Chicago Shirt

Show your love for the Windy City with our collection of Chicago shirts. Designed for comfort and style, these shirts feature soft fabrics and versatile fits perfect for any occasion. Whether you're exploring the city or cheering on your favorite team, our Chicago shirts offer a trendy way to express your pride. With a variety of designs and colors, you can easily find the perfect piece to showcase your Chicago spirit. Elevate your wardrobe and celebrate the vibrant culture of Chicago with every wear.

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165 products
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On Sale
Where I'm From Adult Chicago Gray Striped T-Shirt

Where I'm From Adult Chicago Gray Striped T-Shirt

$11.98

WAS: $32.00*

(1)

Pretty comfortable. ... great shirt, minimal shrinkage after

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5 Woody22
great shirt, minimal shrinkage after washing. Pretty comfortable.

Where I'm From Adult Chicago Natural Flag T-Shirt

Where I'm From Adult Chicago Natural Flag T-Shirt

$32.00

(2)

Great shirt ... Fit was perfect for me. ... The print is lovely though. ... Love the

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5 Russ
Like the shirt. Light weight. Fit was perfect for me.

Obvious Shirts Adult Chicago 1:20 Somewhere T-Shirt

Obvious Shirts Adult Chicago 1:20 Somewhere T-Shirt

$32.99

(3)

The material is soft and comfortable, and the fit is just right. ... The design is fun and nostalgic. ... This Chicago Cubs “ Holy Cow ” t- shirt is a total home

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5 DirtyD41
This shirt is one of 4 obvious shirts I have. It is my 2nd favorite and makes me watch the cubs more.

5 Kevharm
This Chicago Cubs “ Holy Cow ” t- shirt is a total home run! The design is fun and nostalgic. The material is soft and comfortable, and the fit is just right. Whether you ’ re heading to Wrigley or just repping your team around town, this shirt brings great vibes and even better memories. Love it!

5 Carl71
Great shirt for old school Cub Fan! The image gets noticed.

Where I'm From Adult Chicago Flag Black T-Shirt

Where I'm From Adult Chicago Flag Black T-Shirt

$35.00

(4)

Great fit and comfortable fabric ... Fits perfectly, looks great, comfortable, soft. ... Got this shirt to go with some shoes color was spot on. ... This shirt is the perfect color for shoe

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5 Vols guy
Got this shirt to go with some shoes color was spot on..

5 TaJBl
Fits perfectly, looks great, comfortable, soft. I 'm buying a third one

Obvious Shirts Adult Chicago Graphic Light Blue T-Shirt

Obvious Shirts Adult Chicago Graphic Light Blue T-Shirt

$32.99

(4)

Soft material and some cool history ... The store was clean and bright, and all the associates were friendly and made it a great experience. ... I bought this for my

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5 Steele92620
Bought as a gift and they really liked it. Soft material and some cool history

5 Cubbie
Recently had purchased this as a Christmas gift for a relative. The store was clean and bright, and all the associates were friendly and made it a great experience. The share is awesome as well!

5 Cubnm
I bought this for my wife. She loved the simple but true message

4 Ryne23
Theis shirt is a great reminder of one of the most remarkable moments in Chiago sports history.

Where I'm From Adult Chicago Flag Grey T-Shirt

Where I'm From Adult Chicago Flag Grey T-Shirt

$35.00

(1)

Cute and comfy! ... 10/10 recommend! ... Very cute Chi

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5 Vlaveee
Very cute Chi T! Material is so buttery! 10/10 recommend!

Obvious Shirts Men's Chicago Blue 'Favorite Season' T-Shirt

Obvious Shirts Men's Chicago Blue 'Favorite Season' T-Shirt

$32.99

(4)

True cubs fan ... Nice shirt ... She loved the simple but true message ... Theis shirt is a great reminder of one of the most remarkable moments in Chiago sports

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5 Steele92620
Bought as a gift and they really liked it. Soft material and some cool history

5 Cubbie
Recently had purchased this as a Christmas gift for a relative. The store was clean and bright, and all the associates were friendly and made it a great experience. The share is awesome as well!

5 Cubnm
I bought this for my wife. She loved the simple but true message

4 Ryne23
Theis shirt is a great reminder of one of the most remarkable moments in Chiago sports history.

Where I'm From Adult Chicago Archstar Light Blue T-Shirt

Where I'm From Adult Chicago Archstar Light Blue T-Shirt

$32.00

(1)

My husband had worn his old Cubs tee out, so I bought this one for him to wear to a game on a hot summer day. ... His new favorite tee:) ... Husband loves this

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5 cbprseven
Our family was going to a Cubs game together. My husband had worn his old Cubs tee out, so I bought this one for him to wear to a game on a hot summer day. He wore it to the game and continues to wear it again and again. His new favorite tee:)

Obvious Shirts Men's Chicago Grey Score Card T-Shirt

Obvious Shirts Men's Chicago Grey Score Card T-Shirt

$32.99

(4)

The share is awesome as well! ... Bought as a gift and they really liked it. ... Great Christmas

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5 Steele92620
Bought as a gift and they really liked it. Soft material and some cool history

5 Cubbie
Recently had purchased this as a Christmas gift for a relative. The store was clean and bright, and all the associates were friendly and made it a great experience. The share is awesome as well!

