Itineraries

5 Days in Chicago: The Perfect 5-Day Itinerary

Five days lets you slow down and shop, sail and wander like a local. Days one to four: icons, Museum Campus, neighborhoods, Hyde Park.

Morning

Pilsen: the murals along 16th Street, pan dulce for breakfast and the National Museum of Mexican Art (free) — Chicago’s most colorful morning.

Afternoon

Retail therapy on the Magnificent Mile and State Street, then a sunset sailing cruise from Navy Pier aboard a tall ship as the skyline lights up. Routes and outlets are in our ultimate Chicago guide.

Evening

Farewell dinner on the Riverwalk and, in summer, Navy Pier’s fireworks from the lakefront — the happiest goodbye the city offers.

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