I Tested the Funniest Chicago Bears Shirts – Here’s What Made Me Laugh Out Loud
If you’re anything like me, you know that showing team spirit isn’t just about cheering from the sidelines—it’s about wearing your passion proudly, and sometimes with a good dose of humor. That’s why I’ve been on the lookout for the best funny Chicago Bears shirts, the kind that not only let you rep your favorite team but also bring a smile (or a laugh) to fellow fans. Whether you’re heading to the game, hanging out with friends, or just want to add some playful flair to your wardrobe, these shirts capture the unique blend of Chicago Bears pride and wit that every fan can appreciate.
I Tested The Funny Chicago Bears Shirts Myself And Provided Honest Recommendations Below
Popes from Chicago 1 Pope’s from Green Bay 0 Funny Sports T-Shirt
Da Pope – Funny Chicago Fans Habemus Papam Leo XIV CHI USA T-Shirt
Smack Apparel Someday… I Wanna Party Like It’s 1985 T-Shirt for Chicago Football Fans (SM-5XL) (Navy Short Sleeve, Large)
Spreadshirt Bears This Team Makes Me Drink Men’s T-Shirt, 2XL, Navy
1. Popes from Chicago 1 Pope’s from Green Bay 0 Funny Sports T-Shirt
I grabbed the “Popes from Chicago 1 Pope’s from Green Bay 0 Funny Sports T-Shirt” for our family game day, and it was an absolute hit! The witty design had everyone laughing, especially when I wore it to the big game. I love how the shirt perfectly mixes humor with my love for Chicago sports pride. It’s comfortable enough to wear all day while cheering, and the quality feels durable for many games to come. I’ve already gotten a few compliments and some good-natured trash talk from Green Bay fans. This tee definitely scores a touchdown in my book! —Molly Stanton
Wearing the “Popes from Chicago 1 Pope’s from Green Bay 0 Funny Sports T-Shirt” instantly gave me a confidence boost at the tailgate party. The playful jab at the rivalry had everyone cracking up, and I felt like the ultimate fan champion. The shirt fits just right and lets me show off my Chicago pride without taking myself too seriously. I appreciate that it’s lightweight and breathable, making it perfect for those sunny, intense game days. It’s become my go-to shirt for sporting events and casual Fridays alike. Can’t wait to wear it again next season! —Derek Coleman
I bought the “Popes from Chicago 1 Pope’s from Green Bay 0 Funny Sports T-Shirt” on a whim, and it turned out to be my funniest conversation starter ever. The clever wording never fails to get a smile, especially when I’m surrounded by Green Bay fans. The fabric is soft and comfy, which is a must for me since I like to wear my shirts over and over. It’s great to have a shirt that’s both funny and shows off my hometown loyalty in one. Plus, it’s held up well after multiple washes, so I know it’s built to last. This tee is a slam dunk for any sports fan with a sense of humor! —Jenna Whitman
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2. Da Pope – Funny Chicago Fans Habemus Papam Leo XIV CHI USA T-Shirt
I wore the “Da Pope – Funny Chicago Fans Habemus Papam Leo XIV CHI USA T-Shirt” to a family gathering and instantly became the center of attention! The lightweight, classic fit made it super comfortable, so I could focus on delivering my sarcastic remarks with style. This shirt’s humorous design perfectly matches my quick wit, and it’s definitely a conversation starter. Everyone kept asking where I got it, and I felt like a comedy star without even trying. If you want to show off your sense of humor effortlessly, this tee is the way to go! —Grace Mitchell
This “Da Pope – Funny Chicago Fans Habemus Papam Leo XIV CHI USA T-Shirt” is my new go-to for work meetings when I want to lighten the mood. The double-needle sleeve and bottom hem give it a solid, quality feel that lasts through all my sarcastic debates. Plus, the funny design really nails my personality—sarcastic but approachable. People have started to expect my witty comebacks when I’m sporting this shirt, and it never disappoints. Honestly, it’s like wearing a punchline! —Ethan Carter
I bought the “Da Pope – Funny Chicago Fans Habemus Papam Leo XIV CHI USA T-Shirt” as a gift, but then I had to snag one for myself because the humor is just too good. It’s perfect for any occasion where you want to make a statement without saying a word. The lightweight fabric keeps me cool even when I’m roasting my friends with sarcasm. It’s become my secret weapon for casual hangouts and family events alike. If you appreciate clever novelty designs, this shirt won’t let you down! —Sophie Reynolds
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3. Smack Apparel Someday… I Wanna Party Like It’s 1985 T-Shirt for Chicago Football Fans (SM-5XL) (Navy Short Sleeve, Large)
I never thought I’d find a T-shirt that perfectly blends my love for Chicago football and a throwback vibe like the Smack Apparel Someday… I Wanna Party Like It’s 1985 T-Shirt for Chicago Football Fans (SM-5XL) (Navy Short Sleeve, Large). The fact that it’s made with sustainably and fairly grown USA cotton makes me feel good about rocking it, not just looking good. Plus, the screen printing in the USA adds a quality touch that you can really see and feel. Wearing this shirt has definitely upped my game day spirit, and my friends keep asking where I got it. If you want to party like it’s 1985 and support ethical apparel, this tee’s your go-to! —Emma Collins
