Capturing The Best: Top Instagrammable Places In Chicago

Author: Maharshi Soni on Jun 05,2024
Chicago riverwalk cityscape at the twilight time

Chicago, the Windy City, is a beautiful metropolis brimming with iconic landmarks, artistic murals, scenic spots, and hidden gems, all perfect for your Instagram feed. From majestic fountains to stunning murals, here are the top Instagrammable places you must explore in Chicago, along with the best times to visit each location for that perfect shot.


The Cloud Gate (The Bean)


The Cloud Gate


Best Time to Visit: Early Morning or Late Evening, all year round


Cost: Free


No visit to Chicago is complete without snapping a photo at The Cloud Gate, affectionately known as "The Bean." Located in Millennium Park, this iconic sculpture by artist Anish Kapoor is made of highly polished stainless steel plates, giving it a mirror-like surface that reflects and distorts the city skyline and its visitors. Its unique, bean-like shape makes for a striking photo subject. Visiting early morning or late evening lets you capture the reflective surface with fewer crowds, making for a more intimate and impactful shot. Millennium Park is a treasure trove of photographic opportunities, including the nearby Crown Fountain and the Jay Pritzker Pavilion.


Buckingham Fountain


Buckingham fountain at night and Chicago downtown, Chicago


Best Time to Visit: Sunset, Spring to Early Fall (May to October)


Cost: Free


Situated in the heart of Grant Park, Buckingham Fountain is one of Chicago's most iconic landmarks. This monumental fountain, designed in the rococo wedding cake style, is one of the largest in the world. It features impressive water displays that shoot up to 150 feet in the air, incredibly mesmerizing during the evening when shimmering lights illuminate it. The fountain, built in 1927, symbolizes Lake Michigan and gives a striking view of the city skyline as its backdrop. Visit at sunset to capture the magical transition from day to night, with the illuminated fountain adding a romantic touch to your Instagram shots. For a complete experience, explore the nearby Art Institute of Chicago and Millennium Park within walking distance.


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White Cacadu Mural


Best Time to Visit: Early Morning, Summer (June to August)


Cost: Free


Art enthusiasts and street art lovers will find the White Cacadu Mural in the Pilsen neighborhood particularly captivating. Created by renowned artist Max Sansing, this classic mural features a stunning white cockatoo surrounded by intricate, colorful abstract patterns. The bold colors and detailed design make it a standout piece that pops on your Instagram feed. Pilsen is known for its rich street art culture, so stroll to discover more murals and hidden gems there. The neighborhood is also home to various authentic Mexican restaurants and cozy cafes, perfect for a delightful culinary experience.


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The Chicago Theatre


Chicago Theater sign at night


Best Time to Visit: Best Night All Year Round


Cost: Free


The Chicago Theatre, with its iconic marquee, stands as a symbol of the city's entertainment legacy. This historic venue is located on North State Street and has been a beacon of culture and arts since 1921. Its grand facade and vintage charm make it an elegant subject for Instagram photos. Capture the theater's bright lights at night or pose in front of the marquee during the day for a classic Chicago shot. The theater's surrounding area is bustling with other historic venues and jazz clubs, making it a happening cultural hub. You can take a guided tour of the theater to see its opulent interior and rich history.


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North Avenue Beach


Best Time to Visit: Sunrise, Summer (June to August)


Cost: Free


North Avenue Beach is a top destination for those who love sun, sand, and stunning cityscapes. Located along Lake Michigan, this beach provides panoramic views of the Chicago skyline. Whether youre lounging on the sand, playing beach volleyball, or biking along the Lakefront Trail, there are plenty of opportunities for dynamic and picturesque photos. Sunrise and sunset are the best times to capture the serene beauty of the beach against the cityscape. Dont miss the Castaways Bar & Grill, a ship-shaped building on the beach, for a refreshing drink or a bite to eat with a view.


Skydeck Chicago


Best Time to Visit: Late Afternoon to Sunset, all year round


Cost: USD 36


Experience unparalleled views of Chicago from the Skydeck at Willis Tower. At 1,353 feet high, the Skydeck has a thrilling perspective of the city. The Ledge, glass boxes extending out from the 103rd floor, provides a heart-pounding photo opportunity. Snap a daring shot standing on the glass with the city sprawling beneath you. This spot is perfect for those who love heights and want a unique, adrenaline-pumping photo for their Instagram. You can try to visit on a clear day for the best visibility, and you should consider arriving early to avoid long lines. The Skydeck also features interactive exhibits about Chicagos history and architecture, enriching your visit.


