As summer approaches, companies across Chicago and Milwaukee begin planning one of the most anticipated employee events of the year — the corporate summer picnic. More than just a day of fun, a well-executed summer picnic strengthens company culture, boosts morale, and fosters connections among employees and their families. Whether you're planning a small company gathering or a large-scale outdoor celebration, careful planning and attention to detail will ensure a memorable and enjoyable experience for everyone involved.
In this guide, we’ll break down everything you need to consider when organizing a corporate summer picnic in Chicago or Milwaukee, from finding the perfect venue and securing essential rentals to creating engaging activities and thoughtful catering solutions.
Finding the Perfect Picnic Venue in Chicago and Milwaukee
The venue you choose sets the tone for the entire event. Fortunately, both Chicago and Milwaukee offer a variety of outdoor spaces perfect for summer gatherings. From beautiful lakefront parks to lush gardens and scenic pavilions, there are plenty of picturesque settings ideal for your corporate picnic.
In Chicago, popular picnic venues include Lincoln Park, Montrose Beach, Jackson Park, and even private rooftop spaces that offer panoramic city views. Companies looking for a more exclusive experience might also consider renting private garden spaces or event lawns at local museums and cultural centers.
In Milwaukee, venues like Veterans Park, Humboldt Park, Lake Park, and the Boerner Botanical Gardens provide ample space for large groups, along with built-in picnic shelters, walking paths, and scenic views of Lake Michigan. For companies wanting a more private affair, consider renting a pavilion or working with event spaces that allow outdoor catering and customized rental setups.
When selecting a venue, make sure to:
Confirm capacity and available amenities
Check for shade structures and restroom facilities
Review any permit requirements for large groups, tents, or entertainment
Essential Rentals for a Corporate Summer Picnic
A successful summer picnic requires more than just a location — the right event rentals are essential for creating a comfortable, well-organized, and visually appealing event. The right setup also reflects your company’s professionalism and attention to detail, making employees and their families feel valued and cared for.
1. Tent Rentals for Shade and Comfort
Chicago and Milwaukee summer weather can be unpredictable, and having tent rentals on hand ensures that your event runs smoothly, rain or shine. High-peak tents, open-air canopies, and sailcloth tents not only provide necessary shade but also help define the picnic area. Clear-top tents are another stylish option for companies looking for a more elegant setup that still allows natural light to shine through.
2. Comfortable Seating and Tables
Don’t overlook the importance of seating! Provide a mix of round tables with chairs, picnic tables, and casual lounge areas so guests can choose where to relax and dine. High-top cocktail tables can also encourage mingling and make great spots for beverages and snacks. Adding custom linens in your company’s colors can create a cohesive, branded feel.
3. Food and Beverage Stations
Work with caterers or food truck vendors who specialize in summer fare — think grilled entrees, fresh salads, and ice-cold lemonade or craft cocktails. Complement the catering with buffet stations, bar setups, and beverage coolers, all available through rental providers. Don’t forget handwashing stations and waste disposal solutions to keep the picnic clean and comfortable.
4. Audio and Visual Rentals
Music and announcements play a big role in keeping the energy up throughout the day. A professional sound system with microphones and speakers ensures that welcome speeches, raffle drawings, or live entertainment are clearly heard. For larger events, LED screens or portable stages can help you set up presentations or performances with a professional touch.
5. Lawn Games and Entertainment
No summer picnic is complete without fun and engaging activities. Add excitement with rental items like:
Giant Jenga, Connect Four, and Cornhole sets
Inflatable obstacle courses, bounce houses, or slides (perfect if families with kids are invited)
Casino game tables or arcade machines for a unique corporate twist on traditional picnic games
Photo booths with branded backdrops for lasting memories
Catering and Beverage Planning for Corporate Picnics
Food and drinks are at the heart of every great summer picnic. Companies have endless options — from classic BBQ fare and gourmet food trucks to themed buffets featuring international cuisine.
In Chicago, consider trendy food vendors that specialize in Chicago-style hot dogs, Italian beef sandwiches, or farm-to-table picnic spreads. In Milwaukee, tap into local favorites like beer garden-style fare, Wisconsin cheese platters, and bratwurst stations. For a high-end touch, consider offering made-to-order grill stations or live cooking demonstrations that keep guests engaged and well-fed.
Make sure to accommodate a variety of dietary needs by offering vegetarian, vegan, and gluten-free options. Beverage stations should include plenty of water and non-alcoholic options, alongside beer, wine, and signature cocktails if alcohol is permitted at your venue. Adding a portable bar rental with a professional bartender can elevate the experience and encourage guest interaction.
Entertainment and Activities for All Ages
A corporate picnic should be more than just food and seating — it’s an opportunity to bring your team together and create positive, lasting memories. Incorporate entertainment that appeals to all ages and interests.
Live music or DJ performances can set the right mood and encourage dancing.
Raffle drawings, trivia contests, or team-building challenges add excitement and keep guests engaged.
Face painting, balloon artists, and kid-friendly zones ensure families with children have a great time.
Sports tournaments, such as kickball or volleyball, are a great way to promote friendly competition.
Be sure to plan a well-paced schedule that balances downtime with structured activities, and always allow flexibility for guests to participate at their comfort level.
Tips for Successful Corporate Summer Picnic Planning
Start Planning Early: Summer dates fill up fast, and rental companies book out months in advance. Secure your venue and rentals as early as possible.
Have a Backup Plan: Weather can be unpredictable, so always have contingency plans with tents or indoor options if rain is in the forecast.
Plan for Safety and Comfort: Ensure first-aid kits, sunscreen stations, and water stations are readily available.
Promote the Event: Generate excitement by sending invitations early, including clear event details and RSVP instructions. Consider using email reminders and internal communications to keep employees informed.
Capture the Moment: Hire a photographer or videographer to document the day. Share photos on your company’s social media and internal platforms to celebrate the event afterward.
Let Willie Fun Events Help You Plan Your Corporate Summer Picnic
At Willie Fun Events, we specialize in providing luxury rentals and creative solutions for corporate picnics in Chicago and Milwaukee. From elegant tent setups and stylish lounge furniture to professional AV equipment and custom entertainment packages, we help make your summer gathering both memorable and effortless.
If you’re looking to host an unforgettable corporate picnic this summer, let’s talk! We’ll help you design and deliver a well-executed event that leaves your team feeling appreciated and energized.
📞 Call us today to start planning your summer picnic!
📩 Request a quote now and let’s make your event simple, fun, and successful.