What to Do, See and Eat in Chicago


Whether you’re a foodie, a shopping fanatic, an art enthusiast, or a culture buff, the Windy City never disappoints. Welcome to Chicago!

What comes to mind when someone say’s, “Hey I’m going to Chicago what should I do?” Deep dish pizza and the food scene, absolutely! Take in views of the incredible skyline from Lake Michigan, no doubt! Visit locations like millennium park, navy pier and the magnificent mile… well this is just too easy!

After what felt like an eternity, I finally had the opportunity to return to the vibrant and bustling city of Chicago — affectionately known as the “Windy City” alongside the travel group Choose Chicago. Let me tell you, it was an exhilarating experience that left me excited to share every moment.

Perched gracefully along the shores of Lake Michigan, Chicago has always held a special place in the hearts of those who love when city and nature work in harmony.

But beyond its breathtaking natural landscapes, Chicago is a treasure trove of cultural wonders, stemming from its rich history that echoes in every street and neighbourhood. From the vibrant arts scene to the delectable culinary delights, there is something to cater to every taste, quite literally!

Whether you’re a foodie, a shopaholic, an art enthusiast, or a culture buff, the Windy City never disappoints.

Why My Love for Chicago is Deeper Than Their Pizza

As I embarked on my second Chicago trip, I couldn’t wait to rediscover some of my all-time favourite activities and have some new experiences too. Having visited before the pandemic, I wondered if the city had changed, but it embraced me with the same warmth and charm as before.

There is an unmistakable liveliness in the air, as locals and visitors alike weave their way through the dynamic streets, creating an atmosphere that makes you feel right at home and almost part of something.

From indulging in the city’s iconic deep-dish pizzas and savouring mouthwatering dishes from around the world, to exploring the colourful neighbourhoods that hold the city’s beating heart, there’s an abundance of delights awaiting your discovery.

Join me as I take you on a quick tour of Chicago’s endless charm. I promise you’ll fall in love with the Windy City just as I did, all over again!

Where to Go in Chicago

Attractions in Millennium Park

Cloud Gate

📍 201 E Randolph St, Chicago, IL 60602, United States

Nestled in Millennium Park, Cloud Gate, fondly known as “The Bean,” is an enchanting stainless-steel sculpture that perfectly captures Chicago’s charm. Designed by artist Anish Kapoor, this iconic landmark reflects the city’s skyline and the joy of its visitors.

It stands 33 feet tall and 66 feet long, inviting everyone to touch and interact with its smooth surface, creating unforgettable memories. Unveiled in 2006, the Bean’s seamless construction from 168 stainless steel plates makes it an engineering marvel.

As I revisited it, I couldn’t help but be captivated once again by the laughter and delight of people around me. The best part? This free activity is a true symbol of Chicago’s inclusive spirit, welcoming everyone to revel in its gleaming wonder.

Crown Fountain

📍 201 E Randolph St, Chicago, IL 60602, United States

In the heart of Millennium Park lies the captivating Crown Fountain and if you don’t see the water when you arrive just wait! Designed by Jaume Plensa, this urban oasis features two towering glass block towers reflecting the diversity of Chicago’s residents.

The interactive fountain showcases faces of Chicagoans spouting water playfully into a reflecting pool below. Unveiled in 2004, it’s a harmonious blend of art and technology, drawing people of all ages together to cool down and connect in the city’s warm spirit.

As the sun sets, the illuminated portraits create a magical ambiance, leaving visitors enchanted by the fountain’s delightful charm. A true symbol of inclusivity and togetherness, the Crown Fountain embraces everyone with open arms, making it an unforgettable Chicago experience.

Lurie Garden

📍 220 E Monroe St, Chicago, IL 60601, United States

A serene escape amidst the urban bustle of Millennium Park, Lurie Gardens stands as an enchanting oasis that beckons visitors seeking tranquility in the heart of Chicago.

This botanical gem, designed by the renowned Gustafson Guthrie Nichol, is a haven of natural beauty that effortlessly weaves together prairie-style plantings with the city’s majestic skyline as a backdrop and inviting green space.

As I strolled through the winding pathways, I found solace in the meticulously curated landscapes that change with each passing season. Lurie Gardens is more than just a garden; it’s a living tapestry of colours and textures, a place to reconnect with nature amidst the vibrant energy of the city.

