Chicago Corporate Retreats & Offsites
Nature-based experiences in illinoisDiscover illinois
Why choose Chicago for your team retreat?
Chicago combines world-class dining, iconic architecture, and endless waterfront experiences into a retreat destination that’s as exciting as it is accessible. Whether your team is cruising the Chicago River, exploring renowned museums, or taking in Lake Michigan from the water, the city offers something memorable around every corner. With O’Hare International Airport less than an hour away, Chicago makes it easy to bring teams together while delivering an experience that feels distinctly different from the everyday.
RECOMMENDED VENUE
Thompson Chicago
Located in Chicago’s upscale Gold Coast neighborhood, Thompson Chicago offers a boutique retreat experience with the city’s best attractions just outside the front door. The hotel pairs modern, loft-inspired design with sophisticated meeting spaces, luxury accommodations, and views of Lake Michigan, while the Magnificent Mile, Oak Street Beach, and countless restaurants are all within walking distance. It’s a venue that gives teams the flexibility to balance productive meetings with everything that makes Chicago one of America’s great cities.
Destination Snapshot
247 rooms
350/per night
12,000 sq ft of meeting space
50 mins from ORD
May - October
Home to the world's first skyscraperEXCLUSIVELY WILDER
Team experiences
Architecture River Cruise
See Chicago from its most iconic vantage point aboard a guided architecture cruise along the Chicago River. As you glide through the heart of downtown, expert guides share the stories behind the city's famous skyline, showcasing legendary skyscrapers and the innovative designs that helped shape modern architecture.
Art Institute of Chicago
Spend an afternoon exploring one of the world's premier art museums, home to masterpieces spanning thousands of years and countless cultures. Whether wandering through Impressionist galleries or discovering contemporary works, the Art Institute offers teams an inspiring cultural experience in the heart of downtown.
Deep-Dish Pizza Making Class
Roll up your sleeves and learn the secrets behind Chicago's most famous dish during a hands-on pizza-making class led by local chefs. From stretching the dough to layering the perfect deep-dish pie, teams will create and enjoy, a classic Chicago meal together.
Jet Ski Lake Michigan
Experience Chicago from the water on an exhilarating guided jet ski tour across Lake Michigan. Cruise past the city's iconic skyline while enjoying panoramic views of Navy Pier, the beaches, and towering skyscrapers from a perspective few visitors ever get to see.
SAMPLE AGENDA
See what your offsite could look like
Here’s a sample agenda to show how your offsite can come together.
Our experienced team is here to help you tailor the agenda to meet your team’s specific needs.
SAMPLE PRICING
Sample price for 100 people and 3 nights:
Here’s a sample pricing summary based on a group of 100 people:
Wilder’s Growth Framework
Built for Peak Productivity and Employee Retention.
Discovery Call
We begin with a targeted intake session to audit your current organizational challenges. In addition to discussing your favorite destination, we focus on specific business objectives like navigating mergers, resolving friction, or defining a new three-year vision.
Itinerary Design
We curate a high-stakes environment tailored to your goals. By removing the team from the traditional boardroom, we select sites and experiences that create the mental space necessary for divergent thinking and relationship building.
Retreat Experience
We manage all logistics during your retreat so your team can focus exclusively on the agenda. Our job is to ensure the environment eliminates cognitive loops and accelerates the pace of decision-making.
Accelerated Growth
The program concludes with a transition from the retreat environment back to the office. We provide a space for breakthroughs to ensure your team returns with the clarity and unified velocity required for growth.
Discovery Call
We begin with a targeted intake session to audit your current organizational challenges. In addition to discussing your favorite destination, we focus on specific business objectives like navigating mergers, resolving friction, or defining a new three-year vision.
Itinerary Design
We curate a high-stakes environment tailored to your goals. By removing the team from the traditional boardroom, we select sites and experiences that create the mental space necessary for divergent thinking and relationship building.
Retreat Experience
We manage all logistics during your retreat so your team can focus exclusively on the agenda. Our job is to ensure the environment eliminates cognitive loops and accelerates the pace of decision-making.
Accelerated Growth
The program concludes with a transition from the retreat environment back to the office. We provide a space for breakthroughs to ensure your team returns with the clarity and unified velocity required for growth.
Nature-based experiences built for breakthrough.
There's no better way
As a remote team, it's important for us to create an intentional space for us to come together and connect as more than co-workers. We believe there's no better way to do that than in nature and Wilder Retreats helped us do just that.
Chris Clark
CEO
The best experience ever.
We've worked with Wilder Retreats on over three retreats now and it's been the best experience ever. They have great locations in their pocket, work closely with you on budget and details, and are always a step ahead with planning. I don't know how we'd execute on our team offsites without them!
Britt Cooper
VP of Talent
Nothing short of magical!
Our time with Wilder Retreats in Yosemite was nothing short of magical. We explored, we laughed, and we grew together. It was a humbling reminder of the beauty and power of nature, and of the importance of fostering connections with those around us.
Lily Bakour
Head of Communications
We'd choose Wilder Retreats again without hesitation!
Wilder Retreats ran our firmwide offsite this year. It was clear we had a true partner in Wilder. From the earliest planning chats through the final goodbye for the airport, our Wilder Retreats team was responsive, organized, and upbeat, so much so that our own staff who worked with them to plan could simply enjoy the retreat instead of juggling logistics. The result was a relaxed, engaging few days where people could focus on connecting with colleagues and re‑energizing for the year ahead. We came away feeling both cared for and confident that we’d choose Wilder Retreats again without hesitation!
Emma Dyson
Chief of Staff
Highly recommend Wilder Retreats!
Wilder Retreats presented, organized and executed a company retreat in Big Sky for us. The details were communicated in a timely manner both prior to the event and during. Our group had an amazing time! I would highly recommend Wilder Retreats.
Megan Ortman
Business Development
READY TO TRANSFORM YOUR TEAM?
The path to a more aligned team starts here.
GOT QUESTIONS? WE’VE GOT ANSWERS
Frequently Asked Questions
Chicago combines world-class dining, iconic architecture, waterfront experiences, and a vibrant cultural scene into one unforgettable destination. It's an ideal city for teams looking to balance productive meetings with memorable experiences.
May through October offers the best weather for enjoying Chicago's riverwalk, Lake Michigan, outdoor dining, and the city's many festivals and attractions.
Thompson Chicago is located about 45–60 minutes from O'Hare International Airport (ORD) and approximately 30 minutes from Midway International Airport (MDW). Wilder can coordinate group transportation from either airport.
In addition to the featured activities, teams can enjoy rooftop cocktail experiences, improv workshops, guided food tours, live blues or jazz performances, sporting events, and visits to Navy Pier or Millennium Park.
Yes. Thompson Chicago offers 12,000+ square feet of flexible meeting and event space, along with sophisticated accommodations and a prime downtown location that makes it easy to balance meetings with time exploring the city.
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