What to Do in the Windy City

72 Hours in Chicago


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Chicago has always looked ahead. Chicago’s stockyards popularized the time zone and revolutionized commerce. When the streets filled with waste, Chicago lifted itself five feet off the ground so it could build underground sewers. When it burned in 1871, it was rebuilt almost entirely in brick. As the 20th century dawned, it became the fastest-growing city in the world, the aorta of American commerce, a city faced with no choice but to innovate or squander its limitless potential. Its skyline, public parks, and streets are the collective answer of generations of city planners, engineers, and architects to the same question: “what’s next?”

As time passed, the innovative becomes the historically significant, resulting in one of the most architecturally rich cities in the world. From the Chicago School to Frank Lloyd Wright, the history of Chicago is the history of architecture in the United States. As an added bonus Chicago has all the things that make a city great, like nightlife, culture and excellent food.

72-chicago-gear-patrol-stay Where to Stay

The Langham is not only arguably the most luxurious hotel in Chicago, but its central location ensures that guests won’t have to venture too far afield to see and do everything. Plus, it’s in a Miles Van Der Rohe building. If you’re catching a Cubs game, the Old Chicago Inn is place to stay — it’s four blocks from Wrigley Field and has authentic old-school vibes (because it’s old). If you’re looking for a more modern atmosphere, the Ivy Boutique Hotel is an excellent choice for those looking for four-star accommodations. It’s pricey, but the amenities and location (right next to the Magnificent Mile) match the price point.

72-chicago-gear-patrol-pizza Where to Eat

It’s no surprise that a city built on stockyards would have incredible steakhouses. Gene & Georgetti is one of the best. Obviously, no guide to Chicago cuisine would be complete without a pizza place. There are a ton of upscale pizza places in Chicago. Skip them all and go to Pequod’s Pizza, which serves the best deep dish pizza in the city. Their secret? Caramelized crust. Likewise, quality Italian food is also abundant. Bruna’s distinguishes itself through excellent food and by actually being in Little Italy. On the other end of the spectrum, diners seeking more experimental food should head to Alinea, one of only two restaurants in Chicago to be awarded three Michelin stars. For an after-dinner drink, head to The Violet Hour, a Wicker Park cocktail bar with a soft spot for absinthe.

72-chicago-gear-patrol-tower What to Do

Washington, D.C. may set our taxes, but Chicago is the undisputed architectural capital of the United States. The Chicago School of architecture is a genre all its own. There’s everything from New Classical architecture to ultramodern buildings. Millennium Park is an excellent jumping-off point for sightseers. Once a symbol of industrial decay, the area is now one of America’s top public parks. There’s an abundance of sculpture, and its prime location, combined with a bevy of events, ensures that there’s always something to do. Another area worth checking out is the Michigan-Whacker historic district. Besides many of Chicago’s famous bridges, it hosts the Tribune Tower, a triumph of Gothic design and one of the most architecturally significant buildings in the United States. The Magnificent Mile is a 13-block stretch of Michigan Avenue that is considered the top shopping and dining destination in the city.

72-chicago-gear-patrol-wright Venture Out

Travelers looking to experience Chicago’s live music scene would do well to head to The Whistler, a bar on Logan street known for discovering local acts. If you can get a ticket, head to the University of Chicago campus for a guided tour of the Robie House, one of the most famous Frank Lloyd Wright buildings. Craft beer fans may want to take Goose Island’s brewery tour and stop at their taproom afterwards. We’re particular fans of their 312 Wheat Ale. You could spend a week at the Chicago Museum Campus, a pedestrian park on Lake Michigan which connects four of Chicago’s top museums. It also holds Soldier Field, the oldest NFL stadium in existence. North Dunes Nature Park is a beach preserve about an hour north of the city noted for its wildlife, and Kayak Chicago is highly recommended for those looking to explore Lake Michigan. In the summer, they offer kayak trips to see fireworks from the water.