Corporate retreats in Chicago
Architecture, world-class dining, and access you cannot get anywhere else, in a city most of your team can reach in a two-hour flight.
- Best for
- Team offsites, client events, leadership retreats
- Best time to go
- May to October
- Getting there
- Fly into O'Hare (ORD) or Midway (MDW), both 25 to 45 minutes from downtown
- Group size
- 10 to 200
Chicago is our home base, and it is one of the easiest cities in the country to bring a group together. Two major airports, direct flights from almost everywhere, and a downtown where your hotel, meeting space, and dinner can all be within a short walk.
Why it works for groups
The city has hotels at every level, private dining rooms that feel like an event in themselves, and meeting spaces with skyline views. For teams spread across the country, a central location keeps travel time down for everyone.
What to do
Architecture boat tours on the river, private dinners in the West Loop, rooftop receptions, and experiences at Wrigley Field that most visitors never get. In summer, the lakefront turns the city into a resort.
Where to stay
Downtown and River North put your group in the middle of everything. We match the property to your group size, budget, and meeting needs, and we never take a commission from the hotel.
Day one: Arrive and orient
Check in downtown, then a private architecture cruise on the Chicago River before a welcome dinner in the West Loop.
Day two: Work and play
Morning working sessions with a skyline view, lunch nearby, and an afternoon at Wrigley Field with batting practice and an on-field dinner.
Day three: Send-off
A closing session and brunch before flights home, with most of the team back by the afternoon.
retreat questions, answered.
May through October is the sweet spot, with summer being the most lively. Winter works well for indoor programs and often comes with better hotel availability and rates.
Yes. It is one of the easiest cities in the country to fly into, with meeting space, dining, and activities that work for groups of 10 to 200.
Three to six months is comfortable, and more for summer weekends or big convention weeks. Rush planning is available if your dates are closer.
It depends on the season, group size, and hotel level. Planning with Meet&Retreat starts at $8,000, and every proposal includes a complete budget for the trip before you commit to anything.
Tell us about your retreat.
We'll reply within two business days with first thoughts on your trip. Planning with Meet&Retreat starts at $8,000.