Chicago in 3 days

The birthplace of the skyscraper, where bold architecture lines the river and Lake Michigan meets a deep-dish, blues-soaked culture. Best time to visit: May-June and September-October. Average daily budget: $140 to $260 USD.

Day 1, Get oriented

Base: The Loop, The downtown core: skyscrapers, the elevated 'L' train, Millennium Park and the Art Institute.

Morning: Architecture river cruise. The single best Chicago experience: a guided boat tour explaining the skyline from the water.

Afternoon: Explore The Loop, The downtown core: skyscrapers, the elevated 'L' train, Millennium Park and the Art Institute.

Evening: Millennium Park & Cloud Gate. See 'The Bean', stroll the gardens and catch a free concert at the Pritzker Pavilion.

Eat: Deep-dish pizza, the towering Chicago classic

Day 2, Go deeper

Base: River North & Magnificent Mile, Galleries, dining and the famous shopping strip of Michigan Avenue.

Morning: Skydeck or 360 Chicago. Ride up Willis Tower or the John Hancock for vertigo-inducing glass-ledge views over the lake.

Afternoon: Explore River North & Magnificent Mile, Galleries, dining and the famous shopping strip of Michigan Avenue.

Evening: Art Institute of Chicago. One of the world's great museums, home to Hopper, Seurat and an unmatched Impressionist collection.

Eat: A Chicago-style hot dog, dragged through the garden

Day 3, Hidden side

Base: Wicker Park & Bucktown, Hip neighbourhoods of indie boutiques, music venues, cafes and street art.

Morning: Millennium Park and the Bean. See your reflection in Cloud Gate ('the Bean'), then explore the lakefront, Art Institute and the deep-dish pizza and hot dogs that define the city.

Afternoon: Explore Wicker Park & Bucktown, Hip neighbourhoods of indie boutiques, music venues, cafes and street art.

Evening: The 606 elevated trail, a former rail line turned park through the northwest neighbourhoods.. A local favourite most visitors miss, worth the detour.

Eat: Italian beef sandwich, dipped and spicy

Hidden gems

The 606 elevated trail, a former rail line turned park through the northwest neighbourhoods.
The murals and taquerias of Pilsen, far from the tourist trail.
Free Tuesday-evening jazz at the Chicago Cultural Center under its Tiffany dome.
The Garfield Park Conservatory, a vast, free Victorian glasshouse west of downtown.

Getting around

The CTA runs the elevated 'L' trains and buses across the city; a Ventra card or contactless tap covers both, and the 'L' is the easiest way around downtown and to both airports. The Loop and lakefront are walkable, and the lakefront trail is great for cycling. Uber and Lyft are everywhere. The Blue and Orange 'L' lines link O'Hare and Midway airports to downtown cheaply.

Safety

The central, tourist-focused areas (the Loop, Magnificent Mile, lakefront and North Side neighbourhoods) are safe and well-policed. As in any big city, stay aware on transit at night and avoid wandering into unfamiliar South and West Side areas after dark. Winters are bitterly cold and windy, so dress in serious layers.

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