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Q2 Sales Kickoff (SKO) destinations from Chicago

Chicago's Q2 shortlist is Nashville, New Orleans, San Diego and Las Vegas. Each is a nonstop, and each is noticeably warmer than Chicago in April.

By April and May these destinations range from about 69°F in San Diego to the mid 80s in New Orleans. Las Vegas gets very hot by June.

A breakout group gathers around a round wooden table covered with blue cards, sticky notes and markers. Several people write at once as they work through the exercise together.
Photo: Cristian Pedroso / Pexels (Pexels License)

Destinations from Chicago.

From Chicago, the best-weather option is New Orleans, about 2–2.5 hours nonstop by flight.

Downtown Nashville street below skyscrapers.
Photo: Tatiana Bidon

Nashville, TN

Nashville, TN Flight · approx. 1.5–2 hours nonstop, or about 7 hours by road

April
73°F / 49°F (23°C / 9°C)
May
80°F / 58°F (27°C / 14°C)
June
88°F / 66°F (31°C / 19°C)

Nashville is the closest warm-weather option for Chicago in spring. Highs reach about 73°F in April and 80°F in May.

Venue types for about 50–300 people: Large convention hotel (200–300+); Downtown conference hotel; Historic hotel or event hall.

CMA Fest fills Nashville June 10–13, 2027. April and May dates are easier.

Where you could stay

Gaylord Opryland Resort & Convention Center

Nashville, TN

For a Chicago kickoff, Gaylord Opryland puts 2,888 rooms and indoor gardens on one campus.

Local planners for a sales kickoff here

  • Music City Events

    Nashville, TN

    Music City Events is a corporate event planning and destination management company with offices in Nashville and Spartanburg, South Carolina, and it says its team is "led by Certified Meeting Professionals." It plans meetings and conferences, sales kickoffs, incentive travel, executive and leadership retreats, brand activations, celebrations and awards, and team-building programs, and handles transportation and logistics and event production and design. Its site lists featured destinations in Nashville, Charlotte, Greenville–Spartanburg, Charleston, Atlanta, Savannah, Orlando and New Orleans, with reach across Alabama and Mississippi and support for programs nationwide. Case studies on its site describe a three-day Nashville leadership summit for 475 attendees with more than 40 transportation movements, an Atlanta executive retreat for 155 senior executives and an Orlando incentive weekend for 180 top performers. It operates as the destination management division of A Brand Nu Day, led by Aundrea Fogg.

  • OVATION

    Nashville, TN

    OVATION is a corporate event production agency headquartered in Nashville, with a presence in Boston, and its site says it has been producing events for more than 30 years. It keeps strategy, creative, technical production and talent sourcing under one roof, from scenic design, motion graphics and presentation design to AV, live streaming, show calling and technical direction. It works on user conferences, sales kickoffs, medical, educational and association events, expos and product launches, in person, hybrid or virtual, and its FAQ describes events from 50-person sales kickoffs to 5,000-person user conferences. Case studies on its site include general session and expo production for PTC's LiveWorx in Boston, Cracker Barrel's FY24 Managers Conference for more than 1,800 managers and suppliers, Outreach's Unleash 2023, its first in-person user conference after the pandemic, and Brightcove's global sales kickoff. It names Salesforce, PTC, Outreach and YPO among its clients, and says its work has earned six Telly Awards.

  • Simply Golden Events

    Nashville, TN

    Simply Golden Events is a Nashville event planning company co-founded by Keiana Hastings and Hailey Keyees, who both work as lead event producers. The team plans weddings, corporate events and social celebrations across Middle Tennessee, and its site says the team has a combined 18-plus years of experience. For companies it offers two packages: event coordination, which covers a kickoff meeting, venue walkthrough, vendor contact, contract review, the timeline and layout, and a team on site for up to 12 hours, and full event planning, which adds budget management, rental bookings and vendor coordination. Its corporate page names conferences, sales kickoffs and company retreats among the events it handles. In January 2023 the team served as event coordinator for the first Elevate Summit, hosted by NAPCP at Saint Elle and The Graduate Hotel in Nashville and designed by Lemiga Events. Before Simply Golden, Keyees was a venue manager in Nashville.