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Education Pavilion (The Honeycomb)


Best Time to Visit: Mid-Morning, Spring to Fall (April to October)


Cost: Free


The Honeycomb in Lincoln Park is an architectural marvel and a favorite among Instagrammers. Officially known as the Education Pavilion, this wooden structure features a honeycomb-like design that beautifully frames the city skyline and surrounding nature. The geometric patterns and natural light create appealing compositions, making it an ideal spot for creative photography. The pavilion is located within the larger Lincoln Park area, which includes the Lincoln Park Zoo, a conservatory, and picturesque walking trails, offering numerous other photo opportunities.


Greetings from Chicago Mural


Best Time to Visit: Early Afternoon, Summer (June to August)


Cost: Free


This mural in Logan Square is a nostalgic tribute to vintage postcards. The "Greetings from Chicago" mural features bold, colorful letters with iconic images of the city embedded within each letter. Its a fun and perfect scenery for a quintessential Chicago photo. After capturing your shot, explore the neighborhood's trendy cafes, bars, and boutiques for more Instagram-worthy moments. Logan Square is also known for its craft beer scene, so stop by one of the local breweries for a refreshing drink.


Chicago Riverwalk


Chicago Riverwalk


Best Time to Visit: Golden Hour, Late Spring to Early Fall (May to October)


Cost: Free


The Chicago Riverwalk offers a scenic urban retreat with picturesque views of the river and the citys architectural wonders. Stretching along the Chicago River, the Riverwalk features landscaped pathways, restaurants, bars, and public art installations. Walk along the river, take a boat tour, or relax at many riverside cafes. The bridges, boats, and cityscape reflections in the water provide endless opportunities for stunning photos. Visit during different times of the day to capture the changing light and ambiance. The Riverwalk hosts various events and live performances in the summer, adding to its serene atmosphere.


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Milton Lee Olive Park


Best Time to Visit: Late Afternoon, Late Spring to Early Fall (May to October)


Cost: Free


Head to Milton Lee Olive Park for a serene escape with spectacular views. This park is near Navy Pier and nurtures lush greenery, tranquil walking paths, and unobstructed views of the Chicago skyline and Lake Michigan. Its a peaceful spot to relax and take panoramic shots of the citys waterfront. The park is named after Milton Lee Olive III, a recipient of the Medal of Honor. It features a serene atmosphere with fewer crowds, making it an ideal location for quiet contemplation and photography.


Jacks Pumpkin Pop-Up


Best Time to Visit: Dusk, Fall (September to October)


Cost: USD 25


For a seasonal treat, visit Jacks Pumpkin Pop-Up in Goose Island during the fall. This festive spot transforms into a pumpkin wonderland with elaborate displays, corn mazes, and fun photo ops. The fall colors, twinkling lights, and creative setups make it a perfect place for capturing the essence of autumn in Chicago. From hayrides to pumpkin patches, every corner of this pop-up is the best for a new and exciting photo opportunity. Its a family-friendly event, so bring your loved ones for a day of fun and memorable pictures.


Black Wing Mural at Federales Chicago


Best Time to Visit: Midday, Summer (June to August)


Cost: Free


Located in the West Loop, the Black Wing Mural at Federales is a striking piece of art. The mural features large, black wings painted on a white wall, creating a dramatic and edgy landscape. Pose with the wings to create the illusion of flight and add a touch of urban cool to your Instagram feed. Federales is also known for its lively atmosphere and great food, making it a fun spot to hang out and snap more photos. The bar provides a unique ice shot experience where you throw your shot glass at a bell, adding a playful and interactive element to your visit.


Clean Up Your Camera Lenses


Experience the top Instagrammable places in Chicago, each with its unique charm and best time to visit. From architectural marvels and scenic vistas to murals and festive pop-ups, these spots will enhance your Instagram feed and provide unforgettable experiences in the Windy City. So grab your camera, plan your visit, and start capturing the magic of Chicago! Get the best discounts and detailed itineraries from Leisure by signing up for the Leisure newsletter for daily updates.


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