Chicago
Broad shoulders, bold skyline
Chicago is America's architectural cathedral, a muscular grid of skyscrapers hugging a lake the size of a sea. You'll snap your reflection in the mirrored Bean, ride glass ledges 1,300 feet up, devour deep-dish, and feel the city's blues-and-jazz soul on every corner.
How long to stay?
Two days hits the icons: Millennium Park's Cloud Gate and Crown Fountain, the masterpiece-filled Art Institute, and a stroll along the Chicago Riverwalk. Cap it with dizzying views from Skydeck Chicago's glass-floored Ledge.
Big-city swagger without the coastal ego. Chicago is friendly, hardworking, and proud, with world-class culture, a legendary food and music scene, and a stunning lakefront. Summers buzz with festivals; winters are famously brutal.
The Loop and River North keep you central, walkable, and near the sights. Streeterville sits by the lake and Navy Pier. For local flavor and nightlife, Wicker Park and Logan Square deliver bars, boutiques, and great food.
Take an architecture boat tour on the Chicago River; it's the single best way to understand the city and its skyline. Ride the elevated 'L' train, and seek out neighborhood spots for deep-dish over the tourist chains.
Late May through September is prime, with lakefront festivals, patios, and warm days. Fall is crisp and gorgeous. Winters are bitterly cold and windy off the lake, so pack seriously if you brave December through March.
O'Hare (ORD) and Midway (MDW) airports both connect downtown via the CTA Blue and Orange 'L' lines in 30 to 45 minutes. Amtrak trains nationwide arrive at Union Station, a grand Beaux-Arts landmark in the Loop.
The US dollar and tipping culture apply; budget 18 to 20 percent at restaurants and bars. The grid layout makes navigation easy. Lake Michigan acts like an ocean, so check the weather, which swings fast year-round.