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What To Do On A Day Trip To Chicago


Modified: December 28, 2023

by Jorie Andre



Welcome to the vibrant city of Chicago, where a day trip is never short of exciting experiences. Known as the Windy City, Chicago offers a perfect blend of rich history, stunning architecture, world-class museums, and delicious food. Whether you’re a local or a visitor, there’s always something new and exciting to discover in this bustling metropolis.


From the iconic skyline to its diverse neighborhoods, Chicago has a unique charm that appeals to all types of travelers. Whether you’re a history buff, an art enthusiast, a foodie, or simply looking to take in the sights, this city has something for everyone. So, grab your walking shoes and get ready to explore the best that Chicago has to offer on your day trip.


In this guide, we’ll take you through some of the must-see attractions and activities that will make your day trip to Chicago an unforgettable experience. From cultural landmarks to scenic spots, you’ll get a taste of the city’s highlights and immerse yourself in the local culture. So, let’s dive in and discover the wonders that await you in the beautiful city of Chicago.


But first, let’s start with a visit to one of Chicago’s most iconic landmarks – Millennium Park.


Exploring Millennium Park

Millennium Park is a magnificent urban oasis located in the heart of downtown Chicago. Spanning over 25 acres, this iconic park is a popular destination for both locals and tourists alike. It offers a plethora of attractions and activities that showcase the beauty of Chicago and its commitment to art and culture.


One of the standout features of Millennium Park is the Jay Pritzker Pavilion, a stunning outdoor concert venue designed by architect Frank Gehry. The pavilion hosts a variety of free events and concerts throughout the summer months, making it a perfect spot to relax and enjoy live music under the open sky.


No visit to Millennium Park would be complete without a picture in front of Cloud Gate, also known as “The Bean.” This iconic stainless steel sculpture, designed by artist Anish Kapoor, reflects the skyline of Chicago and creates a unique visual experience. Visitors can walk around and underneath the sculpture, marveling at the distorted reflections and capturing incredible photographs.


Another highlight of the park is the Crown Fountain, a pair of 50-foot towers with LED screens displaying the faces of Chicago residents. During the summer months, children and adults alike can cool off in the shallow reflecting pool located between the towers, as water cascades down their faces. The Crown Fountain is a lively interactive artwork that embodies the spirit of community and playfulness.


For those seeking a bit of nature in the city, Lurie Garden is a hidden gem within Millennium Park. This beautifully landscaped garden features a variety of native plants and flowers, providing a peaceful escape from the bustling city streets. Take a leisurely stroll along the winding paths and discover the serene beauty of the garden.


In addition to these attractions, Millennium Park also hosts rotating art installations, temporary exhibits, and seasonal events throughout the year. It’s a dynamic and ever-changing space that offers something new to discover with each visit.


Whether you’re interested in architecture, art, or simply enjoying the outdoors, Millennium Park is a must-visit destination in Chicago. With its stunning sculptures, picturesque gardens, and vibrant atmosphere, this park captures the essence of the city and provides a memorable experience for all who visit.


Visiting The Art Institute of Chicago

Located in Grant Park, The Art Institute of Chicago is a world-renowned museum that houses an extensive collection of artworks spanning thousands of years. With its diverse range of exhibits, it is considered one of the finest art museums in the world.


The museum’s collection includes artworks from various periods and cultures, including ancient Egyptian artifacts, European paintings, American art, contemporary works, and much more. It is home to iconic masterpieces such as Vincent van Gogh’s “The Bedroom,” Grant Wood’s “American Gothic,” and Georges Seurat’s “A Sunday on La Grande Jatte.”


Upon entering the museum, visitors are greeted by the striking bronze lion statues that flank the steps. These majestic sculptures have become symbolic of the Art Institute and are a popular spot for taking memorable photographs.


Once inside, you can explore the museum’s vast collection organized into different galleries. From ancient sculptures to modern installations, there is something to captivate every art enthusiast. The museum also offers guided tours, audio guides, and interactive exhibits to enhance your visit and provide a deeper understanding of the artworks.


A highlight of the Art Institute is the Thorne Miniature Rooms, a collection of intricately designed miniature models of different historical interiors from around the world. These exquisitely detailed rooms give visitors a unique perspective on domestic environments throughout history.


If you’re interested in American art, be sure to visit the newly renovated American Wing. The space showcases American paintings, sculptures, decorative arts, and furniture, providing a comprehensive overview of the nation’s artistic heritage.


