Chicago vs New York: Which City Offers Better Venues for Mid-Market Retreats? (2026)

When planning a corporate retreat, selecting the right city can make all the difference. Did you know that 78% of teams report increased productivity after an offsite? Among the top contenders for mid-market retreats, Chicago and New York stand out for their diverse venue offerings. But which city truly delivers the best value and experience for your team?

Why Choose Chicago or New York for Your Retreat?

Both cities provide unique advantages. Chicago boasts a central location with a lower cost of living, while New York offers unparalleled access to world-class venues and activities. In 2026, with remote work becoming the norm, offsites are more critical than ever for team cohesion and strategy alignment.

Chicago: The Heart of the Midwest

• Best Seasons: Spring (April to June) and Fall (September to November) offer mild weather and fewer crowds.
• Travel Logistics: O'Hare International Airport (ORD) serves as a major hub, with affordable flights from most locations.

New York: The City that Never Sleeps

• Best Seasons: Late Spring (May to June) and Early Fall (September to October) provide beautiful weather and vibrant city life.
• Travel Logistics: Three major airports (JFK, LaGuardia, and Newark) ensure easy access, although travel costs can be higher.

Venue Comparison Table: Chicago vs. New York

| Venue Name | City | Capacity | Price/Person/Night | Best For | Standout Feature | F&B Included | |----------------------------|------------|---------------|---------------------|-------------------|-------------------------------|--------------| | The Langham | Chicago | 150 | $220 | Luxury Retreats | Stunning river views | Yes | | The Palmer House Hilton | Chicago | 300 | $175 | Large Groups | Historic architecture | Yes | | The Drake Hotel | Chicago | 200 | $200 | Upscale Meetings | Iconic Chicago landmark | Yes | | Convene - 101 Park Avenue | New York | 150 | $300 | Executive Retreats | All-inclusive conference space | Yes | | The Westin New York | New York | 400 | $250 | Large Events | Rooftop bar | Yes | | The Standard Hotel | New York | 120 | $275 | Creative Teams | Unique design and vibe | Yes | | The Kimpton Gray Hotel | Chicago | 100 | $210 | Innovative Workshops | Modern amenities | Yes | | The New Yorker Hotel | New York | 250 | $180 | Budget-Friendly | Central location | Yes |

Venue Recommendations by Group Size

Best for Small Teams (Up to 50)

• The Kimpton Gray Hotel, Chicago: Ideal for innovative workshops, offers a modern space with great amenities at $210 per person.
• The Standard Hotel, New York: Perfect for creative teams with a unique vibe priced at $275 per person.

Best for Medium Teams (50-150)

• The Langham, Chicago: A luxury retreat venue with river views at $220 per person.
• Convene - 101 Park Avenue, New York: An all-inclusive space for executive retreats at $300 per person.

Best for Large Groups (150+)

• The Palmer House Hilton, Chicago: Historic venue with a capacity of 300 at $175 per person.
• The Westin New York: Spacious venue for large events at $250 per person.

Our Top Picks for 2026

• Best Value: The Palmer House Hilton, Chicago - Historic charm at an affordable price.
• Best Luxury Experience: Convene - 101 Park Avenue, New York - All-inclusive luxury for executive teams.
• Best Unique Venue: The Standard Hotel, New York - Ideal for creative teams looking for an inspiring environment.

Budget Breakdown for Mid-Market Retreats

Here's a sample budget breakdown for a mid-sized team of 20 people:

| Category | Cost | Percentage Allocation | |----------------|-----------|-----------------------| | Venue | $4,500 | 40% | | Food & Beverage| $2,500 | 25% | | Activities | $1,500 | 15% | | Travel | $1,500 | 15% | | Contingency | $500 | 5% | | Total | $10,500 | 100% |

Timeline for Planning Your Retreat

8-Week Planning Timeline

• Week 8: Set objectives and budget.
• Week 7: Research and shortlist venues.
• Week 6: Request proposals and check availability.
• Week 5: Finalize venue and book.
• Week 4: Coordinate travel arrangements.
• Week 3: Plan activities and meals.
• Week 2: Confirm logistics and finalize agenda.
• Week 1: Send out calendar invites and prepare materials.

Conclusion: Making Your Decision

Both Chicago and New York offer compelling venues for mid-market retreats, but your choice should depend on your team’s needs, budget, and desired experience. Chicago tends to offer more affordable options, while New York provides a vibrant atmosphere with unique venues.

Action Items:

1. Determine your team size and budget.
2. Review the venue options above.
3. Start your planning timeline to secure your preferred venue.