Illinois - Chicago

Chicago, known as the Windy City, is a vibrant metropolis on the shores of Lake Michigan, offering a rich mix of architectural marvels, cultural attractions, and diverse neighborhoods. Its iconic skyline, dominated by skyscrapers like the Willis Tower and John Hancock Center, makes it a haven for architecture enthusiasts and photographers. Chicago’s bustling downtown, with Millennium Park and the famous Cloud Gate sculpture ("The Bean"), provides a dynamic urban landscape perfect for exploration.

The city's cultural scene is equally compelling, with world-class museums like the Art Institute of Chicago, thriving theater districts, and live jazz and blues clubs that pay homage to its musical roots. For food lovers, Chicago is a culinary hub, renowned for deep-dish pizza, diverse cuisine, and vibrant markets. Whether you're exploring the scenic lakefront, taking an architectural boat tour along the Chicago River, or immersing yourself in its lively street life, Chicago offers endless opportunities for photography and discovery.

Things to Do:

Millennium Park:

Millennium Park is a 24.5-acre urban oasis in the heart of downtown Chicago. Known for its innovative art, architecture, and landscape design, the park is home to the famous Cloud Gate, a reflective stainless steel sculpture affectionately called "The Bean." The park also features the Crown Fountain, two 50-foot glass towers with LED screens that display faces of Chicagoans, and the stunning Jay Pritzker Pavilion, an outdoor concert venue designed by Frank Gehry. Millennium Park is a popular spot for cultural events, seasonal outdoor ice skating, and offers plenty of photo opportunities with its modern design and skyline backdrop.

Navy Pier:

Stretching into Lake Michigan, Navy Pier is Chicago's most-visited attraction, offering a mix of entertainment, dining, and cultural experiences. It features the Centennial Wheel, a 200-foot Ferris wheel that provides stunning views of the city and the lake. The pier is home to Chicago Shakespeare Theater, Children’s Museum, and numerous restaurants, making it a destination for all ages. Navy Pier also hosts frequent fireworks shows, festivals, and boat cruises, making it a lively, year-round attraction for locals and tourists alike.

Willis Tower (formerly Sears Tower):

Willis Tower, once the tallest building in the world, remains one of Chicago’s most iconic skyscrapers. Its Skydeck, located on the 103rd floor, offers panoramic views that extend up to four states on clear days. The main attraction is the Ledge, a series of glass boxes that extend 4.3 feet from the building, allowing visitors to look directly down at the streets of Chicago from 1,353 feet above. For thrill-seekers and photographers, this provides a unique, heart-pounding perspective of the city.

Art Institute of Chicago:

The Art Institute of Chicago is one of the oldest and largest art museums in the U.S. and holds a vast collection of over 300,000 works of art. The museum is particularly known for its Impressionist and Post-Impressionist collection, featuring masterpieces such as Georges Seurat's A Sunday on La Grande Jatte, Grant Wood’s American Gothic, and works by Van Gogh, Monet, and Picasso. The museum is also home to extensive collections of ancient, modern, and contemporary art, as well as design, textiles, and sculpture. The stunning Modern Wing, designed by Renzo Piano, adds to the museum’s architectural appeal.

Chicago Riverwalk:

The Chicago Riverwalk is a scenic pedestrian pathway along the Chicago River, offering a unique way to explore the city’s architectural beauty. Stretching from Lake Michigan to Lake Street, it’s lined with cafes, bars, and public art, creating a vibrant atmosphere for visitors to enjoy. The Riverwalk also provides access to boat tours, including the famous Chicago Architecture Boat Tour, where guides explain the history and design of the city’s skyscrapers. For photographers, the Riverwalk offers unparalleled views of Chicago’s stunning skyline, especially at sunset.

Magnificent Mile:

The Magnificent Mile, located along Michigan Avenue, is Chicago’s premier shopping and dining district. Spanning 13 blocks from the Chicago River to Oak Street, the Magnificent Mile features over 450 retailers, ranging from luxury brands like Burberry and Louis Vuitton to department stores like Nordstrom. It’s also home to several historic landmarks, including the Water Tower, one of the few buildings to survive the Great Chicago Fire, and Tribune Tower, known for its unique Gothic Revival architecture. The Magnificent Mile is not just a shopping destination but a cultural experience, with plenty of upscale restaurants, galleries, and seasonal events, all set against the backdrop of Chicago’s towering skyscrapers.

Andy's Jazz Club:

Andy's Jazz Club, located in Chicago’s River North, is a top destination for live jazz, offering an intimate and authentic experience for music lovers. With performances seven nights a week, the club showcases a variety of talented musicians playing everything from classic jazz standards to modern interpretations. The cozy, laid-back atmosphere, paired with excellent acoustics, makes it a great spot for both seasoned jazz enthusiasts and casual listeners alike.

The menu complements the music with a selection of small plates like sliders and flatbreads, along with well-crafted cocktails. The candle-lit tables create a relaxed vibe, perfect for a date night or a casual group outing. Overall, Andy's Jazz Club is a must-visit for anyone looking to experience the best of Chicago’s jazz scene.

Food/Drink

Cabra:

Located on the rooftop of The Hoxton Hotel, Cabra is a lively Peruvian-inspired restaurant led by celebrity chef Stephanie Izard. With a vibrant atmosphere and stunning views of the city skyline, it’s known for its creative ceviche, tapas-style dishes, and refreshing cocktails, all served in a chic, open-air setting. The bright and colorful decor adds to the lively ambiance, making it a great spot for a unique dining experience.

Fulton Market Kitchen:

Blending art and dining, Fulton Market Kitchen is a stylish and eclectic restaurant located in the trendy Fulton Market District. The space feels like an art gallery, with murals, sculptures, and rotating exhibits providing a dynamic backdrop. The menu is equally artistic, offering a fusion of modern American dishes with global influences, paired with craft cocktails. It's a go-to spot for a unique dining experience surrounded by creativity.

Lou Malnati’s Pizzeria:

A staple in Chicago’s deep-dish pizza scene, Lou Malnati’s is famous for its buttery, flaky crust and hearty toppings. This iconic pizzeria offers the quintessential Chicago-style deep-dish pizza, often loaded with layers of cheese, fresh tomatoes, and sausage. It’s a must-visit for anyone looking to experience authentic Chicago pizza in a relaxed, family-friendly setting.

Giordano’s:

Another heavyweight in the Chicago deep-dish pizza rivalry, Giordano’s is renowned for its stuffed pizzas. With a thicker, pie-like crust and a generous amount of cheese and toppings sealed between layers of dough, Giordano’s offers a filling, indulgent take on Chicago’s favorite dish. The cozy atmosphere makes it perfect for enjoying a classic slice of Chicago’s pizza history.

Rose Lounge (for drinks):

A chic and intimate cocktail bar, Rose Lounge is a hidden gem with a sleek, modern vibe. Known for its handcrafted cocktails and upscale atmosphere, it's an ideal spot to enjoy a sophisticated drink in a cozy yet stylish setting. The lounge offers a variety of classic and signature drinks, perfect for unwinding after a day of exploring the city.

Sparrow (for drinks):

Tucked away in the Gold Coast neighborhood, Sparrow is a throwback to the 1920s with its old-world charm and vintage cocktail menu. The intimate, dimly lit space specializes in rum-based drinks and other craft cocktails, making it a favorite for those looking for a unique and atmospheric spot to grab a drink. The bar’s speakeasy vibe and expertly crafted drinks make it a great stop for cocktail enthusiasts.