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Q3 Sales Kickoff (SKO) destinations from Chicago

Chicago's Q3 shortlist is Beaver Creek, Lake Tahoe, San Diego and Monterey. Summer is the season for mountain and Pacific kickoffs, while the desert and the Southeast are at their hottest.

Highs across this list range from the mid 60s in Monterey to the upper 70s in the mountains and San Diego. Rain is rare in California through September.

A small team sits around a long wooden table in a bright meeting room. Papers, water bottles and a vase of flowers sit between them as they talk.
Photo: Tran Nhu Tuan / Pexels (Pexels License)

Destinations from Chicago.

From Chicago, the best-weather option is Lake Tahoe, about 4 hours nonstop to Reno (RNO) by flight.

Chalet-style buildings on Gore Creek Drive, Vail Village.
Photo: Nick Csakany / Wikimedia Commons (CC BY-SA 4.0)

Vail / Beaver Creek, CO

Vail / Beaver Creek, CO Flight · approx. 2.5 hours nonstop to Denver, then about 2–2.5 hours by road

July
77°F / 42°F (25°C / 6°C)
August
74°F / 41°F (23°C / 5°C)
September
67°F / 34°F (19°C / 1°C)

Beaver Creek is a natural Q3 kickoff for Chicago, with cool mountain highs near 77°F in July. Lifts and trails give teams plenty to do outside.

Venue types for about 50–300 people: Mountain resort with conference space; Resort with conference space.

Summer storms often arrive in the afternoon. Opening night of the Vail Dance Festival is July 30, 2027.

Where you could stay

Park Hyatt Beaver Creek Resort and Spa

Vail / Beaver Creek, CO

Chicago groups can hold the plenary and the awards banquet in Park Hyatt Beaver Creek's Sawatch Hall, which has 8,631 square feet and seats up to 600.

Small boats by wooden piers on Lake Tahoe.
Photo: Stephen Leonardi / Pexels (Pexels License)

Lake Tahoe, CA/NV

Lake Tahoe, CA/NV Flight · approx. 4 hours nonstop to Reno (RNO)

July
78°F / 46°F (26°C / 8°C)
August
77°F / 45°F (25°C / 7°C)
September
70°F / 41°F (21°C / 5°C)

Lake Tahoe is at its best in July and August, with highs near 77 to 78°F and very little rain. A Chicago team gets beaches, boats and mountain trails in one place.

Venue types for about 50–300 people: Lakeside mountain resort with conference space; Resort with conference space.

Sand Harbor's outdoor stage hosts Shakespeare on summer evenings. Check 2027 dates once they are announced.

Where you could stay

Hyatt Regency Lake Tahoe Resort, Spa and Casino

Lake Tahoe, CA/NV

Chicago teams get about 17,800 square feet of event space at the Hyatt Regency Lake Tahoe, including the 7,326-square-foot Regency Ballroom, a short walk from the lake.

Local planners for a sales kickoff here

  • Tahoe By Design

    Lake Tahoe, California / Nevada

    Tahoe By Design is a locally owned and operated destination management company with 25 years of corporate meeting and event planning in Lake Tahoe. It plans executive retreats and incentive programs, and handles transportation from Reno and Truckee airports, hotel room blocks, off-site evening events, tours and activities, AV and production, theme décor, VIP management and on-site staffing. Hotel partners include Edgewood Tahoe, the Hyatt Regency Lake Tahoe, the Ritz-Carlton, Everline Resort, Harveys and Harrah's, and the Tahoe Blue Event Center. It charges a percentage management fee on net costs.

Downtown San Diego towers across San Diego Bay.
Photo: Humphrey Jones-Behan / Pexels

San Diego, CA

San Diego, CA Flight · approx. 4–4.5 hours nonstop

July
75°F / 66°F (24°C / 19°C)
August
77°F / 68°F (25°C / 20°C)
September
77°F / 66°F (25°C / 19°C)

San Diego is dry and mild all summer, at about 75 to 77°F. It suits a large Chicago group that wants a city with water on its doorstep.

Venue types for about 50–300 people: Beachfront resort; Resort with conference space; Downtown conference hotel.

Comic-Con takes over the convention district July 22–25, 2027.

Where you could stay

Marriott Marquis San Diego Marina

San Diego, CA

For a large Chicago sales kickoff, the Marriott Marquis San Diego Marina offers about 271,000 square feet of event space beside the bay.

Local planners for a sales kickoff here

  • Cue the Magic

    San Diego, CA

    Cue the Magic is a boutique corporate event studio in San Diego, founded in 2025 by Kelly McCleland, who leads it as founder and creative director. It plans events from strategy through on-site delivery: setting objectives and audience, designing the guest journey and programming, creative direction, communications, and running the room on the day. Its site lists customer events, sales meetings, workshops and trainings, leadership retreats, internal culture moments, and trade shows and conferences among the events it supports, and says it works with a select group of clients rather than at volume. It is based in San Diego and serves teams across the U.S.

