Travel Guide: Top 10 Things to Do in Chicago

Chicago will delight you with its spectacular museums, towering skyscrapers, jubilant skyline, and a host of other attractions. This is our Chicago Travel Guide, offering the top 10 things to do in Chicago. 

Does your idea of a perfect holiday involve shuttling between museums, art galleries, and other historical attractions? Or are you one of those travelers who prefer indulging in a bit of retail therapy during a vacation? Or are you more of a nature lover who craves a touch of greenery and wildlife when you travel? No matter your travel preferences, Chicago will delight you with its spectacular museums, towering skyscrapers, jubilant skyline, and a host of other attractions. Perched on the shores of the picturesque Lake Michigan, it is aptly nicknamed “The Windy City.” The best part is that it is home to plenty of high-end shopping destinations, too.

But the broad spectrum of tourist attractions in Chicago can become overwhelming for new travelers. That is why we have curated a list of the best places to visit and things to do in Chicago. Let us take a look.

Walk the Magnificent Mile

When you think of places to visit in Chicago, the Magnificent Mile is likely the first name that will come to mind. It is not surprising considering that the Magnificent Mile is the city’s hub of retail and commercial activity.

Set on Michigan Avenue, between the Chicago River and Lake Shore Drive, the Magnificent Mile is studded with luxury boutiques and retail stores featuring high-end brands, such as Macy’s, Bloomingdale’s, and Nordstrom.

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While you are there, don’t forget to check out the finest specimens of Chicago’s architecture, including the Wrigley Building, John Hancock Center, Tribune Tower, and Chicago Water Tower.

Chicago Water Tower

There is great architecture in Chicago, including the Chicago Water Tower. Photo by Susan Lanier-Graham

Experience the Architecture River Tour

Chicago is ideal if you are an architecture buff. The Architecture River Tour is going to be the crowning jewel of your trip to Chicago. Organized by the Chicago Architecture Foundation, the 90-minute cruise ride on the Chicago River gives you an insight into the city’s origin and transformation throughout the year.

things to do in Chicago

A great way to see Chicago architecture is with a boat tour. Photo by plusphoto via iStock by Getty Images

You get to witness more than 50 stunning buildings adorning the Chicago skyline. You can take the tour during the morning and evening. And if you are lucky, your docent will share many of the city’s hidden secrets and trivia during the tour.

Take a Stroll Down the Chicago Riverwalk

There isn’t a better way to explore Chicago than by enjoying a stroll through the Chicago Riverwalk. Set on the southern edge of the Chicago River, the 1.25-mile pedestrian walkway offers panoramic views of the city’s scintillating skyline.

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things to do in Chicago

Chicago Riverwalk in downtown Chicago, Illinois. Photo by tifonimages via iStock by Getty Images

Don’t forget to stop by the McCormick Bridgehouse and Chicago River Museum for a closer look at numerous movable bridges situated on the walkway. When you get tired from all the walking around, grab a meal at one of the many restaurants overlooking the Chicago River.

Stay at Selina Hotel, Downtown Chicago

When you look for places to stay in Chicago, you will never run out of options. But if you are looking to catch a closer glimpse of the city’s spirited vibe and happening lifestyle, you can consider staying at the Selina Hotel in Downtown Chicago.

Situated in the heart of the city, Selina Hotel is a stone’s throw away from the city’s top tourist attractions, including the Magnificent Mile and Oak Street Beach. A short drive will take you to other popular attractions, such as Millenium Park, Navy Pier, and Sunset Park Zoo. If you are planning a trip during the Black Friday weekend, the hotel is offering early bird access to their biggest sale of this year. 

Make the most of your time in Chicago by checking out the events and workshops that are regularly organized here. Also, don’t forget to treat your taste buds with local flavors at the on-site restaurant.

Explore the Lakefront Trail in Chicago

The Chicago Lakefront Trail is an 18-mile path on the coast of Lake Michigan. Stretching from 71st Street on the south to Ardmore Street on the north, it is one of the best spots to catch a glimpse of the quintessential Chicago skyline. 

things to do in Chicago

Lake Michigan and the Lakefront Trail in Lincoln Park is open for walking all year round. Photo by James Andrews via iStock by Getty Images

Other attractions on the Lakefront Trail include Navy Pier, Lincoln Park, and Soldier Field. It is also the gateway to Chicago’s glistening beaches and public parks. Take your time to pause and marvel at the numerous art installations located along the path.

