City · Resort or hotel
Chicago Athletic Association
Meeting rooms inside a landmark across from Millennium Park, with seven places to eat and drink. Nonstop flights from almost anywhere.
Group: 20 to 80
Executive retreats · Chicago
Leadership retreats for Chicago teams.
We work with leadership teams across the country, from our home in Dallas–Fort Worth. If your team can get away, take it somewhere great. The right place helps a team slow down and think together. If you’d rather stay close to Chicago, we’ll run it there. Either way, we interview every leader, design the days and run the room in person.
51places across the U.S. in our guide
5within about 3 hours of the Loop, for teams that want to stay close
In personboth founders on site, wherever you go
Fly inO’Hare (ORD) and Midway (MDW)
Get away
Take your team somewhere great.
If your team has the time and the budget, we always encourage getting away. A few days with nowhere else to be gives leaders room to think and talk. A few of the places we’d start with:
Close to home
Or stay near Chicago.
Lake country in southern Wisconsin, the Lake Michigan shore and great rooms in the city itself, most of it an easy drive from the Loop. Every place has room for the whole team to work, eat and stay together.
Countryside · Resort or hotel
Grand Geneva Resort & Spa
Close enough for a team to drive up the morning of, with boardrooms for a leadership group and room to grow to 80. Something to do outdoors in every season.
Group: 20 to 80
Countryside · Resort or hotel
The American Club
A 14-seat boardroom for the senior team and larger rooms for breakouts, in a quiet, polished setting a short drive past Milwaukee.
Group: 20 to 80
Coast · Under one roof
The Wickwood Inn
A team of up to 22 can have the whole inn with its own staff, meals and a meeting room set up for video calls. The beach town is a short walk away.
Group: 8 to 22, the whole inn
Countryside · Under one roof
Allerton Park & Retreat Center
A team can stay and meet in a historic mansion with small rooms sized for 8 to 25, then walk straight into gardens and forest. Run by the University of Illinois, at a fraction of resort prices.
Group: 8 to 17 in the Mansion, up to 33 across the estate
The Everest Climb
How a retreat works for a Chicago team.
We interview every leader before we write a word of the agenda. For a team in Chicago that happens by video in the weeks before. Then we meet you at the place you chose, across the country or close to home, and run the retreat in person.
- 1Discover
Working sessions with you and a one-on-one interview with every leader.
Weeks 1–3 - 2Design
A custom agenda built from what we heard. You sign off before anything is set.
Week 3 - 3Connect
Your team gets to know each other beneath the roles.
Retreat day 1 - 4Clarify
An honest look at what's working and what isn't.
Retreat day 1–2 - 5Align
Two or three priorities and a plan the team wrote together.
Retreat day 2 - 6Sustain
A written readout of what we heard, what the team decided and who owns each priority.
After the retreat
Questions
Retreats near Chicago.
Do you facilitate leadership retreats for Chicago companies?
Yes. Everest Collective is based in Dallas–Fort Worth and works with leadership teams across the United States. We interview every leader before the retreat, usually by video, then the two founders facilitate on site, wherever the team goes.
Should our team travel or stay close to Chicago?
If the team has the time and the budget, we encourage getting away. The place is never the most important part of a retreat, and the right one still helps leaders slow down, step out of the day to day and talk. When travel doesn’t fit, a place within a couple of hours of the Loop works well too.
Where can a Chicago leadership team hold a retreat nearby?
For a team that wants a house to itself, everyone with their own bedroom: The Wickwood Inn, Allerton Park & Retreat Center. For a team that would rather each leader have a room at the same hotel or resort: Chicago Athletic Association, Grand Geneva Resort & Spa, The American Club. All are within about three hours of the Loop.
When is the best time for a retreat near Chicago?
Most of the places on this page are at their best in May, June, July, August, September, October. Each venue page lists its own best months and what to plan around.
How far ahead should we plan?
About eight weeks from the first conversation to the retreat covers the leader interviews and agenda sign-off. Popular venues book group dates months ahead, so pick the place early.
Can you find and book the venue for us?
Yes. Choose full service and we find the venue, book the rooms, plan the meals and run the schedule. Or book it yourself and we bring the interviews, the agenda and the facilitation.
Other cities
You pick the place
We’ll handle the rest.
Tell us about your team and what it needs. We’ll send a short list of places, anywhere in the country or close to Chicago, and how we’d run the days.