Chicago vs New York City: Where to Host Your Next Offsite?

As of February 2026, companies are increasingly recognizing the value of offsite retreats to foster team collaboration and innovation. Did you know that 86% of teams report improved communication and productivity after a well-planned offsite? However, choosing the right city can be a daunting task. In this guide, we’ll compare Chicago and New York City as potential venues for your corporate retreat, focusing on logistics, venue options, and budget considerations.

Why Choose Chicago or New York City for Your Offsite?

Chicago: A City of Opportunities

Chicago is known for its stunning architecture, vibrant cultural scene, and a plethora of unique venues. With a central location and major airport access, it’s an ideal choice for teams coming from various regions. The best seasons to visit are spring (April to June) and fall (September to November) when the weather is pleasant.

New York City: The City That Never Sleeps

New York City offers an unmatched energy and a multitude of iconic venues. The city's cultural diversity and endless activity options make it a compelling choice for offsites. The best times to visit are spring and fall, similar to Chicago, but be mindful of the busy tourist season in summer.

Venue Comparison Table

| Venue Name | Location | Capacity Range | Price/Person/Night | Best For | Standout Feature | F&B Included | |----------------------------------|-------------------|----------------|--------------------|-----------------------|-------------------------------|--------------| | The Langham Chicago | Chicago, IL | 10-400 | $250 | Luxury retreats | Stunning river views | Yes | | The Drake Hotel | Chicago, IL | 20-500 | $200 | Historic charm | Grand ballrooms | Yes | | The Westin New York at Times Square | New York, NY | 20-1,000 | $215 | Large conferences | Proximity to major attractions | Yes | | The Standard High Line | New York, NY | 10-200 | $275 | Creative teams | Rooftop bar with skyline views | Yes | | The Ritz-Carlton Chicago | Chicago, IL | 10-300 | $300 | Executive meetings | Luxurious amenities | Yes | | Convene - 22 Hudson Yards | New York, NY | 10-400 | $350 | Tech-focused teams | High-tech meeting rooms | Yes | | The Kimpton Gray Hotel | Chicago, IL | 10-150 | $180 | Small groups | Modern design | Yes | | 1 Hotel Brooklyn Bridge | New York, NY | 10-300 | $275 | Sustainability-focused | Eco-friendly initiatives | Yes |

Best Venues for Different Needs

Best for Small Teams

• The Kimpton Gray Hotel (Chicago): Capacity of up to 150, ideal for intimate team-building retreats at $180 per person.
• The Standard High Line (New York): Perfect for creative brainstorming with a capacity of 200 at $275 per person.

Best for Large Groups

• The Drake Hotel (Chicago): Accommodates up to 500 guests, great for larger conferences at $200 per person.
• The Westin New York at Times Square: A massive venue that can host 1,000 people at $215 per person.

Best for Luxury Retreats

• The Ritz-Carlton Chicago: For high-end corporate gatherings, capacity of 300 at $300 per person.
• Convene - 22 Hudson Yards: A premium space for tech teams at $350 per person for up to 400 attendees.

Budget Breakdown for a Typical Offsite

Assuming a team of 20 for a 3-day retreat, here’s a sample budget breakdown:

• Venue (40%): $1,800 (based on $225/person for 3 days)
• Food & Beverage (25%): $1,125 (breakfast, lunch, dinner)
• Activities (15%): $675 (team-building exercises)
• Travel (15%): $675 (airfare and transport)
• Contingency (5%): $225

Total Estimated Cost: $4,500

Sample 3-Day Itinerary

Day 1: Arrival & Team Kickoff

• Morning: Arrival and check-in
• Afternoon: Welcome lunch and team-building activity
• Evening: Dinner at a local restaurant

Day 2: Workshops & Strategy Sessions

• Morning: Workshop (venue provided)
• Afternoon: Breakout sessions
• Evening: Group dinner with guest speaker

Day 3: Wrap-Up & Departure

• Morning: Final presentations and feedback
• Afternoon: Lunch and check-out

Conclusion: Making Your Decision

When choosing between Chicago and New York City for your next offsite, consider your team’s needs, budget, and desired experience. Chicago offers unique venues with a slightly lower cost, while New York City boasts iconic locations and endless activities.

Action Items:

1. Determine your budget and team size.
2. Choose a city based on your team's goals and preferences.
3. Select venues from the comparison table and start outreach for availability.