A Chicago Travel Guide: Top 10 Things to Do and Places to Be

Visit the Art Institute of Chicago

If you want to delve deeper into The Windy City’s cultural heritage, there is no better destination than the Art Institute of Chicago.

Lion at Art Institute of Chicago

One of the things to do in Chicago is visit the Art Institute of Chicago. Photo by Susan Lanier-Graham

Set on a sprawling 400,000 sq. ft. campus, the museum is best known for its collection of impressionist paintings. You will also find other forms of artwork, including decorative arts, architectural drawings, and photography.

Applaud the Murals at Hubbard Street

While Chicago is known for its impressive array of museums, the murals at Hubbard Street don’t get the attention they deserve. Spanning five city blocks around Hubbard Street, the vibrant murals are the result of a project started by the students of Ricardo Alonzo in 1971. The open-air museum is a testament to Chicago’s sprightly street art scene and exploring the street art is a must for any list of the best things to do in Chicago.

Explore Garfield Park Conservatory

If you are craving a touch of nature amidst the sky-high buildings, head straight to Garfield Park Conservatory. The twelve-acre glass conservatory is home to exotic plants from all over the world. Apart from the permanent exhibits, this conservatory is also known for its spring flower festivals and holiday displays.

things to do in Chicago

Garfield Park Conservatory in Chicago. Photo by benkrut via iStock by Getty Images

Check Out Shedd Aquarium

Home to more than 32,000 underwater creatures, Shedd Aquarium is one of the best family-friendly destinations in Chicago. It is here that you can enjoy a rendezvous with piranhas, sea lions, stingrays, sharks, and beluga whales. You can even indulge in specialty experiences, such as feeding animals and behind-the-scenes tours.

things to do in Chicago

Shedd Aquarium in Chicago. Photo by benkrut via iStock by Getty Images

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Don’t Miss Lincoln Park Zoo

If a visit to Shedd Aquarium has you craving for more natural wonders, head to Lincoln Park Zoo. Catch a glimpse of more than 200 wildlife species, including zebras, gorillas, and sloths, in their natural habitat. The best part is that you don’t have to pay an entry fee for your visit.

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Whether you are an architecture nerd or an amateur photographer, the Windy City packs plenty of surprises for every traveler. Don’t be surprised if you find yourself extending your Chicago getaway to explore all the tourist attractions the city has to offer. Be sure to check out Wander for more things to see and do when you visit Illinois

A Chicago Travel Guide: Top 10 Things to Do and Places to Be

A Chicago Travel Guide: Top 10 Things to Do in Chicago

Written by Susan Lanier-Graham

Founder and publisher Susan Lanier-Graham has traveled the world for the past twenty years, filling a passport or two along the way. She has wandered through the jungles of Thailand, explored the mysteries of the Great Pyramids, and shared the night with a leopard in Zambia. She sailed in the Mediterranean, sipped her way through Burgundy canals and Champagne caves. She followed Rembrandt’s footsteps through Amsterdam. Susan found her center on the red rocks of Sedona and soaked up an exquisite sunset over the Indian Ocean in Bali. Susan is always looking for wow moments around the world or across the street to share with adventure lovers everywhere. She has authored more than 75 books and hundreds of magazine articles. Susan is an award-winning travel writer and member of the Society of American Travel Writers (SATW) and International Food, Wine and Travel Writers Association (IFWTWA). She is a Certified California Wine Appellation Specialist (CWAS). Susan's work still regularly appears in print and online. Susan is an award-winning travel writer, a member of the Society of American Travel Writers (SATW) and is a Certified California Wine Appellation Specialist (CWAS). Susan has worked as an ambassador for Travelocity and is currently a travel ambassador for Rocky Mountaineer. Her work regularly appears in print and online in a variety of publications. These include various AAA publications, Postcards for Travel Leaders,,,, So Scottsdale, Uptown, Green Living AZ, Life Refined, Modern Luxury,, WHERE Arizona, WHERE Traveler Phoenix + Scottsdale, and more.

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