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Weekend Trip To Chicago: What To Do


Modified: December 28, 2023

by Willi Bentley



Welcome to the vibrant city of Chicago, the bustling metropolis located in the heart of Illinois. Known for its iconic skyline, rich history, and diverse culture, Chicago offers an array of experiences for visitors of all interests. Whether you’re a foodie, an art enthusiast, or an architecture lover, this city has something for everyone.


Chicago is conveniently located in the Midwest region of the United States, making it easily accessible for a weekend trip or a longer vacation. Its central location also allows for easy exploration of other parts of Illinois, including the charming suburbs, picturesque countryside, and tranquil lakes.


With its world-class museums, thriving theater scene, and expansive parks, Chicago is a city that never fails to impress. From strolling along the Magnificent Mile to taking in the breathtaking views at Millennium Park, there are countless attractions to discover during your visit.


When it comes to food, Chicago is renowned for its deep-dish pizza, Chicago-style hot dogs, and diverse international cuisine. Indulge in culinary delights at the city’s numerous famous restaurants and hidden gems, catering to every palate and budget.


Whether you’re a history buff, an outdoor adventurer, or a shopping enthusiast, Chicago has it all. Immerse yourself in the city’s rich history by visiting the iconic landmarks and exploring the vibrant neighborhoods, each with their own unique charm.


Getting around Chicago is a breeze, thanks to its efficient public transportation system. The city offers a variety of transportation options, including buses, trains, and taxis, making it easy to navigate from one attraction to another.


So pack your bags and get ready for an unforgettable weekend trip to Chicago. In this article, we will guide you through the must-visit attractions and share insider tips to make the most of your time in this magnificent city. Let’s dive in and start exploring the wonders of Chicago!


Getting to Chicago

There are several convenient ways to reach the vibrant city of Chicago. Whether you’re traveling by air, train, or car, the city is easily accessible from various locations.


If you’re coming from out of state or abroad, the fastest and most common method of reaching Chicago is by flying into one of the city’s major airports. Chicago is home to two international airports: O’Hare International Airport (ORD) and Midway International Airport (MDW). Both airports are served by numerous airlines, offering a wide range of domestic and international flights.


Once you arrive at the airport, there are several transportation options to get to downtown Chicago. The Chicago Transit Authority (CTA) operates the ‘L’ train system, which provides a convenient and affordable way to travel from the airport to downtown. Both O’Hare and Midway have ‘L’ train stations located within the airport terminals, allowing you to easily transfer to the city center.


If you prefer traveling by train, Chicago is also well-connected by rail. Amtrak operates a number of routes that stop at Chicago Union Station, located in the heart of downtown. Whether you’re coming from neighboring states or you’re planning a cross-country journey, taking the train can be a scenic and relaxing way to reach the city.


For those who prefer driving, Chicago is accessible via several major highways including I-90, I-94, and I-290. However, keep in mind that traffic can be heavy, especially during peak hours. It’s recommended to familiarize yourself with the city’s parking options and consider using public transportation or rideshare services once you arrive in downtown Chicago.


Once you’re in the city, getting around Chicago is relatively easy thanks to its comprehensive public transportation system. The Chicago Transit Authority (CTA) operates an extensive network of buses and trains, covering the entire city and its suburbs. The ‘L’ train system is particularly convenient for navigating the downtown area and reaching popular attractions.


If you prefer a more leisurely way of exploring the city, biking and walking are also great options. Chicago has an extensive network of bike lanes and pedestrian-friendly streets, making it a pedestrian and cyclist-friendly city. You can rent bikes from numerous bike-sharing companies located throughout the city, or simply take a leisurely stroll and enjoy the sights as you explore.


Now that you know how to get to Chicago and navigate the city, it’s time to dive into the exciting attractions and experiences that await you. In the upcoming sections, we’ll guide you through the must-visit places and help you plan an unforgettable weekend trip in Chicago.


