Offers hop-on hop-off tours and private event transport with trolleys and buses.

In-Person

Estimated 2h 0m

Estimated 1+ guests (no max)

Estimated $40 USD per person

Chicago Trolley & Double Decker offers a unique way to explore the city with its "hop on hop off" tour that operates year-round. This service allows participants to visit thirteen different attractions in the downtown area at their own pace. From May through September, additional experiences such as neighborhood tours and night tours are included in the ticket package. Beyond regular tours, the company is heavily involved in providing transportation for more than five thousand private events annually, extending services not only throughout downtown but also to locations in the suburbs and neighboring states.

For businesses looking for creative transportation solutions for company outings or other corporate events, Chicago Trolley & Double Decker provides various options including trolleys, double decker buses, and coach buses. These vehicles are used for a range of corporate needs like convention shuttles or special occasion gatherings. The company's services offer an engaging way for teams to travel together, whether it's for a parade or a party, making it easier to coordinate large group movements across different venues.

Activity Attributes

Key characteristics of this experience.

Core Feel

Energy Level 4/5 How energetic and dynamic is this activity?

Activity Level 2/5 How physically or mentally active are participants?

Challenge Level 2/5 How challenging or complex is this activity?

Team Dynamics

Collaboration 4/5 How much does this require working together?

Icebreaker 4/5 How well does this help people get to know each other?

Bonding 4/5 How well does this build team relationships?

Celebration 5/5 How celebratory or fun-focused is this activity?

Engagement

Problem Solving 2/5 How much critical thinking and problem solving is involved?

Creativity 3/5 How much creative thinking and expression is required?

Learning 2/5 How much new knowledge or skills are gained?

Ratings are based on expert review, AI assist, and community sentiment.

Operating Hours

Monday: 9:00 AM 5:00 PM
Tuesday: 9:00 AM 5:00 PM
Wednesday: 9:00 AM 5:00 PM
Thursday: 9:00 AM 5:00 PM
Friday: 9:00 AM 5:00 PM
Saturday: 9:00 AM 5:00 PM
Sunday: 9:00 AM 5:00 PM

Our Review

Updated August 19, 2025

Our take on Chicago Trolley & Double Decker is that it offers a distinctive team-building experience that combines exploration with convenience. The "hop on hop off" tour is particularly appealing for teams looking to discover Chicago's downtown attractions at their own pace, making it an excellent choice for new teams or those looking to break the ice in a relaxed setting. The flexibility of being able to visit multiple attractions while enjoying the camaraderie of shared travel can foster team bonding in a way that traditional office-based activities might not.

However, one thing to keep in mind is that while this service suits larger groups and established teams who can benefit from the logistical ease of coordinated transportation, it may not be the best fit for smaller or more analytical teams seeking focused interaction or problem-solving activities. The expansive nature of the tours might dilute opportunities for deeper engagement unless supplemented with structured team-building exercises. Overall, Chicago Trolley & Double Decker provides an engaging backdrop for corporate outings but may require additional planning to maximize its potential as a team-building tool.

Chicago Trolley & Double Decker

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