Chicago vs New York: Which City Offers the Best Corporate Retreat Venues? (2026)

Planning a corporate retreat can be daunting, especially when deciding between vibrant cities like Chicago and New York. Did you know that 70% of companies that invest in offsite retreats report a significant boost in team morale and productivity? As a Chief of Staff or HR leader, you want to ensure your investment yields the best results. In this guide, we'll break down the best venues in both cities, comparing their offerings to help you make an informed decision for your 2026 corporate retreat.

Overview: Why Choose Chicago or New York?

Chicago

• Best Seasons: Late spring (April to June) and early fall (September to November) offer mild weather and fewer crowds.
• Getting There: O'Hare International Airport (ORD) and Midway International Airport (MDW) provide easy access to the city.

New York

• Best Seasons: Spring (March to May) for blooming parks and pleasant weather; fall (September to November) for the stunning autumn foliage.
• Getting There: Multiple airports (JFK, LaGuardia, Newark) make it accessible from anywhere.

Venue Comparison Table

| Name | Location | Capacity | Price/Person/Night | Best For | Standout Feature | F&B Included | |-----------------------------|------------------|------------------|---------------------|-----------------------|----------------------------------|--------------| | The Drake Hotel | Chicago | 200 (theater) | $250 | Large groups | Historic elegance | Yes | | The Art Institute of Chicago| Chicago | 150 (theater) | $175 | Creative teams | Unique art backdrop | Yes | | The Langham, Chicago | Chicago | 400 (theater) | $300 | Luxury retreats | River view meeting rooms | Yes | | Convene at 101 Park Avenue | New York | 250 (theater) | $275 | Tech companies | State-of-the-art AV | Yes | | The Standard, High Line | New York | 300 (theater) | $280 | Trendy groups | Rooftop views | Yes | | The Westin New York at Times Square | New York | 500 (theater) | $230 | Large corporate events | Proximity to attractions | Yes | | Chicago Athletic Association | Chicago | 100 (theater) | $220 | Sports-focused teams | Historic venue with sports themes| Yes | | The New Yorker Hotel | New York | 800 (theater) | $210 | Large gatherings | Iconic skyline views | Yes |

Breakdown by Category

Best for Small Teams (Under 50)

• The Art Institute of Chicago: A creative ambiance ideal for brainstorming sessions.
• The Chicago Athletic Association: Offers a sports-focused environment with unique meeting spaces.

Best for Medium Teams (50-150)

• The Drake Hotel: Historic charm with modern amenities, perfect for networking.
• Convene at 101 Park Avenue: A tech-savvy space with great facilities.

Best for Large Groups (150+)

• The Langham, Chicago: Luxury setting with expansive meeting rooms.
• The Westin New York at Times Square: Ample space and ideal location for large gatherings.

Our Top Picks

• Best Value: The Art Institute of Chicago offers a unique setting at $175 per person, ideal for creative teams.
• Most Luxurious: The Langham, Chicago provides top-notch amenities at $300 per person for those looking to impress.
• Best for Large Events: The New Yorker Hotel accommodates up to 800 people at $210 per person, perfect for major corporate gatherings.

Conclusion: Clear Action Items

1. Evaluate Your Needs: Determine the size of your team and the type of atmosphere you want for your retreat.
2. Set a Budget: Consider your budget range and prioritize venues that fit within it.
3. Book Early: Popular venues fill up quickly, especially in peak seasons. Aim to reserve 4-6 months in advance for optimal options.
4. Visit the Venues: If possible, schedule site visits to ensure the venue meets your expectations.

With this guide, you can confidently choose between Chicago and New York for your next corporate retreat. Each city offers unique venues and experiences that can cater to your team's needs.