Aside from its permanent collection, the Art Institute also hosts temporary exhibitions featuring works by renowned artists and themes of cultural significance. These exhibitions offer a chance to explore different artistic styles, movements, and perspectives.


When you need a break, you can indulge in a meal or grab a cup of coffee at one of the museum’s on-site restaurants or cafes. They offer a variety of dining options, from casual bites to fine dining experiences, ensuring you can refuel while enjoying the art-filled atmosphere.


Whether you’re an art aficionado or simply appreciate beautiful and thought-provoking creations, a visit to the Art Institute of Chicago is an enriching and inspiring experience that should not be missed. The museum’s extraordinary collection and stunning architecture make it a cultural gem in the heart of the city.


Taking a Stroll along Navy Pier

Navy Pier is a beloved landmark and entertainment destination on the shores of Lake Michigan. Stretching out into the water, this iconic Chicago attraction offers a wide array of activities, attractions, and stunning views of the city skyline.


One of the main draws of Navy Pier is its lively atmosphere and vibrant energy. As you stroll along the pier, you will encounter a bustling mix of locals and tourists, all eager to explore the various attractions and enjoy the breathtaking scenery.


The Pier boasts numerous shops, boutiques, and souvenir stores, perfect for picking up unique Chicago mementos or indulging in some retail therapy. From clothing and accessories to artwork and collectibles, you can find a wide range of items to suit any taste.


Food lovers will also delight in the diverse dining options available on Navy Pier. From casual food stands to upscale restaurants, there is something for every palate. Enjoy classic Chicago favorites like deep-dish pizza or indulge in international cuisine from around the world.


One of the most iconic features of Navy Pier is the Ferris wheel. Towering over the pier, the Ferris wheel offers panoramic views of the city and Lake Michigan, providing a unique and unforgettable perspective. You can take a ride on the Ferris wheel and take in the stunning vistas while enjoying a gentle breeze off the water.


In addition to the Ferris wheel, Navy Pier offers a variety of other attractions and entertainment options. You can catch a show at the Chicago Shakespeare Theater, visit the Chicago Children’s Museum, or enjoy a thrilling ride at the Pier Park amusement park. The IMAX theater is also a popular destination, offering immersive movie experiences on a massive screen.


For those seeking a more leisurely experience, Navy Pier has several parks and public spaces where you can relax and soak in the ambiance. Whether it’s sitting on one of the many benches, strolling along the water’s edge, or enjoying a picnic in the park, there are plenty of opportunities to unwind and enjoy the beautiful surroundings.


Navy Pier is also a hub for boat tours and cruises, allowing visitors to explore the city’s stunning skyline from the water. From architecture tours to dinner cruises, you can choose from a variety of options to suit your interests and preferences.


Whether you’re looking for entertainment, dining, shopping, or simply a picturesque setting to enjoy the beauty of Chicago, a stroll along Navy Pier is a quintessential experience. With its lively atmosphere, stunning views, and plethora of activities, this iconic destination has something for everyone, making it a must-visit during your day trip to Chicago.


Discovering The Magnificent Mile

The Magnificent Mile is a stretch of North Michigan Avenue in Chicago that is renowned for its upscale shopping, luxurious hotels, renowned restaurants, and iconic landmarks. It is a vibrant and bustling district that offers a unique and memorable experience for visitors.


Stretching over a mile, this iconic avenue is lined with a mix of high-end department stores, designer boutiques, flagship stores, and specialty shops. Whether you’re in search of luxury brands or unique local finds, The Magnificent Mile has it all. From fashion and accessories to home goods and electronics, there’s something for every shopper.


In addition to shopping, The Magnificent Mile is also home to a variety of renowned dining establishments. From fine dining experiences to casual eateries, you can indulge in a wide range of culinary delights. Whether you’re craving a juicy steak, fresh seafood, or international cuisine, you’ll find a restaurant to satisfy your taste buds.


As you explore The Magnificent Mile, you’ll notice the distinctive architecture that defines the area. This stretch of North Michigan Avenue is adorned with historic buildings, modern skyscrapers, and iconic landmarks. Marvel at the Gothic Revival style Tribune Tower or admire the sleek design of the John Hancock Center with its panoramic views from the observatory.


If you’re interested in art and culture, The Magnificent Mile has you covered. The area is home to a number of renowned art galleries, showcasing a diverse range of works from local and international artists. You can also catch a show at one of the theaters or music venues, where you can enjoy performances ranging from Broadway shows to live music concerts.