Whether you seek a peaceful respite or a chance to immerse yourself in the beauty of the outdoors, Lurie Gardens is a must-visit destination that captivates the senses and nourishes the soul.

*If you’re interested in parks check out Hyde Park, Jackson Park, Humboldt Park, Grant Park, Lincoln Park and of course the rest of Millennium Park!

The Architecture River Cruise

📍 112 E Wacker Dr, Chicago, IL 60601 | Website

I almost guarantee that you cannot mention you are visiting Chicago without someone telling you about taking an architecture tour on the Chicago architecture river cruise. I would most definitely be the person saying, “you have to do this!”

Discover the marvels of Chicago’s architecture on Chicago’s First Lady Cruises, operated by the Chicago Architecture Center. With boats accommodating up to 250 passengers, enjoy stunning views from open-air upper decks, comfortable lower cabins, and upscale restrooms.

On this 1.5-hour tour, expert guides will lead you through the city’s iconic landmarks and skyscrapers, revealing the rich architectural history that defines Chicago’s skyline.

The guides are volunteers and ooze charisma and passion for the city’s rich history like the great Chicago fire and what makes Chicago famous.

The loading point is right off the river walk and walking distance from any hotel downtown Chicago. Embrace the urban adventure as you sail along the Chicago River, witnessing the perfect fusion of design and innovation in this captivating city.

The Chicago Botanic Garden

📍 1000 Lake Cook Rd, Glencoe, IL 60022, United States | Website

Escaping the vibrant city life to find solace in the breathtaking beauty of the Chicago Botanic Garden is a true delight and one you might not think of right away. Just a short drive from the bustling streets, this verdant oasis offers a serene retreat.

The Chicago Botanic Garden is ranked among Chicago’s most popular tourist attractions and is a 385-acre living plant museum situated on nine islands in the Cook County Forest Preserves.

As we wandered through its lush gardens, I felt a sense of calm washing over me, far removed from the hustle and bustle of urban living.

Featuring 27 display gardens and five natural habitats including Mary Mix McDonald Woods, Barbara Brown Nature Reserve, Dixon Prairie, the Skokie River Corridor, and the Lakes and Shorelines you are sure to discover something new every season.

The garden’s vast expanse boasts a myriad of themed gardens, each a testament to the wonders of horticulture, showcasing an exquisite array of flowers, plants, and landscapes.

Whether strolling through the vibrant Rose Garden or finding peace in the Japanese Garden’s tranquility, every step offered a new discovery. Embracing the gentle breeze and vibrant colours, I revelled in the joy of reconnecting with nature in this green space.

Chicago Riverwalk

The Chicago Riverwalk is a lively waterfront promenade that weaves its way through the heart of downtown Chicago, offering a captivating experience like no other. You can’t visit Chicago without taking a stroll down the riverwalk!

Quick Note: The Chicago River, famously dyed green on St. Patrick’s Day, is not only a picturesque waterway but also an integral part of the city’s history and transportation network.

This vibrant stretch connects Lake Michigan to the heart of downtown Chicago.

Along the Riverwalk, you’ll find a variety of inviting restaurants and bars, perfect for indulging in the culinary delights of Chicago’s food scene. Whether you’re a food enthusiast or just seeking a leisurely waterfront experience, the Chicago Riverwalk has something for everyone.

From scenic river cruises to the lively ambiance of Navy Pier, there’s no shortage of fun and exploration along this picturesque pathway.

One of the key figures in ensuring the Riverwalk’s public accessibility was former Chicago Mayor Richard M. Daley. His vision for the city included making the waterfront spaces open to the public, emphasizing the importance of public access to Chicago’s natural assets.

Under Mayor Daley’s leadership, the city undertook a series of projects to expand and improve the Riverwalk, investing in its infrastructure and amenities. Through careful planning and collaboration with various stakeholders, the Riverwalk gradually transformed into a lively urban space that attracted locals and visitors alike.

The Chicago Riverwalk offers a unique perspective on the city, where modernity meets nature, and urban living harmonizes with the tranquility of the waterside.

Navy Pier Sunset Dinner Cruise

📍 600 E Grand Ave, Chicago, IL 60611, United States | More Here

A visit to Navy Pier is an absolute must for anyone exploring Chicago. This iconic destination, perched along the shores of Lake Michigan, offers an abundance of entertainment and breathtaking views of the city skyline.

