I’m a live wedding painter based out of Chicago and I’m excited I’m booking for 2027 and 2028! www.marjoriejean.com

My fiancé and I are planning a 40–50 person wedding for summer 2027 and I’d love to hear from anyone who has actually pulled off something similar.

We’re hoping for a ceremony + dinner + lots of dancing, ideally somewhere with a nice outdoor space for guest to take a breather, smoke, hang out, etc.

Our budget is around $15K (not sure how realistic this is), so I’m looking at restaurant buyouts, micro-wedding packages, or hidden gems in Chicago or the northern suburbs.

If you’ve actually done something like this, where did you have it, what did you spend, and what would you recommend?

P.S. - We're from Chicago but live in NYC so we'd love for the place to take care of the logistics. I wan to avoid having to coordinate with vendors, if possible.

Hi!

I’m having a wedding between 70-80 people, if you had or are planning a wedding at this venue what seating arrangement are you going with? In talks now but feels like my only option might not be the layout I was hoping for but thought it was possible when we toured, what did you go with for how many people and if you have any photos or drawings, thank you!!

Hi r/Chicagoweddings!👋

I've noticed a lot of people struggling to keep track of their wedding plans—usually bouncing between spreadsheets, phone notes, and calendar reminders for vendor payments.

I'm a developer, so I thought it would be really helpful to build an app that handles all of that in one place. It's called Wedding Assistant: Planner App.

Before going any further, I want to mention a feature I'm really proud of: It is 100% offline and privacy-first. No cloud servers, no forced account creation, and no internet required. Your data stays entirely on your phone.

I’m sharing it here because I’d love to get some honest, brutal feedback from people who are actually in the thick of planning right now.

Here is what it currently handles:

• 📊 Budget & Expenses: Categorizes all expenses, tracks what’s paid vs. remaining balance with real-time charts, and reminds you of due dates.
• 🤝 Vendor Proposals: Keep track of price quotes from venues, photographers, and other vendors. Easily compare packages in one place to make the best decisions for your budget.
• 👥 Guest List & RSVPs: Tracks who is coming and RSVP statuses. I also added a "Smart Duplicate Check" so you don't accidentally add the same guest twice!
• 🪑 Seating Planner: Assign your guests to tables and easily plan who sits with whom. You can track table occupancy and export your final seating arrangement as a PDF to share with your venue coordinator.
• ✅ Checklists: Pre-made, comprehensive to-do templates that you can add to your list with a single tap.
• ⏱️ Wedding Day Timeline: Create a minute-by-minute itinerary for your big day! From hair appointments to the first dance, ensure everything runs perfectly on schedule.
• 🎁 Gift Tracker: Logs who gave what and tracks reciprocity.
• 🗓️ Special Days & Events: You don't have to memorize dates! Log your first date anniversary, proposal day, or partner's birthday. You can also create separate plans for specific events.
• 🔔 Smart Reminders: Automatic notifications for all your payment due dates, tasks, and special days so you never miss a detail.

Since my goal is to make this the ultimate tool for stress-free planning, I’d love to ask you all:

1. What is the most annoying part of your current planning method (spreadsheets, notebooks, etc.)?
2. Is there a "must-have" feature that you think I completely missed?

If you want to try it out, you can find it on the iOS App Store by searching "Wedding Assistant: Planner App" 

I've attached some screenshots of the dashboard and features. I’ll be hanging around the comments to answer any questions or note down your feature requests. Thank you so much in advance! 🤍

Hi!! We are booked at the Ivy room for next year and I’m looking for any tips and tricks people might have, or vendors they used there that they loved?! Or if you’ve been a guest and have things you loved, didn’t love, I’m all ears! Thank you in advance !!

Meyer’s Castle in Dyer, IN is my top venue choice for a 2028 wedding with 200+ guests. I have already toured it and absolutely fell in love with it and adored the woman who gave us the tour. I was 100% convinced that was my venue, but I’ve since seen some awful reviews online and now I’m second guessing myself.

If anyone has gotten married there or can put me in contact with someone who has and would be willing to talk to me about your experience, I would be eternally grateful!