March 27, 2023

Insider tips for taking in the city’s top sights

For top views of Chicago, head up the Willis (Sears) Tower (the tallest building in the U.S.) or the John Hancock Center Observatory.
Architecture, museums, deep-dish pizza, blues, hot dogs – these are the icons of Chicago. This vibrant, modern Midwestern city is too varied and exciting to be fully explored in just a few days, but you’ll sure have fun trying. Here are the highlights for an Insider weekend in the city.

Friday – City Sights
Stunning architecture is one of Chicago’s most prominent features. Celebrate the city on a tour of its famous buildings, landmarks, public sculptures, and diverse neighborhoods. Chicago Architecture Foundation offers an especially informative tour on the river. After all that exploring, spend some downtime in one of the city’s parks – Grant Park is a favorite along the lake, while Millennium Park offers more beautiful architecture and an expansive garden, and Lincoln Park is known for its zoo and conservatory. And, on your first night, discover the cuisine of the city: grab an iconic slice of deep-dish pizza at Giordano’s or Lou Malnati’s Pizzeria. Finish the night with some live blues or jazz – Joe Segal’s Jazz Showcase or Kingston Mines are classic venues.

Saturday – Local Culture
Chicago’s top-notch museums are not to be missed. Topping the must-visit list are the Art Institute of Chicago, the Museum of Contemporary Art, the Field Museum (of natural history and anthropology), and the Museum of Science and Industry – just take your pick! For lunch, consider a Chicago-style hot dog – meaning mustard, pickle, relish, onion, hot peppers, tomato, and celery salt – at one of Gold Coast Dogs’ many locations. In the afternoon, head to the famous Navy Pier to enjoy parks and gardens, shopping, restaurants, a giant Ferris wheel, a beer garden, and the Chicago Shakespeare Theater. For dinner, go more upscale at MK, serving seasonal, contemporary fare, or Alinea, awarded Michelin 3-Star status.

Sunday – Top Chicago Attractions
Head to downtown today, where a number of great city highlights are within a short distance. Visit the home and studio of renowned architect Frank Lloyd Wright, or Ernest Hemingway’s home in Oak Park. The Chicago Botanic Garden is a 385-acre enclave of charming nature, while the impressive Brookfield Zoo and a Baha’i temple (one of only seven such temples in the world) are among the other draws. For a last meal before you go, Billy Goat Tavern is famous for its double cheeseburgers (and John Belushi’s skits on Saturday Night Live), and Chicago Q dishes out hip, modern barbeque.

Can you already taste the deep-dish pizza? Start planning a luxury Chicago vacation here.

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