'Twas the Night Before Christmas … curated on LTK

Chicago is a city full of charm, history, and vibrant culture, making it the perfect inspiration for thoughtful holiday gifting. Whether you're shopping for a local Chicagoan, a former resident who misses the city, or someone who simply adores the Windy City’s iconic landmarks and unique flair, this curated list of Chicago-themed holiday gifts has something for everyone. From locally crafted treasures to items celebrating the city’s beloved neighborhoods and traditions, these gifts capture the essence of Chicago and are sure to delight anyone on your list.

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Chicago is a city full of charm, history, and vibrant culture, making it the perfect inspiration for thoughtful holiday gifting. Whether you're shopping for a local Chicagoan, a former resident who misses the city, or someone who simply adores the Windy City’s iconic landmarks and unique flair, this curated list of Chicago-themed holiday gifts has something for everyone. From locally crafted treasures to items celebrating the city’s beloved neighborhoods and traditions, these gifts capture the essence of Chicago and are sure to delight anyone on your list. LTKSeasonal LTKGiftGuide LTKHome

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'Twas the Night Before Christmas in Chicago: A Twist on a Classic Christmas Tale and Fun Stocking... | Amazon (US)

MUNI PALS Munipals Chicago Transit Authority Wooden Railway Pink Line–Child Safe and Tested Woo... | Amazon (US)

Season's Greetings From Chicago Soy Candle - Red 15oz | Alice & Wonder

Dibs On Chicago Mug | Alice & Wonder

Chicago Ornament | Anthropologie (US)

Holiday in the City Stoneware Dessert Plate | Anthropologie (US)

Cocoa, Hot Cocoa Mix | The Spice House

On a long-awaited Friday, she wore her thank goodness, it’s almost the weekend uniform: wide-legged jeans that walked the perfect line between effortless and trendy, a black-and-white striped sweater that felt delightfully Parisian, and her new platform sneakers with just enough gold detail to make her feel like she tried (but not too hard). Her everyday gold jewelry added a touch of sparkle as she sipped her latte at a cozy coffee shop story hour, Miles happily perched on her lap. Later, they hit the shops with Grandma in tow, hunting for new toddler clothes (because, apparently, toddlers grow faster than weeds). As they loaded the car with tiny sweaters and pint-sized jeans, she grinned—ready to kick off a weekend that promised family time and maybe, just maybe, a little rest.

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Buying a new red scarf inspired by The Liberty Scarf this year might just be the way to channel the main character energy you’re looking for. More than a pop of color, this scarf represents the hope, resilience, and unity shared by Iris, Geneviève, and Clara in 1917, as they navigate love and loss amid the turmoil of war. As Iris stitches messages into her scarves, she embodies a quiet strength and creativity, making her designs symbols of connection. With a red scarf wrapped around you, you’ll feel linked to the courage of women who’ve used small acts of grace to make a difference. Each time you wear it, this scarf becomes more than just an accessory—it’s a reminder of the fierce and hopeful character within you, carrying a bit of timeless bravery and elegance into every winter day.

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On a blustery Thursday, she pulled together an outfit that said, “I can sip lattes while typing furiously at a coffee shop and still look chic carving a turkey later.” Her wide-legged dark wash jeans and classic black turtleneck served as the perfect base, while the sheer blazer with velvet polka dots added just the right amount of festive flair. New platform sneakers with a subtle gold detail ensured she could power through the day in comfort, from caffeine-fueled productivity in the morning to a cozy family Thanksgiving dinner in the evening. Her everyday gold hoops peeked out from her hair, catching the light with every gust of wind. As she stepped into the warmth of her family’s home, she smiled, silently thankful for the breezy fall weather—far better than the snowy chaos she knew Chicago was getting right now.

