My Chicago Handshake: A Shot, A Beer, A Wink

I’ve done the Chicago Handshake more times than I can count. And yeah, I’m still a little shocked I keep coming back to it. It’s simple: a shot of Jeppson’s Malört and an Old Style beer. A tiny ritual. A little rough. A lot Chicago.

Here’s the thing—I both hate it and love it. I think that’s the point.

First Sip: It Bites Back

Malört tastes like bitter grapefruit peel. Like you chewed a dandelion stem just to prove a point. It hits the tongue, then the jaw, then it drags on for a while. Old Style is there to help you laugh it off. Cold. Light. Friendly. Like a friend who says, “You okay?” when you make a face. Ironically, the long-loved lager even made a comeback to its original Wisconsin brewery, a move that keeps its Midwest street cred intact.

It’s not fancy. It’s not a craft thing. It’s a handshake. Short, sharp, honest.
If you’re curious about how local rituals like this weave into a city’s food-and-drink DNA, Areco’s overview of regional drinking traditions is a surprisingly fun rabbit hole.

Three Real Nights That Sealed It

  • Wrigleyville, Nisei Lounge, Tuesday after a Cubs loss
    I walked in with my cap low and my hopes lower. Bartender slid the shot and the can with a nod, no small talk. Malört burned clean. Old Style cooled it down. A guy at the end of the bar yelled, “Welcome to therapy.” We all laughed. I wasn’t fixed, but you know what? I felt seen.

  • River West, Richard’s Bar, January snow
    The door stuck. My boots squeaked. I ordered the handshake and fed a crumpled bill into the jukebox. A couple in Carhartt coats clinked their shots with me. The Malört felt warmer in the cold. Bitter then sweet then bitter again. The can felt like a mitt around my hand.

  • Wicker Park, Rainbo Club, rainy Sunday date
    We were both trying to act cool. We ordered two handshakes like we meant it. The Malört hit us at different times—her eyes went wide, mine stayed flat, then I coughed a little. We laughed and talked about bad decisions that turned into good stories. That’s the handshake: not a flex, a shrug. If hidden doors and candlelight are more your scene, you’ll appreciate this first-person spin through Chicago’s speakeasy circuit.

How I Handle The Handshake

People argue about the order. I used to sip the beer first. Now I go:

  1. Deep breath
  2. Malört, all in
  3. Wait two seconds for the “oh no” face
  4. Old Style, two pulls
  5. Exhale; nod like you planned it

It’s not a race. It’s a rhythm.

What It Actually Tastes Like (No Poetry, Just Truth)

  • Malört: bitter citrus, herbal, a little like white pepper and pith. It clings.
  • Old Style: crisp, light corn sweetness, bubbly. It clears the lane.

Put together, it’s a fast handshake—firm grip, quick let go.

The Good And The Not-So-Good

What I like:

  • It’s cheap, usually 5 to 10 bucks for the pair.
  • It makes strangers talk, even a little.
  • It feels local without feeling fake.

And hey, if that Malört-fueled banter turns into real sparks, you can take the straight-talking vibe of the bar onto Uber Horny—a no-nonsense site where Chicagoans set up casual meet-ups just as effortlessly as they order the next round.

What bugs me:

  • Warm Malört is rough. Ask for it cold if they’ll do it.
  • Some bars swap the beer. It’s fine, but Old Style just feels right. (Despite its image, Old Style hasn’t been brewed in the city for years, which might surprise first-timers.)
  • If you hate bitter, like truly hate it, this might not be your hill.

Where I’ve Actually Ordered It

  • Nisei Lounge (Wrigleyville)
  • Richard’s Bar (River West)
  • Rainbo Club (Wicker Park)
  • Cole’s Bar (Logan Square)
  • Green Eye Lounge (Bucktown)
  • Maria’s Packaged Goods & Community Bar (Bridgeport)

Different rooms, same idea: you get the nod, you get the glass, you get the can.

If you ever drift south of the city limits, the small-but-lively village of Frankfort has corner taverns that pour the handshake with just as much grit. And for those nights when you want the drink to come with the possibility of meeting someone new in that area, take a look at Backpage Frankfort—its local classifieds make lining up a post-handshake hangout or late-night bite with like-minded neighbors dead simple.

Tiny Tips So You Don’t Grimace (Much)

  • Don’t sniff the Malört. Just don’t.
  • Keep the beer cold and ready.
  • If it’s your first time, say so. Bartenders in Chicago respect the effort.
  • Eat something salty first. Pretzels help.
  • Be 21+. Pace yourself. Water is not a crime.

Is It A Boilermaker?

Not really. A boilermaker’s usually whiskey and a beer. The Chicago Handshake is its own thing. It’s more like a local password. You don’t need it, but it opens doors.

My Take, Plain And Simple

Do I love Malört? Not exactly. Do I love the handshake? Yes. Because it’s more than the taste. It’s the grin after. It’s the shrug. It’s the way the beer softens the blow and the room gets a touch friendlier.

I’ve had it after long days and weird dates, after wins and losses. And each time, I feel a little more like I’m part of the city. A real handshake does that. This one just happens to come with bubbles. And when the night stretches into sunrise, stepping onto a rooftop with the wind in your face can feel just as honest—here’s my unfiltered take on that, for better and worse.

Would I order it again? I already did. Yesterday. Cubs still lost. I still smiled.