Accommodation Options

When it comes to finding the perfect place to stay in Chicago, you’ll be spoilt for choice. The city offers a wide range of accommodation options to suit every budget and preference, ranging from luxury hotels to budget-friendly hostels.


If you’re looking for a luxurious experience, Chicago boasts some of the finest five-star hotels in the world. These hotels offer exceptional amenities, stunning views of the city, and impeccable service. Many of these luxury hotels are located near popular attractions, making it convenient to explore the city on foot.


If you’re traveling on a moderate budget, Chicago also offers a variety of mid-range hotels and boutique accommodations. These hotels provide comfortable rooms, great amenities, and are often located in trendy neighborhoods with easy access to transportation and attractions.


For budget-conscious travelers, there are plenty of affordable accommodation options in Chicago. Hostels and budget hotels can be found in various neighborhoods and offer a range of amenities such as shared dormitories or private rooms. Staying in these budget-friendly accommodations allows you to save money without compromising on comfort.


If you prefer a more unique and immersive experience, you may also consider booking a vacation rental or an Airbnb. With a vacation rental, you can enjoy the comforts of home while exploring the city like a local. These rentals are available in different neighborhoods and cater to various group sizes, making them ideal for families or larger groups.


When choosing your accommodation in Chicago, consider factors such as location, amenities, and proximity to public transportation. The downtown area, known as The Loop, is a popular choice due to its central location and easy access to renowned attractions. However, don’t overlook the vibrant neighborhoods outside of downtown, such as Wicker Park, Logan Square, and Lincoln Park, which offer their own unique charm and a variety of accommodations.


It’s also worth considering the amenities offered by the hotel, such as complimentary breakfast, fitness centers, and on-site dining options. Some hotels even offer spectacular rooftop bars or swimming pools, allowing you to enjoy breathtaking views of the city skyline.


Booking your accommodation in advance is recommended, especially during peak tourist seasons and major events. With a wide range of options available, you’re sure to find the perfect place to stay in Chicago, ensuring a comfortable and enjoyable visit to the Windy City.


Day 1: Exploring the Magnificent Mile

Begin your Chicago adventure by immersing yourself in the iconic Magnificent Mile, one of the city’s most famous and vibrant areas. Stretching along Michigan Avenue, this mile-long stretch is a shopper’s paradise, lined with luxury boutiques, department stores, and designer shops.


Start your day with a visit to the historic Water Tower Place, a multi-level shopping mall that offers a wide range of renowned brands and trendy boutiques. Take your time exploring the various floors, browsing through fashion, accessories, and home goods.


As you stroll along Michigan Avenue, be sure to admire the stunning architecture that Chicago is known for. Marvel at the Tribune Tower and its array of remarkable architectural features, including fragments from famous global landmarks embedded in the façade.


Make a pit stop at one of the many charming cafes or upscale restaurants along the Magnificent Mile for a quick bite to eat. Indulge in some local specialties like deep-dish pizza or a Chicago-style hot dog.


After refueling, continue your exploration by visiting the iconic John Hancock Center. Take the elevator up to the 360 Chicago Observation Deck, where you’ll be treated to breathtaking panoramic views of the city and Lake Michigan. On a clear day, you can even see across the state lines into Indiana and Wisconsin.


If you’re a history enthusiast, don’t miss the opportunity to visit the historic Wrigley Building, located just steps away from the Magnificent Mile. Admire its beautiful architecture and learn about its significance in Chicago’s architectural history.


As the day winds down, take a leisurely stroll along the Chicago Riverwalk and enjoy the scenic views of the river. Experience the picturesque bridges, beautifully landscaped areas, and charming cafes that line this vibrant part of the city.


For an evening of entertainment, consider catching a show at one of the many theaters in the area. From Broadway musicals to cutting-edge performances, Chicago’s theater scene offers a wide range of options to suit all tastes.


End your day by treating yourself to a delicious dinner at one of the Magnificent Mile’s acclaimed restaurants. From fine dining establishments to trendy eateries, you’ll find a culinary experience to delight your taste buds.


