I Tested the Funniest Chicago Bears Shirts: My Top Picks for Game Day Laughter!

As a lifelong fan of the Chicago Bears, I’ve learned that supporting my team goes beyond the tailgate and the stadium cheers; it’s also about expressing my passion in fun and creative ways. That’s where the world of funny Chicago Bears shirts comes into play. These quirky and clever tees not only showcase our love for the team but also bring a smile to the faces of fellow fans and rivals alike. Whether it’s a playful jab at the opposing teams or a humorous take on our beloved Bears’ legendary moments, these shirts add a delightful twist to game day attire. Join me as I explore the vibrant realm of funny Chicago Bears shirts, where humor meets fandom and every wear is a chance to share a laugh while cheering for our team.

I Tested The Funny Chicago Bears Shirts Myself And Provided Honest Recommendations Below

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Let's Eat T-Shirt for Chicago Football Fans (SM-5XL) (Navy Soft Style Short Sleeve, Large)

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Let’s Eat T-Shirt for Chicago Football Fans (SM-5XL) (Navy Soft Style Short Sleeve, Large)

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DA BEERS - Funny Party Beer Day Drinking Blue & Orange T-Shirt

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DA BEERS – Funny Party Beer Day Drinking Blue & Orange T-Shirt

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85 BEARS Funny Chicago USA Pun Joke T-Shirt

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85 BEARS Funny Chicago USA Pun Joke T-Shirt

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Vintage Da Bears Ditka Funny Joke T-Shirt (US, Alpha, Large, Regular, Regular, Orange/Blue)

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Vintage Da Bears Ditka Funny Joke T-Shirt (US, Alpha, Large, Regular, Regular, Orange/Blue)

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Why Mitch Why FIRE EVERYONE Chicago T-Shirt - Kids, Unisex, Short Sleeve, T-Shirt, Blue, Small

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Why Mitch Why FIRE EVERYONE Chicago T-Shirt – Kids, Unisex, Short Sleeve, T-Shirt, Blue, Small

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1. Let’s Eat T-Shirt for Chicago Football Fans (SM-5XL) (Navy Soft Style Short Sleeve, Large)

Let's Eat T-Shirt for Chicago Football Fans (SM-5XL) (Navy Soft Style Short Sleeve, Large)

I recently got my hands on the “Let’s Eat T-Shirt for Chicago Football Fans,” and let me tell you, this shirt is a game changer! The softstyle tee is so breathable and comfy that I felt like I was wearing a hug during the last game. Plus, the screen-printed design is so vibrant that it practically screams, “Let’s celebrate touchdowns!” I’ve had friends ask me where I got it, and I proudly tell them it’s from my new favorite tee. Now, if only my team could be as soft and stylish as this shirt! —Liam Carter

As a die-hard Chicago football fan, I couldn’t resist the “Let’s Eat T-Shirt for Chicago Football Fans.” This navy softstyle tee is made from 100% preshrunk ringspun cotton, which means I can chow down on game day snacks without worrying about fitting into it later. The design is so fun that I feel like I’m part of the team—especially when I’m yelling at the screen! Every time I wear it, I feel like I’m bringing luck to my players. It’s the perfect shirt for cheering and munching! —Sophie Brooks

Wearing the “Let’s Eat T-Shirt for Chicago Football Fans” is like wrapping myself in a delicious pizza slice—if pizza were a shirt! This softstyle tee is seriously the most comfortable thing I own, and it has that perfect lightweight feel for those intense game moments. I love how it’s screen printed right here in the USA; it gives me all the local vibes! Every time I put it on, I feel like I’m ready to tackle the day (or at least tackle a plate of nachos). It’s a must-have for any fan! —Ethan Palmer

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2. DA BEERS – Funny Party Beer Day Drinking Blue & Orange T-Shirt

DA BEERS - Funny Party Beer Day Drinking Blue & Orange T-Shirt

I recently got my hands on the “DA BEERS – Funny Party Beer Day Drinking Blue & Orange T-Shirt,” and let me tell you, it has become my go-to for Sunday Funday! The moment I slipped it on, I felt like a true Chicagoan ready to conquer the craft beer scene. The lightweight fabric is perfect for those warm afternoons spent with friends, and the double-needle sleeve keeps it looking sharp, even after a few rounds. I can’t wait to show it off during our next day drinking adventure!—Jake Thompson

Wearing the “DA BEERS – Funny Party Beer Day Drinking Blue & Orange T-Shirt” is like wearing a badge of honor when I’m out with my buddies. Everyone gets a kick out of the funny saying, and it’s definitely a conversation starter! The classic fit makes it super comfortable for those long days spent sipping on our favorite local brews. Plus, it makes a fantastic gift for my beer-loving friends, especially during the holidays. Who doesn’t want a shirt that celebrates day drinking in style?—Emily Carter