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On a gusty Wednesday that had her hair doing its best impression of a windblown supermodel, she reached for her wide-legged jeans and her effortlessly chic black batwing sleeve sweater—a combination as practical as it was stylish. Her new platform sneakers, with that subtle gold detail she loved, gave her the perfect boost to chase Miles around the adorable indoor play space that looked like a miniature village. With her everyday gold hoops catching the light as she “ordered” a pretend latte at the play café or ducked into the pint-sized post office to “mail” a letter, she couldn’t help but marvel at how utterly charming it all was. Miles was thrilled, she was cozy, and the wind stayed outside where it belonged.

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On a stunningly crisp Tuesday, she dressed for a day of wild adventures and endless photo ops at the zoo with the grandparents. Wide-legged dark wash jeans offered the perfect mix of style and comfort, while her oatmeal sweater wrapped her in cozy vibes that practically begged for a cup of hot cider between exhibits. Her new platform sneakers, with their subtle gold detail, kept her stylish yet zoo-trek ready, and her everyday gold hoops and necklace added a hint of understated glamour. As Miles giggled at the antics of the playful monkeys and his grandparents pointed out the giraffes, she couldn’t help but feel grateful for days like this—family, sunshine, and just enough chill in the air to make her sweater feel like a good idea.

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On a rainy Monday, she embraced a cozy, chic vibe that perfectly balanced weekend exhaustion with weekday ambition. Wide-legged cropped ivory jeans set the stage for her outfit, paired with a chambray shirt layered under a camel sweater vest—like a warm hug of a look that whispered, Let’s keep it low-key today. Her new platform sneakers, with a subtle gold detail, added just enough flair to remind the world she still had her sparkle, rain or shine. Her signature gold hoops and necklace tied it all together as she and Miles strolled into the library, settling into the calm and quiet after their bustling Branson weekend. Sometimes, a little drizzle and a good book are all you need.

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Wearing an ivory and tan striped boat neck shirt, she feels effortlessly stylish, the classic stripes giving her look a hint of Parisian charm. Paired with wide-legged jeans, the outfit flows with a relaxed sophistication, perfectly suited for a quiet moment of unwinding. Gold hoop earrings add a touch of polish, glinting softly as she moves. With a glass of crisp white wine in hand, its flavors grounding her in the moment, she feels like the main character in her own life—embracing a sense of elegance and calm that’s entirely her own, savoring the balance of simplicity and luxury.

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“The world belongs to those who read.” — Rick Holland 2/2)

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My week as a romcom: Friday’s outfit was peak “effortlessly cool mom on the go,” perfect for traveling with a toddler and still looking pulled together. She chose wide-legged jeans and layered a classic white long-sleeve t-shirt under a cozy gray waffle henley, her go-to new sneakers ready for everything from airport sprints to backyard leaf piles. Her gold hoops and necklace gave the look a bit of polish because, even on travel days, she stayed true to her style. After arriving at her family’s house, there was just enough time to drop the bags, bundle up, and head to the local high school football game—where small-town nostalgia and a crisp autumn night felt like the perfect kickoff to the holiday season.

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“The world belongs to those who read.” — Rick Holland (1/2)

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Friday’s outfit was peak “effortlessly cool mom on the go,” perfect for traveling with a toddler and still looking pulled together. She chose wide-legged jeans and layered a classic white long-sleeve t-shirt under a cozy gray waffle henley, her go-to new sneakers ready for everything from airport sprints to backyard leaf piles. Her gold hoops and necklace gave the look a bit of polish because, even on travel days, she stayed true to her style. After arriving at her family’s house, there was just enough time to drop the bags, bundle up, and head to the local high school football game—where small-town nostalgia and a crisp autumn night felt like the perfect kickoff to the holiday season.

