CLIENT REVIEW: 26 GUYS FROM CHICAGO
By Connected Montréal · Dec 03, 2025 · 05 MIN read
A 26-person bachelor party from Chicago with an average age of 31. Here's how we pulled it off — from accommodations booked across our side-by-side Plateau bed-and-breakfasts to coordinated nightlife for a group that size.
Quick Summary
- A 26-person group accommodated across multiple bedrooms in our side-by-side Plateau bed-and-breakfasts.
- The package included full concierge, supper club dinner, and VIP tables with 8 bottles.
- A detailed itinerary was sent 2 weeks before arrival and fine-tuned the week of.
The Setup
The group wanted a classic weekend: a great dinner, a boozy brunch, some clubbing, and a memorable send-off for the groom. The only challenge was the size — 26 guys is a massive bachelor party. Luckily, Connected Montréal has the network to accommodate groups this large without a single logistics hiccup. Read our large group strategies for the playbook.
The Plan
The guys originally wanted to handle accommodation themselves, but took our recommendation and booked across our side-by-side Plateau bed-and-breakfasts — enough bedrooms to fit the entire group in one coordinated setup, all steps from Saint-Laurent. Here's what they booked: full concierge service with a dedicated host (no cover, no lines, no hassles), supper club dinner, group brunch, VIP tables both nights with 8 bottles total, and a private pre-game experience on-site.
Execution
With a group this large, timing is everything. We didn't want them to feel like they were on a field trip, but we needed enough structure to keep 26 guys moving in the same direction. Two weeks before arrival, we sent a detailed itinerary. We fine-tuned it the week of, and locked everything down.
Recap
We won't get anyone in trouble with their significant other, but the weekend went off without a single hiccup. Everyone still has their job. Nobody went to jail. The guys are already planning a return trip. Mission accomplished.
Location Highlights
- Plateau-Mont-Royal: SIDE-BY-SIDE PLATEAU BED-AND-BREAKFASTS — STEPS FROM SAINT-LAURENT
