Chicago Wedding Planning Mistakes: 12 Things to Fix Before Wedding Week

Wedding planning is probably a lot of “Wait, WTF do I do now??” and “How do I know I’m on the right track???” And if that’s the boat you’re in right now… I get it. Trying to balance 20 vendor info packets while also deciding if you want lilies or hydrangeas in your bouquet and also, like, feeding yourself, is a LOT of work. And sometimes things are gonna slip through the cracks. As a Chicago wedding photographer, that’s exactly why I made this guide of wedding planning mistakes to avoid when you’re in the midst of it all. 

Keep reading to find tons of wedding planning tips for your Chicago wedding that’ll save you a TON of stress before your wedding week (or even month) hits. 

How Avoiding Major Wedding Planning Mistakes Makes Your Day Flow WAY Smoother

Maybe you’re super Type B and reading this thinking, “Yeah, it’s fine; it’ll all work itself out even if I do make wedding planning mistakes.” Probably true, but avoiding them in the first place?? It’ll save you a lotttt of headaches later on. 

I say this lovingly: once you hit your wedding week, you’re not gonna want to have to deal with wedding planning anymore. You’re gonna want to greet your guests, celebrate, hang out with your people, get your nails done, and probably also sleep. There’s no time for last-minute timeline changes or realizing that your florist has the wrong address. 

When you focus on it all beforehand, it makes your month, week, and day flow SOOO much easier. I’ve seen the difference between brides who made these wedding planning mistakes vs. those who didn’t, and the latter?? They were calm, relaxed, and had an insane amount of fun for their whole wedding. You can see the vibes allll over my wedding portfolio. 

Top Wedding Planning Mistakes to Avoid for Your Chicago Wedding

Whether you’re a stressed-out bride who just got engaged or your wedding is in 6 months and you can’t sleep because you feel like you forgot something… Take a deep breath. I’ve got you covered. 

Let’s get into the wedding planning mistakes to avoid to make sure that you actually have a good time!! 

Choosing a Venue Before Understanding Guest Count + Logistics

Okay, I know the whirlwind of excitement that is getting engaged. You probably want to do a virtual tour of a venue, book it, and get your wedding date immediately set. And trust me, I get it. 

Listen, though, babes: think about everything before you book it. Because you definitely don’t want to get 5 months down the road and realize that there’s not enough parking for everyone or that it’s wayyy further out of the city than you expected. 

Here’s my list of things to consider before signing any contract with a venue: 

• The guest capacity. At least have a rough draft of your guest list before you book the venue. Please. 
• Parking + transportation
• Guest experience + the movement between spaces
• Accessibility 
• Whether they allow outside vendors or not
• What their rules are as far as decorating, timelines, alcohol, and music
• How long they give you for setup and breakdown
• Nearby accommodations

The best thing you can do, in my opinion, is to look at real weddings from there and see if any look similar to your vision. And then tour it… Please. A floor plan online won’t tell you what moving 120 people from ceremony to cocktail hour actually feels like.

If this is the stage of wedding planning you’re in, check out 10 of my FAVORITE Chicago wedding venues. 

Booking Vendors Too Late

This is a wedding planning mistake that I see firsthand ALL the time. 

I get an inquiry from a couple who’s really excited to work with me… And I’m booked for their date. 

It actually breaks my heart just a little when this happens, and it goes to show that if you have a specific vendor that you know you want to work with, you need to reach out ASAP. 

You can see my entire wedding planning timeline for a month-by-month breakdown of when to book what vendors, but I almost always tell my couples to book 9-12 months in advance to be sure that they’ll have spots available! 

Underestimating Chicago Traffic 

One of my top tips? Don’t underestimate the beast that is Chicago traffic. 

If you have your ceremony, portraits, and/or reception in a different spot across the city… This is me begging you to have a plan and a whole lot of buffer time to get from one place to another. 

Plan out the time of day, any car or shuttle services you’ll need, and your timeline well in advance to account for going approximately 2 miles in the span of 45 minutes. And really, don’t build your transportation around whatever Google Maps says at 11:00 pm on a Tuesday. Saturday traffic, street closures, events, loading a wedding party into transportation, and simply getting everyone out the door take time.

I would rather give you fifteen extra minutes to sit with your person than have twenty people sprinting toward a party bus because portraits ran six minutes late.

Planning Too Many Portrait Locations

Chicago is truly jam-packed with good photo locations. As a Chicago wedding photographer… It’s one of my absolute favorite things about the city. I do, however, see the issues that it causes when wedding planning, because you might want pictures on the river and downtown and in Logan Square. 

Hear me out, though: between the aforementioned nightmarish Chicago traffic and the fact that you probably won’t want your wedding day to turn into a full magazine spread-esque photoshoot… It’s best to stick to two or three photo locations that are close to your venue and close to each other.

Don’t worry, because I do have good news here: we can always plan a photoshoot somewhere in the city after your wedding. It gives you an excuse to get dressed up in your wedding stuff again (score) and gives you a fun little date night. Win-win!! 

Want the editorial photos without building your entire wedding day around photos? That’s exactly how I approach Chicago weddings. You can see what a full wedding day looks like through my lens here!! 

