Chicago vs Boston: Best Cities for Hybrid Working Retreats
Chicago vs Boston: Best Cities for Hybrid Working Retreats
In 2026, a surprising 82% of employees prefer hybrid working models, making retreats more vital than ever for team cohesion and productivity. Choosing the right city for your hybrid working retreat can significantly impact your team's experience and outcomes. This guide compares Chicago and Boston, two vibrant cities that offer unique advantages for hybrid retreats.
Why Choose Chicago for Your Hybrid Retreat?
Chicago, known for its stunning skyline and rich cultural scene, provides a dynamic backdrop for hybrid retreats. The city boasts excellent transportation options, a variety of venues, and a wealth of activities to engage your team.
Best Seasons to Visit
- Spring (April to June): Ideal for pleasant weather and outdoor activities.
- Fall (September to November): Beautiful foliage and mild temperatures.
Getting There
Chicago is accessible via O'Hare International Airport (ORD) and Midway International Airport (MDW), with excellent public transport options to downtown venues.
Why Choose Boston for Your Hybrid Retreat?
Boston, steeped in history and innovation, offers a unique environment perfect for creativity and collaboration. Its walkable neighborhoods make it easy for teams to explore and bond after sessions.
Best Seasons to Visit
- Summer (June to August): Warm weather perfect for outdoor activities.
- Fall (September to November): Vibrant autumn scenery and cultural events.
Getting There
Logan International Airport (BOS) serves Boston, with quick access to downtown via the Silver Line or taxi services.
Venue Comparison: Chicago vs Boston
Below is a comparison table of notable venues in both cities, focusing on capacity, price, and suitability for hybrid retreats.
| Venue Name | City | Capacity | Price/Person/Night | Best For | Standout Feature | F&B Included | |------------------------|-----------|------------------|---------------------|-------------------|----------------------------|--------------| | The Langham Chicago | Chicago | 50-300 | $250-350 | Luxury Retreats | Rooftop terrace | Yes | | The Palmer House Hilton | Chicago | 60-400 | $150-250 | Historic Charm | Grand ballroom | Yes | | Chicago Athletic Association | Chicago | 20-100 | $200-300 | Team Building | Sports facilities | Yes | | The Bostonian Boston | Boston | 30-200 | $200-300 | Corporate Meetings | Waterfront views | Yes | | The Ritz-Carlton, Boston| Boston | 50-150 | $300-450 | Executive Retreats | Luxury spa access | Yes | | The Westin Boston Seaport| Boston | 50-300 | $175-275 | Large Groups | Rooftop bar | Yes | | The Revere Hotel | Boston | 20-150 | $150-250 | Creative Sessions | Art-inspired decor | Yes |
Venue Categories
Best for Small Teams (10-50 people)
- Chicago Athletic Association
- The Bostonian Boston
Best for Large Groups (100+ people)
- The Langham Chicago
- The Westin Boston Seaport
Our Top Picks for Different Scenarios
- Luxury Experience: The Langham Chicago - $250-350/person/night, capacity 50-300.
- Budget-Friendly: The Palmer House Hilton - $150-250/person/night, capacity 60-400.
- Unique Setting: Chicago Athletic Association - $200-300/person/night, capacity 20-100.
Budget Breakdown for Typical Team Size
For a team of 20, here’s a sample budget breakdown for a 3-day retreat:
- Venue (40%): $2,000
- F&B (25%): $1,250
- Activities (15%): $750
- Travel (15%): $750
- Contingency (5%): $250
- Total: $5,000 or $250/person
Sample 3-Day Itinerary
Day 1: Arrival and Team Building
- Morning: Arrive and check-in
- Afternoon: Kick-off meeting (Venue)
- Evening: Team dinner at a local restaurant
Day 2: Workshops and Activities
- Morning: Workshop sessions (Venue)
- Afternoon: Outdoor team-building activity (e.g., scavenger hunt)
- Evening: Networking event at a local brewery
Day 3: Wrap-Up and Departure
- Morning: Final presentations (Venue)
- Afternoon: Lunch and team feedback session
- Evening: Depart
Conclusion
Choosing between Chicago and Boston for your hybrid working retreat will depend on your team's goals and preferences. Both cities offer unique venues and experiences to foster collaboration and creativity. Consider the specific needs of your group when making your decision.
Action Items
- Determine your budget and team size.
- Select preferred dates and book venues at least 4 months in advance.
- Plan activities that align with your retreat goals.
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.