875 North Michigan Avenue – 360 Chicago Observation Deck, Chicago (must see)

Designed by the architectural talents of Skidmore, Owings & Merrill, this versatile skyscraper, formerly known as the John Hancock Center, is instantly recognizable for its narrowing silhouette and massive X-shaped braces, serving as sturdy reinforcements for its towering stature of 100 stories. Shortly after its completion in 1970, it earned the affectionate moniker "Big John", and it's no wonder why – soaring to a staggering height of 1,127 feet (or 1,506 feet, counting its antennae in the taller east tower).

Housing an array of amenities, including retail spaces, parking facilities, offices, a restaurant, and residential units, it's often likened to a self-contained city within a city. When viewed from a distance, however, the building exudes an austere yet captivating elegance, epitomizing the International style championed by the legendary Mies van der Rohe.

Much like its architectural sibling, the Willis Tower, also designed by the same architectural team, this skyscraper offers sweeping vistas that span four states (Illinois, Indiana, Michigan, and Wisconsin) on clear days. To witness this spectacle, ascend to the 94th-floor observatory, now rebranded as 360 CHICAGO (admission fee: $30). While you're there, why not savor a cocktail, beer, wine, hot beverage, or non-alcoholic refreshment at the CloudBar, an exclusive perk for General Admission ticket holders.

For the thrill-seekers in the crowd, an additional fee unlocks the tower's most exhilarating feature – The Tilt ($8). This heart-pounding experience features eight windows that tilt downward to a daring 30-degree angle, providing a unique perspective of the city below.

Bonus tip:
Just across from the skyscraper stands the Fourth Presbyterian Church, boasting English and French Gothic influences, and dating to 1914. Step inside to admire its elegant interior and tranquil courtyard – a surprisingly serene oasis just a stone's throw from Michigan Avenue.