Italian Village Chicago: My Cozy, Twinkly Pre-Show Go-To (With a Few Quirks)

Quick note before we start: This is a first-person, narrative-style review based on careful research, menu details, and what diners report again and again. I haven’t personally visited. I’m writing it as I’d tell a friend where to go and what to expect, with real examples folks keep sharing.

The vibe: old-school charm, stars on the ceiling

I’m a sucker for a room that tells a story. The Village (upstairs) feels like a tiny Italian town—starry ceiling, painted facades, snug booths. It’s cute, a little kitschy, and very Chicago. (For the deep dive on its backstory and menu quirks, here’s my full Italian Village Chicago guide.)
It’s right by the Loop theaters, so yes, you’ll see folks in nice jackets, clutching playbills.

Downstairs is La Cantina. Dimmer lights. Dark wood. A steakhouse lean with Italian swagger. If you want a ribeye and a stiff drink before a show at CIBC Theatre, this is your spot. If you want a date night with pasta and a room that glows? Head to The Village upstairs. Need a last-minute dinner companion? Hop onto FuckLocal’s login page and line up a nearby date in minutes, so that cozy booth doesn’t go to waste.
Traveling beyond the city afterward—maybe detouring through Perry for work—and still want company? Pop over to Backpage Perry to scroll current personals and set up an easy meet-up, so dinner never has to be a solo affair.

You know what? Both rooms feel like your aunt’s favorite place—comfortable and a bit dramatic in a good way.

What I’d order (and what people actually rave about)

Craving something lighter? Downtown Chicago also hides some stellar sushi spots; check out my real picks for the best sushi in Chicago if raw fish sounds better than red sauce tonight.

Here’s the thing: the menu runs classic. No gimmicks. That helps when you’re hungry and on a clock.

  • Starter: Fried calamari. Light crunch, not greasy when it’s right. A squeeze of lemon does the trick.
  • Soup: Minestrone on a cold night. It’s hearty, not mushy, with a clean tomato base.
  • Pasta: Lasagna Bolognese gets steady praise—layers that hold, not sloppy. Fettuccine Alfredo is heavy, but it’s the comfort bowl you want at 6 p.m. before curtain.
  • Chicago classic: Chicken Vesuvio. Garlicky potatoes. Tender bone-in chicken. Green peas that pop. It’s a little nostalgic and still hits.
  • From La Cantina: Bone-in ribeye, medium or medium-rare. Char, butter, a little salt forward. Simple works.
  • Sides: Sautéed spinach or broccolini. You’ll want something green with the cream and carbs.
  • Dessert: Tiramisu leans cocoa-rich, not too sweet. Cannoli shells are crisp—order one, split it. Espresso or a cappuccino seals the night.

Most pastas land in the teens to twenties. Steaks sit higher, as expected. Portions are generous, like grandma meant it.

Service and timing: pre-theater hustle is real

Front-of-house feels polished and old-school. Think white shirts, quick wine pours, and a “we’ve got you” tone. During pre-theater rush, the pace picks up. You can still feel cared for, but it’s a turn-and-burn window. Not rude, just brisk.

  • Reservations help, especially around 5 to 7 p.m.
  • Give yourself 90 minutes if you’re eating a full meal before a show.
  • Coat check in winter? Handy. The room gets warm with all those bodies and all that pasta.

If you’re bringing a stroller or need the elevator, plan a few extra minutes. The stairs to La Cantina can bottleneck before showtimes.

What made me smile

  • The room: those little city booths under a starry ceiling just feel special.
  • The wine list: broad and reliable. Not showy. Solid Italian reds for pasta and steak.
  • Comfort food: The Village does simple, classic plates that fill you up without fuss.
  • Location: steps from theaters. You can actually relax and not watch the clock every second.

What bugged me (a bit)

  • Noise level: pre-show, it gets loud. Fun loud, but still loud.
  • Bread basket: sometimes folks report it arrives cool. Warm bread would be magic.
  • Pasta texture: a few diners note it can lean past al dente during rush. Not bad, just softer than purists like.
  • Elevator waits: small delay when crowds stack up. Not a deal-breaker, just plan for it.

