
easy
2 hours
Suitable for most fitness levels; expect light walking (1–1.5 miles) on flat pavement.
A two-hour walking exploration of Chicago’s best donuts and downtown views. Sample four shops — including Doughnut Vault and Do-Rite Donuts — while learning the local stories behind each bite.
The morning starts with a small crowd and the smell of frying sugar curling through a narrow alley off Franklin Street. A line forms outside Doughnut Vault — a small storefront that feels both irreverent and ritualized — as the guide counts heads and promises you’ll try flavors that don’t show up on menus. You move off the curb, donuts in paper bags, and the city opens up: glass facades reflecting the river, bridges creaking, and the steady hum of downtown waking up.

Donuts are sampled at each stop; skip a big breakfast so you can taste multiple styles and flavors.
Sweet treats and city walking demand hydration — refill stations are available near major public spaces.
You’ll cross the Chicago River and walk busy sidewalks; wear comfortable shoes and keep personal items secure.
Vegan or allergy-friendly options may be limited — tell the operator at booking so they can prepare alternatives.
Donut shops in Chicago reflect waves of immigration and neighborhood bakery culture; the Doughnut Vault became a local ritual by opening limited hours and building long lines that turned into folklore.
Bring reusable containers and avoid excess packaging — downtown food-tour waste is a persistent issue, and many stops partner with local composting programs when possible.
Flat, supportive shoes make the city pavements and short walking distances easier.
Staying hydrated helps counteract the sugar and summer heat.
summer specific
Chicago weather can change quickly — a compact shell keeps you comfortable.
spring specific
Keeps purchases, phone, and layers secure while you walk.