Exploring The Windy City: The Best Things To Do In Chicago

Chicago, often referred to as the “Windy City,” is a vibrant and culturally rich destination that offers an array of exciting attractions and activities for visitors to enjoy. From iconic architecture and world-class museums to lively neighborhoods and delectable cuisine, Chicago has something for everyone. In this blog, we will delve into the top things to do in Chicago, ensuring that you make the most of your visit to this captivating city.

Before we move on, did you know that every week we send out a newsletter featuring:

  • New Destinations on the Tripio app
  • Highlighted Itineraries on the Tripio app
  • Articles from the Tripio blog

Subscribe to Tripio’s Weekly Newsletter!

Explore Millennium Park

 Millennium Park

Photo by Christopher Alvarenga on Unsplash

No visit to Chicago is complete without a visit to Millennium Park. This urban oasis is home to the famous Cloud Gate sculpture, affectionately known as “The Bean,” which provides stunning reflections of the city’s skyline. Enjoy a picnic on the Great Lawn, take in a concert at the Jay Pritzker Pavilion, and admire the artistic fountains and gardens that make this park a true gem.

Visit the Art Institute of Chicago

Art Institute of Chicago

Photo by Patricia Jekki on Unsplash

For art enthusiasts, a visit to the Art Institute of Chicago is a must. This renowned museum houses an extensive collection spanning thousands of years and includes masterpieces from artists like Monet, Van Gogh, and Picasso. Take your time exploring the diverse exhibits, and be sure not to miss the iconic “American Gothic” painting.

Enjoy Navy Pier

Enjoy Navy Pier

Photo by Josh Howard on Unsplash

Navy Pier, located along Lake Michigan, is a popular tourist destination that offers a wide range of entertainment options. Take a ride on the Ferris wheel for breathtaking views of the city, enjoy live performances at the Chicago Shakespeare Theater, or simply stroll along the waterfront and savor the sights and sounds of this lively area.

Experience the Skydeck at Willis Tower

Skydeck at Willis Tower

Photo by Amit Thakral on Pexels

For a bird’s-eye view of Chicago, head to the Skydeck at Willis Tower. Step into the glass boxes that extend out from the 103rd floor, providing a thrilling and unforgettable perspective of the city below. On a clear day, you can see up to four states from this incredible vantage point.

Catch a Game at Wrigley Field

Catch a Game at Wrigley Field

Photo by Heather Maguire on Unsplash

Sports fans won’t want to miss the chance to catch a game at Wrigley Field, the iconic home of the Chicago Cubs. Experience the electric atmosphere, sing “Take Me Out to the Ball Game” during the seventh-inning stretch, and savor the timeless tradition of America’s favorite pastime.

Indulge in Chicago’s Culinary Delights

Giordano;s Pizza

Photo by Jonathan J. Castellon on Unsplash

Deep Dish Pizza Chicago

Photo by Manvi Mathur on Unsplash

Chicago is a food lover’s paradise, offering a wide range of culinary delights. Treat yourself to a classic Chicago-style hot dog or dig into a deep-dish pizza at one of the city’s legendary pizzerias. Don’t forget to sample the city’s diverse dining scene, from upscale restaurants to neighborhood favorites, where you can savor cuisines from around the world.

Immerse Yourself in History at the Museum Campus

Field Museum Chicago

Photo by Chris Nguyen on Unsplash

Visit the Museum Campus, located along the lakefront, and explore three of Chicago’s top museums. Marvel at the dinosaur skeletons at the Field Museum, delve into the wonders of the universe at the Adler Planetarium, and learn about aquatic life at the Shedd Aquarium. These world-class institutions offer fascinating exhibits and educational experiences for visitors of all ages.

Experience the Thrill of Jet Skiing on Lake Michigan

Jet Skiing on Lake Michigan

Photo by Shep McAllister on Unsplash

For adrenaline junkies and water sports enthusiasts, jet skiing on Lake Michigan is an exhilarating adventure. Rent a jet ski and feel the wind in your hair as you cruise along the sparkling waters, enjoying breathtaking views of the city skyline from a whole new perspective. It’s a thrilling way to cool off on a hot summer day and create unforgettable memories.