Exploring the Magnificent Mile is just the beginning of your Chicago adventure. With its luxurious shopping, stunning architecture, and vibrant atmosphere, this iconic area sets the tone for an unforgettable trip to the Windy City.


Day 2: Sightseeing in Millennium Park

On day two of your Chicago itinerary, immerse yourself in the beauty and culture of Millennium Park, a truly iconic destination in the heart of the city. This sprawling green space is home to some of Chicago’s most famous landmarks and offers a multitude of activities for visitors of all ages.


Start your day by exploring the park’s crown jewel, the Cloud Gate, more commonly known as “The Bean.” This massive stainless steel sculpture is a must-see attraction, reflecting the city’s skyline and offering unique photo opportunities. Take your time to stroll around it, marveling at the distorted reflections and interacting with the mirror-like surface.


Adjacent to the Cloud Gate, you’ll find the Jay Pritzker Pavilion, an outdoor concert venue that hosts a variety of performances, from classical concerts to popular music festivals. Check the schedule to see if any events or concerts will be taking place during your visit.


As you continue your walk through Millennium Park, make sure to visit the serene Lurie Garden. This beautifully landscaped area features a variety of plants and flowers, providing a tranquil oasis in the midst of the bustling city.


From there, head to the Crown Fountain, a unique interactive artwork that consists of two towering glass block towers. The towers display digital images of Chicago residents’ faces, spouting water from their mouths. This playful installation is a favorite spot for kids and adults alike to cool off during the summer months.


No visit to Millennium Park would be complete without experiencing a performance at the Harris Theater for Music and Dance. This state-of-the-art venue showcases a range of artistic talents, including ballet, opera, and contemporary dance.


As lunchtime approaches, make your way to the nearby Park Grill, a popular restaurant located right in the park. Enjoy a delicious meal while overlooking the park’s stunning surroundings.


After lunch, take some time to relax and soak in the beauty of the park. Find a spot on the Great Lawn and have a picnic or simply sit back and people-watch as visitors and locals enjoy the green space.


To end your day in Millennium Park, don’t miss the opportunity to catch a free concert or performance at the Jay Pritzker Pavilion. From jazz to classical music, there is always an exciting event happening during the summer months.


Sightseeing in Millennium Park offers a perfect blend of art, nature, and leisure. With its iconic sculptures, beautiful gardens, and vibrant atmosphere, this urban oasis is a true gem in the heart of Chicago.


Day 3: Exploring the Cultural Attractions

On day three of your Chicago itinerary, dive into the city’s rich cultural scene by exploring its renowned museums, galleries, and cultural attractions. Immerse yourself in art, history, and science as you visit some of the city’s most iconic cultural institutions.


Begin your cultural adventure at the Art Institute of Chicago, one of the oldest and largest art museums in the United States. Explore the museum’s vast collection, which spans thousands of years and includes famous works by artists such as Monet, Van Gogh, and Picasso. Don’t miss the opportunity to marvel at Grant Wood’s iconic “American Gothic” or to see the stunning Thorne Miniature Rooms.


Adjacent to the Art Institute is the Chicago Cultural Center, a stunning Beaux-Arts building that offers a variety of free cultural events and exhibitions. Take some time to admire the intricate mosaics, stunning stained glass, and beautiful architecture.


From there, make your way to the Museum of Contemporary Art (MCA), a must-visit destination for modern art enthusiasts. Explore the ever-changing exhibitions featuring works by both emerging and established artists. The MCA also offers engaging programming, including artist talks, performances, and film screenings.


After immersing yourself in contemporary art, it’s time to delve into Chicago’s rich architectural history. Take a guided architecture tour or explore at your own pace, marveling at the city’s iconic skyscrapers such as the Willis Tower (formerly known as the Sears Tower) and the iconic Marina City towers.


