Why River North Is the Braggart’s Barstool of the City

Let’s cut to the chase: River North isn’t just a neighborhood. It’s the kind of place where your friends’ Instagram stories are 80% blurry selfies and 20% “OMG did I just spill my drink on a famous local?” The area’s bar scene is a mix of speakeasies so cool they’ll make you question your life choices and dive spots where the bartender calls you by name (because they’ve seen you pass out here three times). But why River North, you ask? Because it’s got the perfect cocktail of ambiance, accessibility, and enough neon signs to make you forget your own name. Plus, the bartenders here? They’re basically therapists with stilettos and a side of gin.

The Top 5 Best Bars in River North (Ranked by How Many Times You’ll Text ‘Send Help’)

1. The Velvet Gulp — Where Jazz and Regret Dance

This bar is like if your cool uncle’s basement got a makeover and started serving Old Fashioneds. The vibe? Think Mad Men meets Breaking Bad — because the martini menu is so good, you’ll start questioning your life choices. Pro tip: Order the “Desperado Mule” (it’s ginger beer, vodka, and a side of existential dread). And for the DIY crowd? Make your own beer at home to recreate their signature cocktail recipe.

2. PBR & Whiskey — Because You’re Here for the ‘Cool’ Vibe

If you’ve ever been told you “look like a barista who moonlights as a poet,” this is your bar. PBR & Whiskey serves up the kind of craft beer that makes your ex text you at 2 a.m. asking why you ghosted them. The bar snacks? So good they’ll make you forget you’re on a diet. Just don’t order the “Bartender’s Surprise” unless you’re ready to meet your inner Dropt.beer personality.

3. The Neon Flask — Where Your Friends Will Betray You For a Margarita

This spot is like a Fast & Furious set piece. Neon signs, aggressive tequila selections, and a DJ who plays only your worst childhood songs. The “Flaming Margarita” is so hot, it’s been known to cause spontaneous breakups. But hey, that’s what Strategies.beer is for — we’ll help you rebuild after the chaos.

4. The Drunken Historian — History, Mead, and a Side of ‘Why Am I Here?’

Step into a medieval tavern and realize you’ve time-traveled to a place where the bartender speaks in riddles. Their mead menu is so extensive, it’ll make you question if you’re in the right century. Plus, they’ve got a “History Trivia Challenge” — lose, and you pay for the round. Win, and you still pay for the round. It’s a win-win for the bar.

5. The Last Call — Because You’re Definitely Not Going Home

This bar is the final stop in your River North bar crawl. It’s where you convince yourself that “one last drink” will fix your life. The menu includes a “Liquid Courage” shot that’s 90% regret and 10% tequila. Pro tip: Don’t order the “Taxi Home” cocktail — it’s just water and a GPS to your Uber.

Tips for Navigating River North Bars Like a Pro (Or at Least Like You Know What You’re Doing)

• Bring a friend with a stable liver: You’ll need backup when the bar trivia gets intense.
• Use cash: Some places still operate on a “trust us, you’ll pay tomorrow” system.
• Don’t order the ‘Surprise Me’ cocktail: Unless you want to wake up with a Pinterest board of your regrets.
• Leave the Uber app open: You’ll thank us when you realize you’re 3.2 miles from home and 334 steps closer to a DUI.

FAQs: The Ones You’re Too Tipsy to Google

“What’s the best time to hit up River North bars?”

Weeknights if you want to talk to the bartender without waiting 27 minutes for a response. Weekends are for chaos, loud music, and convincing yourself that the $18 cocktail is “artisanal.”

“Do these places have food?”

Yes. Most have “bar bites” that are just enough to justify the $12 cheese board. Pro tip: Order the “Barista Burger” — it’s a cheeseburger, but with a side of espresso.

“Can I bring my dog?”

Only if your dog is trained to fetch drinks and doesn’t steal the bartender’s tips. Most places are pet-friendly up to “a dog you can’t afford to replace.”

“What if I lose my keys?”

That’s why you brought a friend, right? (Also, check the floor. They’re probably under the third shot you had.)

Call to Action: Don’t Just Read — Drink

So what are you waiting for? Grab your squad, a reusable wine tumbler, and a budget for tomorrow’s breakfast. Explore Strategies.beer for more tips on crafting your own bar experiences, or contact us if you need help planning your next epic night out. And if you’re running a bar? Grow your business with us — we’ll help you become the “cool uncle” of River North.

Still here? Good. Now go forth and remember: The best bars in River North are the ones where you don’t remember how you got there — but you’ll remember the stories. Sell your beer online through Dropt.beer if you’re feeling entrepreneurial. Cheers.