Private Group Bike Tours in Chicago: Who Books, What to Ask

A private bike tour turns a scheduled ride into your own: your start time, your group, your pace. This page covers who takes private groups, what they offer, the terms that matter, and the rule that governs a group on the street.

Who runs private tours

Bobby’s Bike Hike. Its classic bike, food, walking and kayak experiences are all available for private bookings.¹ The company helps plan the headcount and the stops, and builds itineraries to fit every occasion and group size.¹

Bike & Roll. Group tours here are for 10 or more participants, on pedal bikes, electric bikes or Segways.² The company was born in Chicago in 1993.² Groups book it for office outings, family adventures, birthday bashes, school field trips and pre-wedding celebrations.² Bike, Eat & Drink Tours are among its group offerings.²

Chicago Bike Adventures. Every ride is custom planned from riders’ answers to a pre-ride questionnaire.⁴ Its site lists custom neighborhood bike rides.⁴

Bobby’s calls itself the nation’s longest running city bike tour operator.⁵

Pick by group size and purpose

Group	Start here
10 or more, mixed ages	Bike & Roll, which quotes groups of 10 or more3
Company outing or team building	Bobby’s, which combines biking, walking and food tastings5
A custom neighborhood ride	Chicago Bike Adventures, which plans each ride from a pre-ride questionnaire4
Any size, food focus	Bobby’s food experiences, available for private booking1

For a corporate outing, Bobby’s can customize any company experience.⁵ Bike & Roll accommodates private group tours for conventions, celebrations, field trips and camps.³

Reference prices

Bike & Roll quotes group tours individually.³ Bobby’s public schedule gives a benchmark for what each format costs.⁶

Public tour	Length	From
Lakefront Neighborhoods Bike Tour	3 hours	$49.996
Chicago’s Ultimate City Bike Tour	3 hours	$49.996
Family & Food Bike Tour of Top Attractions	4 hours	$69.996
Bikes, Bites & Views signature dishes tour	4 hours	$79.996
Chicago’s Westside Foodie Ride	4 hours	$89.996

These are Bobby’s published starting prices, seen October 19, 2026.⁶

Terms to read before you pay

Cancellation is where groups lose money. At Bike & Roll, a refund requires cancelling at least 72 hours before the start, and the refund is less a 10% service fee.³ Under 72 hours, you receive credit only.³

Weather works the other way. Bike & Roll may cancel a tour for weather or other reasons.³ If the tour is cancelled and you cannot reschedule, you are refunded in full.³ When conditions look doubtful, call one to two hours before the start to confirm.³

Two more points go in the group email:

• Arrive 15 minutes before departure.³
• Riders under 18 must wear a helmet on Bike & Roll tours.³

Reservations are recommended for all tours.³

The law for a group on the street

A guided group still rides under Illinois law. Riders may not ride more than two abreast, except on paths or roadway sections set aside for bicycles.⁸ Two abreast must not impede the normal and reasonable movement of traffic, and on a laned roadway the pair must stay within a single lane.⁸

Chicago’s code is worded differently. Riders on a roadway ride single file except on bicycle-only paths or roadway sections, or where two abreast does not impede the normal and reasonable movement of traffic.⁹ Read the full rule at riding two abreast in Illinois.

Joining instead of hosting

If you want company, not a private booking, join an open ride. Chicago Group Rides lists regularly scheduled open group rides for each day of the week, and Half Acre Cycling maintains the list.⁷ The list’s standing rules are helmets required, no tri-bars, bring a flat kit and bring lights for evening rides.⁷

Bike & Roll operates at Chicago’s top attractions by Millennium Park and Navy Pier, which suits a group that wants to start downtown.¹⁰

To compare operators and public tours, see Chicago bike tours compared. For a neighborhood format, read the neighborhood bike tour guide, and for the range of routes start at the Bike Tours hub.