St. Ann Street and the Pontalba Buildings, Jackson Square.
Photo: Jesse James / Wikimedia Commons (CC BY 2.0)

New Orleans, LA

New Orleans, LA Flight · approx. 2–2.5 hours nonstop

April
79°F / 62°F (26°C / 17°C)
May
85°F / 69°F (29°C / 21°C)
June
90°F / 75°F (32°C / 24°C)

New Orleans is a strong spring pick for Chicago, with April highs around 79°F. Food and music fill the evenings without much planning.

Venue types for about 50–300 people: Downtown conference hotel; Historic hotel or event hall; Large convention hotel (200–300+).

Jazz Fest runs April 22–25 and April 29–May 2, 2027. Rates rise on those weekends.

Where you could stay

New Orleans Marriott

New Orleans, LA

Chicago groups get about 84,000 square feet and 50 meeting rooms at the New Orleans Marriott. The French Quarter is a short walk away.

Local planners for a sales kickoff here

  • ACCENT New Orleans

    New Orleans, LA

    ACCENT New Orleans is a destination management company that plans corporate events, incentive trips and VIP experiences in New Orleans, led by president and owner Diane Lyons. Its services span event planning and décor, galas and receptions, meeting planning (site selection, registration, hotel negotiations and AV), transportation including permits and police escorts, entertainment booking, and New Orleans experiences such as second-line parades, marching bands, float rides, dine-arounds, guided tours, team building and CSR projects. According to its site, it has been in business for more than 34 years and has worked with global brands, medical associations and Fortune 500 teams. It is a WBENC-certified women-owned business, a partner of the DMC Network, and says it was one of the first ADME-accredited members in New Orleans. Google reviews on its site describe sales kickoffs featuring drumline openings, second-line bands and Mardi Gras greeters.

  • Live Event Productions

    New Orleans, LA

    Live Event Productions is a New Orleans-area production partner for AV-heavy corporate, association and nonprofit events, founded in 2025 by executive producer Craig A. Trosclair. It describes itself as a production leadership and live event technology partner: it handles production planning, designs and coordinates audio, video, lighting, LED and scenic elements, produces Vectorworks CAD floorplans and 3D renderings, and provides executive producers and show callers. Its corporate page lists sales kickoffs and national meetings, leadership summits, user conferences, product launches, awards programs and trade shows among the events it supports. According to its site, the team brings more than 25 years of live event production experience, and it is certified by the SBA as a Veteran-Owned Small Business. Its LinkedIn posts describe work on the Digital Delta Symposium in Houston and a hybrid program at the JW Marriott Downtown Houston.

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

April
69°F / 57°F (21°C / 14°C)
May
70°F / 60°F (21°C / 16°C)
June
72°F / 63°F (22°C / 17°C)

San Diego is reliably mild in Q2, with highs around 69 to 72°F and very little rain. Chicago teams get outdoor evenings by the water.

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

Late May and June can bring a marine layer, the local "May Gray" and "June Gloom". Mornings may be overcast.

Where you could stay

Marriott Marquis San Diego Marina

San Diego, CA

Chicago teams get about 271,000 square feet of event space at the bayside Marriott Marquis San Diego Marina. Its Grand Ballroom of 35,631 square feet fits a large Chicago general session.

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.

Las Vegas Strip with the Paris Las Vegas tower.
Photo: dumitru bumbu

Las Vegas, NV

Las Vegas, NV Flight · approx. 3.5–4 hours nonstop

April
79°F / 57°F (26°C / 14°C)
May
89°F / 66°F (32°C / 19°C)
June
99°F / 76°F (37°C / 24°C)

Las Vegas suits a large Chicago team in April or May, when the desert is warm and dry. April averages about 79°F with almost no rain.

Venue types for about 50–300 people: Large convention hotel (200–300+); Resort with conference space.

EDC Las Vegas runs May 14–16 and May 21–23, 2027, and pushes up room rates.