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Wearing a dress inspired by Janine Kovac, author of The Nutcracker Chronicles: A Fairytale Memoir, to see The Nutcracker this year just might be the perfect way to embrace your own main character energy. Janine’s journey, from young ballet dancer to wife, mother, and literary curator, mirrors the transformation many of us experience as we grow through different roles in life. A dress that reflects both the grace of a dancer and the strength of a woman who has embraced every stage of her life is an empowering choice. Whether it’s a ballet-inspired tulle gown or something sleek and sophisticated with a touch of sparkle, this look captures the magic of The Nutcracker and the personal evolution Janine writes about. Stepping into that dress, you’ll feel ready to take center stage in your own life, finding joy and balance just as Janine does throughout her unique and inspiring story.

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For mom’s night out last night I made a few changes to my daytime look: I swapped out the t-shirt for a bodysuit and the sneakers for black mules with a gold buckle. I also added my gold necklace for a little more bling. The jeans, cardigan and belt remained the same

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Thursday brought that cozy, autumnal vibe in full force, with dark wash wide-legged jeans and a classic black turtleneck layered under a brown fair isle cardigan—just the right mix of festive and effortlessly cool. Her go-to sneakers were on, of course, ready for anything the day brought, and her everyday gold hoops added a touch of elegance to her cozy look. It was book club day, which meant gathering with her favorite crew of moms, reading sweet Thanksgiving stories, and diving into a table full of acorn crafts. As the toddlers painted and glued (and possibly tried to eat) their acorns, she looked around at the joyful chaos and couldn’t help but feel a warm, pre-holiday glow.

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Wednesday's look was city-mom chic with a touch of “I’ve got this.” She started with her wide-legged jeans, the ones with a subtle front pocket detail that made her feel like she could tackle anything, paired with a navy v-neck long-sleeve under her crisp, white lady jacket cardigan. Her go-to sneakers were ready to hit the ground running, and her everyday gold hoops added that perfect dash of sparkle. They kicked off the morning with a trip to the pediatrician for the two-year check-up (brave little guy!), then headed straight to music class—a sure fix to any morning woes. By the time he was shaking maracas, all was right in the world again.

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Tuesday called for her favorite button-fly skinny jeans, the reliable kind that fits just right (because yes, Millennials still love them!), paired with a sleek black turtleneck layered under a cozy gray sweater. Her go-to sneakers were laced up, and her trusty gold hoops made their daily appearance, adding that touch of “I’ve got this.” Today was all about maximizing time at the daycare/co-working space—him with his mini friends, her powering through projects with a coffee refill or two. It felt like a good balance, like the jeans that hug just right and the hoops that never let her down.

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On Monday, she buttoned up in her wide-legged jeans with a playful front pocket, slipping a navy and camel striped turtleneck under her camel sweater blazer—just the right combo of cozy and chic. Her go-to sneakers were a given, ready for toddler-chasing, and her trusty gold hoops added that everyday polish. The toddler dance party was a hit, with her son pulling out his best wobbly moves, spinning and giggling with abandon. Watching him bop around, his face lit with pure joy, she couldn’t help but feel the beat herself—today’s only dance floor rule: total, uninhibited fun.

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Wearing a beautiful, cozy green sweater that wraps her in warmth, she feels an instant connection to the season’s comfort. Paired with wide-legged jeans, her look is both relaxed and stylish, with just the right balance of casual and chic. The gold hoop earrings add a touch of understated elegance, catching the light as she moves. As she sips on a crisp glass of white wine, the cool, refreshing taste perfectly complements the serene vibe of the moment. In this simple yet perfect scene, she feels like the main character in her own life, embracing the beauty of the everyday with grace and confidence.

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My week as a romcom: Ashley, the effortlessly cool stay-at-home mom, had a week as full as her coffee cup—and twice as strong. She kicked things off with nearly a full day of daycare on Monday, savoring the extra time to catch up on her to-do list (and maybe even a little self-care). Tuesday was Election Day, and between errands and voting, she was feeling all the civic pride. Wednesday brought their favorite music class, where her son clapped along like he was headlining a tiny concert, much to her delight. Thursday’s Little Book Club was the perfect setup for lunch with her mom friends and their kiddos—matching chaos with laughs over lunch, and her heart was full. And that evening? A night out with her oldest friends in the city, which made her feel young and free, just for a bit. By Friday, she was balancing a playdate in the morning with a well-planned daycare afternoon, a little breather to round out the whirlwind week. Ashley’s week had been a perfect mix of mom life and her life, and she was already making plans to do it all over again.