As the sun starts to dip below the horizon, there’s no better way to experience the magic of the Chicago skyline than by embarking on a sunset dinner cruise on Lake Michigan. We had the chance to hop aboard the Spirit of Chicago and it was quite a nice experience. Dinner was buffet style, there was a bar and a DJ to keep things lively.

Sailing through the glistening waters, you’ll be treated to an ever-changing panorama of the city’s architectural wonders, beautifully illuminated against the dusky sky.

Before (or after) setting sail, make sure to stop by the Navy Pier beer garden, where you can savour refreshing brews and indulge in delicious bites, all while basking in the inviting lakefront atmosphere.

The combination of a picturesque Lake Michigan sunset and the city skyline makes for an unforgettable experience that will leave you in awe of Chicago’s timeless beauty. I recommend both this trip and the Architecture river cruise as they both really offer a different view of the city!

The Art Institute of Chicago

📍 111 S Michigan Ave, Chicago, IL 60603, United States | Website

The Art Institute of Chicago, nestled in the heart of Chicago’s downtown loop, is an absolute must-visit location for art enthusiasts and culture seekers alike. I didn’t get a chance to visit this time but it truly was one of my favourite stops the first time I visited Chicago!

The Iconic Lion Statues:

The Art Institute is famously guarded by two magnificent bronze lion statues that flank the main entrance on Michigan Avenue. These majestic lions have become a symbol of the museum and are beloved by both locals and visitors.

Renowned as one of the most celebrated art museums in the world, the Art Institute of Chicago houses an impressive and diverse collection that spans centuries and continents.

Heavily Featured in Pop Culture:

The Art Institute has made several appearances in popular culture, most notably in the 1986 movie “Ferris Bueller’s Day Off.” In the film, the main characters visit the museum to see Georges Seurat’s painting “A Sunday on La Grande Jatte.”

Ferris Bueller’s Day Off is Scotty’s favourite movie so when we were able to visit back in 2019 this was a must visit stop to snap this iconic shot!

If you don’t stop and look. around once in a while, you could miss it.”— Ferris Bueller.

Notable Impressionist Collection:

The museum boasts an impressive collection of Impressionist and Post-Impressionist art, including iconic works by artists such as Claude Monet, Vincent van Gogh, Pierre-Auguste Renoir, and Georges Seurat.

Largest Collection of Thorne Miniature Rooms:

The Art Institute houses the largest collection of Thorne Miniature Rooms, meticulously crafted and exquisitely detailed dioramas that depict historical interiors from various periods and regions. This was one of my favourite exhibits! Truly this one draws you in and leaves you wondering how the artists can create such detail in such a small piece. Amazing!

From priceless masterpieces by renowned artists to thought-provoking contemporary works, the museum offers a rich tapestry of artistic expression. Whether you’re drawn to classical paintings, awe-inspiring sculptures, or mesmerizing photography, the Art Institute of Chicago caters to every artistic taste.

Exploring this treasure trove in the windy city’s downtown Chicago is a journey that promises to ignite your creativity and deepen your appreciation for the transformative power of art.

The museum’s dedication to preserving and showcasing the world’s artistic heritage makes it an indispensable cultural landmark, a true gem that enriches the soul and leaves an indelible mark on every visitor’s heart.

One of the Oldest Museums in the US:

The Art Institute of Chicago was founded in 1879 and is one of the oldest and largest art museums in the United States. Over the years, it has continuously expanded its collection and facilities, solidifying its place as a world-class institution.

If this is something that interests you, you might also be interested in The Chicago Museum of Natural History, The Chicago Cultural Center, Chicago Children’s Museum, Chicago History Museum or The National Museum of Mexican Art (a museum dedicated to Mexican art and the rich culture that is very much alive in the city)

Lincoln Park Zoo

📍 Chicago, IL 60614, United States | Website

Situated in Chicago’s Lincoln Park, the Lincoln Park Zoo is a cherished urban oasis that delights visitors of all ages. On that note, Chicago in my opinion has a ton to offer families with small children. However, it is to be noted I haven’t had a chance to visit this attraction in downtown Chicago but it has been mentioned countless time in my research!

As one of the oldest zoos in the United States, dating back to 1868, this free-admission zoo holds a special place in the city’s history. Home to a diverse array of animal species from around the world, the zoo offers a captivating and educational experience.

