Chicago's Oldest Locale Boasts The Best Of The City With Beaches, Luxe Shops, And Amazing Food

Bordered by the Chicago River to the south and west, and Lake Michigan to the east, the Near North Side tells the story of early Chicago. Its first permanent settlement, at the corner of the Chicago River and the Michigan Avenue Bridge, dates back to the 1780s. Through the following century, property between the river and the lake was bought by New York developers who built fortunes along the sandy shores of the lake. After the fire of 1871 destroyed almost all of early Chicago, the city's wealthiest residents and ambitious architects would come to build, own, and define the streets of the Near North Side, erecting mansions, manors, and later, skyscrapers.

The Frank Lloyd Wright-built Charnley-Persky House, on 1365 N. Astor Street, and the more notorious Playboy Mansion on 1340 N. State Parkway, which dates back to 1899, both highlight the affluence of the Near North Side. And speaking of high-end amenities: Along Lake Michigan, the one-of-a-kind Oak Street Beach is a unique urban space that defines good times on the Gold Coast. Further north, the man-made Foster Avenue Beach is a crowd-free, family-friendly beach that's just out of the district.

There's perhaps no better way to get an overview of the Near North Side and the historic architecture that defines it than with the Chicago Architecture Center's river cruise, which has been rated by USA Today readers as the nation's top boat tour. The 90-minute river cruise, which you can take for a starting price of $54, leaves hourly from 11 a.m. until 7 p.m. It boards at 112 E. Wacker Drive, at the northeast corner of Michigan Avenue and Wacker Drive, close to where the city began.

One micro-neighborhood in the Near North Side, Streeterville, is named for the eccentric skipper, George Streeter, whose boat ran aground in Lake Michigan near Superior Street in 1886. He and his family took up residence on the beached boat, claiming they were in their own jurisdiction outside of the city. Today, Ohio Street Beach's popular Caffe Olivia, (550 E. Grand Avenue) and the dining options of Navy Pier have taken up residence in Streeterville, providing plenty of opportunities to eat and play. Although the Pier might be one of the Chicago tourist traps to avoid (according to Reddit), the restaurants alone provide reasons to check it out anyway.

On the Pier at 700 E. Grand Avenue, Chef Art Smith's Reunion serves notable comfort food made by Oprah's former personal chef, with just a taste of celebrity in every bite. The restaurant is open Sunday through Thursday from 11 a.m. to 8 p.m. and Fridays and Saturdays until 9 p.m.

The district also has two Michelin-starred restaurants: Mexican-inspired Topolobampo at 445 N. Clark Street, and Indienne at 217 W. Huron Street, where Chef Sujan Sarkar uses French techniques to make the food of his homeland. Indienne offers a seven-course seasonal tasting menu starting at $135, while at Topolobampo, you can choose between an exquisitely curated selection of entrées from their menu. Advance reservations are required for both restaurants.

The product of a 1909 plan to redevelop an old row of factory buildings, Chicago's iconic Magnificent Mile provides the true shop-till-you-drop experience — especially when its hundreds of bare-branch trees are lit up at Christmastime. It's technically not the world's largest open-air shopping mall, but it might be close. Besides the endless array of popular storefronts lining each side of the boulevard, the indoor shopping center 900 North Michigan, located at the address of its name, features the outlets of 70 luxury brands on the first seven levels of a Michigan Avenue skyscraper, as well as a vast, six-level Bloomingdale's.

Off the Mile in the prestigious Gold Coast neighborhood, you'll find the upscale boutiques of some of the world's most popular designers and jewelers on Oak Street. Chanel, Marc Jacobs, Cartier, and Prada are among the labels represented. The street is also home to more specialty brands, like Morgenthal Frederics, which provides celebrity eyewear at 129 East Oak Street. Nearby, Rush Street and Walton Street — home to a grand Waldorf Astoria Hotel with an Yves Saint Laurent shop within — complete the high-end shopping trifecta.