Chicago vs New York: Which City Offers Better Value for Team Offsites? (2026)

Did you know that companies that invest in team offsites see a 25% increase in employee engagement? Yet, choosing the right city for your offsite can be a daunting task, especially when comparing costs, venues, and activities. In 2026, Chicago and New York remain two of the most popular cities for corporate offsites, but which one offers better value? Let’s break down the specifics.

Overview: Why Choose These Cities for Offsites?

Chicago: The Heart of the Midwest

• Best Seasons: Spring (April-June) and Fall (September-November) offer mild weather and vibrant city life.
• Getting There: O'Hare International Airport (ORD) is a major hub, making it accessible for teams traveling from across the country.

New York: The City That Never Sleeps

• Best Seasons: Spring (April-June) and Fall (September-November) are ideal for pleasant weather and outdoor activities.
• Getting There: Multiple airports (JFK, LGA, EWR) provide excellent connectivity, but expect higher travel costs.

Venue Comparison: Chicago vs. New York

| Name | Location | Capacity | Price/Person/Night | Best For | Standout Feature | |---------------------|--------------------|----------------|--------------------|-------------------------|------------------------------------| | The Langham | Chicago | 20-300 | $250-350 | Luxury Retreats | Stunning River views | | The Palmer House | Chicago | 10-1000 | $175-275 | Large Conferences | Historic charm | | Spaces at 600 | Chicago | 10-200 | $75-150 | Small Team Meetings | Flexible layouts | | The Standard Hotel | New York City | 20-500 | $300-450 | Trendy Gatherings | Rooftop bar with skyline views | | Convene | New York City | 10-400 | $150-350 | Workshops & Seminars | All-inclusive F&B options | | The New Yorker Hotel| New York City | 15-1000 | $200-300 | Large Groups | Central location in Midtown | | The Gramercy Park | New York City | 30-500 | $250-400 | Executive Retreats | Private park access |

Budget Breakdown for Offsites

Chicago

• Venue: 40% ($100/person average)
• Food & Beverage: 25% ($60/person)
• Activities: 15% ($37.50/person)
• Travel: 15% ($37.50/person)
• Contingency: 5% ($12.50/person)
• Total: $250/person/day

New York

• Venue: 40% ($120/person average)
• Food & Beverage: 25% ($75/person)
• Activities: 15% ($45/person)
• Travel: 15% ($45/person)
• Contingency: 5% ($15/person)
• Total: $300/person/day

Activity Recommendations

Chicago Activities

1. Architectural Boat Tour

   • Time Needed: 1.5 hours
   • Group Size: Up to 150
   • Cost: $50/person
   • Energy Level: Low
   • Skip if: Your team prefers indoor activities.

2. Escape Room Challenge

   • Time Needed: 2 hours
   • Group Size: Up to 12 per room
   • Cost: $30/person
   • Energy Level: Medium
   • Skip if: Your team isn't keen on puzzles.

New York Activities

1. Central Park Team Scavenger Hunt

   • Time Needed: 3 hours
   • Group Size: 10-100
   • Cost: $60/person
   • Energy Level: Medium
   • Skip if: It’s raining or your team prefers indoor settings.

2. Broadway Show Experience

   • Time Needed: 3-4 hours
   • Group Size: Up to 200
   • Cost: $120/person
   • Energy Level: Low
   • Skip if: Your team has no interest in theater.

Sample 3-Day Itinerary

Chicago Offsite

• Day 1: Arrival & Welcome Dinner at The Langham
• Day 2: Morning Meeting, Afternoon Boat Tour, Evening Team Dinner
• Day 3: Wrap-Up Meeting, Depart

New York Offsite

• Day 1: Arrival & Evening Welcome Reception at The Standard
• Day 2: Morning Workshop, Afternoon Scavenger Hunt, Evening Broadway Show
• Day 3: Final Meeting & Depart

Conclusion: Key Takeaways

In 2026, Chicago generally offers better value for team offsites, especially for mid-sized teams looking for a balance of cost and experience. New York excels in unique venues and activities but comes at a premium.

Action Items:

1. Decide on your budget and preferred city.
2. Choose venues based on your team's size and needs.
3. Book your offsite 4-6 months in advance to secure the best rates.