From majestic lions and playful primates to adorable penguins and graceful giraffes, every visit promises an encounter with the wonders of the animal kingdom. As you stroll through its lush pathways, the Lincoln Park Zoo presents the perfect opportunity to connect with nature and engage in conservation efforts.

Whether you’re a family looking for a fun day out or a solo traveler seeking a moment of serenity, this treasured Chicago gem offers a delightful escape from the bustling city and a chance to connect with the beauty and diversity of the natural world.

If this is something that interests you, you might also be interested in the Chicago zoo and don’t forget to save some time to take in Lincoln Park! There are even tours available.

Garfield Park Conservatory

📍 300 N Central Park Ave, Chicago, IL 60624, United States | Website

Somewhere I have on my list for the next time I visit the Windy City is The Garfield Park Conservatory.

The Garfield Park Conservatory is a stunning urban oasis in Chicago, Illinois. With its 2-acre greenhouse and outdoor gardens, it offers a vibrant and lush escape from the city’s hustle and bustle.

Home to thousands of plant species from around the world, the conservatory provides a captivating and educational experience for visitors of all ages. A true gem in the city, Garfield Park Conservatory is a haven of natural beauty and tranquility the photos truly speak for themselves!

Willis Tower Skydeck Chicago (Or 360 Chicago Observation Deck)

📍 233 S Wacker Dr, Chicago, IL 60606, United States (Formally known as the Sears Tower – you’ll learn this on the Architecture Boat Tour!) | Skydeck Website

The Willis Tower Skydeck in Chicago is an iconic attraction that offers breathtaking views and thrilling experiences. As one of the tallest buildings in the Western Hemisphere, it stands as a testament to Chicago’s architectural prowess.

The Skydeck, located on the 103rd floor, provides unobstructed views of the city’s magnificent skyline and Chicago river and extends into the stunning expanse of Lake Michigan. Visitors can step out onto “The Ledge,” a glass balcony that juts out from the building, offering a heart-pounding sensation of floating above the city.

The 360 CHICAGO Observation Deck, formerly known as the John Hancock Center Observatory, is another popular attraction in Chicago. Located on the 94th floor of the 875 North Michigan Avenue building, this observation deck offers stunning 360-degree views of the city.

Visitors can marvel at the city’s skyline, Lake Michigan, and the vast urban landscape from a breathtaking vantage point. One of the highlights of the deck is “TILT,” an exhilarating experience that tilts visitors outward from the building’s façade, providing a unique and adrenaline-pumping perspective.

Whether you’re a first-time visitor or a seasoned local, the 360 CHICAGO Observation Deck and Willis Tower Skydeck promises an unforgettable and awe-inspiring encounter with the Windy City’s beauty.

The Magnificent Mile

📍 Michigan Avenue

The Magnificent Mile in Chicago is a renowned stretch of North Michigan Avenue, running from the Chicago River to Oak Street. It holds significant cultural, commercial, and historical importance, making it one of the city’s most iconic destinations.

Shopping Mecca:

The Magnificent Mile is a shopper’s paradise, boasting a remarkable concentration of luxury boutiques, department stores, and flagship retail outlets. It is home to some of the world’s most prestigious brands, making it a premier shopping destination for both locals and tourists.

Cultural Landmarks:

The Magnificent Mile is dotted with numerous cultural landmarks and attractions. These include the historic Water Tower, one of the few buildings that survived the Great Chicago Fire of 1871, now home to the City Gallery in the Historic Water Tower; and the Chicago Tribune Tower, known for its Gothic Revival architecture and the collection of stones from famous landmarks around the world embedded in its walls.

Hotels and Fine Dining:

The area is brimming with elegant hotels and fine dining establishments, making it a hub for luxury accommodation and culinary experiences. Visitors can enjoy a wide range of world-class dining options, from gourmet restaurants to upscale cafes and bars.

Festivals and Events:

Throughout the year, the Magnificent Mile hosts various festivals, events, and holiday celebrations, including the popular Magnificent Mile Lights Festival during the holiday season.

Tourist Attractions:

The Magnificent Mile is within walking distance of several prominent Chicago attractions, such as Millennium Park, the Art Institute of Chicago, and Navy Pier, making it a central point for exploring the city’s cultural and entertainment offerings.