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On Friday, she slipped into her black moto leggings and a blush-pink cashmere sweater, her go-to sneakers keeping things equal parts comfy and cool. With her everyday gold hoops and necklace catching the morning light, she headed to a playdate with Miles and his best buddies, where toddler laughter and snack crumbs abounded. After their playtime escapades, they parted ways as she swapped playdate energy for a productive afternoon at daycare/cowork. In her effortlessly chic and cozy attire, she felt ready for anything this Friday mom schedule could throw her way.

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Wearing a formal blue dress inspired by Jayne and Meredith from The Memory Dress by Jade Beer just might be the key to feeling like the main character in your own life. A deep blue gown, elegant and timeless, embodies Jayne’s quiet resilience and Meredith’s poise under pressure. The color blue symbolizes trust, loyalty, and calm—qualities both women exude as they navigate mystery, memory, and unexpected connections. Just as Jayne steps into a new world of discovery and Meredith sews her way through a life of elegance and hidden desires, wearing a stunning blue dress allows you to embrace your own strength and grace. This formal look mirrors the courage required to face life’s uncertainties, while channeling the sophistication and history tied to Meredith’s couture masterpiece from Princess Diana. With every step, you’ll feel empowered, ready to tackle the unknown with style and confidence.

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A few simple changes for dinner with the girls: swapped the sneakers for d’orsay flats and added a purse

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On Book Club Thursday, she was wrapped in her camel-colored turtleneck sweater, dark wash wide-leg jeans, and her trusty new sneakers—a look that whispered casual chic with a touch of cozy elegance. Her everyday gold hoops added a glint of warmth as she settled into a morning of good books and even better company. Afterward, she and her mom friends headed out for lunch, laughter filling the table as they shared updates, advice, and encouragement. Sitting there, she couldn’t help but feel a swell of gratitude for this fierce, supportive group of women who offered friendship, grace, and plenty of hugs—today and always.

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On this gentle Wednesday, she reached for her wide-leg jeans and her favorite camel-colored sweater—the one with that hidden pop of hot pink along the collar and a stripe down the back, a little joyful detail only she knew was there. It was a soft embrace of an outfit, paired perfectly with her go-to sneakers and, of course, her daily gold hoops that felt like mini gold hugs themselves. Today, she promised herself, was about kindness and grace: a day for quiet walks, extra deep breaths, and maybe a hug just for her, because sometimes, that's exactly what we all need.

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On Election Tuesday, she dressed in spirited red, white, and blue, feeling both patriotic and—dare she say—stylish. Her navy blue shorts balanced the cheerful plaid turtleneck that, in her opinion, was the perfect blend of festive and cozy. Her go-to sneakers kept her grounded and ready for the long day ahead, from morning drop-offs to polling place lines. Gold hoops and her favorite necklace? Check. But the real MVP was the "I Voted" sticker proudly adorning her top, a small but mighty accessory that spoke volumes about making her voice heard—one chic vote at a time.

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On a drizzly Monday that begged for cozy layers, she reached for her classic camel crew neck sweater—the kind of warm staple that feels like a gentle hug—tucking it just right into her wide-leg jeans. Her go-to sneakers were ready to take on the rain, proving yet again that they were as reliable as any best friend. Her gold hoops and necklace added the familiar touch of sparkle to keep things pulled together as she headed off to daycare drop-off, where Miles trotted inside happily. With a quiet, coffee-fueled day ahead to catch up on blog work, she actually felt almost…dare she say it…relaxed.

