Summer Events in Chicago – 2025 Guide

Planning a summer outing for your company isn’t just about good food and fun in the sun. Done right, these events can offer major ROI in terms of team cohesion, employee retention, and workplace morale.

Benefits of Hosting a Company Summer Event:

• Team Building: Shared activities help foster stronger relationships and break down silos between departments. But remember – team building doesn’t necessarily mean required or organized activities, so think about your goals and needs for mandates as you plan.
• Employee Retention: Meaningful, well-executed events make employees feel valued, improving engagement and loyalty. Allowing employees to bring family members or friends can reinforce these benefits even more.
• Company Culture: Reinforces your brand and values in a social, memorable way. Especially important for companies with hybrid or significant remote workforces.
• Networking: Gives employees across departments and locations the chance to connect. Even better, inviting clients or potential customers can allow for relationship building outside of a formal sales process.
• Recognition: Use the event as a moment to celebrate milestones or shout out top performers. With an environment of celebration, there’s no better time to add shout outs and recognition.

Common “Fails” to Avoid for Summer Event Planning in Chicago:

• Waiting too long to book: Summer venues fill up quickly in Chicago, and especially potential retreat locations where you’ll compete with summer vacationers.
• Not accounting for weather: Always have an indoor backup or shade/rain plan, but even better – make sure things like umbrellas, sunscreen, comfortable seating, water, and more are available. Summers in Chicago are hot!
• Failing to consider accessibility: Ensure transportation and accommodations work for everyone. Especially for locations outside of the city, providing buses, Metra passes, Uber rides, etc. can help boost attendance.
• Overplanning: Leave room for downtime; not every moment needs to be scheduled. Since corporate outings often involve fun, scheduling every moment can become self-defeating!
• Missing dietary needs: Offer diverse menu options or dietary accommodations in advance. Also, consider choosing catering or food options that aren’t a norm at the office already!

Top 5 Tips to Maximize Summer Event Attendance

• Early and Clear Communication: Announce the event well in advance with all necessary details. Be clear about the ability to bring family or friends, travel logistics, agenda or scheduled activities, and send confirmations and reminders as needed.
• Engaging Invitations: Use creative and personalized invites to generate interest. This is a great time to go beyond an Outlook or Google calendar invite and add a little excitement to the event with a custom invite.
• Incentivize Participation: Offer perks like raffles, giveaways, or recognition to encourage attendance. Make sure to highlight the venue itself – if you choose the right one, venues can be incentive enough.
• Flexible Scheduling: Choose dates and times that accommodate the majority of your team. One pro tip? Propose multiple dates or times to find the right date for the majority of potential attendees.
• Solicit Feedback: Involve employees in the planning process to ensure the event meets their interests. Ask for preferences on potential venues, activities, and times/dates to design a summer event that makes the majority of your company or team happy.

Top Chicago Summer Corporate Event Venues for 2025

For Large/Full Company Outings

• Wrigley Field: A historic and iconic setting for large-scale corporate events. Options range from private suites to full stadium buyouts.
  Best For: Large companies seeking a unique and memorable venue.
• Lincoln Park Zoo: An urban oasis offering indoor and outdoor spaces and tailored experiences.
  Best For: Companies looking for an engaging and family-friendly environment.
• Millennium Park: Versatile spaces like the Jay Pritzker Pavilion and Wrigley Square for large gatherings.
  Best For: Formal events, concerts, and large corporate celebrations.
• Six Flags Great America: Amusement park experience with group packages, catering services, and exclusive event areas.
  Best For: Companies aiming for a fun-filled, high-energy outing.

For Smaller Companies or Team Outings

• Chicago Architecture Cruise: A 90-minute river cruise with guided tours and customizable private charters.
  Best For: Teams seeking a relaxed and educational experience.
• North Avenue Beach: A vibrant beachfront venue with private cabanas, catering options, and stunning lake views.
  Best For: Casual team gatherings and summer parties.
• District Brew Yards: A self-pour brewery collective with a laid-back atmosphere.
  Best For: Informal team-building events and happy hours.
• Topgolf: An interactive golf and entertainment venue suitable for all skill levels.
  Best For: Competitive team outings and client entertainment.
• Rivers Casino: A dynamic venue offering gaming, dining, and event spaces.
  Best For: Companies seeking a mix of business and leisure.
• Ravinia Festival: An outdoor music venue set in a picturesque park setting.
  Best For: Cultural outings and client appreciation events.

For Company Retreats

• New Buffalo, Michigan: A charming lakeside town with retreat venues like The Neighborhood Hotel for tailored corporate experiences.
• St. Joseph, Michigan: A scenic destination with luxury resorts and beachfront access, perfect for balancing relaxation and productivity.
• Lake Geneva, Wisconsin: A resort town with lakeside charm, team-building activities, and immersive retreat experiences.

How to Leverage Event Software like RSVPify for Events in Chicago

Event software like RSVPify can significantly reduce the headaches that come with planning corporate outings. Here’s how:

• Custom Branded Event Invitations: Set a polished tone with custom logos, colors, and messaging for your summer event.
• Mobile-Friendly RSVP Forms: Capture attendance easily with personalized forms accessible from any device.
• Guest List Management: Track who’s attending, send reminders, and manage sub-events like breakout activities or team awards.
• QR Code Check-In: Skip the paper and streamline arrival with fast, contactless check-in tools.
• Meal + Transportation Selection: Ask for meal preferences, allergies, or shuttle needs upfront to simplify day-of logistics.
• Sub-Event Management: Coordinate optional sessions like golf tournaments, group tours, or happy hours with individual RSVPs.
• Email + SMS Communication: Schedule or send reminders and updates via built-in tools without needing another platform.
• Real-Time Analytics: Monitor registration trends, optimize messaging, and forecast attendance confidently.
• Exportable Data Reports: Share lists with vendors or exec teams quickly using downloadable spreadsheets.
• Privacy & Permission Controls: Keep event information internal to your team or company with customizable access settings.