New York vs Chicago for Team Retreats: Which City Wins?
New York vs Chicago for Team Retreats: Which City Wins? (2026)
When it comes to planning corporate retreats, choosing the right city can make all the difference. Did you know that 85% of employees report increased productivity after attending an offsite retreat? With that in mind, let’s dive into a head-to-head comparison of New York and Chicago to determine which city is better for your next team retreat in 2026.
Overview: Why Choose New York or Chicago?
New York
New York City is a bustling metropolis filled with iconic landmarks, diverse culture, and endless entertainment options. It’s the perfect backdrop for inspiring creativity and teamwork. Best seasons to visit are spring (April to June) and fall (September to November) when the weather is mild.
Chicago
Chicago boasts a rich history, stunning architecture, and a vibrant food scene. It provides a more laid-back atmosphere compared to NYC, making it an excellent choice for teams looking to bond without the hustle and bustle. The best seasons to visit are late spring (May to June) and early fall (September to October).
Getting There
- New York: Major airports include JFK, LaGuardia, and Newark. Expect about 30-60 minutes of travel time from the airport to downtown.
- Chicago: O'Hare and Midway are the primary airports. Travel time to downtown Chicago is typically around 30-45 minutes.
Venue Comparison Table
| Venue Name | Location | Capacity | Price/Person/Night | Best For | Standout Feature | |---------------------------|-------------------------|----------------|---------------------|---------------------|-----------------------------------| | The Westin New York | Times Square, NYC | 500 | $250 | Large Teams | Rooftop terrace with skyline views | | The Langham | Midtown, NYC | 100 | $400 | Luxury Retreats | Award-winning spa | | Convene | Financial District, NYC | 200 | $200 | Workshops | All-inclusive meeting packages | | The Drake Hotel | Gold Coast, Chicago | 300 | $180 | Elegant Events | Historic charm | | The Kimpton Gray Hotel | Loop, Chicago | 150 | $220 | Modern Teams | Rooftop bar and lounge | | Virgin Hotels Chicago | Loop, Chicago | 200 | $200 | Creative Retreats | Unique meeting spaces | | The Palmer House Hilton | Loop, Chicago | 500 | $195 | Large Groups | Historic ballroom |
Our Top Picks for Different Scenarios
1. Best for Large Teams
- Venue: The Westin New York
- Location: Times Square, NYC
- Capacity: 500
- Price: $250/person/night
2. Best for Creative Retreats
- Venue: Virgin Hotels Chicago
- Location: Loop, Chicago
- Capacity: 200
- Price: $200/person/night
3. Best for Luxury Experience
- Venue: The Langham
- Location: Midtown, NYC
- Capacity: 100
- Price: $400/person/night
Activity Recommendations
New York
-
Central Park Team Scavenger Hunt
- Time Needed: 3 hours
- Group Size: 10-50
- Cost: $50/person
- Energy Level: Moderate
- Logistics: Requires a guide.
-
Broadway Show Experience
- Time Needed: 3 hours
- Group Size: 10-100
- Cost: $150/person
- Energy Level: Low
- Logistics: Book tickets in advance.
Chicago
-
Chicago River Architecture Boat Tour
- Time Needed: 1.5 hours
- Group Size: 10-100
- Cost: $40/person
- Energy Level: Low
- Logistics: Reserve private boats for larger groups.
-
Cooking Class at The Chopping Block
- Time Needed: 3 hours
- Group Size: 10-20
- Cost: $125/person
- Energy Level: Moderate
- Logistics: Book early for group classes.
Sample 3-Day Itinerary
Day 1: Arrival and Welcome
- Morning: Arrival at the venue
- Afternoon: Icebreaker activities
- Evening: Welcome dinner at a local restaurant
Day 2: Team Building and Planning
- Morning: Workshop session
- Afternoon: Group activity (e.g., scavenger hunt or cooking class)
- Evening: Free time to explore the city
Day 3: Wrap-Up and Departure
- Morning: Final meeting and feedback session
- Afternoon: Departure
Budget Breakdown for a Team of 20
| Category | Estimated Cost | |------------------|------------------| | Venue | $4,000 | | F&B | $2,500 | | Activities | $1,500 | | Travel | $3,000 | | Contingency | $1,000 | | Total | $12,000 |
Conclusion: Making the Choice
Both New York and Chicago offer excellent venues and activities for team retreats. Consider your team’s size, budget, and desired atmosphere when making your choice.
Action Items:
- Decide on your preferred city.
- Select a venue based on your team's needs.
- Book your venue at least 4 months in advance for best rates.
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