Los Angeles vs Chicago for Team Retreats: A Comprehensive Analysis

As of May 2026, team retreats have become a vital part of fostering collaboration and creativity within organizations. In fact, 72% of employees report feeling more engaged after attending an offsite retreat. However, choosing the right city for your team's retreat can be daunting. This guide offers a detailed comparison between Los Angeles and Chicago, focusing on venues, activities, and logistical considerations to help you make an informed decision.

Why Choose Los Angeles or Chicago?

Los Angeles: The Allure of the West Coast

Los Angeles is known for its sunny weather, diverse culture, and vibrant arts scene. Ideal for teams looking to combine work with leisure, LA offers unique venues that can cater to a variety of needs.

Best Season: Late spring and early fall are ideal, with temperatures ranging from 70°F to 85°F.

Getting There: Los Angeles International Airport (LAX) is a major hub, making it accessible for teams traveling from various locations.

Chicago: The Windy City Experience

Chicago boasts a rich history, stunning architecture, and a robust food scene. It’s perfect for teams that appreciate urban culture and want a blend of business and exploration.

Best Season: Late spring and early fall provide pleasant weather, with temperatures typically between 60°F and 75°F.

Getting There: O'Hare International Airport (ORD) and Midway International Airport (MDW) serve as primary gateways, with numerous domestic and international flights.

Venue Comparison: Los Angeles vs. Chicago

Los Angeles Venues

| Venue Name | Location | Capacity | Price per Person/Night | Best For | Standout Feature | |-----------------------------|---------------------|--------------------|------------------------|------------------|----------------------------------| | The LINE Hotel | Koreatown | 100+ | $250-300 | Creative Retreats | Rooftop views and outdoor space | | The Ritz-Carlton | Downtown LA | 50-300 | $350-450 | Luxury Retreats | Full-service spa on-site | | The Maimon Group | Santa Monica | 20-100 | $200-275 | Small Teams | Beachfront access | | The Hollywood Roosevelt | Hollywood | 50-200 | $150-250 | Historic Themes | Vintage charm and décor | | The Westin Bonaventure | Downtown LA | 200-500 | $175-225 | Large Groups | Iconic revolving restaurant |

Chicago Venues

| Venue Name | Location | Capacity | Price per Person/Night | Best For | Standout Feature | |-----------------------------|---------------------|--------------------|------------------------|------------------|----------------------------------| | The Drake Hotel | Magnificent Mile | 50-300 | $250-350 | Elegant Retreats | Historic architecture | | The Field Museum | South Loop | 100-400 | $200-300 | Cultural Retreats | Access to exhibits | | The Chicago Athletic Association | Loop | 20-150 | $175-225 | Boutique Retreats | Unique sports-themed spaces | | The Langham | River North | 50-200 | $300-400 | Luxury Retreats | Stunning river views | | The W Chicago - City Center | Loop | 100-500 | $200-275 | Modern Retreats | Trendy design and nightlife |

Our Top Picks

Best for Small Teams

• Los Angeles: The Maimon Group (Santa Monica)
• Chicago: The Chicago Athletic Association (Loop)

Best for Large Groups

• Los Angeles: The Westin Bonaventure (Downtown LA)
• Chicago: The Field Museum (South Loop)

Best for Luxury Retreats

• Los Angeles: The Ritz-Carlton (Downtown LA)
• Chicago: The Langham (River North)

Activity Recommendations

Los Angeles Activities

1. Beach Volleyball at Santa Monica

   • Time Needed: 2 hours
   • Group Size: Up to 20
   • Cost: $20/person
   • Energy Level: High
   • Logistics: Venue must provide nets and balls.
   • Skip if: Your team prefers low-energy activities.

2. Studio Tour at Universal Studios

   • Time Needed: 3 hours
   • Group Size: Up to 30
   • Cost: $80/person
   • Energy Level: Moderate
   • Logistics: Book 4-6 weeks in advance.
   • Skip if: Team members are not fans of theme parks.

Chicago Activities

1. Architectural Boat Tour

   • Time Needed: 90 minutes
   • Group Size: Up to 50
   • Cost: $45/person
   • Energy Level: Low
   • Logistics: Book ahead for large groups.
   • Skip if: Team prefers more active options.

2. Cooking Class at The Chopping Block

   • Time Needed: 3 hours
   • Group Size: Up to 20
   • Cost: $90/person
   • Energy Level: Moderate
   • Logistics: Reservations required.
   • Skip if: Team has dietary restrictions.

Sample 3-Day Itinerary

Day 1: Arrival and Team Bonding

• Morning: Arrive and check into the venue.
• Afternoon: Icebreaker activities.
• Evening: Dinner at a local restaurant.

Day 2: Workshops and Activities

• Morning: Workshop session.
• Afternoon: Team activity (choose from recommendations).
• Evening: Group dinner at the venue.

Day 3: Wrap-Up and Departure

• Morning: Final meeting to discuss takeaways.
• Afternoon: Depart.

Budget Breakdown

For a team of 20, the estimated budget is as follows:

| Category | Cost Estimate ($) | Percentage Allocation | |-----------------|-------------------|-----------------------| | Venue | $4,000 | 40% | | F&B | $2,500 | 25% | | Activities | $1,500 | 15% | | Travel | $1,500 | 15% | | Contingency | $500 | 5% |

Conclusion

Choosing between Los Angeles and Chicago for your team retreat depends on your team's preferences, budget, and goals. Both cities offer unique venues and activities that can enhance your offsite experience.

Action Items:

1. Determine your team size and budget.
2. Choose your preferred city based on the analysis.
3. Start contacting venues to secure your dates.