Chicago vs New York: Best Cities for Large Team Retreats (2026)

Did you know that 85% of employees report feeling more engaged after attending a well-planned team retreat? However, planning such an event can be overwhelming, especially when choosing the right city that aligns with your team's needs. In 2026, both Chicago and New York City stand out as prime locations for large team retreats, each offering unique venues and experiences. Let’s dive into the specifics to help you make an informed decision.

Why Choose Chicago for Your Retreat?

Chicago is known for its midwestern charm, affordable venues, and a vibrant culture. The city boasts a range of spaces suitable for large gatherings, often at lower price points than its coastal counterparts. Spring and fall are particularly pleasant, with mild weather perfect for outdoor activities.

Venue Options in Chicago

| Venue Name | Location | Capacity | Price/Person/Night | Best For | Standout Feature | |--------------------------------|----------------------|--------------|---------------------|-------------------------------|--------------------------------------| | The Westin Chicago River North | River North | 800 | $175-225 | Conferences, Workshops | Scenic river views | | Chicago Marriott Downtown | Loop | 500 | $200-250 | Large Meetings, Banquets | Central location, modern amenities | | The Hyatt Regency O'Hare | Rosemont | 1,200 | $160-210 | Conventions, Trade Shows | Proximity to O'Hare Airport | | The Field Museum | Museum Campus | 1,000 | $150-200 | Unique Experiences | Access to world-class exhibits | | The Merchandise Mart | Near North Side | 700 | $175-225 | Networking Events, Showcases | Historic venue with flexible spaces |

Why Choose New York for Your Retreat?

New York City is a global hub with unparalleled resources, venues, and activities. The city is ideal for teams looking to inspire creativity and innovation. Spring and autumn provide the best weather, while summer can be hot and humid.

Venue Options in New York

| Venue Name | Location | Capacity | Price/Person/Night | Best For | Standout Feature | |--------------------------------|----------------------|--------------|---------------------|-------------------------------|--------------------------------------| | The New York Hilton Midtown | Midtown | 1,500 | $250-300 | Large Conferences | Close to major attractions | | Convene at 101 Park Avenue | Midtown | 400 | $200-250 | Corporate Meetings | High-end amenities | | The Glasshouse | Chelsea | 500 | $225-275 | Networking Events | Stunning views of the skyline | | The Brooklyn Botanic Garden | Brooklyn | 300 | $175-225 | Outdoor Retreats | Beautiful gardens for inspiration | | The Times Center | Times Square | 400 | $200-250 | Presentations, Workshops | State-of-the-art AV capabilities |

Venue Comparison Table

| Venue Name | Location | Capacity | Price/Person/Night | Best For | F&B Included | AV Quality | |--------------------------------|----------------------|--------------|---------------------|-------------------------------|--------------|----------------| | The Westin Chicago River North | River North | 800 | $175-225 | Conferences, Workshops | Yes | High | | Chicago Marriott Downtown | Loop | 500 | $200-250 | Large Meetings, Banquets | Yes | High | | The Hyatt Regency O'Hare | Rosemont | 1,200 | $160-210 | Conventions, Trade Shows | Yes | Moderate | | The New York Hilton Midtown | Midtown | 1,500 | $250-300 | Large Conferences | Yes | High | | Convene at 101 Park Avenue | Midtown | 400 | $200-250 | Corporate Meetings | Yes | High | | The Glasshouse | Chelsea | 500 | $225-275 | Networking Events | Yes | High | | The Field Museum | Museum Campus | 1,000 | $150-200 | Unique Experiences | Yes | Moderate |

Our Top Picks

Best for Budget-Conscious Teams

• Chicago Marriott Downtown: $200/person/night, capacity 500, ideal for meetings and banquets.

Best for Creative Teams

• The Glasshouse, New York: $225/person/night, capacity 500, great for networking with skyline views.

Best for Large Conferences

• The New York Hilton Midtown: $250/person/night, capacity 1,500, perfect for large gatherings and close to attractions.

Conclusion

Both Chicago and New York offer a wealth of options for large team retreats, each with its unique advantages. Chicago provides more budget-friendly venues with a relaxed atmosphere, while New York boasts high-energy environments that can inspire creativity. Consider your team's specific needs, budget, and the type of experience you want to create.

Action Items

1. Determine your budget and expected team size.
2. Review the venue options and their standout features.
3. Book a venue at least 4-6 months in advance for the best rates.
4. Create an itinerary that includes activities that align with your team’s goals.