The Ultimate Guide to Planning Your Groovy Chicago Wedding with Soul & Style

Planning your groovy Chicago wedding? First of all hell yeah! This city is amazing! You’ve got the skyline, the lake, the dive bars, the vintage record stores, the late-night tacos… and a wild kind of beauty that makes every moment feel like magic. So if you’re dreaming up a wedding that’s more “soulful and weird in the best way” than stiff and traditional, you’re in the right place!! Your wedding day should feel like an extension of who you are not a performance, not a Pinterest checklist. Let’s make it groovy. Let’s make it yours. Here are 10 unapologetically fun and totally essential tips for planning your groovy Chicago wedding!

#1 Pick a Venue with Soul (Not Just a View)

Sure, skyline views are stunning but you know what’s even better? A venue that feels like a reflection of your story. Picture saying your vows in an industrial loft in Pilsen, dining under string lights in a Wicker Park courtyard, or dancing the night away on a West Loop rooftop. When you’re planning your groovy Chicago wedding, it’s all about energy. Go for spaces with character, texture, and stories built into their walls. Some of the best weddings I’ve photographed have happened in places no one expected, a cozy record shop, a dive bar, a backyard with twinkle lights and vintage rugs. If it feels like you, it’s the right spot!

#2 Expect the Unexpected (Because Chicago Weather Doesn’t Play)

If you’ve lived here even a week, you already know. Chicago’s weather is pure chaos, in the best and most frustrating way. It can be 75° and sunny at noon, and pouring by 3 p.m. (even in July). When planning your groovy Chicago wedding, don’t assume anything about the forecast especially if you’re outdoors. Make backup plans that still feel special, embrace clear umbrellas, and prep your guests for anything. And hey, if a little weather shows up? Let it! Some of the most iconic photos and best memories come from dancing in the rain or running through the wind with your veil flying behind you.

#3 Book Local, Funky, and Fabulous Vendors

Chicago is a creative goldmine. Your perfect team is out there you just have to look past the traditional vendor lists. Think: florists who mix blooms with wild textures and fruits, DJs who blend disco and hip-hop, or planners who dream in technicolor mood boards. When planning your groovy Chicago wedding, you want vendors who aren’t just talented, but who truly get you! Ask to see full galleries. Chat about your weirdest ideas. The best vendor matches are the ones who light up when you share your vision and can’t wait to bring it to life with you.

#4 Ditch the Rulebook

Who says you need a first dance? Or a white dress? Or cake at all? If that doesn’t feel like you, toss it out! Planning your groovy Chicago wedding means curating a day that celebrates your love, not just follows a script. Whether that means eloping at City Hall and throwing a warehouse dance party after, or walking down the aisle to Fleetwood Mac in roller skates do what feels right! Chicago is built for boldness. This is a city that loves personality, so don’t hold back. Make it yours. All the way.

#5 Make It a Whole Vibe (Not Just a Day)

Let’s be real, your people are flying in, booking hotels, clearing calendars. So why not make it more than just one event? Turn your wedding into a full-on Chicago weekend experience. Think: welcome drinks at a speakeasy, brunch on the riverwalk, late-night karaoke in Lincoln Park, or a Cubs game for your out-of-town guests. Not only does this stretch the celebration, but it also gives everyone time to actually connect, not just wave at each other between ceremony and cake!

#6 Build in Time to Just… Breathe

Your timeline doesn’t need to be packed down to the minute. In fact, please don’t do that!! When planning your wedding, leave space for breath, moments to reset, laugh, sip your drink, or sneak in an impromptu dance with your person. The magic often lives in the unscripted pauses, the quiet car ride between venues, the ten minutes hiding behind a curtain before the ceremony, the deep breath before you walk into your reception. Those are the moments that stay with you!

#7 Invest in What Lasts

Tacos will be devoured. Flowers will wilt. But your photos and video? That’s your forever. When it comes to documenting your wedding, don’t settle for just “technically good.” Find someone whose work makes you feel something. Someone who hypes you up, captures the chaos and the calm, and makes you look like the main character you are. Your wedding gallery should make you laugh, cry, gasp, and relive every second again and again!

#8 Steal a Moment for Just the Two of You

At some point in the whirlwind, sneak away. Just five minutes. Find a quiet street corner, a rooftop, a dimly lit hallway wherever you can be alone. Let yourselves exhale. Laugh. Cry. Just be. This day is about the two of you, after all. One of my favorite moments to capture is that golden hour stroll, where the world fades out and it’s just the two of you, soaking in the joy before the next chapter begins!

#9 Let the City Be Part of Your Story

Don’t just get married in Chicago, let Chicago be part of your story. Take photos under the ‘L’ tracks. Grab late-night snacks from your favorite diner. Have your portraits in the alley behind your go-to bar or on the steps of the Art Institute. Planning your groovy Chicago wedding means saying yes to spontaneity and city energy. Let the skyline, the grit, the glam, and the heartbeat of the city weave its way into your memories.

#10 Own Your Weird. Own Your Groovy. Own Your Story.

Here’s the big one: lean in. Go bold. If you’ve been dreaming of disco balls, leather jackets, or an all-vinyl reception playlist, this is your moment. Forget about what’s trendy or what your cousin did last year. Your wedding should feel like the best parts of you turned up loud. Groovy isn’t a theme. It’s a feeling. And when your wedding reflects your joy, your love, and your vibe? That’s when the magic happens!

Ready For Your Groovy Chicago Wedding? Let’s Chat!

Wren And Rose Photography | Chicago Wedding Photographer

You deserve a wedding that feels like a soul-filled celebration, not a carbon copy. If you’re planning your groovy Chicago wedding and want a photographer who’ll dance in the rain with you, chase golden hour through the city, and capture every bold, weird, wonderful moment, you know where to find me! If you want to learn more about me and what I do, click here. Can’t wait to hear from you!