In addition to shopping and culture, The Magnificent Mile also offers a variety of events and festivals throughout the year. From holiday parades to summer concerts and art fairs, there’s always something happening along this vibrant avenue.


For those looking for a break from shopping and sightseeing, there are several parks and public spaces along The Magnificent Mile where you can take a leisurely stroll or relax and soak in the atmosphere. The beautiful Chicago Riverwalk is also nearby, offering scenic views and outdoor dining options.


Whether you’re a fashion enthusiast, a food lover, an art connoisseur, or simply looking to soak in the vibrant atmosphere, exploring The Magnificent Mile is a must during your day trip to Chicago. With its blend of upscale shopping, iconic landmarks, and a lively ambiance, this district is synonymous with style and luxury.


Enjoying a Cruise on the Chicago River

One of the best ways to experience the beauty and architectural wonders of Chicago is by taking a cruise on the Chicago River. Embarking on a river cruise allows you to marvel at the city’s stunning skyline and learn about its fascinating history and architectural achievements.


As you glide along the Chicago River, you’ll be treated to breathtaking views of the city’s iconic skyscrapers, including the Willis Tower (formerly known as the Sears Tower), the Tribune Tower, and the Trump International Hotel and Tower. The river provides a unique perspective, allowing you to see the intricate details and design elements of these majestic structures up close.


One of the highlights of a river cruise is the opportunity to learn about Chicago’s architectural history from knowledgeable tour guides. They will point out significant buildings and explain their architectural styles, influences, and historical significance. You’ll gain a deeper understanding of how Chicago has evolved and become a hub for innovative and groundbreaking architecture.


During the cruise, you’ll also pass through the iconic Chicago River bridges. These engineering marvels play a crucial role in the city’s transportation system, allowing boats to navigate through the river and connecting different parts of the city. As the bridges open and close to accommodate passing boats, it’s an exciting and unique sight to witness.


As you enjoy the river cruise, you can choose from a variety of options and experiences. There are architectural tours that focus specifically on Chicago’s renowned buildings and their architects, highlighting their architectural significance. Other cruises offer a combination of architecture, history, and even sunset or fireworks views, providing a memorable and scenic experience.


Many river cruise companies provide comfortable seating, panoramic windows, and informative commentary in multiple languages, ensuring an enjoyable and educational experience for all visitors. Snacks and beverages are often available onboard, allowing you to relax and soak in the beauty of the city as you cruise along the river.


Whether you’re a history buff, an architecture enthusiast, or simply looking for a unique way to explore Chicago, a river cruise is a must-do activity. It offers a different perspective of the city, showcasing its architectural wonders and providing insights into its rich history. So sit back, relax, and enjoy the breathtaking views as you cruise along the Chicago River.


Touring The Field Museum

The Field Museum is a world-renowned natural history museum located in Chicago. With its extensive collection and educational exhibits, it offers a fascinating glimpse into the natural world and the rich cultural history of different civilizations.


Upon entering the museum, visitors are greeted by Sue, the largest and most complete T. rex skeleton ever discovered. This iconic exhibit sets the stage for the awe-inspiring journey that awaits inside the museum.


The Field Museum’s collection spans millions of years, covering a wide range of disciplines including paleontology, anthropology, botany, zoology, and geology. From ancient fossils to intricate artifacts, there is something to captivate every visitor.


One of the highlights of the museum is the Ancient Egypt exhibit, which takes visitors on a journey through one of the world’s most fascinating ancient civilizations. Explore the tombs of pharaohs, marvel at intricate jewelry and hieroglyphics, and learn about the fascinating rituals and beliefs of the ancient Egyptians.


For those interested in dinosaurs and prehistoric creatures, the Evolving Planet exhibit is a must-visit. It showcases the incredible diversity and evolution of life on Earth, featuring fossil specimens and interactive displays that bring extinct creatures back to life.


The museum also houses the Grainger Hall of Gems, which showcases a stunning collection of rare and beautiful gemstones from around the world. Marvel at the vibrant colors and exquisite craftsmanship on display, and learn about the geological processes that create these precious treasures.


Another fascinating exhibit is the Hall of Native North Americans, which explores the rich cultural heritage and diversity of indigenous peoples in North America. From intricately woven textiles to intricately carved totem poles, this exhibit provides a deeper understanding and appreciation of the Native American cultures.


