Best 10 Venues for Remote Team Retreats in Chicago 2026

Planning a remote team retreat can be daunting, especially when considering logistics, budget, and the ultimate goal of team bonding. Did you know that 70% of teams report improved collaboration and communication after offsite retreats? If you're looking to boost your team's synergy in 2026, Chicago offers a wealth of venues that cater to various needs and budgets. Here’s a practical guide to help you choose the best spot for your next corporate offsite.

Why Choose Chicago for Your Team Retreat?

Chicago is not just known for its deep-dish pizza and stunning skyline; it’s also a hub for innovation and collaboration. With a rich culture, diverse activities, and excellent connectivity (O'Hare International Airport is a major hub), it makes for an ideal location for remote teams to gather. The best times to visit are spring (April to June) and fall (September to November) when the weather is pleasant, and hotel rates are more reasonable.

Venue Comparison Table

| Venue Name | Location | Capacity | Price/Person/Night | Best For | Standout Feature | F&B Included | |-----------------------|------------------------|----------------|---------------------|------------------------|----------------------------|--------------| | The Gwen | Near North Side | 150 | $200-300 | Large Teams | Rooftop terrace | Yes | | The Drake Hotel | Gold Coast | 200 | $175-250 | Luxury Experience | Historic charm | Yes | | Spaces - River North | River North | 100 | $75-150 | Creative Meetings | Flexible layouts | No | | The Chicago Athletic Association | Loop | 250 | $150-225 | Team Building | Historic sports club | Yes | | The Westin Chicago River North | River North | 180 | $180-260 | Relaxed Retreat | River views | Yes | | Hotel Chicago Downtown | Loop | 120 | $125-200 | Budget-Conscious | Central location | Yes | | The Field Museum | Museum Campus | 500 | $100-250 | Unique Experiences | Access to exhibits | Yes | | The Art Institute of Chicago | Grant Park | 300 | $200-350 | Cultural Immersion | Art tours available | No | | The Langham, Chicago | River North | 150 | $300-400 | High-End Retreat | Spa services | Yes | | Navy Pier | Near North Side | 500 | $50-100 | Large Gatherings | Iconic views | No |

Our Top Picks

For Large Teams:

The Gwen - This venue offers a stunning rooftop terrace and ample space for large gatherings. Ideal for teams looking to combine work and leisure.

For Budget-Conscious Groups:

Hotel Chicago Downtown - A central location with essential amenities at a competitive price, ensuring you don't break the bank.

For Unique Experiences:

The Field Museum - Engage your team with a retreat surrounded by fascinating exhibits. Perfect for sparking creativity and teamwork.

Conclusion

Choosing the right venue for your remote team retreat in Chicago can set the tone for a productive and enjoyable experience. Here’s a quick action plan:

1. Determine your budget: Use the price ranges provided to set a realistic budget.
2. Consider your team size and needs: Review the venue capacities and unique features to find the best fit.
3. Book early: Venues can fill up quickly, especially in peak seasons. Aim to book at least 3-4 months in advance.
4. Plan activities: Incorporate team-building activities that align with your retreat goals.

Ready to take the next step?