Chicago — Five-Day Local Itinerary

Where locals run and bike with the best free views of the skyline.

💡 Best at sunrise or sunset.

A Route 66 institution since 1923; they give free donut holes to people waiting in line.

💡 Classic breakfast spot. Don't skip the marmalade.

The definitive version of the Italian Beef sandwich.

💡 Order it 'dipped' with hot giardiniera.

A stunning, quiet sanctuary inside the Art Institute that most tourists walk right past.

💡 Requires check-in at the desk, but open to the public.

Abandoned rail line turned elevated park; the local alternative to the High Line.

💡 Accessible from multiple points in Wicker Park and Logan Square.

Solid neighborhood stand for a proper dragged-through-the-garden dog.

💡 Try the cheese fries too.

A world-class museum in the heart of Pilsen that is free to all.

💡 Closed on Mondays.

The local bonfire spot and the best view of the skyline looking North.

💡 Limestone steps are great for sitting and reading.

One of the largest glasshouse conservatories in the world; a tropical escape from the city grit.

💡 The Fern Room is world-famous among botanists.

A no-TV, no-children beer mecca in Andersonville. Famous for mussels and frites.

💡 Cash or credit, but note it is strictly 21+.