The Field Museum also hosts special exhibitions that cover a wide range of topics, from ancient civilizations to biodiversity and climate change. These temporary exhibits offer a chance to explore new and exciting areas of science and culture.


In addition to its exhibits, the museum also offers educational programs and interactive displays that engage visitors of all ages. From hands-on activities for children to lectures and workshops for adults, there are opportunities to learn and discover at every turn.


Before you leave, be sure to visit the museum’s gift shop, where you can find unique souvenirs, books, and educational toys related to the exhibits.


A visit to The Field Museum is a journey through time and a celebration of the wonders of the natural world. With its diverse collection and engaging exhibits, it offers a memorable and educational experience for all who visit, making it a must-see destination during your day trip to Chicago.


Experiencing Skydeck Chicago

If you’re looking for a thrilling and panoramic view of the city, a visit to the Skydeck Chicago is a must. Situated on the 103rd floor of the iconic Willis Tower, formerly known as the Sears Tower, the Skydeck offers breathtaking views of the Chicago skyline and beyond.


One of the main attractions at the Skydeck is The Ledge. These glass-floored observation decks extend out from the building, providing an exhilarating experience as you step onto the transparent floor and look down at the bustling city below. The Ledge offers a unique perspective and unparalleled photo opportunities, allowing you to capture stunning images with the cityscape as your backdrop.


As you take in the panoramic views, interactive exhibits and displays throughout the Skydeck provide interesting information about the history and architecture of Chicago. Learn about the construction of the Willis Tower and the engineering feats that made it possible to create such a tall and impressive structure.


In addition to the breathtaking views, the Skydeck also offers multimedia presentations and telescopes that allow you to zoom in and explore specific points of interest in the city. You can learn about the different neighborhoods, landmarks, and historical sites that make Chicago unique.


For an extra touch of excitement, consider visiting the Skydeck during sunset or in the evening. The changing colors of the sky as the sun sets and the city lights illuminate create a magical atmosphere that is truly unforgettable.


While the views are undoubtedly the main attraction, the Skydeck also houses a gift shop and a variety of dining options. From grabbing a quick snack to enjoying a full meal with a view, you can relax and take in the surroundings as you indulge in some delicious food or pick up a souvenir to remember your visit.


Given its popularity, the Skydeck can get crowded at times. To avoid long lines and ensure a smoother experience, consider purchasing your tickets in advance or visiting during off-peak hours. This way, you’ll have more time to soak in the breathtaking views and fully appreciate the beauty of Chicago from above.


With its thrilling elevation, breathtaking views, and immersive exhibits, the Skydeck Chicago offers a one-of-a-kind experience that should not be missed. Whether you’re a local or a visitor, stepping onto The Ledge and witnessing the awe-inspiring vistas will leave you with lasting memories of your time in the Windy City.


Trying Deep Dish Pizza

No visit to Chicago would be complete without indulging in the city’s most famous culinary creation – deep dish pizza. Known for its thick, buttery crust and generous layers of cheese, sauce, and toppings, deep dish pizza is a true Chicago institution.


Deep dish pizza is a unique style of pizza that originated in the city in the 1940s. It is characterized by its deep, round pan, which allows for a substantial amount of toppings and cheese to be piled on top of the buttery crust. The sauce is usually rich and chunky, creating a delicious combination of flavors.


When it comes to trying deep dish pizza, Chicago offers a plethora of renowned pizzerias that have perfected this iconic dish. From long-standing institutions to new and innovative pizza joints, there’s no shortage of options to satisfy your deep dish pizza cravings.


One of the most famous spots is Pizzeria Uno, where the deep dish pizza was first created. Their original recipe is still a fan favorite, with a tall, crispy crust and layers of gooey cheese. Lou Malnati’s Pizzeria is another beloved institution that is known for its buttery crust and tangy tomato sauce.


Giordano’s is another popular choice, famous for its stuffed deep dish pizza. This style takes the traditional deep dish concept to the next level by adding an additional layer of dough and more filling, creating a truly indulgent experience.


If you prefer a thinner crust, there are also pizzerias that offer a “thin crust” version of deep dish pizza. These pizzas still feature a slightly thicker crust compared to traditional thin crust, but they offer a lighter and crispier alternative for those who prefer a less doughy experience. Some notable thin crust deep dish pizza spots include Gino’s East and Pequod’s Pizza.


