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The star of scenic Streeterville is without question Chicago’s historic Navy Pier. Sometimes referred to as the “People’s Pier,” this more than 100-year-old stretch of spectacular lakefront encompasses more than 50 acres of parks, restaurants, sightseeing and dining cruise boats, retail shops, and other attractions. Chief among these offerings is Offshore Rooftop & Bar, the world’s largest rooftop venue. Measuring a staggering 36,000 square feet (including a 20,000 square foot terrace), this convivial all-season/all-weather venue boasts seven fire pits, a full-service bar, a world class restaurant helmed by Executive Chef Michael Schrader and, most impressively, jaw-dropping views of Lake Michigan and the Chicago skyline.


Another nearby attraction is 360 Chicago, an observation deck offering sensational views of Chicago from the 94th floor — 1,000 feet above the famed Magnificent Mile. While there enjoy Bar 94, a modern bar and café, serving classic cocktails and mouthwatering nibbles, and TILT, a patently ‘not for the faint at heart’ experience that literally tilts visitors out from the 94th floor so that they can look down on Chicago’s legendary architecture and lakefront.


Other highlights of Streeterville include the Museum of Contemporary Art where guests can take in innovative and experimental exhibits. Winter’s Jazz Club offers a classic listening room where live singers perform six nights a week. Ohio Street Beach is one of Chicago’s rare north-facing beaches and don’t miss the Peninsula Hotel’s rooftop Z Bar, which was recently named one of World’s Best Hotel Bars thanks to stellar hand-crafted cocktails and even more stellar views of Chicago’s many wonders.

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