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Wearing her favorite old sweater with a timeless black-and-white pattern, she feels an instant sense of comfort and nostalgia. Paired with wide-legged jeans, the look blends cozy with a touch of effortless chic, while her gold hoop earrings add a subtle hint of elegance. As she takes a sip of crisp white wine, the refreshing taste matches the simple pleasure of her outfit. It’s a quiet, reflective moment, yet it makes her feel like the main character in her own life—unrushed, authentic, and perfectly at ease with the beauty of the present.

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“When you lose yourself in a book the hours grow wings and fly.”— Chloe Thurlow (2/2)

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“When you lose yourself in a book the hours grow wings and fly.”— Chloe Thurlow (1/2)

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“No. I can survive well enough on my own – if given the proper reading material.” — Sarah J. Maas

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My week as a romcom: Ashley, the effortlessly cool stay-at-home mom, had planned Halloween week down to the last candy corn. Monday kicked off with a half-day daycare drop-off to ease into the week, followed by a warm-up round of trick-or-treating in the bustling business district, where her little one charmed shop owners with his tiny costume and enthusiastic “trick-or-treat!” Tuesday’s toddler fitness class had him hopping through obstacles like a Halloween pro, while she mentally ran through the candy stockpile already growing at home. By Wednesday, they were off to a Halloween-themed music class, shaking maracas to spooky tunes and adding to the festive chaos. Thursday was all about pumpkins at Little Book Club, followed by an evening round of trick-or-treating that felt like a mini Halloween marathon. And on Friday? A nearly full daycare day—Ashley’s brilliant idea to reclaim a few hours of sanity after a week of costumes, candy, and nonstop festivities. It was chaotic, it was sugary, and Ashley was already wondering if it was too early to start planning next year’s costumes.

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The Friday after Halloween called for comfort, and she delivered in dark wash wide-leg jeans and a chunky blue sweater that practically hugged her back. Her go-to new sneakers were on duty, perfect for balancing the laid-back look with a hint of mom-on-the-go style. With her gold hoops—because even in post-Halloween recovery mode, the details matter—she navigated the day mostly at daycare, where everyone was still a little sugared-up and sleepy. It was a cozy, low-key day, just what she needed after a week of costumes, candy, and toddler antics.

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A holiday look inspired by Josephine Reynolds or her great-grandmother Alma from The Vanishing of Josephine Reynolds by Jennifer Moorman might be just the ticket to feel like the main character in your own life. Channel Josephine's quiet resilience and newfound sense of purpose with a look that’s both elegant and timeless, perhaps a vintage-inspired dress in soft, wintry tones paired with modern accessories for a nod to both the past and present. Alternatively, embrace the bold, Jazz Age glamour of Alma with a daring flapper-style dress, adorned with sequins or fringe, paired with a faux fur stole or sparkling accessories. Each look carries a sense of transformation, evoking the spirit of stepping through time, just as Josephine did, and celebrating your own ability to rewrite the story with courage, style, and grace.

For Halloween at Little Book Club, she leaned into cozy-chic vibes with a pair of wide-leg jeans and the coziest ivory and camel sweater she snagged from her friend’s boutique—one of those perfect finds that manages to look casual yet thoughtfully put together. Her new favorite sneakers made chasing tiny costume-clad readers around a breeze, and, of course, her everyday gold hoops and necklace added that signature touch. With storytime shivers and giggles aplenty, it was a Halloween she’d never forget, filled with tiny superheroes, dinosaurs, and witches discovering the magic of books.

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On this unexpected, balmy Wednesday in late October, she went for a balance of festive-meets-practical: green pleated shorts paired with a crisp long-sleeve white tee, a nod to Halloween without sweltering in a full autumn ensemble. Her go-to new sneakers kept up with her toddler’s endless enthusiasm, and her everyday gold hoops and necklace added just the right bit of polish. She couldn’t help but laugh at her weather-defying “fall” outfit—perfectly suited for chasing down mini ghost-and-goblin dance partners at music class while the sun shone like summer.

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