If you’re planning an out-of-the-box wedding day, Sophie and Jack’s unforgettable Chicago wedding is chock full of creative wedding ideas (plus a few laughs) that you never knew you needed. (But first, be sure to start at the beginning of their story with their iconic Chicago Riverwalk engagement session.)

Making Your Wedding Weekend Feel Like an Epic Reunion

Sophie and Jack kicked things off at one of my very favorite spots in Chicago: the Publishing House Bed & Breakfast. With its chic charm and nostalgic nooks, it feels like a thoughtfully curated home, rather than just another “getting ready” venue. The couple, along with their family and close friends, arrived in town on Thursday—and this was no throwaway buffer day! They kicked off the weekend-long celebration with a welcome dinner followed by a city scavenger hunt that had everyone reconnecting, exploring, and laughing. (And yes, there was a bit of friendly competition in there, too.)

Expert Tip: A collaborative game or event before the wedding day is a great way to bring people together and provide natural conversation starters. Instead of guests talking about the weather, economy, or business, you’ll hear snippets like, “Remember when Rachel swore the last clue was at Millennium Park, and we all raced over there?” That’s a lot more fun, if you ask me.

A Day That Was So Them — and Then Some

On the big day, the ceremony took place at Loft Lucia, an urban retreat with exposed brick walls, large industrial windows, and a rooftop terrace that offers a polished yet personal loft-style ambiance with plenty of light.  

After “I do,” guests drifted into cocktail hour. But instead of a string quartet or a DJ, they were treated to a live magician! It wasn’t your typical wedding fanfare, but it was exactly the kind of surprise you’d expect from Sophie and Jack.

After hors d’oeuvres, everyone sat down to dinner crafted by the brilliant team at Ilixr Creative, who brought in warmth, flavor, and heart to every dish. Then—and this is where it gets delightfully unconventional—instead of a dance floor, the newlyweds opted for a trivia night. Yep, each table became its own trivia team; laughter was the main anthem.

But they didn’t stop there. There was a “him-or-her” game that had friends guessing fun facts about the happy couple, lottery tickets tucked under place cards (because why not?), and a custom puzzle with a photo of the couple that each table solved together. They even had a crossword with clues about them, their story, and their quirks. The evening felt intimate, playful, and contagiously fun.

Creative Wedding Ideas that Will Make the Best Memories

1. Make the lead-up part of the party.
   By arriving early and hosting a welcome dinner + scavenger hunt, Sophie and Jack made their wedding less “event” and more “weekend with friends.” It’s a great option if you want to lengthen the fun without stretching your budget, or if you want to deepen connections. (After all, how often are you able to get the whole crew together?)
   
2. Choose a venue that matches your vibe.
   Loft Lucia’s industrial-chic-meets-rooftop-garden setup made it a canvas for them. The space is flexible, bright, and full of character.  
   
3. Replace traditions with intentional experiences.
   A magician at cocktail hour? Brilliant. It’s interactive, unexpected, and gets people talking. And then swapping dancing later for trivia night? That switch felt totally aligned with who Sophie and Jack are—not a compromise, but a choice.
   
4. Put your mark on it.
   The games, crosswords, and puzzles weren’t just filler. They were a way for guests to learn about Sophie and Jack, connect with their story, and be part of the fun. If your goal is to make every person feel involved, small interactive elements like these go a long way. It’s a wedding experience that’ll live on in fond memories long after the send-off.

Planning Your Own Unconventional (But Totally Yours) Celebration

If Sophie and Jack’s day has your wheels turning, here are some creative wedding ideas—from luxe to nearly free—for couples dreaming of a wedding that breaks the mold:

• Entertainment
  • Hire a magician or illusionist (like they did).
  • Book an improv troupe or comedian for cocktail hour.
  • Set up a karaoke corner.
  • Rent a vintage video-game console.
    
• Games + activities
  • Put a different classic game on each table. No need to buy new ones! Use what you have and ask friends to pitch in. Ideas include Apples to Apples, dominoes, playing cards, Scrabble, Jenga, Trivial Pursuit, Clue, Pictionary, Uno, Skipbo, Backgammon, Checkers, and more! Guests can mix it up after dinner.
  • Trivia night is a star, but you could also do a “guess the memory” game, or “how well do you know the couple” bingo. There are endless options here.
  • Scavenger hunts don’t just belong in the welcome weekend: create one as part of the reception (photo hunt, clue-based roaming, etc.).
  • Personalized puzzles and crosswords are more affordable than you think. You might even have a creative friend or family who could create it for you.
    
• Interactive food and drink
  • Instead of a standard bar, do a mocktail or cocktail “flight” tasting that’s personalized (maybe a drink named after how they met, or a shared takeaway).
  • For dinner, a chef’s station or interactive food bar gives people something to engage with instead of just sitting down.
  • You can never go wrong with a taco truck, hotdog cart, or sweet treat station.
    
• Budget-friendly personal touches
  • Print out crossword or trivia sheets yourself (or hire a student designer).
  • Use mass-producible items like lottery tickets, personalized matchboxes, or even custom coasters as fun place-card extras.
  • Ask a friend or family member to MC/host the games. If they’re charismatic, it makes everything feel more authentic and fun (especially if they have some stories to share).

A Shout-Out to the Dream Team Behind Their Day

Every great wedding leans on a few key people, and Sophie and Jack had a stellar crew. Here’s the team who took their creative wedding ideas and ran with them:

Photographer: @megadamikcreative
Venue: @loftlucia
Planning: @plan_and_gather_events
Florals: @flowersfordreams
Catering: @ilixrcreative
Bakery: @chicago.sugardaddy
DJ: Okyne Entertainment Group
Magician: Luis Carreon

Trading Tradition for Trivia

Instead of following a traditional wedding checklist, Sophie and Jack made every last detail feel like them. They leaned into joy, playfulness, and a little gentle rebellion against tradition. If you’re imagining a wedding that’s less ballroom and more living-room-party-meets-escape-room, I say run with it!

Whether you have the budget for professional entertainment, or you’re more into DIY nostalgia, you can absolutely pull off a day that’s quirky, warm, and full of real connection. Trade the dance floor for trivia, sneak in a magician, and plan a scavenger hunt for kicks. Your wedding should feel like a celebration of you, and your friends and fam will love it, too!