For lunch, head to the vibrant neighborhood of Pilsen, known for its Mexican heritage and vibrant arts scene. Enjoy a delicious meal at one of the neighborhood’s many authentic Mexican restaurants, and then take a stroll along 18th Street, where you’ll find vibrant murals and art galleries showcasing the works of local artists.


In the afternoon, visit the Field Museum of Natural History, known for its extensive collection of artifacts and exhibits that explore the natural world and human history. Marvel at the massive T. rex skeleton named “Sue,” discover ancient Egyptian mummies, and learn about cultures from around the world.


To end your day, take a leisurely walk along the stunning Chicago Riverwalk, where you can enjoy scenic views of the river and the city’s impressive architectural skyline. Relax at one of the many waterfront cafes or bars, taking in the beauty of the surroundings.


Exploring Chicago’s cultural attractions offers a glimpse into the city’s rich heritage and artistic expressions. From world-class museums to vibrant neighborhoods filled with art, your day will be filled with inspiration and discovery in the Windy City.


Day 4: Enjoying the Lakefront and Navy Pier

On day four of your Chicago adventure, embrace the beauty of Lake Michigan by exploring the city’s stunning lakefront and paying a visit to the iconic Navy Pier. With its picturesque views and exciting attractions, this day promises a memorable experience.


Start your day by taking a leisurely stroll along the lakefront path, which stretches for miles and offers breathtaking vistas of the city skyline and the sparkling waters of Lake Michigan. Breathe in the fresh air and enjoy the peaceful ambiance as you walk or jog along the scenic route.


As you continue your walk, make your way to Navy Pier, one of Chicago’s most popular attractions. This historic landmark offers a mix of entertainment, dining, and outdoor activities for visitors of all ages.


Explore the various attractions that Navy Pier has to offer, such as the Ferris wheel, which provides stunning views of the city and the lake. Take a ride on the carousel or test your skills at the outdoor mini-golf course. For thrill-seekers, there are also thrilling rides and games to enjoy.


Treat yourself to a delicious lunch at one of the many restaurants located on Navy Pier. From casual eateries to upscale dining options, there are plenty of choices to satisfy any craving.


After lunch, visit the Chicago Children’s Museum, located on Navy Pier. This interactive museum offers a wide range of exhibits and activities designed to engage and educate young visitors.


Continue your exploration by taking a relaxing boat tour of Lake Michigan. Choose from a variety of options, including architectural cruises or leisurely sightseeing tours. These tours offer a unique perspective of the city’s skyline and provide interesting insights into Chicago’s rich history and architecture.


In the evening, enjoy the vibrant atmosphere on Navy Pier, especially during the summer months when the pier hosts free concerts, fireworks displays, and cultural events. Grab a seat at one of the outdoor patios, indulge in a refreshing drink, and soak in the lively ambiance.


Before leaving Navy Pier, be sure to catch the nightly fireworks display, a spectacular show that lights up the sky over Lake Michigan. Find a comfortable spot along the pier or on the Ferris wheel for the best views of this dazzling spectacle.


End your day by taking a leisurely stroll along the lakefront, watching as the city lights reflect on the water. The combination of the lakefront’s natural beauty and Navy Pier’s excitement makes for a memorable Chicago experience.


Day 5: Discovering the Historic Neighborhoods

On day five of your Chicago getaway, venture beyond the downtown area and explore the city’s vibrant and historic neighborhoods. Chicago is known for its diverse communities, each with its own distinct character and charm.


Start your day by visiting the neighborhood of Lincoln Park, which is not only known for its beautiful namesake park but also for its charming tree-lined streets and historic homes. Take a leisurely stroll through the park, stopping by the Lincoln Park Zoo, one of the oldest zoos in the country, to see a variety of animals from around the world.


From there, make your way to Old Town, one of the city’s most historic and lively neighborhoods. Wander through its picturesque streets lined with Victorian-era buildings, boutique shops, and eclectic restaurants. Explore Second City, a renowned comedy club that has launched the careers of many famous comedians.


