Chicago Apparel and Accessories

Sweatshirts, t-shirts, hats and other accessories are great souvenirs for visitors, Chicago residents and anyone else who loves our city.

62 products

62 products

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A woman wears the Touchdown, Chicago! Women’s Luxe Lounge Set by Kiki + Lulu, featuring blue bamboo pajamas with sports-themed cartoon prints like footballs, hats, foam fingers, and the number 18. A close-up highlights the detailed pattern of these comfortable Mom Jams or nursing pajamas. Shown on a white background.
A woman smiles while wearing the Touchdown, Chicago! Women’s Luxe Lounge Set from Kiki + Lulu, featuring blue bamboo fabric decorated with cartoon bears, footballs, and foam fingers. Her right hand is in her pocket. The image is cropped from the nose down.
Touchdown, Chicago! Women's Luxe Lounge Set
$84.00
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The Daily Disco ‘chicago’ Chainstitch Embroidered Beanie in gray features red lowercase “chicago” lettering on the cuff in a vintage chainstitch design, and is displayed on a gray tiled surface.
'chicago' Chainstitch Embroidered Beanie - gray + red thread
$35.00
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A ‘chicago’ Chainstitch Embroidered Beanie by Daily Disco, featuring gray knit material with “chicago” stitched in rainbow thread on the folded brim, is displayed on a gray tiled surface.
'chicago' Chainstitch Embroidered Beanie - gray + rainbow thread
$35.00
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The ‘chicago’ Chainstitch Embroidered Baby & Toddler Beanie from Daily Disco, crafted in cozy gray knit and accented with vibrant rainbow chainstitched lettering on the cuff, sits atop a sleek gray tiled surface. This adorable winter hat also features a small white tag with a blue logo on the side—perfect for little ones in chilly weather.
'chicago' Chainstitch Embroidered Baby & Toddler Beanie - gray + rainbow thread
$32.00
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The ‘chicago’ Chainstitch Embroidered Baby & Toddler Beanie by Daily Disco, featuring cream knit fabric and “chicago” stitched in rainbow thread on the cuff, is shown on a gray tiled surface—an ideal and stylish Chicago toddler beanie.
'chicago' Chainstitch Embroidered Baby & Toddler Beanie - cream + rainbow thread
$32.00
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A Chicago Chainstitch Sweatshirt in flo blue by Daily Disco, made from soft ring-spun cotton with a relaxed fit, is displayed flat on a white, wrinkled fabric surface. The neckline is accented with “chicos” and small colorful shapes chainstitched in rainbow thread.
Chicago Chainstitch Sweatshirt - Flo Blue with Rainbow Thread
$68.00
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The Chicago Chainstitch Sweatshirt by Daily Disco features “chicnyc” chainstitched in rainbow thread on the collar. Crafted from heavyweight fleece with soft ring-spun cotton, this cream-colored sweatshirt is shown against a blue sky with light clouds.
Chicago Chainstitch Sweatshirt - Cream with Rainbow Thread
$68.00
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The Daily Disco Chicago Chainstitch Sweatshirt in chambray features “chicago” embroidered in red thread on the left shoulder and is crafted from heavyweight fleece and ring-spun cotton for exceptional comfort, displayed on a white wooden surface.
Chicago Chainstitch Sweatshirt - Chambray with Red Thread
$68.00
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A white Daily Disco ‘chicago’ Chainstitch Embroidered Beanie features “chicago” stitched in vibrant rainbow thread across the front and rests on a gray textured surface. A small logo tag is attached to the cuff, showcasing its playful vintage-inspired chainstitch detail.
'chicago' Chainstitch Embroidered Beanie - white + rainbow thread
$35.00
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The Southern N Savvy “good, better, best!” embroidered knit beanie features the phrase stitched in vibrant orange thread on the folded brim. Displayed on a tiled gray surface, this classic black beanie is designed as a one-size-fits-most style for comfortable everyday wear.
good, better, best! embroidered knit beanie
$28.00
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A heathered royal chicago embroidered knit beanie from Southern N Savvy, featuring “chicago” in red cursive on the folded brim, displayed on a gray tiled surface. This one-size beanie combines style and comfort for everyday wear.
chicago embroidered knit beanie - heathered royal
$28.00
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A DA BEARS embroidered baseball cap by Southern N Savvy, featuring bold orange lettering on beige and black premium cotton with classic snap closure, is displayed on a gray tiled surface.
DA BEARS embroidered baseball cap
$38.00
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A Chicago Bears unisex raglan shirt in soft tri-blend gray and navy blue by tori grace outfitters, featuring the iconic bear logo on the front, is displayed on green artificial turf near a white field line—perfect for game day.
A man and a young girl, both sporting tori grace outfitters’ Chicago Bears unisex raglan shirts made from soft tri-blend fabric, smile at each other on a football field, sharing a joyful game day moment.
Chicago bears unisex raglan shirt - soft tri-blend
$38.00
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A light pink ‘chicago’ Chainstitch Embroidered Beanie by Daily Disco, featuring “chicago” stitched in rainbow colors across the front cuff, is displayed on a gray tiled surface. This beanie brings a playful pop of color to any outfit.
'chicago' Chainstitch Embroidered Beanie - light pink
$35.00
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Bundle includes two tori grace outfitters Chicago flag baby & toddler faux fur pom beanies—one in white, one in navy—each featuring the iconic Chicago flag patch on the cuff. These cozy hats are perfect for your little one’s winter wardrobe and add a touch of Windy City pride to any baby or toddler’s look.
