Babes, a beach and breakfast nachos: A bachelorette weekend in Chicago

This weekend, I celebrated my upcoming wedding with a bachelorette party in Chicago!

Highs: Amazing food, beautiful gifts, a glamorous hotel, belly laughs and even a few happy tears

Lows: Parading around the city wearing phallic jewelry

Katharine, Molly and I arrived in Chicago on Friday evening, where we met Laura and were welcomed into Anna’s impressive big-city apartment. After catching up and cleaning up, the six of us indulged in sushi and sake at a secret restaurant near Anna’s home, where I was even served a belated fish-shaped 30th birthday dessert! (When asked what it was, the waiter accurately described it as, “Uhh, I don’t know, something Asian?”) IMG_2706 IMG_2712 IMG_2713 We followed dinner with tasty Moscow Mules at a neighboring bar before walking back to Anna’s place to meet Courtney, who arrived bravely via Mega Bus.


We ended the night with Prosecco, frozen pizza, a photo session with Molly’s selfie stick, Cards Against Humanity and rolling on the floor, clasping our bellies in laughter. (Cards Against Humanity champion? Jillian: 11. Sorry Molly.) IMG_2711IMG_2710 IMG_2709 IMG_2708 On Saturday morning, we awoke and brunched at Two Sparrows, where I stuffed my face with one of the best meals I’ve ever eaten. I kept referring to it as “breakfast nachos,” but Anna didn’t like that description.

CHILAQUILES: tortilla chips, fire roasted tomatillo salsa, 2 sunny side farm fresh eggs, queso-cheddar blend, black beans and roasted anaheim aioli – add shredded chicken or pork chorizo

(And yes, you should add the shredded chicken.)

From brunch, we gathered our bags and cabbed to Saturday night’s destination: The Palmer House Hilton. IMG_2729 IMG_2728 Since we were too early to check into our room, we hijacked a bathroom and changed into our bikinis (which is exactly what you want to do after you’ve stuffed yourself sick with breakfast nachos + $4.00 shredded chicken.) Maria arrived in time to join our bathroom party, and we headed off to the beach.

We lazed around in the sun, drinking fancy frozen lemonades and pina coladas poured from spinning machines and taking more photos with the selfie stick. Ashley arrived and met us at the beach, and we chatted a few hours away in the warmth of the sun. IMG_2717 IMG_2714 IMG_2718 IMG_2719 IMG_2715 Finally, it was time for the big event! We returned to the hotel to check into our room and get ready for the evening. First up? My friends shut me in the bathroom while they decorated the hotel room with streamers before allowing me to re-enter. IMG_2722 IMG_2721 IMG_2720 Once I made it through the decor, they showered me with lacy, racy gifts. Oh, and also a necklace, veil and garter carefully garnished with tiny plastic penises and a tastefully-sequined sash that screamed BACHELORETTE!

Then, we played my ultimate favorite game in which I tried to guess Bryan’s answers to a list of questions Laura had sent him a few days prior to the party. In his responses, Bryan revealed his deepest, darkest, most romantic emotions, including things like, “I plead the fifth,” and “We don’t have a song.”

(He did have some heartfelt answers, and even some surprising ones, on which I’ve been smiling and reflecting since Laura read them to me. I knew I loved that man!) IMG_2723 IMG_2724 IMG_2725 IMG_2726 After all the gifts had been opened and the answers had been guessed, we packed our pretty selves up and headed to another tasty meal at Hubbard Inn. In the rustic, dimly-lit restaurant, we dined on small plates of spicy scallops, buttery whitefish and chorizo, rich bacon-wrapped dates and tangy watermelon and gorgonzola salad. And surprise! I was given a second 30th birthday dessert – chocolate mousse topped with sour cherry syrup. IMG_2727 We wrapped up the evening by heading around the street corner to The Baton, where we showered impressive drag queens with our remaining dollar bills.

Finally, we drug ourselves back to the hotel. One of us called every pizza restaurant she could think of trying (unsuccessfully) to order “cheese pizza with multiple sauces!” for delivery. Before I knew it, we had peeled off our dresses for comfier pajamas, set our lashes carefully on the bathroom counters, finished off the chip crumbs at the bottom of the snack bag and tucked ourselves into bed.

A bachelorette weekend success!

I had the very best weekend with my girlfriends, and I’m reflecting on it now with a full heart. Over the last few years, I have struggled some days with feeling alone and abandoned. But these ladies – Ashley, Laura, Katharine, Courtney, Molly, Maria, Anna (and Megan, Bess, Lauren and Janel who couldn’t make it to Chicago this weekend) – helped me find brighter days.

They have walked with me through difficult times, listened to my worries, insecurities and complaints with open ears and celebrated with me in my successes. They have been some of my biggest cheerleaders and confidantes, helping me to realize redemption and grace. I am so thankful for them and praise God that he put these ladies in my life when I needed them the most.

And now, high on love for my friends and for my handsome fiance, it’s time to look forward to my wedding day – only 67 days away!

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