Chicago vs New York: Which City is Better for Corporate Retreats? (2026)

Did you know that companies that invest in offsite retreats see a 20% increase in team productivity? However, choosing the right city for your corporate retreat can be a daunting task. Chicago and New York each offer unique advantages, but which is better for your team? In this guide, we’ll break down the venue options, activities, and logistics to help you make an informed decision.

Overview: Why Choose Chicago or New York?

Both cities are vibrant, offering diverse cultural experiences and excellent venues for corporate retreats.

• Chicago: Known for its stunning architecture and deep-dish pizza, Chicago boasts a more affordable cost of living compared to New York, making it an attractive option for budget-conscious teams. The city is also centrally located, making it accessible for teams from all over the U.S.

• New York: As a global hub for business and culture, New York offers unparalleled networking opportunities and world-class venues. However, it tends to be more expensive, especially during peak seasons like the summer and holiday months.

Venue Comparison Table

| Venue Name | Location | Capacity | Price/Person/Night | Best For | Standout Feature | F&B Included | |-----------------------|---------------------|----------------|---------------------|-----------------------|-------------------------------------|--------------| | The Langham | Chicago | 10-500 | $250-400 | Luxury retreats | Stunning river views | Yes | | The Drake | Chicago | 50-300 | $175-300 | Historic charm | Iconic ballroom | Yes | | Hyatt Regency | Chicago | 10-1,200 | $175-250 | Large groups | Rooftop terrace | Yes | | The Westin New York | New York | 20-700 | $275-450 | Corporate conferences | Central Park views | Yes | | The New Yorker Hotel | New York | 10-1,000 | $200-350 | Mid-range groups | Art Deco style | Yes | | Conrad New York | New York | 30-1,200 | $300-500 | Luxury experiences | Rooftop bar with skyline views | Yes | | The Peninsula | New York | 20-400 | $400-600 | High-end gatherings | Award-winning spa | Yes | | The Kimpton Gray Hotel| Chicago | 30-200 | $150-250 | Intimate teams | Modern design | Yes |

Venue Recommendations by Category

Best for Large Groups

• Hyatt Regency Chicago

  • Location: Chicago
  • Capacity: 10-1,200
  • Price: $175-250
  • Best For: Large corporate gatherings
  • Standout Feature: Rooftop terrace

• The Westin New York

  • Location: New York
  • Capacity: 20-700
  • Price: $275-450
  • Best For: Corporate conferences
  • Standout Feature: Central Park views

Best for Intimate Retreats

• The Kimpton Gray Hotel

  • Location: Chicago
  • Capacity: 30-200
  • Price: $150-250
  • Best For: Small teams
  • Standout Feature: Modern design

• The New Yorker Hotel

  • Location: New York
  • Capacity: 10-1,000
  • Price: $200-350
  • Best For: Mid-range groups
  • Standout Feature: Art Deco style

Our Top Picks

1. Budget Version: The Kimpton Gray Hotel, Chicago - $150/person/night
2. Standard Version: The Drake, Chicago - $175-300/person/night
3. Premium Version: The Peninsula, New York - $400-600/person/night

Activity Recommendations

Chicago Activities

1. Architecture Boat Tour

   • Time Needed: 1.5 hours
   • Group Size: Up to 100
   • Cost: $40/person
   • Energy Level: Low
   • Notes: Great for team bonding; skip if your team prefers active experiences.

2. Escape Room Experience

   • Time Needed: 1-2 hours
   • Group Size: Up to 12
   • Cost: $30/person
   • Energy Level: Medium
   • Notes: Excellent for problem-solving; skip if team members dislike puzzles.

New York Activities

1. Broadway Show

   • Time Needed: 3 hours
   • Group Size: Varies
   • Cost: $100-200/person
   • Energy Level: Low
   • Notes: Perfect for entertainment; skip if your team prefers outdoor activities.

2. Central Park Team Scavenger Hunt

   • Time Needed: 2 hours
   • Group Size: Up to 50
   • Cost: $50/person
   • Energy Level: High
   • Notes: Great for engagement; skip if weather is poor.

Sample 3-Day Itinerary

Day 1: Arrival & Welcome

• Afternoon: Check-in at venue
• Evening: Welcome dinner at a local restaurant

Day 2: Workshops & Activities

• Morning: Team-building workshop
• Afternoon: Activity (choose from options above)
• Evening: Dinner & networking event

Day 3: Wrap-Up & Departure

• Morning: Reflection session
• Afternoon: Check-out and depart

Budget Breakdown for a 10-Person Team

| Category | Allocation | Total Cost | |-------------------|------------|-------------| | Venue | 40% | $2,000 | | F&B | 25% | $1,250 | | Activities | 15% | $750 | | Travel | 15% | $750 | | Contingency | 5% | $250 | | Total | 100% | $5,000 |

Conclusion: Making Your Decision

Both Chicago and New York offer compelling options for corporate retreats. Chicago tends to be more budget-friendly, while New York provides unmatched networking opportunities.

Action Items:

1. Determine your budget and team size.
2. Select a city based on your priorities.
3. Review the listed venues and activities.
4. Begin the booking process—consider booking 4+ months in advance for peak seasons.