Pre-Retreat Engagement

1. Collaborative Planning: Ask for their input on the retreat agenda to make them feel involved.
2. Personalized Invitations: Send creative, budget-friendly invitations—like digital designs or hand-written notes with small gifts (e.g., branded items or custom postcards).
3. Exclusive Communication: Create a group chat or email thread to build excitement and connection before the event.

During the Retreat

1. Affordable Venue: Look for unique but budget-friendly venues like coworking spaces, Airbnbs, or local parks for workshops or photo ops.
2. Swag Bags: Curate thoughtful swag bags with samples from sponsors or local businesses.
3. Content Opportunities: Organize activities that provide great content for their channels—e.g., a mini photo walk, themed meals, or a rooftop sunset session.
4. Networking Time: Build in free time for them to connect organically, which will also strengthen their ties to your brand.
5. Recognition: Give shoutouts or small awards to each influencer to make them feel valued.

Maximizing Impact on a Budget

1. Sponsor Partnerships: Seek sponsors for meals, accommodations, or swag. Offer the influencers' exposure in return.
2. DIY Efforts: Handmake elements like decor or photo backdrops to save money while adding a personal touch.
3. Leverage Chicago’s Free Attractions: Use scenic spots like Millennium Park, the Chicago Riverwalk, or free-entry museums for activities.

Post-Retreat Engagement

1. Highlight Reel: Share a thank-you video or compilation of their content from the retreat.
2. Follow-up Content: Create challenges or campaigns that build on the retreat’s themes to maintain momentum.
3. Feedback Loop: Ask for their feedback to show you value their opinion and improve future events.

With the right planning and creativity, you can deliver a memorable retreat that energizes and inspires your influencers while staying within budget.

There are some great low cost things to do in Chicago to keep them engaged while they are there! 

I would start by welcoming them with a swag bag using any items you can spare from your side business (stickers, mugs, socks, etc). I would also put together a “welcome to chicago” card which you can make and print yourself, include things like historical facts about chicago, things to do, any current events for that weekend, and best restaurants in the area. 

While they’re there, you can keep them entertained with activities like a beach afternoon on Lake MI--add in a lunch picnic to make it even better! Do a short walking tour of the loop or the architecture boat tour, you can find discounted tickets on Groupon. Make sure to stop by the Dusable Bridge and have them do a photo shoot by the Wrigley Building on Kinzie St&Michigan Ave for a memorable photo. A donut tour with stops at Do-Rite Donuts and Stans Donuts is fun and low-cost. 

I would end the weekend with some Chicago themed thank you cards and maybe a small gift, like a small bag of Garrett’s popcorn. Good luck! 

Ok wow both of these responses were a huge help and got me thinking long term as I work to meet my goal!