Economic and Tourism Hub:

The Magnificent Mile is a significant economic engine for Chicago. Its high concentration of retail and dining establishments, coupled with its popularity among tourists, contributes significantly to the city’s tourism and economy.

Overall, the Magnificent Mile is not only a shopper’s delight but also a symbol of Chicago’s vibrant energy, rich history, and thriving cultural scene. Its importance as a premier destination for shopping, dining, and cultural experiences has cemented its status as one of the most famous and celebrated streets in the United States. We were so impressed with the gardens along the mile and the way the city takes care of their streets!

What to Eat in Chicago

Deep Dish Pizza

Lou Malnati’s for Deep Dish Pizza | Instagram | Website

📍 439 N Wells St, Chicago, IL 60654, United States (The location we visited)

Deep dish pizza, a beloved culinary masterpiece, has become synonymous with the city of Chicago. Its roots can be traced back to the 1940s when a pair of Italian immigrants, Ike Sewell and Ric Riccardo, sought to create a pizza that would stand out from the thin-crust versions commonly found in the United States. In 1943, they opened Pizzeria Uno, offering a unique twist on the classic pizza by crafting a pie with a deep, thick crust that resembled more of a pie than a traditional flat pizza.

Why You Should Visit Lou Malnati’s

Lou Malnati’s is a legendary name in the world of Chicago deep dish pizza. Established in 1971 by the son of Rudy Malnati, one of the original creators of deep dish pizza at Pizzeria Uno, Lou Malnati’s continues to be a beloved institution in the city’s food scene.

With a commitment to quality and using the finest ingredients, Lou Malnati’s has garnered a loyal following of pizza enthusiasts who flock to its various locations across Chicago and beyond. This is also now a chain so you can find this restaurant wherever you are in the city!

The restaurant’s deep dish pizza, known for its buttery crust, generous layers of mozzarella cheese, and zesty tomato sauce made from fresh tomatoes, has become a hallmark of the Chicago-style deep dish experience. I have to say the individual size was the PERFECT serving size for one person and I can’t recommend their signature pies enough!

Over the years, Lou Malnati’s has expanded its menu to include a variety of toppings and options, but its commitment to the authentic deep dish tradition remains unwavering.

Lou Malnati’s has played a significant role in preserving and popularizing Chicago’s deep dish pizza heritage, ensuring that this culinary masterpiece continues to be celebrated and cherished by generations to come.

For locals and tourists alike, a visit to Lou Malnati’s is an essential stop on their journey through Chicago’s rich food history and a chance to savour the unmistakable taste of this iconic dish in the city where it all began! I was hesitant at first thinking this meal might be too heavy but trust me, you’ve got to try it!

*A lot of other people will tell you Giorgano’s is also a great option! I haven’t been there but through the grape vine I’ve heard good things.

Chicago Style Hot Dogs

📍 *Really all over downtown Chicago

Hot dogs are big in Chicago due to a combination of historical factors, cultural influences, and the city’s unique culinary traditions. One of the key reasons is the significant influence of immigrants, particularly from Germany and Poland, who brought their sausages and hot dog recipes to the city in the late 1800s and early 1900s.

Chicago’s diverse population embraced these sausages and adapted them to suit local tastes, leading to the creation of the “Chicago-style hot dog.”

This iconic version typically includes an all-beef frankfurter served on a poppy seed bun and topped with a specific combination of toppings, such as yellow mustard, chopped onions, bright green relish, sliced tomatoes, a dill pickle spear, sport peppers, and a sprinkling of celery salt.

The result is a colorful and flavorful combination that has become synonymous with Chicago’s hot dog scene.

Additionally, the hot dog became a popular street food during the early 20th century, especially during the Great Depression when it was an affordable and filling meal. It also gained popularity at sporting events and local attractions, further solidifying its place in the hearts of Chicagoans. Hello Chicago Cubs!

Over time, Chicago’s hot dog culture has grown into a cherished culinary tradition that locals take pride in, and visitors eagerly seek out as a quintessential Chicago experience.

From classic hot dog stands to gourmet variations, hot dogs remain an integral part of the city’s food culture, reflecting the fusion of immigrant influences and Chicago’s vibrant culinary scene.

Garrett Popcorn and the “Chicago Mix”

📍 173 Michigan Ave, Chicago, IL 60601, United States (This is the one on Michigan Avenue but there are many more if you search in Google Maps) | Instagram | Website

If you’ve never had Chicago style popcorn you can now purchase it at Costco but there is nothing like the true popped goodness of the OG Garrett Popcorn in Chicago!

