Category: Places

I’m Kayla, and I went to Wild ’N Out Live in Chicago at Wintrust Arena. Saturday night. Cool wind off the lake, lines around the block, and folks in Bulls jerseys. I wore my Sox cap, because of course I did. You could feel the buzz. Like pre-game at the UC, but sillier.

(If you’re hunting for the longer, photo-heavy play-by-play—including my shameless beanie regret—you can always skim the full recap right here.)

Getting in: a quick play-by-play

We got there about 6:30. Doors said 7. The line moved, then stalled. Classic. Security was firm but kind. The bag check was smooth. The merch table? Packed. Hoodies were nice but steep. I eyed a beanie, then backed away. Twenty minutes later, I wanted the beanie again. That’s how they get you.

The show started late by about 40 minutes. Not cute. But the DJ kept us warm with Chief Keef and Lil Durk. Once “Love Sosa” hit, the whole bowl woke up. Even the ushers were nodding.

The cast, the bits, the Chicago jabs

Nick Cannon came out in a red jacket and a grin. DJ D-Wrek set the mood. The core crew rolled in—DC Young Fly, Justina Valentine, Chico Bean, Karlous Miller, Conceited. Hitman Holla too. Big cheers for him, even though he’s from St. Louis. Chicago is petty, but we clap for funny.

• Got Props: They tossed out a big orange traffic cone. DC held it up and yelled, “I got ya CTA home!” Then he wore it like a hat. Another prop was a giant foam pizza slice. Justina called it “deep dish, back pain edition.” We groaned, then laughed.

• Pick Up and Kill It (Chicago): Beat drops, and they rhyme in turns. Justina went, “You got Lou Malnati’s, I got extra cheese. But this crust so thick it brought me to my knees.” Corny? Yes. Funny? Also yes. Chico clapped back, “You said thick crust? Girl, you brave. In January wind you’ll still misbehave.” The rhyme wasn’t pretty, but it worked.

• Let Me Holla: They pulled a volunteer from Pilsen. DC slid over and said, “Girl, you like Garrett? Cuz I’m cheesy and sweet and I get stuck in your teeth.” Everyone booed and laughed. He cracked up too.

• Wildstyle: This part always cooks. Conceited pointed at a guy in a zebra jacket and said, “You dressed like a CTA seat and still missed your stop.” The camera cut to the dude. He stood up and bowed. Peak Chicago energy.

Real Chicago flavor, for real

They roasted the snow. They roasted the Bears. They even roasted the Bean. Karlous said, “We got a big shiny bean and nothing to season it with.” A South Side section yelled back, “Put lemon pepper on it!” I’ll admit, I snorted.

During a quick break, the DJ played “Footworkin.” Two teens in our aisle broke out a little footwork battle by the stairs. Security let it rock for a minute. House lights hit them by accident, and the crowd gave a tiny standing O. It felt like a block party for 30 seconds. You know what? That was my favorite moment.
If you want to dig into how live shows like this pump money and energy into neighborhood arts scenes, swing by ARECO for some nerdy-but-cool data.

(Pre-show pro tip: if you’re looking to carb-load and bask under fairy lights first, duck into the Italian Village a few blocks north—red-sauce comfort meets old-school charm.)

(Still amped after the confetti drops? Slide into the Loop for a nightcap—this speakeasy-style narrative maps out a few hidden bars where the party keeps humming behind unmarked doors.)

If the post-show adrenaline has you feeling flirty instead of thirsty, check out this local fling finder where you can scroll through nearby singles who are also looking to keep the night spontaneous—perfect for turning that leftover laugh energy into a real-time connection before heading home.
And hey, if your spontaneous streak has you hopping down to Florida’s Panhandle for a quick sun-soaked getaway, bookmark the bustling classifieds at Backpage Crestview — the up-to-date listings there make it a breeze to see which events, meet-ups, and late-night hangouts are vibing so you can keep the party mood alive even miles from the Chi.

The show flow: tight, but not spotless

The sound was strong—mics were hot, bass thumped. I work events sometimes, so I notice the mix. The highs weren’t harsh. No big feedback squeals. Stage blocking was clean. They used both wings, plus a center runway. The screens helped if you were up top. The camera crew was sharp—tight reaction shots, no awkward dead air.

But not every bit felt fresh. You can tell some lines live in their pockets. I get it. It’s live improv plus a plan. Still, a few jokes felt canned. Also, one roast about a person’s weight went flat. The crowd cooled a little. They moved on fast, but I clocked it.

Crowd work and care

Nick kept checking the crowd, row by row. “Where the West Side at?” Huge scream. “South Side?” Louder. A guy behind me kept yelling “Harold’s!” like it was a prayer. A woman near the tunnel held a sign that said “I babysat for this.” Relatable. They brought two fans on stage for a quick game. One kid from Bronzeville hit a clean one-liner: “Y’all jokes weak like my Wi-Fi.” The whole arena howled. Pay that child.

(Still amped after the confetti drops? Slide into the Loop for a nightcap—this speakeasy-style narrative maps out a few hidden bars where the party keeps humming behind unmarked doors.)

Snacks, seats, and sticker shock

• Drinks were pricey. My friend paid $16 for a beer. I took a sip out of spite.
• Popcorn was fresh, but they ran low on napkins.
• Seats were fine for two hours, but legroom is still legroom. I stretched during the DJ set.
• Bathrooms were clean, line moved quick at halftime. Bless the venue crew.

What I loved

• Fast pace, real crowd work, and Chicago jokes that hit home.
• DC and Chico together. They bounce like cousins at a reunion.
• DJ D-Wrek kept the beats tight. No awkward gaps.
• The camera on audience fits created mini-stories. A grandma in a Bulls jacket stole the show with a smirk that said “Don’t try me.”

What bugged me

• Late start. If you say 7, try 7:20, not almost 8.
• Merch prices. Cute gear, wild tags.
• A few bits felt too rehearsed.
• One mean-spirited roast. Short, but still.

Tips if you’re going

• Eat before. Harold’s, Portillo’s, whatever—just not arena hot dogs.
• CTA is your friend. Green Line to Cermak-McCormick Place worked great.
• Bring a light jacket. Arena AC plus lake breeze equals cold knees.
• Show is PG-13 plus. Not for little kids who repeat everything.

Final call: Should you go?

If you like the show on TV, you’ll have a blast live. It’s louder, looser, and way more Chicago. I smiled a lot. I laughed for real. I left hoarse. That’s the metric, right?

Score: 4.2 out of 5. Cut the late start and shave five bucks off that beanie, and it’s a 4.6.

Quick hits

• Funniest line I heard: “You built like a CTA seat.” Still makes me chuckle.
• Best crowd moment: Footwork by the stairs. Pure city joy.
• Most Chicago thing: Someone eating Garrett Mix like it was medicine.
• Would I go again? Yep. With two friends and a budget for snacks.

I walked out into that cool night air, Sox cap tilted, and thought, yeah. That felt like home—loud, warm, a little messy, and very us.

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.