Chicago vs New York: Which City is Best for Your Next Corporate Retreat? (2026)

Did you know that 86% of employees believe that offsites significantly improve team morale and collaboration? As leaders in HR and corporate strategy, choosing the right city for your next corporate retreat can make all the difference. In this guide, we'll compare Chicago and New York City—two vibrant hubs for corporate gatherings—so you can make an informed decision for 2026.

Why Choose Chicago for Your Corporate Retreat?

Chicago, known for its stunning architecture and rich history, boasts a variety of venues that cater to corporate needs. The city is often more budget-friendly than New York, making it ideal for teams looking to maximize their investment.

Best Seasons to Visit

• Spring (April - June): Mild weather with beautiful flowers blooming, perfect for outdoor activities.
• Fall (September - November): Stunning autumn colors, great for team-building activities and explorations.

Getting There

Chicago O'Hare International Airport (ORD) is one of the busiest airports in the U.S., offering numerous direct flights. The city is easily accessible via public transportation, and many venues provide shuttle services.

Why Choose New York for Your Corporate Retreat?

New York City, the bustling metropolis, is a cultural melting pot with a plethora of venues that can accommodate any corporate need. From high-end luxury to unique spaces, NYC is perfect for teams looking to impress.

Best Seasons to Visit

• Spring (April - June): The city comes alive with events and activities; great for networking.
• Fall (September - November): Ideal for experiencing the vibrant arts scene and outdoor events.

Getting There

With three major airports (JFK, LaGuardia, and Newark), New York is a breeze to reach from virtually anywhere. The extensive subway system makes getting around easy, though traffic can be a challenge.

Venue Comparison Table

| Venue Name | Location | Capacity | Price/Person/Night | Best For | Standout Feature | F&B Included | |-------------------------|-------------------|--------------|---------------------|-----------------------|--------------------------|--------------| | The Langham Chicago | Chicago, IL | 10-400 | $250-350 | Luxury retreats | Stunning river views | Yes | | The Drake Hotel | Chicago, IL | 20-600 | $175-275 | Historic charm | Iconic architecture | Yes | | The Art Institute | Chicago, IL | 50-200 | $150-200 | Unique experience | Private gallery access | Yes | | Convene at 101 Park Ave | New York, NY | 20-500 | $300-450 | Corporate events | State-of-the-art tech | Yes | | The New York EDITION | New York, NY | 10-200 | $350-600 | High-end gatherings | Luxury accommodations | Yes | | The Glasshouse | New York, NY | 50-300 | $250-400 | Modern ambiance | Panoramic city views | Yes | | The Bowery Hotel | New York, NY | 10-150 | $400-600 | Boutique experience | Unique artistic decor | Yes |

Venue Recommendations by Group Size

Best for Small Teams (10-50)

• The Art Institute (Chicago, IL): Unique experience, $150-200/person, capacity 50-200.
• The Bowery Hotel (New York, NY): Boutique experience, $400-600/person, capacity 10-150.

Best for Medium Teams (50-200)

• The Drake Hotel (Chicago, IL): Historic charm, $175-275/person, capacity 20-600.
• The Glasshouse (New York, NY): Modern ambiance, $250-400/person, capacity 50-300.

Best for Large Teams (200+)

• The Langham Chicago (Chicago, IL): Luxury retreats, $250-350/person, capacity 10-400.
• Convene at 101 Park Ave (New York, NY): Corporate events, $300-450/person, capacity 20-500.

Our Top Picks for Different Scenarios

1. Budget-Friendly Option: The Drake Hotel, Chicago
2. Luxury Experience: The New York EDITION, New York
3. Unique Venue: The Art Institute, Chicago

Conclusion

As you weigh the options between Chicago and New York for your next corporate retreat, consider your team's size, budget, and desired experience. Both cities offer unique venues that cater to various needs, ensuring a successful offsite.

Action Items:

1. Determine your budget and team size.
2. Choose your preferred city based on your team's needs.
3. Book your venue at least 4-6 months in advance for the best rates.