Take a Jet Speed Boat Ride

Jet Speed Boat Ride

Photo by Ray Miller on Pixabay

If you’re craving an adrenaline rush with a touch of adventure, hop on a jet speed boat for a thrilling ride along the Chicago River and Lake Michigan. Hold on tight as the boat zips through the water, making sharp turns and twists, while your experienced captain provides commentary on the city’s iconic architecture. It’s a fast-paced and exciting way to explore the city’s waterways.

Be Titled Over the Edge

360 Chicago Tilt

Photo by Patrick Foreman on Unsplash

Located on the 94th floor of the John Hancock Center, 360 CHICAGO offers visitors breathtaking views of Chicago’s iconic skyline, the picturesque lakefront, and even glimpses of four different states. It stands as the ultimate destination to experience the city’s remarkable height and grandeur. One of the most thrilling attractions at 360 CHICAGO is TILT, an exhilarating ride that takes visitors on a heart-pounding journey. Step onto a giant moving platform that gently tilts you over the edge of the building, providing an adrenaline-pumping perspective like no other. It’s a truly unforgettable experience that will leave you in awe of the city’s stunning panorama.

Ice Skate in Millennium Park

During the winter months, lace up your skates and glide across the ice at Millennium Park’s McCormick Tribune Ice Rink. Set against the backdrop of the city skyline, this picturesque outdoor rink offers a delightful winter activity for locals and visitors alike. Enjoy the festive atmosphere, the twinkling lights, and the joy of ice skating in the heart of Chicago.

Discover Chicago’s Architectural Gems

Boat tour Chicago

Photo by Dylan LaPierre on Unsplash

Chicago is renowned for its breathtaking architecture, and one of the best ways to admire it is through a boat architecture sightseeing tour. Cruise along the Chicago River and learn about the city’s rich architectural history as you pass by iconic buildings such as the Wrigley Building, the Tribune Tower, and the Willis Tower. It’s a fascinating journey that showcases the innovative designs and structures that define the city’s skyline.

Step Back in Time at a Speakeasy

Speakeasy Chicago

Photo by Laure Noverraz on Unsplash

Experience the allure of the Prohibition era by visiting one of Chicago’s hidden speakeasies. These covert establishments pay homage to the clandestine drinking spots of the 1920s and offer a unique ambiance, craft cocktails, and live entertainment. Step through secret entrances, sip on creatively concocted drinks, and immerse yourself in the vintage charm and mystique of the roaring twenties.

Embark on a Gangster Tour

Chicago has a notorious history associated with gangsters and organized crime. Embark on a gangster tour and explore the city’s dark past as you visit infamous sites like the St. Valentine’s Day Massacre, former speakeasies, and the spots where legendary gangsters once operated. Learn about Al Capone, John Dillinger, and other infamous figures who left their mark on the city’s history.

Whether you’re seeking cultural enrichment, outdoor adventures, or a taste of Chicago’s history, the Windy City delivers. As you explore the best that Chicago has to offer, remember to savor the city’s renowned cuisine, from deep-dish pizza and Chicago-style hot dogs to international culinary delights.

Chicago is a city of endless possibilities. With its captivating architecture, vibrant neighborhoods, world-class museums, thrilling water activities, and intriguing history, it promises a memorable experience for all. So, pack your bags and get ready to discover the wonders of the Windy City. Chicago awaits, ready to enchant and delight you at every turn.

Interested in more of what the East Coast has to offer, check out: Discovering The Gems Of Washington D.C

or how about The Top 10 Hidden Beaches You Never Knew Existed

and The Ultimate Guide To Must-See Sites On Your First Visit To New York City

and more of the Windy City: Gangsters & Bears

-Liam, Tripio Guru


Download the free Tripio app on iOS and Android!


2 replies

Trackbacks & Pingbacks

  1. … [Trackback]

    […] Info on that Topic: blog.tripioapp.com/exploring-the-windy-city-the-best-things-to-do-in-chicago/ […]

  2. … [Trackback]

    […] Here you will find 19298 more Information to that Topic: blog.tripioapp.com/exploring-the-windy-city-the-best-things-to-do-in-chicago/ […]

Leave a Reply

Want to join the discussion?
Feel free to contribute!

Leave a Reply