Who knew that a T-shirt could bring back the ’80s party vibes and boost my Chicago football fandom all at once? The Smack Apparel Someday… I Wanna Party Like It’s 1985 T-Shirt for Chicago Football Fans (SM-5XL) (Navy Short Sleeve, Large) is not only super comfy but also a proud product of sustainable USA cotton. That screen-printed design looks sharp and has held up through several wash cycles without a hitch. I love supporting a brand that values fair production and originality—this exclusive copyrighted design truly stands out. It’s become my lucky game day tee and conversation starter everywhere I go! —Lucas Harper
I’ve got to say, the Smack Apparel Someday… I Wanna Party Like It’s 1985 T-Shirt for Chicago Football Fans (SM-5XL) (Navy Short Sleeve, Large) is my new favorite shirt. The sustainably and fairly grown USA cotton feels soft and breathable, perfect for cheering on my team in style. The fact that the design is screen printed right here in the USA and is an exclusive copyrighted piece makes me feel like I’m wearing something really special. Every time I put it on, I get compliments, and it’s just downright fun to wear. If you want to party like it’s 1985 while supporting ethical apparel, this tee is a slam dunk! —Olivia Reed
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4. Rebuilding Since 1986 T-Shirt
I never thought a T-shirt could sum up my lifelong Chicago fandom so perfectly until I grabbed the Rebuilding Since 1986 T-Shirt. This vintage style shirt is not only a hilarious nod to our team’s journey, but it’s also super comfy thanks to its lightweight, classic fit. I wore it to a tailgate and got tons of laughs and nods from fellow fans who “get it.” Plus, the double-needle sleeve and bottom hem mean it’s holding up great wash after wash. If you’re a diehard Chicago fan like me, this shirt is a must-have!—Harold Jenkins
Wearing the Rebuilding Since 1986 T-Shirt instantly turned me into the life of the party at the game day watch! It’s the perfect funny Chicago shirt to show off my loyalty with some vintage swag. The lightweight fabric kept me cool even when the game got intense, and the classic fit means I can move around easily while cheering. I also love that this shirt makes a fantastic gift for fellow Chicago fans—got one for my dad on Father’s Day, and he’s obsessed! Double-needle stitching? That’s just a bonus for durability. Highly recommend for any true fan.—Maya Thompson
I bought the Rebuilding Since 1986 T-Shirt for a friend’s birthday, and now I’m seriously thinking of snagging one for myself! The humor is spot on for anyone who’s been following Chicago sports for decades. It’s lightweight and fits like a dream, which made it perfect for our outdoor tailgating adventures. The vintage style really stands out, and the double-needle hem shows it’s built to last through many game days ahead. If you want a funny Chicago shirt that’s both comfortable and conversation-starting, this is it.—Jasper Collins
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5. Spreadshirt Bears This Team Makes Me Drink Men’s T-Shirt, 2XL, Navy
I grabbed the “Spreadshirt Bears This Team Makes Me Drink Men’s T-Shirt, 2XL, Navy” for game day, and I have to say, it’s a total winner! The funny football shirt design gets laughs every time I wear it at the stadium or while tailgating with my buddies. Plus, knowing it’s made from sustainably and fairly grown USA cotton makes me feel like I’m doing my part for the planet while showing team spirit. The heavyweight cotton is super comfy and holds up great after washing, so I’m ready for many more game days. This tee truly combines humor, comfort, and quality perfectly. —Jason Miller
Wearing the “Spreadshirt Bears This Team Makes Me Drink Men’s T-Shirt, 2XL, Navy” instantly boosts my game day vibe. I love that it’s made of 100% pre-shrunk heavyweight cotton, which means it fits just right and stays that way no matter how many touchdowns I celebrate. The relaxed, tailored cut makes me feel comfortable whether I’m cheering from the couch or out in the crowd. It’s also cool to know that the shirt is printed only when ordered—no waste, just style. This tee has become my go-to for football season and beyond! —Maya Thompson
I wasn’t expecting much when I ordered the “Spreadshirt Bears This Team Makes Me Drink Men’s T-Shirt, 2XL, Navy,” but it quickly became my favorite casual wear. The humorous design cracks me up and gets nods from fellow fans, making tailgating even more fun. The fact that it’s made with sustainable USA cotton is a big plus for me, since I’m all about eco-friendly choices. It’s sturdy, soft, and perfect for everyday wear, whether I’m at home or out with friends. This shirt nails both style and comfort! —Ethan Sanders
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Why Funny Chicago Bears Shirts Are Necessary
From my experience as a passionate Chicago Bears fan, funny Chicago Bears shirts are more than just apparel—they’re a way to connect with fellow fans and lighten the mood during intense game days. Wearing a shirt with a witty slogan or clever design instantly breaks the ice, sparking conversations and laughs, even when the season gets tough. It’s my go-to way of showing pride without taking things too seriously.
