Hi there! My name is Rifat Sheerin. I’m a dreamer who took the leap and left my career in architecture to explore the world and live life on my own terms!

I’m here to share my love for travel, and inspire you to embark on new adventures and discover the world!

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Fun Things to Do in Chicago on a Weekend

Chicago is a bustling metropolis located in the heart of the United States. Its prime location makes it an ideal destination for a weekend getaway, with easy access from various parts of the country. There are endless fun things to do in Chicago, and a quick trip will treat you to remarkable architecture, vibrant neighborhoods, culinary delights, world-class museums, etc. It’s a cool and exciting city that offers something to everyone! 

Chicago, known as the “Windy City,” is one of the best cities to visit in the USA. Nestled along the sparkling shores of Lake Michigan, this vibrant urban hub captures the essence of a truly cosmopolitan experience. It’s a must-visit destination with a breathtaking skyline, architectural wonders, and iconic landmarks. Whether you’re interested in art, culture, history, or food, or just want to experience a great city, Chicago has it all!

Are you planning a weekend escape to the Windy City? If so, don’t miss out on these fun things to do in Chicago:

1. Explore Millennium Park and Take a Selfie with "The Bean"

Bean sculpture at Millennium Park, Chicago

Millennium Park is a dynamic urban space located in the heart of Chicago. It is a beautiful park with a variety of things to see and do. This vast green oasis is not just a park but a cultural hub that seamlessly blends art, architecture, and nature. Some of the attractions you can explore here include Cloud Gate (The Bean), Crown Fountain, Jay Pritzker Pavilion, Maggie Daley Park, and Lurie Garden.

The park’s most famous attraction and a must-see is the “Bean” sculpture, officially known as Cloud Gate. Its polished surface reflects the city skyline, creating intriguing visual distortions and serving as a perfect spot for creative photos. Take a moment to marvel at the reflections and colors, and snap a selfie!

2. Stroll Along Navy Pier and Enjoy the Ferris Wheel, Carousel, and Lake Views

Navy Pier, Chicago

The iconic Navy Pier is a great place to hang out, whether you are seeking some family fun or a romantic night out by the water. You can enjoy a variety of activities and attractions here, all set against the stunning backdrop of Chicago’s lakefront. Stroll along the pier and ride the Ferris wheel for a bird’s-eye view of the city and lake. Unleash your inner child with a ride on the carousel, marvel at the shimmering waters, and soak up the lively atmosphere!

3. Indulge in a Chicago Architecture Tour While Cruising Along the Chicago River

Architecture River Cruise in Chicago showing the blend of old and new buildings.

Take a Chicago Architecture River Cruise for a fun and educational way to appreciate the Windy City’s architecture. You are in for a treat here as you gaze upon the city’s skyline coming alive with iconic architectural marvels, from towering skyscrapers to historic landmarks! It’s a great way to see the city and learn about its past at the same time.

As you cruise along the river, you’ll witness the remarkable blend of old and new, where historic buildings stand side by side with contemporary structures. It’s a visual feast that celebrates the seamless integration of architectural styles and the dynamic evolution of Chicago’s skyline.

4. Marvel at the Panoramic View of the City from the 360 Chicago Observation Deck

Breathtaking view of Chicago's skyscrapers from 360 Chicago Observation Deck.

Check out 360 Chicago Observation Deck for an expansive view of one of the most captivating cityscapes in the world. It’s perched high above the city, on the 94th floor in the John Hancock Center. You can take in breathtaking 360-degree views of the soaring skyscrapers, Lake Michigan, and bustling streets from this vantage point.

If you’re feeling adventurous, try the TILT experience at 360 Chicago Observation Deck for an extra dose of thrill! This one-of-a-kind attraction allows you to step onto a glass balcony that gradually tilts outward from the building, giving you an exhilarating sensation of leaning out over the edge high above the ground!

5. Enjoy a Stroll Along the Chicago Riverwalk at Night

One of the most fun things to do in Chicago at night is to take a stroll along the stunning Chicago Riverwalk. As the sun sets and the city illuminates, the Riverwalk transforms into a magical promenade, adorned with dazzling lights and an atmosphere brimming with enchantment.

As you walk along the Riverwalk, you’ll come across many charming cafes, lively restaurants, and trendy bars, offering a delightful array of culinary experiences and lively entertainment! The beautifully landscaped pathways, thoughtfully embellished with captivating public art installations, provide a picturesque and immersive backdrop for your nighttime adventure. Soak in the sweeping vistas of the illuminated skyscrapers, the architectural wonders that line the river’s edge, and the occasional passing boats gliding serenely through the water!

6. Satisfy Your Sweet Tooth at Nutella Cafe

Treat your taste buds at Nutella Cafe, where dreams are made of chocolate and hazelnut! It’s the ultimate sweet tooth destination, with a mouthwatering array of Nutella specialties. You’ll experience the ultimate paradise of temptation here, where Nutella takes center stage. Feast on a variety of Nutella-infused dishes, such as fluffy pancakes, velvety gelatos, and irresistible crepes, to satisfy your sweet tooth. So, if you want to add a touch of sweetness to your Chicago trip, Nutella Cafe is the place to go!

7. Embark on a Culinary Adventure and Sample Diverse Cuisines

Set off on a one-of-a-kind culinary adventure as you explore the dynamic city of Chicago. With a rich multicultural heritage and a melting pot of flavors, the Windy City offers a delectable feast like no other! From Michelin-starred establishments to innovative fusion cuisine, Chicago boasts a vibrant food scene that caters to every palate. Delight in the iconic deep-dish pizza for a quintessential Chicago experience! Or venture into a world of diverse cuisines that will tantalize your taste buds.

These are just a handful of the countless exciting and fun things to do in Chicago. I’ve curated this list to focus on the most enjoyable experiences, leaving out the less exciting museums! Chicago’s central location, impressive architecture, and diverse attractions make it a perfect destination for a weekend getaway. From exploring iconic landmarks like Millennium Park and Navy Pier to soaking in the breathtaking views from 360 Chicago and indulging in culinary delights, the Windy City has something for everyone to enjoy within a short visit!

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