Forgetting Permits, Rules, or Restrictions

Listen, I hate rules and restrictions as much as the next gal. When it comes to your wedding, though, you probably won’t want to be looking at a fine because you didn’t read the fine print of your contract. 

Different locations have different rules for photos, decor, alcohol laws, and permitting. Always, always, always check with any locations you’ll be going to and read all the fine print on any contracts before you sign them. Let’s maybe not get you kicked out of your wedding venue for lighting a candle, K? 

As your Chicago wedding photographer, I can help you out a little here. I’ve captured days at SO many different Chicago wedding locations that I know a lot of their rules, and if we need anything like permits to take pics at a location, I know exactly how to go about it. 

Choosing a Ceremony Time Without Considering Seasonal Light

Every time I see a late fall or winter wedding timeline with a 5:00 pm ceremony, an angel loses its wings. 

Seriously, though, from a photography perspective, always consider the lighting and sunset time for the current season when you’re planning your timeline. You want there to be enough light throughout the ceremony, into the cocktail hour, for good, well-lit portraits. 

There isn’t one ceremony time that works year-round in Chicago. A 4:00 pm ceremony in June gives us a completely different amount of daylight than a 4:00 pm ceremony in December, which is why I always look at your actual date, sunset time, venue, portrait plan, and whether you’re doing a first look before recommending when photos should happen.

Not Having a Weather Backup Plan

I know that no one wants to think about rain on their wedding day… But having a Plan B is always a good idea. Just in case. Chicago weather can get a little shifty, so just think about it before it’s too late. 

Know that this is NOT me saying to freak out over a 15% chance of rain a month out from your wedding. There’s a happy medium between that and waking up on your wedding day to gray skies and thinking, “Oh no… I don’t have a backup at all.” 

This can be something as simple as booking a venue with indoor and outdoor options, or even just having a backup tent on hand. And believe me when I say that it saves a LOT of stress, time, energy, and money when you think about it in advance. 

Overloading Your Timeline With Traditions You Don’t Even Care About

I’m a self-proclaimed nontraditional wedding photographer (learn all about me if that sounds like you, too), so I feel very strongly about not including wedding traditions that you could not care less about. 

I actually wrote a whole blog on how to pick what wedding traditions to keep and which ones to toss, but know that at the end of the day, you deserve for your wedding to feel like you. Don’t just include things because your great-aunt Judy says that she did it, so you should too!! 

Not Budgeting for Hidden Costs

When you’re planning your wedding budget breakdown, this is your friendly reminder not to forget about little hidden costs. Things like transportation, rentals, tips, overtime, bar costs, and hidden vendor costs can really add up, so save a little bit of your budget for your wedding day. 

Not Communicating With Vendors

As a wedding vendor myself… This is me begging you to please let us know of any surprises or sensitive family situations in advance. It’s uncomfortable for everyone when I ask your mom and dad to kiss in a picture and then find out they’re divorced. And it’s also really tough to jump up out of my dinner chair, mouth full of food, to photograph a last-minute surprise band that you added. 

This is said with love… Both for you and for myself, babes. 

Building a Pinterest Wedding Instead of One That Feels Like You

I love scrolling on Pinterest, saving dreamy wedding Pins just as much as the next person does. And if I’m honest, I love wedding trends just as much as everyone else does, too!

What I don’t love, though, is when you include Pinterest trends in your day just because you feel like you have to. I always suggest looking deeep down and seeing if the calla lilies and the butter yellow feel like who you are or have any special meaning to you. 

Forgetting to Build a Buffer Between Major Events

One of the biggest planning mistakes I see is building a timeline with zero buffer. I saved this one for last because it might just be the most detrimental wedding planning mistake for how your day feels. 

I have a whole breakdown on wedding day regrets that goes more into this (and shows what a relaxed day-of timeline can look like), but if you take nothing else from this blog… Make sure you build enough time into your timeline so that you’re not rushing between moments, getting stressed AF, or missing out on the most important moments of the day. 

As a Chicago wedding photographer, it’s really important to me that you enjoy your wedding, and this is one of the easiest things to do to make sure that you do. 

How to Be Sure You’re Not Making Wedding Planning Mistakes

If you’re feeling overwhelmed by all of this, I understand. Wedding planning is a lot. 

If you want to make sure you’re not missing any crazy steps or making huge wedding planning mistakes, you can use this and my entire Chicago wedding planning guide together to create the day of your dreams. 

Also, though… This is your sign to book a wedding planner. They’re kind of life-savers, I can’t lie! 

Wren and Rose | Chicago Wedding Photographer

I didn’t write this post to stress you out. In fact… It’s totally the opposite. I genuinely want you to enjoy your day, and avoiding these wedding planning mistakes can really help make that happen. 

If you miss a step or two or make a tiny little mistake, don’t beat yourself up over it. Honestly… Everyone messes up or forgets something. It’s just the way it is!! As long as you enjoy your day (and keep a positive mindset, even if something goes wrong), it’s a success. And I love that for you. 

If you’re still looking for a Chicago wedding photographer to be on your team throughout wedding planning, click to inquire about booking me right here. Can’t wait to chat about your vision, babes.