A young Chicago toddler wears the tori grace outfitters’ Chicago flag baby & toddler faux fur pom beanie, bundled in a warm coat and gloves while squatting on grassy park terrain scattered with autumn leaves. A toy is clasped in their hands, with the city’s skyline and tall buildings stretching across the background.
Chicago flag baby & toddler faux fur pom beanie
$34.00
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Introducing the tori grace outfitters Bears logo faux fur pom beanie, a navy blue cable knit hat accented with a brown faux fur pom-pom on top and finished with a Chicago Bears logo patch on the folded brim.
A smiling woman wears a tori grace outfitters Bears logo faux fur pom beanie in navy blue while standing in a football stadium filled with fans and an ongoing game.
Bears logo faux fur pom beanie
$40.00
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The Chicago Bears inspired onesie by tori grace outfitters features dark gray fabric with white striped sleeves and an orange and blue bear head logo on the chest, laid flat on a white background—perfect for baby gifts.
A smiling baby wearing a Chicago Bears inspired onesie with striped sleeves from tori grace outfitters sits on a green football field near white yard lines, enjoying the sunny day—an adorable choice for memorable baby gifts.
Chicago bears inspired onesie, striped sleeve
$30.00
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A “da bears” Chainstitch Embroidered Beanie by Daily Disco, featuring custom orange embroidery on the front cuff, is displayed on a gray tiled floor.
'da bears' Chainstitch Embroidered Beanie
$34.00
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A royal blue ‘chicago’ Chainstitch Embroidered Baby & Toddler Beanie from Daily Disco, featuring “chicago” chainstitched in red thread on the cuff and a small white tag on the right side, is displayed flat on a gray textured surface. Perfect as a Chicago kids or toddler beanie.
'chicago' Chainstitch Embroidered Baby & Toddler Beanie - royal blue + red thread
$32.00
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A royal blue ‘chicago’ Chainstitch Embroidered Baby & Toddler Beanie by Daily Disco, featuring the word “chicago” stitched in colorful thread on the front, displayed on a gray textured background.
'chicago' Chainstitch Embroidered Baby & Toddler Beanie - royal blue
$32.00
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The Daily Disco ‘chicago’ Chainstitch Embroidered Baby & Toddler Beanie in light pink features “chicago” stitched in rainbow colors on the cuff, making it perfect for little ones and shown here against a gray textured background.
'chicago' Chainstitch Embroidered Baby & Toddler Beanie - light pink
$32.00
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Dress your little one in the Chicago Icons & Hearts Baby Onesie from EnjoyMyDesign—a cream-colored baby bodysuit adorned with colorful illustrations of iconic Chicago landmarks, hearts, pizza, a hot dog, a sailboat, and “Chicago” boldly printed in blue. It’s the perfect unique Chicago gift or addition to any little one’s Windy City wardrobe.
Chicago Icons & Hearts Baby Onesie
$28.00 $21.00 Save $7.00
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A streetwear staple from Funky Junque, the 2 Tone Upside Down Trucker Cap in Navy/Beige features a contrasting navy bill and bold orange "CHICAGO" embroidery displayed upside down on the front. This snapback hat seamlessly blends sporty style with contemporary flair.
2 Tone Upside Down Trucker Cap - Chicago - Navy/Beige
$30.00
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The Kiki + Lulu Chicago Football Convertible Footies, featuring blue bamboo fabric with football, foam finger, and bear mascot prints, long sleeves, navy cuffs, and a front zipper, are laid flat on a wooden surface.
Chicago Football Convertible Footies
$39.00
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The "Chicago flag baseball hat - youth" by tori grace outfitters features a light blue design with a hand-embroidered patch of four red stars and two blue stripes, shown against a white background.
Introducing the Chicago flag baseball hat - youth from tori grace outfitters: a stylish white cap featuring the iconic Chicago flag design with blue stripes and four red stars, all hand-embroidered on the front. Set against a crisp white background, this hat is perfect for kids who want to show off their Chicago pride in style.
Chicago flag baseball hat - youth
$29.00
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The Chicago Unisex T-Shirt by Nobullwoman Apparel hangs on a wooden hanger, crafted from a soft cotton blend. “Chicago” is written in bold, navy blue script across the chest. This t-shirt is easy to care for and machine-wash friendly.
Size chart for Chicago Unisex T-Shirt in XS-2XL, making it easy to find your perfect fit in our comfortable cotton blend shirts. Features a how-to-measure guide and Nobullwoman Apparel branding at the top. White background with black and pink text for clear, easy reading. All Chicago Unisex T-Shirts are machine wash friendly.
Chicago Unisex T-Shirt
$40.00
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The Chicago Puff Print Cropped Sweatshirt with Elbow Stripes by Nobullwoman Apparel, made from a soft cotton-polyester blend, showcases bold embossed "CHICAGO" lettering on the front and striking white stripes on the sleeves. This navy blue cropped sweatshirt is displayed hanging on a wooden hanger indoors.
Chicago Puff Print Cropped Sweatshirt with Elbow Stripes
$74.00
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The Chicago Puff Print Cropped Sweatshirt by Nobullwoman Apparel is a light blue, ultra-soft and comfy top with embossed 3D red cursive lettering that spells "Chicago," displayed on a wooden hanger against a white wall.
A Nobullwoman Apparel display mannequin wears the Chicago Puff Print Cropped Sweatshirt, featuring soft light blue fabric and 3D embossed
Chicago Puff Print Cropped Sweatshirt – Embossed 3D Lettering
$58.00