It’s become somewhat of a tradition now — when a close friend or a family member sets a wedding date, I get a text within seconds of the ink drying on the contract. You’re the first to know, they’ll tell me, considering my crazy calendar — so you better be there! How could I not comply?

When my cousin Kirsten, who is really more like a sister, called to let me she and her high school sweetheart Steve had set a date — a mere twenty years later — I wouldn’t have missed it for the world.

Cindy's Rooftop Chicago

After a fun — and food-filled — few days exploring Chicago tourist-style with Ian, it was time to get back into marriage mode. We checked out of the Freehand and shifted over to the Swissotel, the official wedding hotel where my mom had generously reserved rooms for the whole family. While the hotel felt like your standard business hotel compared to the quirky lodging we’d just moved from, we luxuriated in the generously sized rooms and the views stretching out all the way to Navy Pier.

Chicago Wedding Weekend

Chicago Wedding Weekend

We didn’t linger long though — as soon as my mom and Miller arrived from Decatur (yes, this was the second decades-later wedding of Illinois high school sweethearts I attended in two weeks), we hopped in an Uber and rushed up to Ravenswood for the rehearsal. Lollapalooza traffic was insane, and we ended up arriving just as the wedding party was headed to the rehearsal dinner. Oops.

Chicago Wedding Weekend

Chicago Wedding Rehearsal Dinner

The super low-key rehearsal involved taking over nearby sports bar Tavern on Little Fort for a surprisingly delicious buffet, a bevy of champagne toasts, and an impromptu family reunion as I caught up with family members I hadn’t seen in eons.

I even got to give one of those champagne toasts. A few years ago, when Kirsten and my mom and my sister Olivia and I went to Central America, I penned ‘Twas The Night Before Belize in celebration. Kirst loved it so much she asked me to write a rehearsal dinner version, ‘Twas The Night Before the Wedding — how fun is that!

Finally, we took family photos. This next set of the new cousins is my favorite — first, the one you frame, second, the one you pull out and laugh at for years to come. Isn’t Steve, over on the left there, lucky to join this crew!

Chicago Wedding Rehearsal Dinner

Chicago Wedding Rehearsal Dinner

As with most rehearsal dinners, we stayed up way later than we vowed to — I feel like there’s a real flaw in this whole wedding weekend plan that means you always wake up exhausted on the big day!

One of the bridedsmaids told me that her brother had held his rehearsal on a Thursday and then had a quiet, low key bride-and-groom-only night on that Friday. I loved that idea — consider it mentally filed for any future wedding I might be a host of.

Chicago Wedding Rehearsal Dinner

Chicago Wedding Rehearsal Dinner

But beauty waits for no woman — especially not a sleeping one. We dragged our bums out of bed and up to the bridal suite for a morning of hair, makeup, and girly giggles.

This is always one of my favorite aspects of participating in a wedding. Things get so crazy once the whole walking down the aisle thing happens — I love having a little bit of alone time with the ladies to freak out over what’s about to go down.

Chicago Wedding Getting Ready

This wedding, we had a lot of tiny adorable company! Kirsten is beloved honorary aunt to a whole gaggle of cute kiddos, and they truly couldn’t have looked sweeter. The moms of all these munchkins were part of our amazing Nashville bachelorette weekend — we sure clean up nice, eh?

Chicago Wedding Getting Ready

Chicago Wedding Getting Ready

Chicago Wedding Getting Ready

Chicago Wedding Getting Ready

Chicago Wedding Getting Ready

Chicago Wedding Getting Ready

Once the bridal party headed off on the trolly for photos, Olivia and Ian and I reunited for a little photo fun of our own. I’d yet to show Ian the major tourist tick-offs The Bean and Millennium Park, so we strolled over for a gander and an iconic Chicago photo backdrop.

Wedding Guest Portraits at The Bean

Wedding Guest Portraits at The Bean

Wedding Guest Portraits at The Bean

Wedding Guest Portraits at The Bean

No surprise — the crowds were insane! It was Lollapalooza weekend, and we could actually hear some of the music extending all the way to The Bean.

Wedding Guest Portraits at The Bean

Wedding Guest Portraits at The Bean

Once we snapped a few shots, we sought refuge from the street up at Cindy’s Rooftop. Cindy’s is one of the most sought-after reservations in Chicago, but we managed to squeeze into a spot at the bar for a pre-wedding drink and snack in our finest formal wear. With tons of festival-goers crammed in for a pre-show drink, it was a lively and full crowd and a fun atmosphere.

While we were on the balcony, we even ran into an Alex in Wanderland reader — how fun! Usually when that happens I’m in my sweatpants and no makeup and haven’t slept for three days, so it was very exciting to meet someone on a day I wasn’t embarrassed to appear in photos, ha!

Cindy’s truly has the best views in the city — if you can’t get in for a meal, just stop by for a drink and the best aerial photo of Millenium Park around!

Cindy's Rooftop Chicago

Cindy's Rooftop Chicago

Cindy's Rooftop Chicago

Cindy's Rooftop

Cindy's Rooftop Chicago

Cindy's Rooftop Chicago

Cindy's Rooftop Chicago

And then we were in an Uber singing “Going To The Chapel…” except we were going to Ravenswood Event Center! I absolutely fell in love with this industrial chic space the moment my cousin sent me photos of it, and I couldn’t wait to see it transformed into her and Steve’s vision on that day.

We made our way up to the third floor, where a full wall of windows would frame the “I do’s.” And just as the sun began to set, the procession began.