For lunch, head to the neighborhood of Wicker Park. This trendy area is known for its hipster vibe and vibrant arts scene. Indulge in a delicious meal at one of the neighborhood’s many unique and trendy restaurants, and take some time to browse through the boutique stores and vintage shops that line the streets.


After lunch, visit the Ukrainian Village, a neighborhood rich in history and culture. Explore the vibrant community and admire the neighborhood’s stunning Ukrainian Orthodox churches, colorful murals, and quaint shops.


Continue your neighborhood exploration by making your way to the historic Pullman district. This well-preserved neighborhood offers a fascinating glimpse into Chicago’s industrial history. Take a guided tour to learn about the success and struggles of the Pullman Company and the significance of the area.


End your day in Hyde Park, a neighborhood located on the south side of Chicago and home to the prestigious University of Chicago. Visit the Museum of Science and Industry, the largest science museum in the Western Hemisphere, and explore its interactive exhibits that cover a wide range of scientific disciplines.


For dinner, indulge in a delicious meal at one of Hyde Park’s many restaurants that offer diverse cuisines from around the world. Enjoy a relaxing evening before heading back to your accommodation.


Exploring Chicago’s historic neighborhoods allows you to experience the city’s rich cultural heritage while immersing yourself in its vibrant communities. From picturesque streets to unique shops and mouthwatering cuisine, each neighborhood offers its own delightful surprises.


Day 6: Shopping and Dining Experiences

On day six of your Chicago itinerary, indulge in a day of shopping and dining, immersing yourself in the city’s vibrant culinary and retail scenes. Chicago offers a plethora of options, from luxury shopping districts to diverse culinary delights.


Start your day by exploring the iconic shopping district of Oak Street. Known as the “Rodeo Drive of Chicago,” Oak Street is home to high-end boutiques, designer shops, and luxury brands. Spend some time browsing through the offerings and treat yourself to a few indulgent purchases.


After shopping, it’s time to satisfy your appetite at one of Chicago’s renowned eateries. Head to Fulton Market, a trendy neighborhood known for its culinary scene. Enjoy a leisurely brunch or lunch at one of the chic restaurants that offer a variety of cuisines, from farm-to-table fare to international fusion dishes.


Once you’ve refueled, make your way to the Magnificent Mile, a shopper’s paradise. This renowned stretch of Michigan Avenue is lined with department stores, luxury retailers, and flagship stores, offering a wide range of shopping options. Take your time exploring the various shops and landmarks along this iconic avenue.


As the day continues, make a detour to the vibrant neighborhood of Bucktown. This trendy area is known for its unique boutiques and independent shops, offering a wide array of clothing, accessories, and home decor items. Discover hidden gems and support local businesses as you browse through the eclectic offerings.


While you’re in the area, take some time to explore Wicker Park, a neighboring hipster enclave. Here, you’ll find a mix of vintage stores, record shops, and quirky boutiques. Spend some time wandering through the streets, appreciating the artistic and bohemian atmosphere of the neighborhood.


For dinner, immerse yourself in Chicago’s diverse culinary scene by visiting one of the city’s many internationally influenced neighborhoods. Consider trying authentic Italian cuisine in Little Italy, devouring Middle Eastern flavors in Andersonville, or savoring Mexican delights in Pilsen.


End your day with a nightcap at one of Chicago’s renowned cocktail bars or rooftop lounges. Sip on handcrafted cocktails while enjoying stunning skyline views or cozy up in a speakeasy-style bar for a more intimate experience.


Shopping and dining experiences in Chicago offer a blend of luxury, diversity, and culinary delights. From high-end boutiques to unique local shops, and from world-class restaurants to hidden neighborhood gems, this day is sure to satisfy your shopping cravings and culinary desires.


Day 7: Outdoor Adventures and Parks

On the final day of your Chicago itinerary, immerse yourself in the city’s outdoor beauty by exploring its parks and engaging in various outdoor activities. Chicago is blessed with a multitude of green spaces, offering opportunities for relaxation, recreation, and exploration.


