Boston vs Chicago: Which City is Best for Your Next Offsite?

Did you know that 83% of executives believe offsite meetings are critical for team cohesion and productivity? Yet, planning the perfect offsite can often feel overwhelming, especially when choosing between vibrant cities like Boston and Chicago. Each city offers unique venues and experiences, making your decision not just about location, but about the kind of offsite experience you want to create for your team in 2026.

Overview: Why Choose Boston or Chicago?

Boston: A Hub of History and Innovation

Boston is known for its rich history and educational institutions. The city’s walkable neighborhoods and waterfront views provide a picturesque backdrop for corporate retreats. Best seasons for offsites are late spring (May-June) and early fall (September-October) when the weather is mild and pleasant.

Chicago: The Windy City Experience

Chicago offers a dynamic urban landscape with a vibrant arts scene and iconic architecture. The best times for offsites are late spring (May-June) and early fall (September-October) as well, providing an ideal climate for both indoor and outdoor activities.

Venue Comparison Table

| Venue Name | Location | Capacity | Price/Person/Night | Best For | Standout Feature | AV Quality | |--------------------------|-----------------------|--------------|---------------------|-------------------------|-------------------------------------|-------------------| | The Bostonian Boston | Boston, MA | 50-200 | $175-250 | Small to medium teams | Rooftop views of the city | Excellent | | Seaport Hotel | Boston, MA | 200-500 | $200-300 | Large groups | Waterfront location | High-end AV | | Kimpton Gray Hotel | Chicago, IL | 100-300 | $180-260 | Medium teams | Trendy design and rooftop bar | Good | | The Drake Hotel | Chicago, IL | 50-400 | $150-250 | Grand events | Historic charm | Excellent | | Boston Harbor Hotel | Boston, MA | 150-400 | $220-320 | Large groups | Harbor views and luxury amenities | High-end AV | | The Westin Chicago River | Chicago, IL | 100-350 | $175-225 | All team sizes | Scenic river views | Good | | Boston Convention Center | Boston, MA | 500+ | $85-150 | Major conferences | Versatile space | Excellent | | Hyatt Regency Chicago | Chicago, IL | 300-600 | $170-240 | Large groups | Central location | Good |

Venue Highlights

Best for Small Teams

• The Bostonian Boston: Capacity of 50-200, great for intimate gatherings. Price: $175-250 per person. Standout feature: Rooftop views of the city.

Best for Medium Teams

• Kimpton Gray Hotel: Capacity of 100-300, trendy atmosphere. Price: $180-260 per person. Standout feature: Rooftop bar.

Best for Large Groups

• Boston Convention Center: Capacity of 500+, flexible spaces. Price: $85-150 per person. Standout feature: Versatile space for various setups.

Activity Recommendations

Boston Activities

1. Harbor Cruise: 2 hours, 20-150 people, $45/person. Great for team bonding with stunning views.
2. Escape Room: 1.5 hours, 6-12 people, $35/person. High engagement, suitable for smaller teams.
3. Historical Walking Tours: 3 hours, 10-30 people, $25/person. Perfect for history buffs.

Chicago Activities

1. Architecture River Cruise: 1.5 hours, 20-120 people, $50/person. High energy, great for larger groups.
2. Cooking Class: 3 hours, 10-20 people, $85/person. Fun, collaborative experience.
3. Team Building Workshop: 2 hours, 15-50 people, $75/person. Focused on collaboration and communication.

Sample 3-Day Itinerary

Day 1: Arrival and Team Building

• Morning: Arrival and hotel check-in
• Afternoon: Ice breaker activities
• Evening: Welcome dinner at venue restaurant

Day 2: Workshops and Activities

• Morning: Workshop on team dynamics
• Afternoon: Choose between cooking class or architectural cruise
• Evening: Group dinner at a local favorite restaurant

Day 3: Wrap-Up and Departure

• Morning: Final team meeting to recap
• Afternoon: Optional activity (escape room or historical tour)
• Evening: Departure

Budget Breakdown

For a team of 20 people, a typical budget might look like this:

| Category | Cost (Total) | Percentage | |----------------------|---------------|--------------| | Venue | $4,000 | 40% | | F&B | $2,500 | 25% | | Activities | $1,500 | 15% | | Travel | $1,500 | 15% | | Contingency | $500 | 5% |

Risk Mitigation

• Venue Cancellation: Book flexible cancellation policies.
• Weather Issues: Have a backup plan for outdoor activities.
• Travel Delays: Schedule buffer time for arrivals and departures.

Conclusion and Action Items

Choosing between Boston and Chicago for your next offsite ultimately depends on your team’s preferences and objectives. Review the venues and activities listed, and consider your budget and logistics.

1. Select your city and preferred venues.
2. Draft a preliminary budget.
3. Reach out to venues for availability.

Ready to take the next step?