19 Most Popular Wedding Dates in Chicago for 2025

There definitely are days that are already proving to be incredibly popular for weddings in 2025 and there are some that have many reasons for popularity here in Chicago. We have listed out some of the wedding dates in Chicago that seem to have popularity with their reasons as well.

Valentine’s Day Weekend

It’s no wonder that these dates are popular - With Valentine’s Day being a Friday this year and the following day being a Saturday, some people are going to want to up the romance and lean into the holiday about couples. Next year, this will probably be even more true because of the actual holiday landing on a Saturday in 2026!

2/14/25

2/15/25

Memorial Day Weekend

Memorial Day weekend is always popular in Chicago for weddings because it typically marks one of the first weekends in Chicago that the weather is pretty nice! This is when folks have been hibernating for 6 months so they are ready to go outside and be in the sun. That means that folks will be extra excited to celebrate with you too!

5/24/25

5/25/25

Palindromes

Dates that have catchy numbers are also going to be popular because they are easy and fun to remember! These two dates might be busy for weddings because the weather might shape up to be nice in the spring and is sure to be nice in the fall even though it’s a Friday.

5/5/25

10/10/25

Good Weather

This is a LONG list of dates that we see popping up often for inquiries, and we know it’s because the weather is generally good in this timeframe in Chicago. If you’re looking to get married in or around the Chicago area, May through October is always booked and busy for weddings. These are definitely going to be big ones and the highlighted ones are ones we see more often than the rest.

5/31/25

6/14/25

6/21/25

6/28/25

7/19/25

8/16/25

9/6/25

9/27/25

10/4/25

10/11/25

Fall Leaves

In Chicago, the last few years we have seen the last weekend of October as the best weekend for having the pretty fall colors as your wedding photo backdrop. We have seen some leaves still into the early week of November, but we definitely think it’s likely that the October 25 date here will be the best Saturday for the fall vibes.

10/25/25

11/8/25

New Year’s Eve

You can’t help but have couples want to have their wedding on New Year’s Eve because of how exciting it is for you and your guests! Everyone is looking to have a good time, it gives your guests a plan they don’t have to make, and it also encourages your guests to actually stay past midnight instead of leaving early! We highly recommend New Year’s Eve weddings personally because it always seems to be a great time for everyone involved.

12/31/25

Wedding dates in 2025 are already filling up, and wedding dates in 2026 are also starting to get picked up! It’s most important to book the vendors and get the things that you really want for your wedding as soon as possible, especially if you are looking at any of these wedding dates. If you need more help planning your 2025 or 2026 wedding, reach out to us at our contact page and we can help make sure you have everything you are hoping for for your wedding day!