Chicago vs New York: Which City Offers Better Venues for Financial Services Retreats?

Did you know that 74% of employees believe that offsite retreats improve team communication and collaboration? As leaders in the financial services sector, planning an impactful retreat can be a daunting task. Choosing between Chicago and New York, two bustling hubs with unique offerings, can further complicate the decision. In this guide, we’ll break down the best venues for financial services retreats in both cities, providing you with specific details to help you make an informed choice in 2026.

Venue Comparison Overview

When considering venues for financial services retreats, factors such as capacity, price, location, and amenities play crucial roles. Below is a comparison of venues across both cities, categorized by budget and suitability.

Venue Comparison Table

| Venue Name | City | Capacity | Price/Person/Night | Best For | Standout Feature | F&B Included | |------------------------|--------------|---------------|--------------------|-----------------------|------------------------------|--------------| | The Langham | Chicago | 50-200 | $275-400 | Luxury retreats | Riverside views | Yes | | Swissotel Chicago | Chicago | 30-300 | $200-350 | Mid-sized teams | Rooftop terrace | Yes | | The Palmer House | Chicago | 20-500 | $150-300 | Large groups | Historic architecture | Yes | | The Ritz-Carlton | Chicago | 60-400 | $300-450 | High-end clients | Award-winning dining | Yes | | Convene at 101 Park Ave| New York | 10-300 | $250-450 | Corporate training | Customizable meeting spaces | Yes | | The Standard, High Line| New York | 50-200 | $300-500 | Creative teams | Scenic rooftop bar | Yes | | The New York EDITION | New York | 40-300 | $275-450 | Executive retreats | Central Park views | Yes | | The Westin New York | New York | 50-400 | $180-320 | Large conferences | Large breakout spaces | Yes |

Best for Small Teams

1. The Langham, Chicago

   • Capacity: 50-200
   • Price: $275-400/person/night
   • Best For: Luxury retreats
   • Standout Feature: Riverside views
   • Insider Tip: Book direct for 15% savings.

2. The Standard, High Line, New York

   • Capacity: 50-200
   • Price: $300-500/person/night
   • Best For: Creative teams
   • Standout Feature: Scenic rooftop bar
   • Insider Tip: Reserve the rooftop for sunset events.

Best for Large Groups

1. The Palmer House, Chicago

   • Capacity: 20-500
   • Price: $150-300/person/night
   • Best For: Large groups
   • Standout Feature: Historic architecture
   • Insider Tip: Request a guided tour of the property.

2. The Westin New York

   • Capacity: 50-400
   • Price: $180-320/person/night
   • Best For: Large conferences
   • Standout Feature: Large breakout spaces
   • Insider Tip: Utilize their planning services for seamless coordination.

Activity Recommendations

For a successful retreat, integrating engaging activities is essential. Here are some tailored options for both cities:

Chicago Activities

1. Architecture River Cruise

   • Time Needed: 90 minutes
   • Group Size: Up to 100
   • Cost: $40/person
   • Energy Level: Low
   • Skip if: Your team dislikes being outdoors or has mobility issues.

2. Cooking Class at The Chopping Block

   • Time Needed: 3 hours
   • Group Size: 10-30
   • Cost: $100/person
   • Energy Level: Medium
   • Skip if: Dietary restrictions are extensive.

New York Activities

1. Escape Room Experience

   • Time Needed: 1.5 hours
   • Group Size: Up to 12 per room
   • Cost: $50/person
   • Energy Level: High
   • Skip if: Team members are introverted or prefer quieter environments.

2. Central Park Team Scavenger Hunt

   • Time Needed: 2 hours
   • Group Size: 10-100
   • Cost: $45/person
   • Energy Level: Medium
   • Skip if: Weather conditions are poor.

Budget Breakdown

Planning a retreat involves careful financial consideration. Here’s a typical budget breakdown for a group of 20 in 2026:

• Venue: 40% ($2,000)
• F&B: 25% ($1,250)
• Activities: 15% ($750)
• Travel: 15% ($750)
• Contingency: 5% ($250)

Total Estimated Cost: $5,000

Timeline for Planning

1. 8-12 Weeks Out

   • Define goals and objectives for the retreat.
   • Establish budget and get approvals.

2. 6-8 Weeks Out

   • Select and book the venue.
   • Finalize travel arrangements.

3. 4-6 Weeks Out

   • Confirm catering and activity details.
   • Send out invites to attendees.

4. 2-4 Weeks Out

   • Coordinate A/V requirements.
   • Prepare materials and agendas.

5. 1 Week Out

   • Confirm final headcount with the venue.
   • Conduct a final check of logistics.

Conclusion

Choosing between Chicago and New York for your financial services retreat ultimately depends on your team’s needs, budget, and desired experiences. Both cities offer unique venues and engaging activities that can enhance team collaboration and communication.

Action Items

• Review the venue comparison table and shortlist your top picks.
• Consider the activity recommendations to enhance team engagement.
• Create a timeline to ensure a smooth planning process.

For personalized assistance in finding the perfect venue and activities for your financial services retreat, reach out to us today!