Chicago Favorites: Ultimate Food and Walking Tour of Downtown
Difficulty
easy
Duration
2.5–3 hours
Fitness Level
Suitable for most fitness levels; expect light walking (about 1.5 miles) and standing at tasting stops.
Overview
Walk the Loop with a local guide and sample Chicago’s essential eats—deep-dish, Italian beef, a Chicago-style dog and the original brownie—while passing Millennium Park, the Riverwalk, and more. This 2.5–3 hour tour pairs history, architecture, and insider tips with a free 2-hour bike or kayak rental.
Chicago Favorites: Ultimate Food and Walking Tour of Downtown
Select participants and date
The city opens like a map under your feet: glass towers throwing long mirrors across the Chicago River, the lake breeze tugging at your jacket, and the smell of frying oil and melted cheese drifting from a nearby pizzeria. On Bobby’s Bike Hike Chicago Favorites Ultimate Food and Walking Tour, a guide in a branded shirt becomes both storyteller and taste tester, steering a small group through the Loop and along Michigan Avenue between canonical landmarks and the counters where the city’s working-class dishes were born.
Adventure Photos
Adventure Tips
Arrive early to the meeting point
Plan to arrive 15 minutes before departure at the Plaza of the Americas (day) or Gino’s East (evening) to check in and use nearby restrooms.
Bring cash for gratuities
A suggested $10 per person gratuity is customary; there’s no on-site ATM at some stops.
Notify dietary needs in advance
Email reservations@bobbysbikehike.com after booking to confirm accommodations—gluten-free and vegan options are limited.
Use your free rental within three days
Bike rentals are year-round; kayaks operate seasonally—book your 2-hour bike or kayak soon after the tour to secure availability.
Local Insights
Wildlife
- Ring-billed gulls along the lakefront
- Urban squirrels and occasional migrating ducks on the river
History
Chicago’s food culture grew from its meatpacking and immigrant labor roots; the original brownie and many staple dishes trace back to the city’s 19th- and early-20th-century industrial growth.
Conservation
Choose reusable bottles and refuse single-use utensils when possible; support independent eateries that source responsibly to reduce waste and food miles.
Select participants and date
Adventure Hotspots in Chicago
Frequently Asked Questions
Recommended Gear
Comfortable walking shoes
Streets, plazas, and occasional Pedway surfaces require supportive footwear for up to 1.5 miles of walking.
Reusable water bottle
Keeps you hydrated between tastings—refill at public fountains or cafes.
summer specific
Layered jacket
Chicago weather shifts quickly; layers keep you comfortable from lake breezes to heated interiors.
fall specific
Small daypack
Carries purchases, souvenirs, and any extras like sunscreen or a camera.