Start your day by visiting Grant Park, often referred to as “Chicago’s front yard.” This expansive park is home to several famous landmarks, including Buckingham Fountain, one of the largest fountains in the world. Take a leisurely stroll around the fountain and admire its magnificent displays.


From Grant Park, head to the nearby Museum Campus, a picturesque area nestled along the lakefront. Take a walk along the waterfront, enjoying the stunning views of Lake Michigan and the city skyline. Visit the Field Museum and the Shedd Aquarium, both located within the Museum Campus, to learn about natural history and marine life.


Continue your outdoor adventure by making your way to the Chicago Lakefront Trail, a scenic path that stretches for 18 miles along the shore of Lake Michigan. Rent a bike and pedal along the trail as you take in the breathtaking views and feel the refreshing lake breeze. Alternatively, you can also opt for a leisurely walk or jog along the well-maintained pathway.


For a unique experience, visit Northerly Island, a peninsula located along the lakefront that has been transformed into a nature park. Explore the prairie-like landscape, hike the trails, and enjoy the serene beauty of the area. Keep an eye out for bird sightings, as Northerly Island is known for its diverse bird population.


For lunch, have a picnic in one of the city’s beautiful parks. Pack a basket with delicious treats and find a cozy spot in Lincoln Park or Millennium Park. Enjoy the tranquility of the green spaces as you savor your meal.


In the afternoon, make your way to the 606 Trail, a unique elevated park that was once an elevated railway line. Walk or bike along this urban oasis as you take in the sights and sounds of the surrounding neighborhoods.


To end your day, head to one of Chicago’s scenic beaches along Lake Michigan. Relax on the sandy shores, soak up the sun, or take a refreshing swim in the lake. Juneway Beach, North Avenue Beach, and Oak Street Beach are popular choices, offering a lively atmosphere and beautiful views.


As your day comes to a close, reflect on your outdoor adventures in Chicago and the beauty of its parks and lakefront. From peaceful green spaces to exhilarating bike rides, this day allows you to connect with nature and appreciate the outdoor splendor of the city.



Congratulations! You have reached the end of your exciting and fulfilling journey through the vibrant city of Chicago. Over the course of seven days, you have explored iconic landmarks, delved into the city’s rich cultural scene, enjoyed shopping and dining experiences, and immersed yourself in the beauty of Chicago’s outdoor spaces.


From the bustling streets of the Magnificent Mile to the tranquil parks and lakefront, Chicago has showcased its diverse offerings and captivating charm. The city’s deep cultural roots, stunning architecture, and thriving neighborhoods have provided you with a truly unforgettable experience.


Throughout your adventure, you have discovered the wonders of Millennium Park, explored the city’s renowned museums and cultural institutions, and indulged in the culinary delights of Chicago’s diverse neighborhoods. You have embraced the energy of downtown Chicago and ventured beyond, uncovering the hidden gems of historic districts and vibrant communities.


As you reflect on your time in Chicago, you will carry with you memories of iconic landmarks like “The Bean” in Millennium Park, the scenic views of Lake Michigan from Navy Pier, the cultural treasures found in the city’s museums and galleries, and the vibrant atmosphere of neighborhoods filled with art, history, and culinary delights.


Whether it was your first time visiting Chicago or a return trip, this city has undoubtedly left a lasting impression on you. The Windy City has showcased its unique blend of Midwest charm, cosmopolitan allure, and warm hospitality, making it a destination that captivates the hearts of visitors from around the world.


As you bid farewell to Chicago, take with you the memories, experiences, and newfound fondness for this dynamic city. Keep the spirit of adventure alive and carry the lessons learned during your time here wherever your future travels may take you.


Thank you for embarking on this journey through Chicago with us. We hope your time in the city has been filled with joy, discovery, and countless unforgettable moments. Until we meet again, safe travels and may your future adventures be as remarkable as your experience in the vibrant city of Chicago!