While deep dish pizza is undoubtedly the star of the show, many pizzerias in Chicago also offer other delicious menu items such as classic thin crust pizza, Italian pasta dishes, and salads. This ensures that there is something for everyone, even if deep dish pizza isn’t your go-to choice.


Whether you’re a pizza connoisseur or simply a food lover looking to try a quintessential Chicago dish, trying deep dish pizza is a must during your day trip to the Windy City. Be prepared for a hearty and satisfying meal that will leave you craving another slice. Just be sure to bring your appetite because this pizza is not for the faint of heart.


Exploring Grant Park and Buckingham Fountain

Grant Park, often referred to as Chicago’s “front yard,” is a sprawling urban green space located in the heart of the city. It offers a peaceful retreat from the bustling streets and a variety of attractions to enjoy. One of the park’s most iconic features is the stunning Buckingham Fountain.


Buckingham Fountain is a grand centerpiece that stands as one of the largest fountains in the world. This majestic fountain features intricate sculptures and a central jet that shoots water up to 150 feet in the air. The fountain is particularly enchanting during its hourly water displays, when streams of water dance to the sounds of music and colorful lights illuminate the surroundings.


Adjacent to Buckingham Fountain is the Clarence F. Buckingham Memorial Plaza, a beautifully landscaped area that provides a serene setting for leisurely strolls or picnics on the lush grass. From here, you can enjoy panoramic views of both the fountain and the Chicago skyline as a backdrop.


As you explore Grant Park, you’ll come across numerous well-maintained walking paths and gardens to wander through. The park is home to various monuments, sculptures, and art installations that add to its allure. You may encounter the impressive Agora, a collection of 106 massive iron sculptures, or the serene Cancer Survivors’ Garden, a peaceful oasis that honors those who have battled cancer.


For art enthusiasts, the Art Institute of Chicago is conveniently located within Grant Park. This world-class museum houses an extensive collection of artworks spanning various periods and cultures. A visit to the museum allows you to delve into the realm of art and discover masterpieces from around the world.


Grant Park is also a popular venue for outdoor concerts, festivals, and events. During the summer months, you can catch live music performances, film screenings, and cultural celebrations in the park. The Taste of Chicago festival, an annual culinary event featuring a vast array of local food vendors, is also held in Grant Park, attracting food lovers from near and far.


When you need a break, there are several outdoor seating areas and designated picnic spots where you can relax and soak in the tranquil atmosphere. Pack a blanket, some snacks, and enjoy a leisurely picnic while taking in the beauty of the surrounding nature.


Exploring Grant Park and admiring the grandeur of Buckingham Fountain is an essential experience during your day trip to Chicago. Whether you’re interested in art, nature, or simply seeking a peaceful escape, Grant Park offers a perfect blend of scenic beauty and cultural attractions that will leave you mesmerized.



As we come to the end of our day trip to Chicago, it’s clear that this vibrant city has so much to offer. From iconic landmarks to world-class museums, from delectable cuisine to breathtaking views, Chicago truly has something for everyone.


We started our journey by exploring Millennium Park, immersing ourselves in its unique art installations and enjoying the serene beauty of its gardens. Next, we ventured into The Art Institute of Chicago, where we were captivated by the vast collection of artworks spanning centuries and cultures.


We then took a stroll along Navy Pier, savoring the lively atmosphere and soaking in the stunning views of the city skyline. The magnificence of The Magnificent Mile awaited us with its upscale shopping, renowned restaurants, and architectural wonders.


Continuing our adventure, we experienced the thrill of a river cruise, marveling at the impressive buildings and bridges that dot the Chicago River. The Skydeck at the Willis Tower provided us with a breathtaking perspective of the city, its towering skyscrapers, and the beauty of Chicago’s urban landscape.


Indulging in deep dish pizza, we satisfied our taste buds with a beloved Chicago culinary tradition. And finally, we explored Grant Park and admired the beauty of Buckingham Fountain, reveling in the serenity of this urban oasis.


Chicago has proven to be a city that seamlessly blends history, culture, architecture, and natural beauty. Its welcoming atmosphere, vibrant energy, and endless opportunities for exploration make it a perfect destination for a day trip.


Whether you’re a local or a visitor, Chicago offers a multitude of experiences that will leave lasting memories. So, when you find yourself in the Windy City, be sure to embark on this day trip itinerary, and you’ll be treated to a delightful adventure through the best the city has to offer.