Where you could stay

Mandalay Bay Resort & Casino

Las Vegas, NV

Mandalay Bay keeps a Chicago program in one building, with 3,209 rooms and over 2 million square feet of meeting space.

Local planners for a sales kickoff here

  • Corporate Events Las Vegas

    Las Vegas, NV

    Corporate Events Las Vegas is an independent corporate event planner in Las Vegas, where Daniel Herschman has been Director of Events since 2004. It plans corporate meetings, sales kickoffs, conferences, receptions, product launches and convention-related programs, with one point of contact from venue search to on-site execution. Much of its work is finding and negotiating venues: restaurants, lounges, nightclubs, rooftops, pools, ballrooms and hospitality suites, including food and beverage minimums, venue fees, event hours and contract terms. Its site describes a 200-guest welcome reception at The Chandelier Bar at The Cosmopolitan for a corporate client attending a conference, where it negotiated the food and beverage minimum down from $40,000 to $30,000. Example programs it lists include a 500-person sales kickoff at Wynn, a 300-person annual summit at Fontainebleau and a 250-person awards dinner at Bellagio. It also provides destination management support, including hotel room blocks, group transportation, dine-arounds and entertainment. Clients quoted on its site include Velocitor Solutions, whose president says they have done more than 30 events with the team over 20 years.

  • JET The Agency

    Las Vegas, NV

    JET The Agency is a Las Vegas event planning and destination management company that works nationwide and also designs and builds trade show booths. Its DMC page lists venue sourcing, event design and management, staffing, dining, transportation, furniture and decor, entertainment and activities, for corporate events, incentive trips, business meetings, sales kickoffs, annual conferences and team building. It started as a boutique entertainment agency, and today handles booth design and in-house fabrication and rents event and trade show furniture. On its site, Aruba Networks' global event director says the team was hired as DMC for the Airheads/ATMOSPHERE conference, a 2,500-person customer and partner event, handling entertainment, acts, staffing and themes. Other testimonials describe custom booths for AgentSync since 2022 and a conference sponsorship for XUP Payments, a KeyBank brand. Its site says it has worked on more than 1,500 events.

  • MyRSVP

    Las Vegas, NV

    MyRSVP is a Las Vegas nightlife and dining concierge that also runs corporate programs in the city: sales kickoffs, client appreciation events, customer summits, multi-day off-sites, incentive trips, executive retreats and holiday parties. It acts as a single point of contact across restaurants, nightclubs, pool clubs, transportation and room blocks, and, according to its site, sends one consolidated invoice. Its corporate page says it works directly with events teams at nine Strip resorts and with the major nightlife and dayclub operators, and that it handles programs from 10-person executive retreats up to 2,000-attendee summits. It charges a flat or per-attendee fee agreed up front, and says comped tables and venue concessions often offset it. Clients listed on its site include Davis Polk, Crexi, Golub Capital and DocuSign. According to its site, it was founded by Adam Sadie, who has 25 years in hospitality, including opening director roles at Nikki Beach, Hakkasan and Sphere, and it has operated since 2014.

Staying local.

No warm-weather Q2 option is within easy driving range of Chicago. Nashville is about seven hours by car, so most teams will fly.

A sample two- to three-day agenda.

In San Diego, put a session outdoors on the bay. Nashville and New Orleans both suit a music night. In Las Vegas, run everything in one resort and keep travel time low.

  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.

Which is the shortest flight from Chicago?

Nashville, at about 1.5 to 2 hours nonstop.

Which destination has the most reliable weather?

San Diego, with highs around 69 to 72°F and less than an inch of rain a month in Q2.

What is May Gray?

A marine layer that often leaves San Diego mornings overcast in late spring. Afternoons usually clear.

Which 2027 events affect these dates?

Plan around Jazz Fest's two weekends in late April, EDC in Las Vegas in mid-May, and CMA Fest in Nashville from June 10 to 13.

Which venue has the largest ballroom?

The Marriott Marquis San Diego Marina, with a 35,631-square-foot Grand Ballroom.

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