Chicago vs Miami for Summer Team Retreats: Which City is Right for You? (2026)

Planning a summer retreat for your team can feel overwhelming, especially when choosing between two vibrant cities like Chicago and Miami. Did you know that 88% of companies that invest in team offsites report improved collaboration and morale? With those numbers, making the right choice is crucial. In this guide, we’ll dive deep into comparing Chicago and Miami for your summer team retreat, providing specific venues, budgets, and logistics to help you decide.

Overview: Why Choose Chicago or Miami?

Chicago

• Best Seasons: Summer (June to August) offers pleasant weather, perfect for outdoor activities.
• Getting There: Chicago O'Hare International Airport (ORD) is a major hub with numerous direct flights.

Miami

• Best Seasons: Summer is warm and sunny, ideal for beach activities, but be mindful of humidity and occasional rain.
• Getting There: Miami International Airport (MIA) provides extensive flight options and is about 20 minutes from most venues.

Venue Comparison: Chicago vs. Miami

Chicago Venues

| Venue Name | Location | Capacity | Price/Person/Night | Best For | Standout Feature | |---------------------------|-----------------------|---------------|---------------------|-----------------------|-------------------------------------| | The Langham | River North | 10-600 | $250-350 | Luxury retreats | River views, top-notch service | | The Palmer House Hilton | Loop | 10-1,000 | $200-300 | Large groups | Historic charm | | The Chicago Athletic Association | Loop | 10-300 | $175-275 | Team bonding | Unique sports facilities | | Virgin Hotels Chicago | Loop | 10-400 | $200-300 | Modern retreats | Rooftop bar and lounge | | The Drake Hotel | Gold Coast | 10-500 | $225-325 | Formal meetings | Historic elegance |

Miami Venues

| Venue Name | Location | Capacity | Price/Person/Night | Best For | Standout Feature | |---------------------------|-----------------------|---------------|---------------------|-----------------------|-------------------------------------| | The Fontainebleau Miami Beach | Mid Beach | 10-1,500 | $300-500 | Luxury retreats | Oceanfront views | | Kimpton EPIC Hotel | Downtown Miami | 10-500 | $200-400 | Trendy gatherings | Rooftop pool and bar | | Miami Beach Convention Center | Miami Beach | 50-10,000 | $150-300 | Large conventions | Versatile spaces | | The Ritz-Carlton Key Biscayne | Key Biscayne | 10-500 | $275-425 | Upscale retreats | Private beach access | | The Biltmore Hotel | Coral Gables | 10-1000 | $200-350 | Historic elegance | Stunning golf course |

Activity Recommendations

Chicago Activities

1. Architectural Boat Tour

   • Time Needed: 90 minutes
   • Group Size: 15-150
   • Cost: $50/person
   • Energy Level: Low
   • Indoor/Outdoor: Outdoor
   • Skip if: Team prefers more active options.

2. Escape Room Experience

   • Time Needed: 2 hours
   • Group Size: 6-12
   • Cost: $35/person
   • Energy Level: Medium
   • Indoor/Outdoor: Indoor
   • Skip if: Team dislikes puzzles or challenges.

Miami Activities

1. Beach Volleyball Tournament

   • Time Needed: 2 hours
   • Group Size: 6-30
   • Cost: $20/person
   • Energy Level: High
   • Indoor/Outdoor: Outdoor
   • Skip if: Team prefers low-energy activities.

2. Art Deco Walking Tour

   • Time Needed: 2 hours
   • Group Size: 10-50
   • Cost: $25/person
   • Energy Level: Low
   • Indoor/Outdoor: Outdoor
   • Skip if: Team is not interested in history or architecture.

Sample 3-Day Itinerary

Day 1: Arrival and Welcome

• Morning: Arrive at chosen venue, check-in.
• Afternoon: Team lunch at venue restaurant.
• Evening: Welcome reception with cocktails.

Day 2: Team Building and Workshops

• Morning: Outdoor team-building activities (e.g., Escape Room in Chicago, Beach Volleyball in Miami).
• Afternoon: Workshops or brainstorming sessions.
• Evening: Group dinner at a local restaurant.

Day 3: Explore and Depart

• Morning: Optional activity (Architectural Boat Tour in Chicago, Art Deco Tour in Miami).
• Afternoon: Wrap-up session, feedback collection.
• Evening: Depart.

Budget Breakdown for a Team of 20

| Category | Estimated Cost | Percentage of Total | |-------------------|------------------|---------------------| | Venue | $4,000 | 40% | | Food & Beverage | $2,500 | 25% | | Activities | $1,500 | 15% | | Travel | $1,500 | 15% | | Contingency | $500 | 5% | | Total | $10,000 | 100% |

Conclusion: Action Steps

Choosing between Chicago and Miami for your summer retreat depends on your team's preferences, budget, and desired activities. Both cities offer unique venues and experiences to enhance team bonding and productivity.

• Step 1: Determine your budget and team size.
• Step 2: Choose the city that aligns with your goals.
• Step 3: Book your venue at least 4 months in advance for best rates.

Ready to plan your summer retreat?