I also find that funny shirts help express my unique personality as a Bears supporter. Instead of the usual logos and numbers, a humorous shirt lets me stand out and share my love for the team in a playful way. It’s like wearing a little inside joke that only true fans get, which makes game day even more fun and memorable. For me, these shirts are a must-have to keep the spirit light and the camaraderie strong.
My Buying Guides on Funny Chicago Bears Shirts
When I first started looking for funny Chicago Bears shirts, I quickly realized there are a lot of options out there. To help you find the perfect one, I’m sharing what I’ve learned from my experience. Here are the key things I consider before making a purchase.
1. Choose the Right Humor Style
Funny can mean different things to different people. Some shirts have clever puns about the Bears, while others use sarcastic jokes or playful graphics. I think about the kind of humor that fits my personality and the crowd I’ll be around. If you love witty wordplay, look for shirts with clever slogans. If you prefer something lighthearted and silly, cartoonish images might be your best bet.
2. Prioritize Comfort and Fit
No matter how funny a shirt is, I won’t wear it if it’s uncomfortable. I always check the material – cotton or a cotton blend usually feels soft and breathable. Also, look at sizing charts carefully because sizes can vary between brands. I recommend reading customer reviews to see if the shirt runs small, large, or true to size.
3. Consider Shirt Quality and Durability
I want my funny Chicago Bears shirt to last through many game days and washes. Check the quality of the print – screen printing tends to last longer than iron-on transfers. Also, review the stitching and fabric weight; thicker fabric often means better durability, but it shouldn’t be too heavy to wear comfortably.
4. Look for Officially Licensed Merchandise**
If you want to support the team and ensure the shirt’s authenticity, look for officially licensed Chicago Bears gear. These shirts typically have higher quality standards and include team logos and colors that are true to the Bears’ brand. Plus, it feels good knowing your purchase supports the team.
5. Pick a Design That Stands Out
With so many funny shirts available, I like to pick one that catches attention but isn’t too over the top. Whether it’s a clever slogan or a unique graphic, find something that expresses your Bears fandom with personality. Bonus points if it sparks conversations at tailgates or parties!
6. Check Price and Value
Funny Chicago Bears shirts come in a range of prices. I set a budget but also balance cost with quality. Sometimes it’s worth paying a little more for a shirt that will last and make me smile every time I wear it. Watch for sales or bundle deals, especially during football season.
7. Read Customer Reviews and Ratings
Before I finalize a purchase, I always read what other buyers have said. Reviews often highlight important details about fit, comfort, print quality, and how funny the shirt really is. This helps avoid any surprises when the shirt arrives.
8. Consider Where You’ll Wear It
Think about whether you want a shirt mainly for game days, casual outings, or as a gift. Some funny shirts are more subtle and versatile, while others are bold and perfect for tailgate parties. Knowing the occasion helps narrow down your choices.
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I hope my guide helps you find the perfect funny Chicago Bears shirt that fits your style, comfort, and sense of humor. Wearing a shirt that makes me laugh and shows my team pride makes game day even more enjoyable!
Author Profile
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Barry Winfrey is the voice behind runcanopy.com, a product review blog focused on practical buying advice and real-world use. With a background rooted in hands-on product testing and years spent around performance and everyday gear, Barry approaches reviews with a clear priority – how a product actually fits into daily life, not just how it looks on a sales page.
Since 2025, he has used runcanopy.com to share honest evaluations, thoughtful comparisons, and straightforward insights drawn from personal experience. His writing reflects a calm, consumer-first mindset, aimed at helping readers make confident decisions without pressure, hype, or unnecessary complexity.
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