Corporate Retreats in Chicago
A lakefront city with standout dining and architecture, and nonstop flights from almost everywhere.
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Why choose Chicago for a corporate retreat
Chicago is one of the easiest cities in the country to bring a team together. Two major airports put almost every US city a nonstop flight away, and the Gold Coast and Magnificent Mile keep lodging, dinners and the lakefront within walking distance. Days can start with a run along Lake Michigan and end with an architecture cruise and a chef’s table dinner.
Recommended venues
Where your team could stay
Three venues we trust in Chicago, all within a few blocks of each other on the Gold Coast and the Magnificent Mile.
Gold Coast, off Lake Shore DriveThompson Chicago
Park Hyatt Chicago
Sofitel Chicago
Nightly rates: $$ $200 to $300 · $$$ $300 to $450 · $$$$ $450 and up
EXCLUSIVELY WILDER
Corporate Team Experiences
Architecture River Cruise
See Chicago’s skyline from the river on a private architecture cruise with an expert guide.
Art Institute of Chicago
A private guided visit to one of the world’s great art museums, steps from Millennium Park.
Deep-Dish Pizza Class
Learn to make Chicago’s most famous dish in a hands-on class with local chefs.
Wrigley Field Batting Practice
Step into the cage for a private, behind-the-scenes batting practice at Wrigley Field, with a tour of the dugouts and clubhouse.
SAMPLE AGENDA
Sample Chicago Corporate Retreat Agenda
Here’s how three days in Chicago could come together. We tailor every agenda to your team’s goals.
SAMPLE PRICING
What 3 nights could cost
Sample group sizes vary by venue.
60 people · 3 nights · One room each
| Per person | Cost |
|---|---|
| Lodging ($400 a night × 3 nights) | $1,200 |
| All meals | $1,100 |
| Team experiences | $200 |
| Airport transfers | $80 |
| Meeting space and A/V ($5,000 for the group) | $83 |
| Total per person | $2,663 |
| Group total (60 people) | $159,780 |
60 people · 3 nights · One room each
| Per person | Cost |
|---|---|
| Lodging ($650 a night × 3 nights) | $1,950 |
| All meals | $1,200 |
| Team experiences | $200 |
| Airport transfers | $80 |
| Meeting space and A/V ($5,000 for the group) | $83 |
| Total per person | $3,513 |
| Group total (60 people) | $210,780 |
100 people · 3 nights
| Per person | Cost |
|---|---|
| Lodging ($375 a night × 3 nights) | $1,125 |
| All meals | $1,100 |
| Team experiences | $200 |
| Airport transfers | $80 |
| Meeting space and A/V ($8,000 for the group) | $80 |
| Total per person | $2,585 |
| Group total (100 people) | $258,500 |
Sample only. Most Wilder retreats run $750 to $1,500 per person per day, depending on season, group size and experiences. Your proposal includes exact costs.
How It Works
From first call to back at the office
Discovery call
We learn your goals, group, budget and timing, plus the business challenge behind the offsite.
Itinerary design
We match you with a destination and agenda built to get your team out of the boardroom and thinking big.
Retreat experience
A Wilder expert runs every detail onsite, so your team can focus on the work and each other.
Back to work, aligned
Your team returns with the clarity and momentum to act on what they decided together.
In their words
Why teams keep booking with Wilder
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 ClarkCEO
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 CooperVP of Talent
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 BakourHead of Communications
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 DysonChief of Staff
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 OrtmanBusiness DevelopmentChicago retreat questions
Frequently asked questions
Chicago is easy to reach, with nonstop flights from almost every US city into O’Hare and Midway. Teams can stay in walkable neighborhoods on the lake, meet in hotels with strong service and spend evenings at some of the best restaurants in the country.
It depends on your group and style. Thompson Chicago has 247 rooms on a quiet Gold Coast street near the lake, a strong fit for teams of up to about 60 that want a boutique feel. Park Hyatt Chicago has 182 rooms on Water Tower Square with a polished, five-star setting, best for leadership teams. Sofitel Chicago Magnificent Mile has 415 rooms and a 4,600-square-foot ballroom, the best fit for groups of 100 or more. We’ll recommend the best fit for your group size, goals and budget.
May through October is the most popular, with warm days on the lake and patio dining. September is often the best month of all. Winter is cold but festive, and hotel rates are lower.
Fly into O’Hare (ORD), about 40 minutes from all three hotels, or Midway (MDW), about 30 minutes. We handle all ground transfers.
Yes. Teams can run or bike the 18-mile Lakefront Trail, kayak the Chicago River, sail Lake Michigan or take a day trip to the Indiana Dunes.
Beyond the featured experiences, teams can take a private sailing charter, visit the Chicago Botanic Garden, take a food tour of the West Loop or catch a show at a comedy club.
Yes. Sofitel Chicago can host groups of 100 or more, and the city has hundreds of private venues for larger dinners and events.
Yes. In summer and early fall we use rooftop terraces and private lakefront spaces for sessions and receptions, with an indoor room held as a backup.
Yes. The architecture cruise, museum visit, pizza class and batting practice need no experience. There is always an easier option.
Bring comfortable walking shoes and layers, since the wind off the lake can be cool even in summer. From November through March, bring a heavy coat, hat and gloves.
Most retreats run $750 to $1,500 per person per day on average, depending on the venue, season, group size and experiences. The sample pricing above shows what three nights could cost at each venue, and we’ll build a custom proposal for your team.
START WITH A SHORT BRIEF
Let's build your retreat
What happens next
- 1
Share your brief
Two minutes. Goals, group size and timing.
- 2
Talk with a Wilder expert
Pick a time for a discovery call about the business challenge behind the offsite.
- 3
Get your custom proposal
Destination, agenda and pricing built around your goals.
“Wilder transformed our entire company retreat in Vail from a standard corporate offsite into a deeply restorative adventure. Our team left the mountains feeling truly connected and inspired for the year ahead.”
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