Garrett Popcorn is famous in Chicago for several reasons, including its rich history, high-quality ingredients, and unique flavours. The story of Garrett Popcorn began in 1949 when a small family business opened its doors near Chicago’s iconic State Street. They perfected their signature blend of sweet and savoury popcorn, which quickly gained popularity among locals and visitors alike.

One of the key factors contributing to its fame is the exceptional quality of the popcorn. Garrett’s uses only premium, non-GMO kernels and cooks them in small batches using copper kettles. The result is popcorn with a perfect balance of crunchy texture and buttery flavour, setting it apart from other popcorn varieties.

Another reason for Garrett Popcorn’s fame is its distinctive and mouthwatering flavours. The “Chicago Mix” is their most famous offering, which combines the sweet and crunchy Caramel Crisp with the savoury and cheesy Cheese Corn. This delectable combination of flavours has become a symbol of Chicago’s unique popcorn culture.

“Chicago-style popcorn” typically refers to the Garrett Popcorn “Chicago Mix,” as well as other popcorn creations in the city that blend sweet and savoury flavours. It has become an essential treat for locals and a popular souvenir for visitors to take home.

Moreover, Garrett Popcorn has established a strong connection with the city, becoming an integral part of Chicago’s food scene and a treasured tradition. The distinct flavours, high-quality ingredients, and the story of this family-owned business have made Garrett Popcorn an enduring icon in Chicago’s culinary landscape, earning its place as a must-try delicacy for anyone visiting the Windy City.

Coffee Shops Downtown (Blue Bottle Café)

📍 435 N Michigan Ave, Chicago, IL 60611, United States

Blue Bottle Cafe is a popular coffee shop chain with locations across the United States, including one in Chicago. Blue Bottle Cafe is known for its commitment to serving high-quality, freshly roasted coffee. They source their beans from carefully selected coffee farms around the world and roast them in-house to ensure maximum freshness and flavour.

The cafe offers a variety of coffee beverages, including espresso-based drinks, pour-over coffee, and cold brew. They also provide a selection of pastries and snacks to complement their coffee offerings.

Blue Bottle Cafe places a strong emphasis on the art of coffee brewing, and their baristas are skilled in preparing each cup with precision and care. The cafe’s minimalist and modern aesthetic provides a relaxed and inviting atmosphere for coffee enthusiasts and casual visitors alike.

There are so many lesser known coffee shops in Chicago and many patios to enjoy in the summer months. I loved the aesthetic of this one and the matcha we ordered was extremely smooth!

*In 2019 Scotty and I also went to Hero Coffee Bar and loved it!

The Purple Pig

📍 444 Michigan Ave, Chicago, IL 60611, United States | Purple Pig Instagram | Website

This is the restaurant I still dream about to this day – actually I think Scotty mentioned the other day he was there in a dream haha. I don’t know if it was our hunger at the time but The Purple Pig for me is a must visit restaurant in downtown Chicago.

The Purple Pig is a popular and renowned Mediterranean-inspired eatery that has gained a significant following among locals and tourists alike for its unique and flavourful dishes.

The Purple Pig has been praised for its creative and inventive menu, which focuses on seasonal ingredients and a celebration of Mediterranean flavours. Their menu features a wide array of small plates, cheeses, charcuterie, and main dishes that are perfect for sharing and exploring a diverse range of tastes.

The restaurant’s location on North Michigan Avenue, close to the Magnificent Mile, makes it a popular destination for both locals and visitors exploring the downtown area. This city is extremely walkable!

Over the years, The Purple Pig has garnered numerous accolades and recognition in the culinary world, solidifying its place as one of Chicago’s must-visit dining establishments. Its history of offering unique and delightful dishes has made it a cherished part of Chicago’s vibrant food scene. As with any restaurant, please check for the most up-to-date information and operating status before planning a visit.

Beatnik on the River

📍 180 N Upper Wacker Dr, Chicago, IL 60606, United States | Beatnik Instagram | Website

I wish we were able to go back to Beatnik on the River but sadly time didn’t allow for it. However, I loved it so much the first time I had to include it!