5 Cubnm
I bought this for my wife. She loved the simple but true message

4 Ryne23
Theis shirt is a great reminder of one of the most remarkable moments in Chiago sports history.

On Sale
Where I'm From Adult Chicago Black Six Seven T-Shirt

Where I'm From Adult Chicago Black Six Seven T-Shirt

$10.97

WAS: $32.00*

(2)

I bought this tee for my cousin and he loves the fit and style, also comfortable. ... I was looking everywhere for a shirt like this, and DSG was the only place that had

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5 Lil spender
I bought this tee for my cousin and he loves the fit and style, also comfortable.

5 CANESWAG
I was looking everywhere for a shirt like this, and DSG was the only place that had it.

Where I'm From Unisex Chicago White Golf T-Shirt

Where I'm From Unisex Chicago White Golf T-Shirt

$32.00

(2)

Soft and fashionable! ... Great

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5 Lil spender
I bought this tee for my cousin and he loves the fit and style, also comfortable.

5 CANESWAG
I was looking everywhere for a shirt like this, and DSG was the only place that had it.

Where I'm From Adult Chicago Gray Repeat Cropped T-Shirt

Where I'm From Adult Chicago Gray Repeat Cropped T-Shirt

$32.00

(1)

This one is super soft. ... Exactly what I wanted ... And I miss the “ Indians ” so I love that this shirt simply says “ Cleveland

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5 Jlr67
I ’ m petite, so I prefer cropped t- shirts. This one is super soft. And I miss the “ Indians ” so I love that this shirt simply says “ Cleveland ”.

Where I'm From Men's Chicago Light Blue Flag 2Hit T-Shirt

Where I'm From Men's Chicago Light Blue Flag 2Hit T-Shirt

$32.00

(7)

The material is lightweight and SO incredibly soft and the print quality is fantastic! ... He is 5'11ish and can wear an XL, but likes his shirts a little bigger, so I got him a 2Xm and it is n't too baggy so I would say the fit is just right for

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5 Dzales
Great Shirt awesome fit and price not bad at all they going fast

5 hmfRVT82
I bought this t- shirt for my husband and he absolutely loves it! The fit is just the way he likes it. He is 5'11ish and can wear an XL, but likes his shirts a little bigger, so I got him a 2Xm and it is n't too baggy so I would say the fit is just right for size. The material is lightweight and SO incredibly soft and the print quality is fantastic! We both love this shirt!

5 Chief
I bought this football shirt for my wife and she loves it.

5 InTheBag
Love this shirt... got on sale at a great price with super fast shipping!

5 Lindsj32
Loved it and the material is amazing. I would buy it again.

On Sale
Where I'm From Youth Chicago Black Six Seven T-Shirt

Where I'm From Youth Chicago Black Six Seven T-Shirt

$11.97

WAS: $25.00*

(1)

Highly recommend! ... Cute vintage t ... Very soft, great price( bought it on sale) and very different compared to the other Williamsport

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5 GRB0721
Very soft, great price( bought it on sale) and very different compared to the other Williamsport tshirts! Highly recommend! I bought a youth size( much cheaper) I am 103lbs, 4'11 height.

Where I'm From Women's Chicago City Bar Cropped T-Shirt

Where I'm From Women's Chicago City Bar Cropped T-Shirt

$32.00

Quick Facts

The material is so soft and very comfortable boxy shirt ... Fav new crop

Where I'm From Adult Chicago Blue 2Sided Diamond T-Shirt

Where I'm From Adult Chicago Blue 2Sided Diamond T-Shirt

$35.00

(1)

I bought this last month and the fit& feel was great ... Great

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5 Jayc23
I bought this last month and the fit& feel was great

Where I'm From Women's Chicago Light Blue Script Cropped T-Shirt

Where I'm From Women's Chicago Light Blue Script Cropped T-Shirt

$32.00

(1)

Cropped to a good length. ... Cute stylish shirt ... Good design and stylish top for a young

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5 Spurs crop top
Good design and stylish top for a young lady. Cropped to a good length.

Obvious Shirts Adult Chicago Holy Cow T-Shirt

Obvious Shirts Adult Chicago Holy Cow T-Shirt

$32.99

(3)

Clever and fun Cubs shirt ... Great style and fit. ... It is my 2nd favorite and makes me watch the cubs more. ... Love it! ... Great shirt for old school Cub Fan! ... Whether you ’ re heading to Wrigley or just repping your team around town, this shirt brings great vibes and even better

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5 DirtyD41
This shirt is one of 4 obvious shirts I have. It is my 2nd favorite and makes me watch the cubs more.

