Summary of Attractions in Chicago’s Loop
When you visit Chicago, make your way to the downtown district known as The Loop. This area transcends a mere urban sprawl of towering skyscrapers and cultural venues; it offers a wealth of opportunities for exploration and enjoyment.
The Loop encompasses a community area covering over one and a half square miles, bordered by the picturesque shoreline of Lake Michigan and the Chicago River. It features scenic lakeside trails, riverside promenades, expansive parks, museums, art galleries, and historical monuments.
Although you may find yourself in the heart of the city, the proximity of several beaches might lead you to believe you are in a coastal resort. Downtown Chicago truly is a vibrant area that offers an abundance of attractions. Here are fifteen exceptional activities to experience during your visit, ensuring you do not overlook any highlights.
1. Boat Cruise
Whether during the day or at night, one of the most remarkable ways to experience the Loop skyline is by taking to the water. Embark on a boat at Navy Pier, where you’ll be offered stunning views of Downtown Chicago as you navigate past. Opt for a cruise along the Chicago River or Lake Michigan to enjoy breathtaking and memorable panoramic vistas of iconic buildings and significant monuments in the Loop.
Choices range from lunch, brunch, or dinner cruises to sightseeing tours that provide educational insights into the city’s architecture. For those seeking a thrill, speedboat tours deliver an exhilarating experience as you zoom across the water at speeds of 45 mph.
For a romantic evening, witness the fireworks display at Navy Pier illuminating the night sky from a cruise boat, perhaps accompanied by dinner onboard and some dancing for a truly memorable night in the Loop.
2. The Picasso
Be sure to take a moment to appreciate The Picasso, an intriguing and unnamed sculpture that dominates Daley Plaza. Standing at approximately fifty feet tall, this substantial steel structure has been the subject of a long-standing debate regarding its intended representation.
Is it a depiction of a winged horse, a dog, or a Cubist interpretation of a chosen model? The interpretation remains subjective. The sculpture, a gift from the renowned French artist to the city, serves as an unusual yet captivating feature in the plaza. Additionally, it has made appearances in several notable films and, despite its unconventional design, proves to be surprisingly photogenic.
This striking sculpture provides a compelling focal point during festive events, farmers’ markets, and musical performances regularly held in the plaza.
3. Pizza, Popcorn & Pumpkin Pie
During your stay in Downtown Chicago, three items of local cuisine should not be missed. These iconic delicacies are either unique to the city or have been embraced by its culinary culture.
Chicago-style pizza is characterized by its double deep-dish design, with slices as thick as a slice of cake. Overflowing with rich tomato sauce, melted cheese, and a variety of other ingredients according to preference, this dish has been a beloved comfort food for over seventy years. Indulge in a slice at Pizano’s on Madison Street or Giordano’s on Randolph Street.
Equally noteworthy is Chicago-style popcorn, a delightful fusion of cheesy kernels combined with caramel-coated pieces, creating a unique flavor experience that has captivated not only Chicago but the entire state of Illinois. The origins remain somewhat of a mystery, yet the continued production of this treat brings joy to many. You can find yourself a bucketful at Garrett’s on E Madison Street.
Additionally, pumpkin pie holds the title of the official pie of Illinois. Infused with cinnamon and encased in a pastry crust to retain the creamy custard, this indulgent dessert is a must-try while in the Loop.
4. Willis Tower Skydeck
The Willis Tower, also known as Sears Tower, once claimed the title of the tallest building in the world. Although many structures have since overtaken it, its observation deck remains the highest in the US, reaching an impressive one thousand three hundred and fifty-three feet. Visitors are treated to spectacular views of Chicago and Lake Michigan through the deck’s expansive windows.
For those seeking an extra thrill, consider stepping onto The Ledge, a glass-enclosed and glass-floored platform extending four feet beyond the building – precisely one hundred and three floors above ground.
If you find yourself on The Ledge and experience a sense of vertigo, rest assured it is merely the sway of the building in the wind.
5. Lakefront Trail
The Lakeside Trail offers a picturesque nineteen-mile-long pathway crafted from asphalt and concrete, running parallel to the Lake Michigan shoreline, stretching from the South Shore Cultural Center to Kathy Osterman Beach. A portion of the trail meanders through the Loop, making it an excellent location for outdoor activities and fresh air.
For those preferring an alternative to walking or jogging, renting a bicycle or inline skates is a fun option. Access points to the trail can be found at Grant Park, E Monroe Street, and various locations throughout the Loop.
Riding or walking to the Adler Planetarium is particularly recommended, as it provides magnificent views of the Loop skyline.
6. Historic Route 66 Sign
Make your way to East Adams Street, situated just off South Michigan Avenue, and look up to discover a notable historic marker perfect for capturing a memorable photo. The iconic Route 66 sign offers a personal keepsake of this legendary highway.
Known as perhaps the most famous highway globally, Route 66 has been immortalized in various films, songs, and stories. The original highway spanned nearly four thousand miles, connecting Chicago to Santa Monica in California, beginning and concluding within the Loop.
