Chicago vs New York: Which City Offers the Best Venues for Executive Retreats?
Chicago vs New York: Which City Offers the Best Venues for Executive Retreats?
Did you know that 70% of companies report increased productivity and morale after conducting an executive retreat? With the stakes so high, choosing the right city and venue is crucial for your next offsite. In 2026, both Chicago and New York boast a plethora of options, but which city offers the best venues for executive retreats? Let's break down the specifics.
Why Choose Chicago?
Chicago is known for its vibrant culture, stunning architecture, and accessibility. The city boasts a central location, making it convenient for teams coming from various regions. The best time to visit is during spring (April to June) or fall (September to November) when temperatures are mild, and the city is buzzing with activity.
Venue Options in Chicago
| Venue Name | Location | Capacity | Price/Person/Night | Best For | Standout Feature | |--------------------------------|--------------------|------------------|---------------------|-------------------------|---------------------------------| | The Langham Chicago | River North | 20-300 | $300-450 | Luxury retreats | Rooftop terrace with skyline views | | The Palmer House Hilton | Loop | 50-1000 | $200-350 | Large groups | Historic ballroom | | The Chicago Athletic Association| Loop | 10-200 | $250-400 | Small to medium teams | Private rooftop bar | | The Hyatt Regency O'Hare | Rosemont | 10-1000 | $150-300 | Tech-focused retreats | State-of-the-art AV equipment | | The Ritz-Carlton, Chicago | Magnificent Mile | 10-200 | $500-700 | High-profile clients | Exceptional catering options |
Why Choose New York?
New York City is the epicenter of business and innovation, offering unparalleled networking opportunities. The best seasons to visit are spring (March to June) and fall (September to November) when the city is alive with events and activities.
Venue Options in New York
| Venue Name | Location | Capacity | Price/Person/Night | Best For | Standout Feature | |--------------------------------|--------------------|------------------|---------------------|-------------------------|---------------------------------| | The Standard, High Line | Meatpacking District| 10-300 | $350-500 | Trendy retreats | Rooftop bar with views | | The Conrad New York Downtown | Financial District | 50-600 | $250-400 | Corporate gatherings | Spacious event space | | 1 Hotel Brooklyn Bridge | Brooklyn | 20-200 | $300-450 | Eco-conscious teams | Green building design | | The Westin New York at Times Square | Midtown | 50-2000 | $200-350 | Large conferences | Proximity to major attractions | | The Bowery Hotel | Lower East Side | 10-150 | $400-600 | Creative teams | Chic, artsy decor |
Venue Comparison Table
| Venue Name | Location | Capacity | Price/Person/Night | Best For | F&B Included | AV Quality | |--------------------------------|--------------------|------------------|---------------------|-------------------------|--------------|---------------| | The Langham Chicago | River North | 20-300 | $300-450 | Luxury retreats | Yes | High | | The Palmer House Hilton | Loop | 50-1000 | $200-350 | Large groups | Yes | Medium | | The Standard, High Line | Meatpacking District| 10-300 | $350-500 | Trendy retreats | Yes | High | | The Conrad New York Downtown | Financial District | 50-600 | $250-400 | Corporate gatherings | Yes | High | | The Chicago Athletic Association| Loop | 10-200 | $250-400 | Small to medium teams | Yes | Medium | | The Ritz-Carlton, Chicago | Magnificent Mile | 10-200 | $500-700 | High-profile clients | Yes | High | | The Westin New York at Times Square | Midtown | 50-2000 | $200-350 | Large conferences | Yes | Medium |
Our Top Picks
For Small Teams
- Chicago: The Chicago Athletic Association - Ideal for intimate discussions.
- New York: The Bowery Hotel - Perfect for creative brainstorming.
For Large Groups
- Chicago: The Palmer House Hilton - Ample space for big gatherings.
- New York: The Westin New York at Times Square - Great for large conferences.
For Luxury Experiences
- Chicago: The Langham Chicago - A touch of elegance with top-notch service.
- New York: The Standard, High Line - Trendy atmosphere with stunning views.
Budget Breakdown for Typical Team Size
For a team of 10, here's a sample budget for a 3-day executive retreat:
- Venue: $300/person/night x 3 nights = $9,000
- Food & Beverage: $100/person/day x 3 days = $3,000
- Activities: $75/person/day x 3 days = $2,250
- Travel: $150/person (average flight) = $1,500
- Contingency (5%): $1,175
Total Estimated Cost: $16,925
Conclusion
Both Chicago and New York offer exceptional venues for executive retreats, each with its unique advantages. Chicago's affordability and spacious venues make it a strong contender, while New York's vibrant atmosphere and networking opportunities are hard to beat.
Action Items:
- Assess your team's needs: size, budget, and goals.
- Select your preferred city based on the information provided.
- Reach out to venues early to secure the best rates and availability.
Get a Free Custom Offsite Proposal
Tell us your team size, dates, and goals. We'll send venue options, activity ideas, and a full budget breakdown within 48 hours.