5 Kevharm
This Chicago Cubs “ Holy Cow ” t- shirt is a total home run! The design is fun and nostalgic. The material is soft and comfortable, and the fit is just right. Whether you ’ re heading to Wrigley or just repping your team around town, this shirt brings great vibes and even better memories. Love it!

5 Carl71
Great shirt for old school Cub Fan! The image gets noticed.

Where I'm From Women's Chicago Windy City Cropped T-Shirt

Where I'm From Women's Chicago Windy City Cropped T-Shirt

$32.00

(1)

The boxy fit is comfy and still flattering. ... Cute and comfy ... I ’ ve worn this a few times now and I really love

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5 Katherine
I ’ ve worn this a few times now and I really love it. The boxy fit is comfy and still flattering. I ’ m 5 ’ 7 ” 125# and ordered a small. Washes well.

Where I'm From Unisex Chicago Black 2-Hit Golfball T-Shirt

Where I'm From Unisex Chicago Black 2-Hit Golfball T-Shirt

$35.00

(4)

Material is buttery soft and fit is cute! ... Soft and great quality. ... Love this shirt ... Love the material! ... The quality and fit of this shirt is so great! ... I purchased this brand a few years ago and have loved

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5 William
Soft and great quality. Does run a bit smaller and shrinks, but up a size

5 CDizzle
So happy I got a shirt to represent my favorite place. Material is buttery soft and fit is cute!

5 Znorris11
I purchased this brand a few years ago and have loved it. The quality and fit of this shirt is so great!

Retro Brand Youth Chicago Fire Red Logo T-Shirt

Retro Brand Youth Chicago Fire Red Logo T-Shirt

$26.00

(1)

this shirt is perfect to wear to a game in all weather. ... perfect for

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5 victoriaricci
this shirt is perfect to wear to a game in all weather.

chicka-d Women's Chicago Fire Cardinal The Band T-Shirt

chicka-d Women's Chicago Fire Cardinal The Band T-Shirt

$50.00

(1)

I bought this a month ago and the quality is amazing! ... Great

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5 Hmk904
I bought this a month ago and the quality is amazing!

Nike Men's Chicago White Max90 City T-Shirt

Nike Men's Chicago White Max90 City T-Shirt

$45.00

(15)

Very comfortable feel and great fit! ... It is simple yet catchy with the city name embroidered. ... Comfortable and seems durable. ... Perfect heavyweight cotton Nike Dallas Tee, I get to represent my city and be super comfortable in this Nike

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5 vboyz69
People know where you from when you where this great looking shirt in public.

5 mikeyboy
Great quality shirt, made with good fabrics and can go with almost anything

5 Dallas Tee
Perfect heavyweight cotton Nike Dallas Tee, I get to represent my city and be super comfortable in this Nike tee! 5 stars yet again Nike!

5 Rdub
This is a solid Nike white tee. Comfortable and seems durable.

5 Chuckie P
Very satisfied with purchase. Item was as advertised.

ALLCITY Men's Chicago Cubs Blue 'Hot Dog' T-Shirt

ALLCITY Men's Chicago Cubs Blue 'Hot Dog' T-Shirt

$34.99

(4)

Purchased for my wife and she loves the softness of the shirt. ... Comfortable, fun shirt, good way to support one of my favorite teams. ... Good idea ... Christmas gift for my wife that loves die hard

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5 Pancho
Purchased for my wife and she loves the softness of the shirt.

5 Jmart
Christmas gift for my wife that loves die hard movie

5 Wine girl 66
Comfortable, fun shirt, good way to support one of my favorite teams.

5 Cjh23
I bought this shirt less than a month ago getting ready for the cubs season. Excited to wear it to games and throughout the season to show support for the team.

Nike Men's Chicago Black Core Cotton Shoebox T-Shirt

Nike Men's Chicago Black Core Cotton Shoebox T-Shirt

$40.00

(15)

Very comfortable and great design ... Love wearing very comfortable ... My son bought this shirt from the Dick's from Washington Square and loves it since he's from

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5 Ryan
Great shirt I would recommend for anyone who likes the Vols

5 JH96
My boys loved this shirt, unique and great colors!

5 Tkaz03
My son bought this shirt from the Dick's from Washington Square and loves it since he's from LA.

5 Danielle
My son loves his Nike Baltimore Orioles t- shirt with the Maryland State outline

5 Bdubs9999
Shorts looks great! Very comfortable and great design

Columbia Men's Chicago Bears Grey Tamiami Shirt

Columbia Men's Chicago Bears Grey Tamiami Shirt

$74.99

(6)

New shirt ... GO BILLS ... So this shirt will still allow him to rep the best team ever! ... Bought shirt two weeks ago fits perfect. ... He loves it ... I own multiple Columbia shirts and I love them

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5 KH825
I bought this shirt for my boyfriend because he is n't a fan of jerseys. So this shirt will still allow him to rep the best team ever!

