Flat Fall Bike Rides on Chicago's Lakefront

Pedal past tree-lined blocks and the waterfront with a guide, pausing for deep-dish pizza and Italian beef between views.

Plan a fall ride along the lake.

🚲 A Rolling Fall Tasting Tour

Cool fall mornings suit a slow ride along the lake. Bobby's Bike Hike, the city's longest-running tour operator, leads guided rides that keep to a flat, easy-paced route through tree-lined residential streets and along the waterfront, with the skyline stacked up across the water.

Food itineraries turn the ride into a rolling tasting menu of deep-dish pizza, Chicago hot dogs, Italian beef, and bakery sweets. Walking tours cover the same appetite on foot.

The shop sits at 540 N Lake Shore Dr, opening at 9:00 AM Monday through Thursday and 8:30 AM Friday through Sunday. Reviewers rate it 4.9 from more than 2,300 reviews.


🌊 More Lakefront Outings

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