Beatnik on the River is a stylish restaurant located in Chicago, Illinois, situated along the Chicago River. It is the sister restaurant of the original Beatnik in the West Town neighborhood of Chicago.

The history of Beatnik on the River begins with the success and popularity of the original Beatnik, which is known for its bohemian and eclectic atmosphere, inspired by the Beat Generation of the 1950s and ’60s. The original Beatnik became a beloved dining spot in Chicago, known for its vibrant decor, exotic cocktails, and globally inspired cuisine.

Building on the success of the first location, Beatnik on the River opened its doors to patrons seeking a similar experience but with a unique waterfront setting. The restaurant’s location along the Chicago River offers picturesque views and a serene ambiance, adding to the allure of the dining experience.

Beatnik on the River’s menu features a blend of Mediterranean, Middle Eastern, and North African influences, resulting in a diverse array of dishes with bold flavours and unique combinations. The menu includes a variety of small plates, shareable dishes, and enticing entrees, all prepared with fresh and seasonal ingredients.

The restaurant’s interior design is so eye catching and showcases an eclectic and bohemian style, with a mix of vintage and modern elements, plush fabrics, and lush greenery, creating an inviting and enchanting atmosphere for diners.

Beatnik is a hip place to go anytime of year but with the patio over looking the Chicago River it is must visit during the warmer months.

Cindy’s Rooftop

📍 12 S Michigan Ave, Chicago, IL 60603, United States | Instagram | Website

One of the coolest spots for a view of Millennium Park is Cindy’s Rooftop! I wish I could have ordered a cocktail here again so it’s back on my list for my third visit!

Cindy’s Rooftop is a popular rooftop bar and restaurant located atop the Chicago Athletic Association Hotel in downtown Chicago. The rooftop is named after Cindy Pritzker, an American philanthropist and member of the prominent Pritzker family, who was involved in the development of the hotel.

The history of Cindy’s Rooftop is tied to the Chicago Athletic Association building, which was originally constructed in 1893 as a private men’s club for Chicago’s elite. The building itself is a historic landmark and a fine example of Venetian Gothic architecture. For many years, the Chicago Athletic Association was a hub for social activities, sports, and exclusive events.

Courtesy of Condé Nast Traveler

In 2015, the hotel underwent a major renovation and was transformed into a boutique hotel, carefully preserving its historic charm while adding modern amenities. As part of the restoration, the rooftop was converted into a stunning and stylish open-air space, which is now known as Cindy’s Rooftop.

Cindy’s Rooftop quickly became a must-visit destination for locals and tourists alike due to its spectacular views of Millennium Park, Lake Michigan, and the city’s skyline. The rooftop bar and restaurant offer a sophisticated yet relaxed atmosphere, making it a perfect spot to enjoy cocktails, shareable plates, and breathtaking vistas.

The significance of Cindy’s Rooftop lies in its unique location and the breathtaking views it offers. The rooftop provides an unparalleled perspective of some of Chicago’s most iconic landmarks, including Millennium Park’s Cloud Gate (“The Bean”) and the Art Institute of Chicago.

Surf and Turf at Smith and Wollensky

📍 318 N State St, Chicago, IL 60654, United States

Smith & Wollensky Chicago is a well-established steakhouse located in the heart of downtown Chicago, Illinois. The history of Smith & Wollensky dates back to 1977 when Alan Stillman and Ben Benson founded the first Smith & Wollensky restaurant in New York City.

In 1997, the Chicago location of Smith & Wollensky opened its doors along the Chicago River, offering stunning views of the city’s iconic skyline. The restaurant quickly became a favourite destination for locals and visitors seeking high-quality steaks and a classic American steakhouse experience.

Smith & Wollensky is renowned for serving premium USDA Prime steaks, which are hand-cut and dry-aged on-site to achieve exceptional tenderness and flavour. Their menu features a variety of steak cuts, including filet mignon, ribeye, New York strip, and porterhouse, along with other classic steakhouse offerings like prime rib and lamb chops.

In addition to their steaks, Smith & Wollensky also serves an array of seafood dishes, including fresh oysters, lobster, and salmon, providing options for guests with varied tastes.

The restaurant’s elegant and sophisticated ambiance, combined with its commitment to serving top-quality meats and seafood, has earned Smith & Wollensky Chicago a reputation as one of the city’s premier steakhouses. It continues to be a favoured destination for business dinners, special occasions, and steak enthusiasts looking for an unforgettable dining experience in downtown Chicago.