5 Big Tony
Wife bought me this shirt for Christmas and I love it! I own multiple Columbia shirts and I love them all!

5 LynnT1
. Perfect style for summer days and combined with his favorite team made this a great gift

On Sale
Nike Youth Chicago Sky Logo T-Shirt

Nike Youth Chicago Sky Logo T-Shirt

See Price in Cart

WAS: $30.00*

(7)

Very simple, but cool WNBA t- shirt ... My daughter loves the WNBA and represents her fanhood in this comfortable t- shirt ... Nice soft cotton, bright color design I ordered her the size medium and it fits

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5 red__2
Daughter loves it. Fits well. Good quality. Please make more in other sizes.

5 Mall214
Great buy.........................................

5 KRay
My daughter is excited to wear this on the first day of school. Fits true to size and she loves the design.

5 bhac88
My daughter loves the WNBA and represents her fanhood in this comfortable t- shirt

5 Dolphin
Was very happy with my shirt I just wish it was on sale

Obvious Shirts Adult Chicago W Stands For Win T-Shirt

Obvious Shirts Adult Chicago W Stands For Win T-Shirt

$32.99

(1)

The quality is superior and soft and well a few words go a long way. ... Cubbies fan for life! ... Simple and Great Quality ... Bought this as a gift and the recipient loved

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5 Francescax
Bought this as a gift and the recipient loved it. The quality is superior and soft and well a few words go a long way. Cubbies fan for life!

On Sale
Nike Youth Chicago Red Stars Graphic Black T-Shirt

Nike Youth Chicago Red Stars Graphic Black T-Shirt

$21.60

WAS: $36.00*

(7)

Staff were very friendly. ... Nice regular tshirt for our new favorite NWSL team. ... Great shirt and true to size. ... Happy with this product. ... Super cool shirt love the

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5 Lwest444
Great shirt and true to size. My son loves it and Nike lasts.

5 KateFtW
My daughter loved wearing this at a game. Nice size and washed well.

5 Ygana
This shirt has everything Cleveland! It'ss really cool shirt, my son loves it!

5 Bob Juan 27
Nice regular tshirt for our new favorite NWSL team.

5 Chan
Happy with this product. Order pick up online went into the Crofton Dick ’s and easy pick up process. Staff were very friendly.

Columbia Men's Chicago Bears Navy Low Drag Button Down Shirt

Columbia Men's Chicago Bears Navy Low Drag Button Down Shirt

$90.99

(8)

Nice and comfy! ... Its comfortable and fits great. ... Comfortable as well ... Nice design, colors, and fits well. ... Great Columbia PFG short sleeve polo. ... Looked great ... Great fit and nice

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5 Nickylee
Great fit and nice quality. Washes well. I hang to dry.

5 Lynns view
I bought this for my husband and he loves the design and fabric.

5 Papa Henry
Nice design, colors, and fits well. Comfortable as well

5 Blaw
I thought this a month ago and bought another for a gift!

5 Brownswon
Bought for a Brown ’s game. Nice and comfy! Looked great

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Chicago Shirt

On this page...

  • What styles of Chicago shirts are available?
  • What materials are commonly used in Chicago shirts?
  • Are Chicago shirts suitable for all seasons?
  • What occasions are Chicago shirts appropriate for?
  • How do I choose the right size for a Chicago shirt?

Frequently Asked Questions For Chicago Shirt

Chicago shirts come in various styles, including short sleeve, long sleeve, and graphic tees. You can find options featuring iconic Chicago symbols, such as the city flag or sports team logos. This variety allows you to choose a shirt that fits your personal style and the occasion.

Chicago shirts are typically made from comfortable and breathable materials like cotton or cotton blends. These fabrics are ideal for everyday wear, providing a soft feel against the skin. Some shirts may also incorporate moisture-wicking technology for added comfort during active use.

Yes, Chicago shirts can be worn year-round. Short sleeve options are great for warmer weather, while long sleeve shirts provide extra warmth during cooler months. Layering with jackets or hoodies can also enhance comfort during transitional seasons.

Chicago shirts are versatile and can be worn for various occasions, including casual outings, sporting events, or as part of everyday attire. They make a great choice for showing off your city pride or supporting local teams.

To choose the right size for a Chicago shirt, it's important to refer to the sizing chart provided by the retailer. Consider your usual fit preferences, whether you like a more relaxed or fitted style. Trying on different sizes or styles can also help ensure the best fit for your body type.