Chicago vs New York: Which City Offers Better Team Retreat Venues?
Chicago vs New York: Which City Offers Better Team Retreat Venues? (2026)
Did you know that 80% of employees report feeling more connected to their team after an offsite retreat? Choosing the right city for your corporate retreat can significantly impact your team’s experience and productivity. In 2026, Chicago and New York stand out as top contenders for hosting corporate retreats, each offering unique venues and experiences. But which city truly offers better options for your team? Let’s dive into a detailed comparison.
Why Choose Chicago for Your Team Retreat?
Chicago is known for its rich architecture, vibrant culture, and accessibility. With venues that range from historic buildings to modern spaces, it caters to diverse corporate needs. Best seasons for retreats are spring and fall when the weather is mild. The city is easily accessible via O'Hare International Airport (ORD) and Midway International Airport (MDW).
Venue Options in Chicago
| Venue Name | Location | Capacity | Price/Person/Night | Best For | Standout Feature | |-----------------------|--------------------|---------------------|--------------------|-------------------|------------------------------------| | The Langham Chicago | River North | 10-300 | $250-400 | Luxury retreats | Stunning river views | | The Merchandise Mart | Near North Side | 20-1000 | $100-250 | Large conferences | Versatile event spaces | | The Drake Hotel | Gold Coast | 10-500 | $200-350 | Classic elegance | Historic charm | | Venue SIX10 | Loop | 10-400 | $150-300 | Creative workshops | Rooftop terrace | | The Chicago Athletic Association | Loop | 15-300 | $175-300 | Team-building | Unique sports amenities | | The Art Institute of Chicago | Grant Park | 20-200 | $200-350 | Cultural retreats | Access to world-class art |
Why Choose New York for Your Team Retreat?
New York City is the epitome of energy and innovation, making it a fantastic choice for corporate retreats aimed at creativity and networking. With a plethora of venues in diverse neighborhoods, NYC shines during the spring and fall. The city is accessible via three major airports: JFK, LaGuardia, and Newark.
Venue Options in New York
| Venue Name | Location | Capacity | Price/Person/Night | Best For | Standout Feature | |-----------------------|--------------------|---------------------|--------------------|-------------------|------------------------------------| | The Standard, High Line | Meatpacking District | 10-500 | $250-500 | Trendy retreats | Rooftop bar with skyline views | | The New Yorker Hotel | Midtown | 20-800 | $150-300 | Large gatherings | Historic architecture | | 99 Scott | Bushwick | 30-300 | $100-200 | Creative workshops | Industrial chic vibe | | Convene - 22 W 38th St| Midtown | 10-500 | $200-400 | Corporate meetings | All-inclusive packages | | Brooklyn Grange | Brooklyn | 10-200 | $150-250 | Outdoor retreats | Rooftop farm experience | | The Bowery Hotel | Bowery | 10-150 | $300-600 | Boutique retreats | Intimate atmosphere |
Chicago vs. New York: A Comparison Table
| Venue Name | Location | Capacity | Price/Person/Night | Best For | F&B Included | AV Quality | |-----------------------|--------------------|----------|--------------------|-------------------|--------------|--------------| | The Langham Chicago | River North | 10-300 | $250-400 | Luxury retreats | Yes | Excellent | | The Standard, High Line | Meatpacking District | 10-500 | $250-500 | Trendy retreats | Yes | Excellent | | The Merchandise Mart | Near North Side | 20-1000 | $100-250 | Large conferences | Yes | Good | | The New Yorker Hotel | Midtown | 20-800 | $150-300 | Large gatherings | Yes | Good | | Venue SIX10 | Loop | 10-400 | $150-300 | Creative workshops | Yes | Good | | 99 Scott | Bushwick | 30-300 | $100-200 | Creative workshops | No | Fair | | The Drake Hotel | Gold Coast | 10-500 | $200-350 | Classic elegance | Yes | Excellent | | Convene - 22 W 38th St| Midtown | 10-500 | $200-400 | Corporate meetings | Yes | Excellent | | The Chicago Athletic Association | Loop | 15-300 | $175-300 | Team-building | Yes | Good | | Brooklyn Grange | Brooklyn | 10-200 | $150-250 | Outdoor retreats | Yes | Good | | The Art Institute of Chicago | Grant Park | 20-200 | $200-350 | Cultural retreats | Yes | Excellent | | The Bowery Hotel | Bowery | 10-150 | $300-600 | Boutique retreats | Yes | Excellent |
Our Top Picks
- For Luxury Experience: The Langham Chicago vs. The Standard, High Line
- For Budget-Friendly Options: The Merchandise Mart vs. 99 Scott
- For Large Groups: The New Yorker Hotel vs. The Drake Hotel
Conclusion
Both Chicago and New York offer exceptional venues for team retreats, each with its unique advantages. Chicago is ideal for those seeking comfort and historic charm, while New York excels in trendy, vibrant environments. Consider your team’s objectives, budget, and desired atmosphere when making your choice.
Action Items:
- Determine your team size and budget.
- Select your preferred city based on the analysis above.
- Reach out to your top venue choices for availability and pricing.
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