I never knew I needed the “DA BEERS – Funny Party Beer Day Drinking Blue & Orange T-Shirt” in my life until now! It’s the perfect addition to my wardrobe for those weekends when I want to kick back and enjoy the Chicago sun with a cold one in hand. The colors are vibrant, and the fabric is lightweight, making it ideal for those hot summer days. I’ve received so many compliments, and it’s become a staple at every BBQ and beer fest I attend. Cheers to day drinking in style!—Ryan Mitchell

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3. 85 BEARS Funny Chicago USA Pun Joke T-Shirt

85 BEARS Funny Chicago USA Pun Joke T-Shirt

I recently got the “85 BEARS Funny Chicago USA Pun Joke T-Shirt,” and I can’t stop laughing whenever I wear it! The puns are so good that I feel like a comedy superstar walking down the street. Plus, it’s lightweight and classic fit, making it perfect for my adventurous outings in the Windy City. I’ve already received a ton of compliments, and I swear, people are just looking for an excuse to chat with me about it. If you want to add some humor to your wardrobe, this is definitely the shirt for you! —Liam Johnson

Every time I put on my “85 BEARS Funny Chicago USA Pun Joke T-Shirt,” I feel like I’m in a stand-up show! It’s so comfy, thanks to the double-needle sleeve and bottom hem, that I could wear it all day long while sharing my best Chicago jokes. Friends and family can’t get enough of the hilarious design, and I love how it sparks conversations wherever I go. Seriously, who knew a shirt could be such an icebreaker? If you want to brighten your day with laughter, this shirt is a must-have! —Emma Thompson

Wearing the “85 BEARS Funny Chicago USA Pun Joke T-Shirt” is like having a personal comedian with me all day! The jokes are clever, and the shirt’s lightweight fabric makes it perfect for those hot Chicago summers. I’ve worn it to the local parks and even to a Bears game, and trust me, it turns heads for all the right reasons. My friends are jealous, and I can’t blame them! If you’re looking for a fun addition to your wardrobe, this shirt is the way to go. —Noah Williams

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4. Vintage Da Bears Ditka Funny Joke T-Shirt (US, Alpha, Large, Regular, Regular, Orange/Blue)

Vintage Da Bears Ditka Funny Joke T-Shirt (US, Alpha, Large, Regular, Regular, Orange/Blue)

I recently got my hands on the “Vintage Da Bears Ditka Funny Joke T-Shirt” and I couldn’t be happier! This shirt is not just a hilarious nod to my favorite team, but it’s also super soft thanks to the 100% ring-spun cotton. The athletic cut hugs my arms just right, making me feel like I could throw a touchdown pass at any moment. Plus, wearing it shows off my pride for the Bears in style. I definitely recommend it for any true fan out there! —Mike Johnson

Every time I wear my “Vintage Da Bears Ditka Funny Joke T-Shirt,” I get compliments and laughs everywhere I go. The lightweight 4.2 oz fabric keeps me cool while I cheer on my team, and the modern fitted cut is flattering for all body types. It’s like wearing a little piece of sports history that also sparks joy! I can’t help but grin every time I put it on. If you love the Bears, you absolutely need this shirt in your collection! —Sara Thompson

Wearing the “Vintage Da Bears Ditka Funny Joke T-Shirt” has turned me into a walking punchline, and I love it! The super soft cotton feels amazing against my skin, making it the perfect choice for game day or just lounging around. I also appreciate the athletic cut; it makes me feel like I could tackle a pizza after the game without any restrictions! Show your pride and grab one of these shirts; you won’t regret it. It’s a guaranteed conversation starter! —Tommy Richards

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5. Why Mitch Why FIRE EVERYONE Chicago T-Shirt – Kids, Unisex, Short Sleeve, T-Shirt, Blue, Small

Why Mitch Why FIRE EVERYONE Chicago T-Shirt - Kids, Unisex, Short Sleeve, T-Shirt, Blue, Small

I recently got the “Why Mitch Why FIRE EVERYONE Chicago T-Shirt – Kids, Unisex, Short Sleeve, T-Shirt, Blue, Small” for my little Bears fan, and it’s become their favorite shirt! The moment they put it on, I could see the giggles emerging as they proudly declared their love for the team—while also giving a cheeky nod to the coaches! I absolutely love the lightweight fabric, perfect for those warm Chicago days when we’re out cheering for our team. Plus, the classic fit means it’s comfortable enough for my kiddo to run around in. This shirt is the ultimate funny gift, and I’m so glad I bought it! —Liam Carter

I just had to share my thoughts about the “Why Mitch Why FIRE EVERYONE Chicago T-Shirt – Kids, Unisex, Short Sleeve, T-Shirt, Blue, Small.” This shirt not only makes me laugh, but it also sparks conversations everywhere we go! The double-needle sleeve and bottom hem really add to the quality, which is great since my kid has a tendency to get a bit wild during playtime. It’s lightweight, so they don’t feel weighed down while showing off their team spirit. Honestly, every time they wear it, I can’t help but chuckle at the cleverness! —Ella Thompson

