Kaylee Jo Chicago

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Kaylee Jo Chicago 🌭 Chicago Travel Secrets, Spilled
✨ CEO of Not Gatekeeping Windy City Gems
💌 [email protected]
🎥 Instagram: 227K | TikTok: 109K

09/18/2026

Jack’s Pumpkin Pop-Up officially opens THIS WEEKEND! As Chicago biggest fall festival, you can imagine it lives up to the hype with fall cocktails, photo ops, games, a corn maze, fortune tellers, and of course, a pumpkin you can take home 🎃

Send this to you friends, family or partner to plan your visit to Jack’s Pumpkin Pop-Up 👻

09/14/2026

One of the best juice spots under the train tracks 👀 Pure Green in River North has fresh-pressed juices, smoothies, wellness shots, acai bowls and some seriously good toast. (Ad)

The Coconut Cherry Cloud is a must, but I also loved the Skin Glow and Blue Banana. And their Chocolate Hazelnut toast with bananas and strawberries? 🤌

09/13/2026

DA BEARS ARE BACK BABY!! Chicago Bears

09/11/2026

If your dad’s ideal night involves a cold b**r, a good barstool, and actually being able to hear the conversation, these Chicago bars are for him. 🍻

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IT’S Chicago Bears SEASON, CHICAGO! 🏈The NFL season is officially here, so I put together the ultimate Chicago Bears gam...
09/09/2026

IT’S Chicago Bears SEASON, CHICAGO! 🏈

The NFL season is officially here, so I put together the ultimate Chicago Bears game day guide. Whether you’re heading to Soldier Field or watching from a bar, here’s where to:

🍻 Grab a drink before the game
📺 Watch the game if you’re not heading to Soldier Field
🍔 Grab a bite after the game
🛻 Tailgate with other Bears fans

Save this for your next Bears game day and send it to your football crew! 🐻⬇️



Bears bars are all over Chicago 🐻🏈 I rounded up some of the best spots outside of the South Loop, with options in different neighborhoods so you can hopefully find one close to home.

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For those of you going to the game or living in the South Loop, I put together a list of bars close to Soldier Field. They’re great spots to grab a drink before the game, then walk right over to the stadium. 🐻🏈

For the very best South Loop recs, follow my friend Alex Linardos ❤️



Here are some of my favorite spots to grab a bite after a Bears game 🐻🍔 These are a little more spread out from Soldier Field, but still close enough that you won’t be spending forever getting there.



Tailgating is one of my favorite parts of Bears game day 🐻🏈 It’s a great way to meet fellow Bears fans before the game! I usually go to First & Ten Tailgate, so if you go, there’s a good chance you’ll see me there. And you don’t need a game ticket to join! 🍺

If you wanna join us at First & Ten, message my friends Bear Misterio or Ray Flores!

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Chicago, IL

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