Chicago

America's third-largest city is a architectural masterpiece with iconic skyscrapers, world-class museums, and vibrant neighborhoods along Lake Michigan. The Art Institute, Millennium Park, and deep-dish pizza culture make it an essential Midwest destination.

Things to do

• Millennium Park — Explore Chicago's 24-acre urban oasis featuring the famous Cloud Gate sculpture, Crown Fountain, and free concerts in the Jay Pritzker Pavilion.
• Art Institute of Chicago — One of the oldest and largest art museums in the US, housing masterpieces by Monet, Grant Wood's American Gothic, and extensive photography collections.
• Navy Pier — A historic landmark on Lake Michigan offering restaurants, shops, an iconic Ferris wheel, and stunning skyline views.
• Willis Tower Skydeck — Ascend to the 103rd floor of Chicago's second-tallest building for panoramic city views and the thrilling Ledge glass boxes extending over the street.
• Chicago Architecture Foundation Boat Tour — Experience the city's architectural heritage from the Chicago River, where expert guides explain the design and history of iconic buildings.
• Field Museum — Explore natural history and the famous fossil Sue the T. rex in one of the world's largest and most visited natural history museums.
• Second City Comedy Club — Catch improv and sketch comedy shows at this legendary training ground for Saturday Night Live stars and comedic talent.

Food to try

• Deep-Dish Pizza — Chicago's signature thick-crust pizza with layers of cheese and toppings, best sampled at iconic spots like Lou Malnati's or Pequod's.
• Chicago-Style Hot Dog — An all-beef frank topped with mustard, relish, onions, tomatoes, pickles, peppers, and celery salt on a poppy seed bun—never ketchup.
• Italian Beef Sandwich — Thin-sliced seasoned beef piled on a long roll, typically dipped in gravy and topped with hot peppers, a messy local favorite.
• Garrett Popcorn — Chicago's famous caramel corn and cheese popcorn mix, a sweet and savory treat sold at multiple locations around the city.
• Chicago Steakhouse Experience — Dine at legendary establishments like Gibsons or Morton's for dry-aged steaks, classic cocktails, and old-school elegance.

Local customs & good to know

• Lake Michigan is Central to Life — Locals spend summers along the lakefront beaches and the 26-mile Lakefront Trail; dress in layers as lake breezes cool the city even in warm months.
• Neighborhood Pride Runs Deep — Chicago's distinct neighborhoods like Wicker Park, Logan Square, and Hyde Park each have unique character and loyal residents; asking where someone is from reveals much about their identity.
• Public Transit Efficiency — The CTA 'L' train system is affordable and extensive; purchase a Ventra card for seamless navigation, though service can be crowded during rush hours.
• Winter is Serious — Harsh winters (November through March) mean dress warmly and expect snow; many cultural attractions and restaurants keep visitors entertained indoors.