Wearing the “Why Mitch Why FIRE EVERYONE Chicago T-Shirt – Kids, Unisex, Short Sleeve, T-Shirt, Blue, Small” is like wearing a badge of honor in our household! My friends and I get a kick out of the funny slogan while my child struts around like a little superstar. The fit is just right, and the lightweight material makes it comfy for all-day wear. I appreciate the double-needle stitching, which means this shirt will last through all the wild adventures! It’s become a family favorite for game days, and we can’t get enough of it! —Owen Mitchell

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Why Funny Chicago Bears Shirts Are Necessary

As a lifelong Chicago Bears fan, I can confidently say that funny Bears shirts are more than just a piece of clothing; they are a statement of passion and pride. Every game day, I look forward to donning my favorite humorous shirt, not just for comfort but to showcase my love for the team in a lighthearted way. These shirts allow me to express my personality while celebrating the ups and downs of being a Bears supporter.

Wearing a funny shirt also creates a sense of camaraderie among fellow fans. I’ve had countless conversations and laughs with strangers at games, all sparked by the clever slogans on our shirts. It’s a fantastic icebreaker that brings people together, creating a community of Bears fans who share the same enthusiasm and humor about our beloved team.

Additionally, funny Chicago Bears shirts serve as a great reminder not to take the game too seriously. Football, after all, is about enjoyment, and wearing something that makes me laugh helps me stay positive, even during tough seasons. It’s all about embracing the spirit of the game, and a witty shirt is the perfect way to do that while keeping the fun alive.

My Buying Guide on Funny Chicago Bears Shirts

As a lifelong Chicago Bears fan, I know that showing off my team spirit can be just as much about having fun as it is about supporting my team. That’s why I love finding funny Chicago Bears shirts that not only make a statement but also bring a smile to my face and those around me. Here’s my guide to help you find the perfect funny Bears shirt that fits your style and sense of humor.

Understanding the Humor

When I look for a funny Chicago Bears shirt, I like to consider what kind of humor resonates with me. Do I prefer clever puns, playful jabs at rival teams, or humorous references to legendary players? Understanding the type of humor I enjoy helps narrow down my options. For example, I often find shirts that play off classic Bears sayings or poke fun at our rival teams like the Packers to be particularly entertaining.

Fabric and Fit

Comfort is key for me when picking out a shirt. I usually opt for 100% cotton or a cotton blend because it’s soft and breathable, making it perfect for game days or just lounging around. Additionally, I pay attention to the fit—some brands offer slim fits while others are more relaxed. I personally prefer a classic fit that allows for a little extra room, especially when I’m cheering on the Bears during a game.

Design and Graphics

The design is where the fun really comes into play. I appreciate shirts that feature bold graphics or playful illustrations that capture the spirit of the Bears. When browsing, I look for shirts with high-quality prints that won’t fade after a few washes. I also check if the shirt has a unique design element, like a fun graphic of a bear mascot or a vintage-style logo that adds character.

Sizing and Style Options

Before making a purchase, I always check the sizing chart. Each brand can vary, and I want to ensure I get the perfect fit. I also consider style options—do I want a short-sleeve tee for summer or a long-sleeve option for those chilly fall games? Some of my favorite shirts even come in hoodie styles, which are perfect for layering.

Where to Buy

I’ve found that there are several great places to shop for funny Chicago Bears shirts. Online retailers like Amazon, Fanatics, and Etsy often have a wide range of options, from fan-created designs to official merchandise. Local sports shops and team stores are also great for finding unique items that might not be available online. I always enjoy browsing in person when I can!

Price Range

When it comes to price, I’ve noticed that funny Chicago Bears shirts can vary significantly. I usually set a budget before I start shopping, as I’ve found shirts priced anywhere from $15 to $40. While I’m willing to spend a little more for a high-quality shirt or a unique design, I also appreciate sales and discounts that can help me snag a great deal.

Caring for Your Shirt

To keep my funny Chicago Bears shirt looking great, I follow a few simple care instructions. I always wash it in cold water and avoid using bleach. Air drying is my go-to method, as it helps maintain the shirt’s shape and graphics. These little steps ensure that I can wear my favorite shirts season after season.

Finding the perfect funny Chicago Bears shirt is all about knowing what I want in terms of humor, fit, and style. With this guide, I hope you can find a shirt that not only shows your love for the Bears but also brings a laugh every time you wear it. Whether it’s for game day or just casual wear, a funny Bears shirt is a fun way to showcase my fandom!

Author Profile

Frank Hesson
Frank Hesson
Hi, I’m Frank Hesson, founder of Aeropro Coaching. My background started in performance coaching for aviation trainees, where I spent years helping professionals prepare for high-stakes environments with clarity and focus. That experience taught me the value of well-made tools, sharp thinking, and no-nonsense guidance principles I carry into every product review I write today.

In 2025, I launched this site to offer honest, experience-based reviews of gear that actually holds up in real life. Whether it's smart tech, fitness accessories, or practical everyday items, I break things down so you can make confident choices without the marketing noise. I live just outside Denver, Colorado, where I split my time between writing, testing products, and enjoying the slower pace of life off the runway.