Windy City Admirer Gifts

Looking for a special gift for a Windy City admirer? Our collection celebrates Chicago's iconic spirit with witty, heartfelt designs on mugs, t-shirts, pillows, and prints. Show them how much you appreciate their love for the Windy City and bring a piece of Chicago into their everyday life with thoughtfully crafted, amusing items that capture the city's essence.

All Products Prints T-Shirts Mugs Pillows

'Don't worry - all tall buildings sway a little in the wind.'

'Don't worry - all tall buildings sway a little in the wind.' mockup

'Don't worry - all tall buildings sway a little in the wind.'

from $19.00

Large Dollar Sign Office Block

from $19.00

"Of all the buildings I've designed, it's probably the most handsome."

"Of all the buildings I've designed, it's probably the most handsome." mockup

"Of all the buildings I've designed, it's probably the most handsome."

from $19.00

"Some day, son, all this will be yours. ... Actually, you know what? You can have it now."

"Some day, son, all this will be yours. ... Actually, you know what? You can have it now." mockup

"Some day, son, all this will be yours. ... Actually, you know what? You can have it now."

from $19.00

“It's $195 million. Now, I know what you're thinking: 'OK, what's the catch?'”

“It's $195 million. Now, I know what you're thinking: 'OK, what's the catch?'” mockup

“It's $195 million. Now, I know what you're thinking: 'OK, what's the catch?'”

from $19.00

"Looks like a pretty quiet night out there, huh, girl?"

"Looks like a pretty quiet night out there, huh, girl?" mockup

"Looks like a pretty quiet night out there, huh, girl?"

from $19.00

Country farmhouse loaf / Inner city highrise loaf.

Country farmhouse loaf / Inner city highrise loaf. mockup

Country farmhouse loaf / Inner city highrise loaf.

from $19.00

"Makes me wish I'd kept that gorilla suit."

"Makes me wish I'd kept that gorilla suit." mockup

"Makes me wish I'd kept that gorilla suit."

from $19.00

"Hey, I just consider myself very fortunate to be getting paid for something I'd be doing anyway."

"Hey, I just consider myself very fortunate to be getting paid for something I'd be doing anyway." mockup

"Hey, I just consider myself very fortunate to be getting paid for something I'd be doing anyway."

from $19.00

Sick Building Syndrome

from $19.00

'We're very tight on space right now but we'll have you in an office as soon as we can. Meanwhile...'

'We're very tight on space right now but we'll have you in an office as soon as we can. Meanwhile...' mockup

'We're very tight on space right now but we'll have you in an office as soon as we can. Meanwhile...'

from $19.00

Manhattan Cat atop the Woolworth Building

Manhattan Cat atop the Woolworth Building mockup

Manhattan Cat atop the Woolworth Building

from $19.00

"You look pretty shifty in the getup. . . even for the subway."

"You look pretty shifty in the getup. . . even for the subway." mockup

"You look pretty shifty in the getup. . . even for the subway."

from $19.00

'It's amazing that with all the things I've done that I haven't gotten a big head.'

'It's amazing that with all the things I've done that I haven't gotten a big head.' mockup

'It's amazing that with all the things I've done that I haven't gotten a big head.'

from $19.00

"With great power comes great, great stress."

"With great power comes great, great stress." mockup

"With great power comes great, great stress."

from $19.00

Statue of Liberty With Face Mask

from $19.00

"It is just as the Oracle foretold!" mockup

"It is just as the Oracle foretold!"

from $19.00

Architectural Messages Through the Ages.

Architectural Messages Through the Ages. mockup

Architectural Messages Through the Ages.

from $19.00

"And, yet another plus, it will block out the sun's harmful ultraviolet rays from a considerable portion of the city."

"And, yet another plus, it will block out the sun's harmful ultraviolet rays from a considerable portion of the city." mockup

"And, yet another plus, it will block out the sun's harmful ultraviolet rays from a considerable portion of the city."

from $19.00

"We call it, 'Green meadows' because that's what it was before we decided to build on it."

"We call it, 'Green meadows' because that's what it was before we decided to build on it." mockup

"We call it, 'Green meadows' because that's what it was before we decided to build on it."

from $19.00

Jasper's Limo Service.

from $19.00

'Boy, these vast grassy plains are great, but some shade in full Summer would be good too...'

'Boy, these vast grassy plains are great, but some shade in full Summer would be good too...' mockup

'Boy, these vast grassy plains are great, but some shade in full Summer would be good too...'

from $19.00

"Sarah, get me my own billboard right across the way. I'd like an office with a nice view."

"Sarah, get me my own billboard right across the way. I'd like an office with a nice view." mockup

"Sarah, get me my own billboard right across the way. I'd like an office with a nice view."

from $19.00

Gambling on office building construction

Gambling on office building construction mockup

Gambling on office building construction

from $19.00

Yeah? Delivery! Come on up!

from $19.00

The Gilmore Girls

from $19.00

"Honey, my boss moved me upstairs – way upstairs!"

"Honey, my boss moved me upstairs – way upstairs!" mockup

"Honey, my boss moved me upstairs – way upstairs!"

from $19.00

'It's not really rsutling, it's rebranding."

'It's not really rsutling, it's rebranding." mockup

'It's not really rsutling, it's rebranding."

from $19.00

'It's like having our own private luxury box in the game of life.'

'It's like having our own private luxury box in the game of life.' mockup

'It's like having our own private luxury box in the game of life.'

from $19.00

Working Vacation.

from $19.00

"Sorry, y'all — no locals. This is a tourists-only bar."

"Sorry, y'all — no locals. This is a tourists-only bar." mockup

"Sorry, y'all — no locals. This is a tourists-only bar."

from $19.00

'I love it when it's windy and we do a Mexican wave!'

'I love it when it's windy and we do a Mexican wave!' mockup

'I love it when it's windy and we do a Mexican wave!'

from $19.00

"You are not what I expected."

from $19.00

"Chew. I don’t want you getting a stomachache."

"Chew. I don’t want you getting a stomachache." mockup

"Chew. I don’t want you getting a stomachache."

from $19.00

"I can't say I love New York, but I can say New York loves me."

"I can't say I love New York, but I can say New York loves me." mockup

"I can't say I love New York, but I can say New York loves me."

from $19.00

Windy City Admirer Gifts Collection

Windy City Admirer Mugs

Explore our collection of Chicago-themed mugs and find the perfect gift for Windy City fans who love starting their morning with a city-inspired smile.

Windy City Admirer Pillows

Check out our Chicago-themed pillows—perfect for cozying up with a bit of city pride in every nap or lounge.

Windy City Admirer Prints

Discover striking Chicago prints—beautiful artwork celebrating the city’s landmarks and vibrant culture, ideal for fans and decor lovers alike.

Windy City Admirer T-Shirts

Browse our Chicago-inspired t-shirts collection—fun, trendy designs for those proud of their Windy City roots.