This was our “going all out dinner” and it absolutely did not disappoint!

Where to Stay in Chicago

The Loews Hotel Chicago

📍 455 N Park Dr, Chicago, IL 60611, United States | Book Your Stay Here

Loews Chicago Hotel is a luxurious and stylish hotel located in the Streeterville neighbourhood of downtown Chicago, Illinois. The hotel is situated just steps away from the Magnificent Mile, providing guests with easy access to some of the city’s most popular shopping, dining, and cultural attractions.

I found that this hotel was not only affordable but central to everything we wanted to access downtown.

Loews Chicago Hotel offers upscale accommodations and a wide range of amenities for both leisure and business travellers. The hotel features modern and well-appointed guest rooms and suites, providing a comfortable and inviting stay for guests. The rooms are equipped with modern conveniences, including high-speed internet access and flat-screen TVs. The beds were comfortable and I found the hotel as a whole to be extremely clean and well maintained (note this location is new).

One of the highlights of the hotel is its stunning views of Lake Michigan and the city skyline, offering guests picturesque vistas right from their rooms.

In addition to its luxurious rooms, Loews Chicago Hotel offers a variety of on-site dining options. The hotel’s flagship restaurant, ETA Restaurant + Bar, serves contemporary American cuisine with a focus on locally sourced ingredients. We ate at ETA both mornings and our meals were incredible!


If you are looking for a patio experience this location also has their aptly named Streeterville Social Eatery. Streeterville Social is an outdoor rooftop terrace serving up alfresco dining, libations, and the perfect scene for a table for two or a celebration. When we were there, there was also a retirement party taking place!

Loews Chicago Hotel also provides excellent facilities for meetings, events, and weddings. The hotel offers several versatile event spaces equipped with state-of-the-art technology and a dedicated events team to ensure a successful and memorable experience.

The hotel’s amenities include a fully equipped fitness centre, perfect for guests looking to stay active during their stay. But I’m also sure you will get this grind while walking the city! Looks at steps on health tracker.

Overall, Loews Chicago Hotel offers a sophisticated and upscale experience in the heart of downtown Chicago, making it an excellent choice for both leisure and business travellers looking for a chic and convenient stay in the Windy City.

As with any hotel, I recommend checking with Loews Chicago Hotel directly or visiting their website for the most up-to-date information on their amenities and services! We loved our stay and I would absolutely book again at this hotel.

Some Final Thoughts

In conclusion, Chicago is undeniably a city like no other, beckoning travellers with its unique charm and boundless energy. From the iconic Magnificent Mile and its luxury shopping to the cultural gems found within world-class museums like The Art Institute of Chicago and the vibrant flavours of deep dish pizza and the famed Chicago-style hot dogs, the city offers an abundance of experiences that cater to all interests.

Beyond the bright lights and towering skyscrapers, Chicago’s rich history and architectural heritage shine through its diverse neighbourhoods and storied landmarks. Millennium Park’s Cloud Gate and Crown Fountain, the serenity of Lurie Gardens, and the picturesque Riverwalk paint a vivid tapestry of a city that continuously evolves while honouring its past.

But it’s not just the sights that make Chicago extraordinary; it’s the people and their warm Midwest hospitality. Whether you’re indulging in a sunset dinner cruise on Lake Michigan, exploring the bustling Navy Pier, or savouring the delights of The Purple Pig, the city’s dynamic energy is always palpable.

So, whether you’re a first-time visitor or returning to the Windy City after a hiatus, Chicago has something for everyone to enjoy and cherish. Its diverse offerings, unmatched culinary scene, and thriving cultural landscape make it a destination that captures the hearts of all who wander its streets.

So, pack your bags and let Chicago sweep you off your feet. Embark on a journey that will leave you with unforgettable memories and a lasting love for this vibrant and inviting city.

Chicago awaits you with open arms, ready to share its warmth and wonders with all who dare to explore. Come and discover the magic of the Windy City – a place where every moment is an invitation to experience something extraordinary.

And let me know what you think!

Want more travel content? Check out the 15 Most Instagrammable Places in Paris for your next visit!

Safe Travels!


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I'm Amanda – blogger, content creator, photographer,  videographer,  and founder of Below the Blonde: a space for vibrant, ambitious women who are looking to live their best lives in style.









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