7. Grant Park
Grant Park constitutes a sprawling three-hundred and nineteen-acre green space nestled by Lake Michigan. Its broad boulevards invite leisurely strolls, complemented by numerous flower gardens, fountains, monuments, and even a three-acre skate park.
Within its framework, Grant Park encompasses three additional parks: Millennium, Maggie Daley, and Hutchinson Field, all of which provide access to various sporting facilities and artistic installations. Moreover, two marinas, a university campus, and the esteemed Art Institute of Chicago can be found here, as well as the Petrillo Music Shell, Cloud Gate, and Buckingham Fountain. All of these attractions will be explored further on.
Throughout the year, the park plays host to vibrant food and music festivals. Consider timing your visit to coincide with events such as The Taste Chicago, Lollapalooza, or the Chicago Blues Festival, where you will witness the park bustling with visitors.
Additionally, do not overlook the Agora, an intriguing sculpture comprising over one hundred headless and armless figures, sure to offer a unique photo opportunity.
8. Buddy Guy’s Legends
While in Downtown Chicago, experiencing live Blues music is essential, and one of the premier venues to do so in the Loop is Buddy Guy’s Legends.
This establishment is owned by the venerable Blues musician Buddy Guy, a seven-time Grammy winner who has influenced countless artists throughout his illustrious career. Although he may not perform regularly at the age of eighty-one, the club showcases many other exceptional Blues musicians each night.
Additionally, the venue features an in-house restaurant serving authentic Louisiana soul food in tribute to Buddy’s heritage.
9. Cloud Gate
The Cloud Gate is a striking public sculpture that cannot go unnoticed. This one hundred-ton, polished stainless steel “bean,” inspired by a droplet of mercury, captivates all who see it.
Located in AT&T Plaza in Millennium Park, walking beneath the arch of the Gate to gaze upward reveals a unique, distorted reflection of yourself and others nearby—an unusual yet intriguing experience.
For the best perspective, position yourself at a distance from Cloud Gate to capture a stunning photograph of the Loop’s twisted skyscrapers reflected on the sculpture’s gleaming surface.
10. Loop Retail Historic District
The Loop Retail Historic District encompasses far more than conventional department stores. Spanning over twenty-six acres, this section features historic buildings and landmarks that captivate with their architecture, intriguing both inside and outside.
If shopping appeals to you, visit Macy’s on State Street, boasting eight floors of retail space, ranking as the second-largest store globally. Prior to entering, take note of the impressive two seven-ton timepieces adorning the building’s corners; once inside, the experience will undeniably consume your attention.
11. Riverside Walk
As you stroll along the Loop’s Riverside Walk, you’ll discover more than just a towpath running beside the water.
This mile and a quarter-long paved promenade is lined with beer gardens, restaurants featuring terraces, and charming cafés. More than merely a riverside walk, the Riverside Walk acts as one of the most vibrant social hubs in Downtown Chicago.
Be sure to sample a traditional handmade Italian ice cream from the nostalgic handcart, as their flavors are truly delightful.
12. The Art Institute Of Chicago
The Art Institute of Chicago, located on South Michigan Avenue within Grant Park, may appear imposing, yet within its walls lies a treasure trove of artistic masterpieces.
A full day is recommended for browsing, as there is a vast array of items to explore. The museum boasts over three hundred thousand permanent collections and regularly hosts numerous temporary exhibits throughout the year.
Notably, the artworks are not confined to American artists; the institute showcases an eclectic mix of artworks from renowned creators worldwide, encompassing various mediums such as oil paintings, watercolors, photographs, prints, textiles, and furniture.
13. Buckingham Fountain
The Clarence Buckingham Memorial Fountain, as it is formally known, stands not only as the focal point of Grant Park but as a symbolic feature of Chicago itself, ranking among the largest fountains globally.
This stunning fountain, tiers of pink marble adorned with eight seahorses, features a central jet that propels water to an impressive height of one hundred and fifty feet.
Be sure to catch the hourly water shows from mid-April through mid-October, or the evening performances when the water sprays dance in sync with lights and music—an awe-inspiring sight.
14. Petrillo Music Shell
For outdoor music festivals within the Loop, the Petrillo Music Shell in Grant Park serves as the venue of choice.
This impressive facility features a large stage and state-of-the-art sound and lighting systems designed to meet the demands of both performers and audiences. Its tiered seating accommodates five thousand guests, with additional lawn seating for thirty thousand more.
Whether enjoying live music during the Taste of Chicago or the Chicago Blues Festival, the atmosphere is sure to be electric.
15. Miller’s Pub
Indulge in dining, beverages, and perhaps even spot a celebrity at one of the Loop’s oldest establishments. Miller’s Pub, located on S Wabash Street, has been a staple in the area since 1935, with its current owners taking over in 1950.
Explore the gallery of famous personalities showcased on the walls, and then relax in one of the booths while savoring a rack of Miller’s renowned ribs or the signature HenryJ corned beef hash, accompanied by a slice of Key Lime Pie.
Visiting Miller’s Pub is a cherished tradition in the Loop; it’s an experience you won’t want to miss.
