Smaller than Los Angeles, less crowded than New York and arguably one of the cleanest metropolitan areas in the U.S., Chicago has come into its own as a major tourist destination. With historic sights, specialty food and cultural options for the whole family, it offers a diverse array of things to see and do. Here, find a two-day itinerary to get the most out of a weekend stay in America’s Second City.
Saturday morning: In a city lined with historic buildings and modern skyscrapers, there’s no better way to see Chicago than get an introduction via a guided architecture tour. Along the river, several companies sell tickets for on-the-water tours, perfect for a sunny summer day when the weather is warm and the breeze blows a cool mist over the boat. Navigate the river with a knowledgeable guide, who can point out must-see landmarks like the Civic Opera House, the Sun-Times building, Willis Tower (formerly the Sears Tower) and Frank Lloyd Wright homes. During the autumn and winter months, when the weather is too brisk for an outdoor excursion, hop aboard a tour bus and stay warm while learning about the city’s rich architectural history.
Saturday afternoon: Chicago is a food-lover’s paradise, but perhaps more famous than any other staple is the deep-dish pizza—a great option for a first meal in the city. Inches of cheese, sauce and toppings are layered high and finished with a crispy crust. Restaurants across the city serve up the delicacy, but a topic hotly debated among locals is where to find the best Chicago-style pizza. Some say Uno, others say Giordano’s—but one of the original pie recipes comes from the family behind Lou Malnati’s, renowned for its buttery, savory crust and sausage blend. Chicago is also a city known for its many craft breweries, so wash down the pizza with a Goose Island ale or 312—that’s three-one-two, not three-twelve—and sign up for a walking beer tour around the Lincoln Park and Wicker Park neighborhoods. The perfect way to finish out an afternoon, the Chicago Beer Experience gives participants four samples of brews at four bars that are frequented by locals for a true taste of the city’s beer scene.
Saturday evening: For an once-in-a-lifetime dinner, the Lincoln Park area boasts many of Chicago’s premier restaurants. The experience comes with a high price tag, but many say it’s worth the splurge if celebrating a special occasion. Alinea is known across the country for its fine American cuisine, and features specialty tasting menus for those who wish to put their palates in the chefs’ hands. More budget-friendly options are also available in the neighboring streets, with restaurants ranging from Spanish tapas to Mexican and Greek. From Alina, walk a few blocks east to catch a show at the original Second City, where comics like John Belushi and Dan Ackroyd got their start. With two stages and a troupe of talented performers who will surely make it big in the not-too-distant future—some go on to star on shows like “Saturday Night Live”—the theater will keep audiences on the edge of their seats.
Sunday morning: While most of the city is still sleeping, take an early morning stroll down Magnificent Mile. Shops of all types line the streets, but the ones making up the famed stretch of Michigan Avenue include luxury brands such as Tiffany & Co., Cartier, Louis Vuitton, Burberry and Prada. During peak hours on the weekdays and weekend afternoons, the Magnificent Mile area is a center of activity with interesting landmarks such as the Chicago Water Tower, one of the few structures remaining in the city after the great fire of 1971. Continue walking down Michigan Avenue toward the lake to Millennium Park, where there’s much to see in this area. Here you’ll see the Pritzker Pavilion designed by Frank Gehry as well as rotating public art sculptures, but the featured attraction is the “Cloud Gate” sculpture, better known as the Bean for it’s rounded shape. Designed to reflect the Chicago skyline in its silvery finish, the sculpture is a favorite place for locals and tourists alike to take a quintessential self-portrait. Just a few miles away—a walk-able distance in comfortable shoes—is Grant Park, where Buckingham Fountain stands proudly amongst the surrounding greenery to represent Lake Michigan. While its nighttime display is a sight to be seen, it’s just as enchanting during the day—just be sure to visit during the spring and summer months, as it’s turned off during the winter so the water won’t freeze.
Sunday afternoon: A visit to Chicago isn’t complete without a visit to one of its many museums. The Art Institute of Chicago is a popular attraction, as is the Museum of Science and Technology on the south side, but travelers with children have two great options that are within walking distance of Grant Park. Double back to the Navy Pier to take a ride on the Ferris wheel before visiting the children’s museum, or continue south to Museum Campus to find two beloved Chicago institutions. Adler Planetarium is the first planetarium built in the Western Hemisphere, while Shedd Aquarium was at one point the largest indoor aquarium in the world (it was surpassed in 2005 by the Georgia Aquarium).
Sunday evening: Before catching a plane, train or car back home, head to one of the city’s iconic towers. Although it’s not the tallest in the city, the John Hancock building is a favorite spot for visitors to Chicago who wish to see an aerial view of the city. Instead of purchasing an expensive ticket to the top, plan to have a cocktail—virgin or otherwise—at the Signature Lounge where you can watch the sun set from the 96th floor at one of the high tables lining the windows. Women who visit the Signature Lounge are also in for an extra surprise: In the restroom, floor to ceiling windows offer dramatic views of city lights.
It’s possible for visitors to Chicago to get a taste of the city—literally and figuratively—in just two days. From food and beer to architecture and museums, Chicago offers an experience for all to enjoy.