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Chicago, Illinois: Planning The Perfect Weekend

Chicago, the birthplace of the skyscraper, is considered the most influential architectural city in the world. Founded in 1837, between the Great Lakes and the Mississippi River watershed, the city was rebuilt after the Great Chicago Fire of 1871, which led to the establishment of the Chicago School of Architecture, the integration of the City Beautiful Movement, and the first skyscrapers. The city hosts a number of free festivals, mostly in the summer, including the Chicago Blues Festival, the Taste of Chicago, the Chicago Jazz Festival and the World Music Festival Chicago. The city is also known for its enthusiastic sports fans, who enjoy Chicago Bears football games at Soldier Field, Chicago Cubs baseball games at Wrigley Field, and Chicago Bulls basketball games at the United Center.

Pequod’s Pizza

Via Eater Chicago

Pequod’s Pizza in Lincoln Park and Old Town specializes in pan-style deep dish pizza, a Chicago staple and a must-try for visitors to the Windy City. Named after Captain Ahab’s ship in Moby Dick, this casual eatery has the feel of a sports bar with Blackhawks memorabilia adorning the walls. Aside from pizza, Pequod’s serves traditional appetizers, such as wings, mozzarella sticks and jalapeño poppers, as well as meatball and Italian sausage sandwiches. The standouts at Pequod’s, though, are the thin-crust and deep-dish pan pizza offerings. The toppings,which include Canadian bacon, pepperoni, anchovies, spinach, and black olives, among others, are layered over zesty tomato sauces and handfuls of mozzarella. For meals on the go, the restaurant also serves slices and take-out.

Chicago Architecture River Cruise

Via Chicago Architecture Foundation

The Chicago Architecture River Cruise, a 75-minute guided tour on the Chicago River, gives visitors a unparalleled perspective on the city’s spectacular architectural gems. The ship, which boards at Navy Pier, sails past the Willis Tower, formerly the Sears Tower, the old Post Office Building, the John Hancock Center and the Wrigley Building before exploring all three branches of the Chicago River with views of countless structures, such as the Aon Center, the IBM Building and Boeing World Headquarters, among countless others. The guide will lead you through the historical events that shaped the city, such as the invention of balloon-frame construction and the Great Fire of 1871, as well as the designs of world-renowned architects, including Mies van der Rohe, Helmut Jahn and Skidmore, Owings and Merrill. The ship also includes a full bar for guests to enjoy a cocktail as they cruise the Chicago River.

Hopleaf

Via UrbanMatter

Hopleaf, a European restaurant in Andersonville and Uptown, is a favorite among gourmands. A Belgian-inspired beer bar, owned by Michael Roper, that serves great food, this Chicago eatery features an unparalleled selection of craft beers that pair perfectly with the simple yet satisfying menu. Favorites include Atlantic mussels with frites and aioli, which can be ordered Belgian-style, steamed in Blanche de Chambly, or with a San Marzano tomato and white wine broth. Other standouts include the steak frites - wood-grilled grass-fed NY Strip with pommes frites, and the pan-seared Atlantic salmon with freekeh, carrot cream, braised radish, green pea-almond pesto and aji dolce coulis. Beer lovers will especially enjoy the ale menu, which includes De Koninck, Kwak and Delirium Tremens on tap. Each beer is served in its own custom-made glass. Casual yet inviting, Hopleaf is great for a relaxed lunch or an informal dinner.

Chicago, considered a city of neighborhoods, each with its own appeal, such as the bustling Loop downtown, the elegant River North, or the stylish Wicker Park, has something for everyone. From comedy and jazz clubs to skyscrapers and top-notch restaurants, the city is thoroughly modern yet steeped in history. With an outstanding selection of upscale hotels, such as The Drake, Palmer House Hilton, the Thompson and the Virgin Hotel, visitors can make their weekend getaway a truly memorable occasion. Its best to visit Chicago in the spring or fall, when temperatures are warm and the city offers an array of festival options, yet in the summer, travelers can enjoy the numerous terrace or rooftop patio spaces in the evening, including the rooftop at the Chicago Athletic Association, which occupies a Art Deco-styled Gothic era building. Museums include the Field Museum of Natural History, the Museum of Science and Industry, the Frank Lloyd Wright Home and Studio, the Art Institute of Chicago and the Museum of Contemporary Art, among others. So let us know what you think of our suggestions or feel free to offer your own.

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