  • GoGather

    Escondido, CA

    GoGather is a full-service corporate event management agency based in Escondido, in San Diego County, co-founded in 2008 by Brian Kellerman (Partner & CEO) and Dave Wagner (Partner & President). It plans sales kickoffs, conferences, corporate meetings, and employee and channel-partner incentive trips, handling strategy, site selection, budgeting, vendor management, production and A/V, and on-site management. Its case studies include a 3,000-person, eight-division sales kickoff, a sales kickoff for more than 300 people in Puerto Rico, a franchise conference at The Cosmopolitan in Las Vegas and a first user conference for an AI software company in San Francisco. According to its site, it works with Fortune 1000 companies in manufacturing, trucking and transportation, home services, construction and franchising, and has managed more than 1,000 events. It says clients get an online project plan and budget they can view anytime, plus KPI-setting and post-event reporting.

  • The Private Event Company

    San Diego, CA

    The Private Event Company is a female-owned San Diego event planner that specializes in group dining and evening events: corporate and client dinners, dine-arounds, restaurant buyouts, block parties and holiday parties. For groups in town for a conference, incentive trip or sales meeting, its destination management page describes handling the ground program, including group dinners, off-site evenings, transport, hotel coordination and excursions, with one dedicated contact. It says it works with more than 100 venues across the Gaslamp, Little Italy and Downtown, handles everything from 20-person dinners to 5,000-guest block parties, and charges no planning fee because the venues pay it. Case studies on its site include a 245-guest VIP dinner for the California Cattlemen's Association, a cocktail reception and group dinner for Marsh, dinners for Ryvu Therapeutics and AstraZeneca Brazil, and a Taco Bell brand activation.

Cliffs meeting the Pacific at Monterey.
Photo: Abhishek Navlakha

Monterey / Carmel, CA

Monterey / Carmel, CA Flight · approx. 4.5 hours nonstop to San Jose or San Francisco, then about 1.5–2 hours by road

July
66°F / 54°F (19°C / 12°C)
August
67°F / 55°F (19°C / 13°C)
September
68°F / 54°F (20°C / 12°C)

Monterey stays cool in summer, with highs around 66 to 68°F and coastal fog on many mornings. It suits a Chicago group that prefers golf and the coast to heat.

Venue types for about 50–300 people: Resort with conference space; Downtown conference hotel; Golf resort.

Car Week brings collectors from around the world, and its closing Concours at Pebble Beach is on August 15, 2027. Rooms are scarce that week.

Where you could stay

Hyatt Regency Monterey Hotel and Spa on Del Monte Golf Course

Monterey / Carmel, CA

The Hyatt Regency Monterey sits on 22 acres along Del Monte Golf Course. Chicago teams can choose among more than 43,000 square feet of meeting rooms.

Local planners for a sales kickoff here

  • Karissa Paxton Events

    Carmel, California

    Karissa Paxton Events is a boutique planning and production company on California's Central Coast, serving Carmel, Carmel Valley, Pebble Beach, Big Sur, Santa Cruz and Half Moon Bay. With more than 20 years of experience, the team offers full-service planning, design and event management, and produces corporate, social and nonprofit events, from venue sourcing to on-site execution. Its related company, Paxton Entertainment, handles entertainment.

Staying local.

Chicago has no cool, scenic summer kickoff within easy driving range that matches these picks. Most teams will fly, and Beaver Creek via Denver is the shortest trip.

A sample two- to three-day agenda.

Start early in Beaver Creek and Tahoe and keep the afternoons free. Monterey suits a golf outing or a coastal drive. In San Diego, plan a dinner on the bay.

  1. Day 0. Arrivals and a welcome reception.
  2. Day 1. CEO or CRO keynote, product and compensation-plan sessions, segment breakouts, and a team dinner.
  3. Day 2. Enablement workshops and role-play, a customer or partner panel, and an awards night.
  4. Day 3, optional. A half-day leadership session, then departures.

Why a local planner, with Vantly.

A local planner knows which rooms are actually free in high season. Vantly is how the company runs the event after that.

Local planners and designers know venue availability, seasonal patterns, and vendors. Vantly adds centralized billing, a shared agenda, guest registration, an AI event builder, and multi-currency support.

Questions planners ask first.

Short answers for a Q1 sales kickoff.

Why are Scottsdale and Miami off the Q3 list?

Scottsdale averages about 107°F in July, and Miami is hot, wet and in hurricane season. Both return for Q4.

Which Q3 destination is coolest?

Monterey, where summer highs average 66 to 68°F.

What is the busiest week to avoid in Monterey?

Car Week. Car Week's last day, August 15, 2027, belongs to the Pebble Beach Concours d'Elegance.

Which 2027 events should Chicago plan around?

Comic-Con in San Diego (July 22–25), the Vail Dance Festival (opening July 30) and Monterey Car Week (Concours on August 15).

Which venue has the most space?

Chicago's largest groups can fill San Diego's bayfront Marriott Marquis, some 271,000 square feet.

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