Wedding at Ravenswood Event Center

Wedding at Ravenswood Event Center

Wedding at Ravenswood Event Center

Wedding at Ravenswood Event Center

When Kirsten walked down the aisle, I couldn’t help it — I cried!

Wedding at Ravenswood Event Center

Wedding at Ravenswood Event Center

Olivia and I were honored to be asked to read in the ceremony, along with Steve’s cousin — I shared a passage from my man Mark Twain. It was a beautiful and heartfelt ceremony with vows that left us laughing and smiling. From their first kiss at thirteen to their wedding kiss a few years later, it was a beautiful moment to see these two crazy kids finally make it official.

Five stars on Yelp, for sure.

Wedding at Ravenswood Event Center

Wedding at Ravenswood Event Center

Wedding at Ravenswood Event Center

Wedding at Ravenswood Event Center

Wedding at Ravenswood Event Center

And then the party got started! I was a little too distracted by the fun of being at a wedding with not only Ian but also my immediate and extended family and a whole bunch of Chicago folk I’ve known since I was wee. Which means I didn’t get photos of the cute champagne cork place cards or the wall of vintage family photos. But suffice it to say, no detail went forgotten!

Wedding at Ravenswood Event Center

Wedding at Ravenswood Event Center

Wedding at Ravenswood Event Center

Wedding at Ravenswood Event Center

I love loft weddings. When I worked doing wedding set up and tear down for extra cash in New York City in college, these were our speciality and I was always swooning at the amount of creativity allowed by a big blank slate like this!

The reception room at Ravenswood was once home to an industrial printing and binding machinery warehouse — now, it houses a collection of vintage neon signs and sports cars (I couldn’t help but think of the much-beloved Neon Museum in Las Vegas!)

Wedding at Ravenswood Event Center

Wedding at Ravenswood Event Center

Time to party! Dinner was crazy good, which meant I had plenty to dance off in the ensuing hours. Even better? The bride’s mother is a talented baker and made an overflowing dessert table for over three-hundred guests, by hand! I almost went into a sugar coma, a hospitalization I wouldn’t have regretted in the slightest.

Wedding at Ravenswood Event Center

Wedding at Ravenswood Event Center

Wedding at Ravenswood Event Center

Wedding at Ravenswood Event Center

What a night! The next morning, we gathered at Kirsten and Steve’s beautiful new home to wish them well on their honeymoon to Bali. While I strongly weighed the pros and cons of trying to hide in their suitcases, I had a flight to New Orleans to catch, and that was a pretty enticing trip as well.

Next stop, NOLA!

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21 Comments...
  • Marni
    September 15 2017

    Weddings seems to go in waves where there will be plenty one year and hardly any the next. I can’t get over how many you attended in such a short time!

    • Alex
      September 22 2017

      Ha yep, this was a crazy summer for nuptials — just one next year, though!

  • Danie
    September 16 2017

    Had to skip down before I finished reading the post- I LOVE your rehearsal dinner dress. OMG.

    Okay. Gonna finish reading now.

    • Alex
      September 22 2017

      Haha! Thank you — hand-me-down from my little sister 🙂 I’ve been wearing it all over the place lately!

  • Nathan George
    September 20 2017

    looks like you had a great time in windy city chicago…. love your post and thanks for sharing

    • Alex
      September 22 2017

      You’re so welcome Nathan — thanks for reading!

  • Dominique
    September 22 2017

    I loved the outfits, I loved the setting! I went wedding dress shopping with a friend of mine last week, and I have to say… I never considered myself to be a “wedding” kind of girl, but I’m starting to get swayed 😉

    • Alex
      September 22 2017

      Dress shopping will do that to anyone, I think 🙂 I’ve yet to get to go wedding dress shopping with any of my girlfriends… hoping the opportunity comes soon!

  • Anuj Agarwal
    September 23 2017

    Hi Alexandra,

    My name is Anuj Agarwal. I’m Founder of Feedspot.

    I would like to personally congratulate you as your blog Alex In Wanderland has been selected by our panelist as one of the Top 100 Solo Female Travel Blogs on the web.

    I personally give you a high-five and want to thank you for your contribution to this world. This is the most comprehensive list of Top 100 Solo Female Travel Blogs on the internet and I’m honored to have you as part of this!

    Best,
    Anuj

    • Alex
      September 25 2017

      Hey Anuj! Thanks so much for sharing — thrilled to be on the list. Happy blogging!

  • Naveen Kumar
    October 3 2017

    What a beautiful wedding. I love all the pics!

    • Alex
      October 3 2017

      It really was a stunner! Beautiful couple, gorgeous event.

      • Naveen Kumar
        October 4 2017

        Yeah! 🙂

  • Teresa Rocha
    March 6 2019

    I like how you blended the blue on your make up and dress and the skyline. This was interesting. A nice color palete!

    • Alex
      March 8 2019

      Thanks Teresa — I love dressing up!

  • Emery Ocampo
    May 3 2019

    What a lovely wedding. 🙂 You all look amazing!!!

    • Alex
      May 11 2019

      You’re too kind. Thank you!

  • Steve
    October 27 2019

    What incredible photos of a gorgeous couple. great job!

    • Alex
      October 30 2019

      Thanks, Steve! Appreciated.

  • Esther Diaz
    February 9 2020

    The wedding looks really fun and yet simple. Thank you for sharing this. It is something to add to my ideas when planning one. Cheers!

    • Alex
      February 14 2020

      You’re welcome Esther! Thanks for reading!

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