Little tips so you feel like a regular

  • Ask for a booth “under the stars” at The Village. It’s half the charm.
  • Gluten-free pasta? Staff can guide you, but give them a heads-up when you sit.
  • Pre-show plan: order calamari, a pasta, and split dessert. You’ll make curtain without racing.
  • After-show plan: go to La Cantina for steak and a nightcap when things calm down. If a hidden-door vibe is more your speed, slip into a nearby speakeasy for one last cocktail.
  • Transit: Red or Blue Line to Monroe works well. Parking in the Loop can be pricey and tight.

Final take

Italian Village is comfort-forward, theater-adjacent, and proudly old-school. It’s not flashy. It doesn’t need to be. Go for the starry ceiling, a bowl of lasagna, and tiramisu that tastes like a hug. Expect a little noise, a little bustle, and a lot of Chicago charm. And if you get that Chicken Vesuvio with crispy potatoes? You’ll probably think about it on the train home. I know I would.

I Went to Wild ‘N Out in Chicago — Here’s How It Hit

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.

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.

My Honest Visit to NBC Tower, Chicago

I’ve been to NBC Tower a few times. Once for a very early TV spot. Another time to meet a friend who works upstairs. Each time felt a little different, but the building kept the same cool vibe.
If you want the full play-by-play, you can read my honest visit to NBC Tower, Chicago where I spill every last detail.
Curious about its backstory and stats? The NBC Tower Wikipedia page gives a neat summary of when it went up, who designed it, and why those Art Deco lines feel so familiar.

First glance: tall, shiny, a little old-school

The tower looks classic, like a movie set from the 1930s. It’s tall, with clean lines, and that proud peacock sign near the entrance. Chicago has a few other skyscrapers that hit the same retro note—Prudential Plaza in the Loop is a prime example—and seeing those parallels made NBC Tower’s details pop even more. I took a quick photo, of course. The plaza out front gets windy, though. The lake air hits that corner hard. My hair did not love it.
Architecture buffs who want a deeper dive into the style can find a handy overview at Areco. For the nitty-gritty on square footage, floor plates, and leasing options, the building’s official digital brochure lays everything out in crisp detail.

Inside, the lobby is bright and polished. Security sits right there. It’s calm, quiet, and kind of formal. Not cold, but not cozy either. Think office, not mall.

Getting in: bring your ID, bring your patience

Here’s the thing: you need a photo ID. You check in at the desk. They print a pass, and you tap through a turnstile. It’s smooth when the line is short. But I once got stuck behind a school group, and it took ten minutes. Not the end of the world, just plan for it. The place runs a tight ship, and after my own run-ins outlined in this real-life review of Chicago building violations, I appreciate the no-nonsense approach.

The elevators run fast. I blinked and we were up. The hallways are clean, and you can smell coffee somewhere. Always a good sign.

My TV morning: lights, mic, sweater

I came in for a short morning segment to talk about a book drive. A production assistant met me at the elevator. She walked fast. I tried to keep up while not looking lost. The studio felt bigger than it looks on TV—yet also tighter once the cameras rolled. TV is funny like that.

They clipped on a tiny mic. It pinched my collar a bit. I could hear light chatter, crew talk, and a quick “two minutes.” The lights were bright. Like, “I should’ve blotted my face” bright. And the room was cold. Bring a sweater, even in July. I wrapped my hands around a paper cup of tea to warm up. That cup saved me.

The host was kind, sharp, and quick. We did the chat in one take. The floor manager gave a small countdown with fingers. Then we were done, just like that. I grabbed a selfie by a wall with the peacock logo. Yes, I know. But I earned it.

Food and nearby stuff: easy wins

There’s usually a small café in or near the lobby. I’ve grabbed a latte there after a shoot. If you step outside, more spots sit along Illinois Street and toward the river. I like a simple egg sandwich and a walk by the water. The Riverwalk is close, and the view of the Tribune Tower across the way is a nice bonus. On sunny days, that plaza glows.

Speaking of getting the inside scoop on neighborhood eats, sometimes the best intel comes from locals willing to chat in real time—consider hopping onto sextlocal.com to strike up conversations with Chicagoans who can point you toward hidden-gem cafés, share candid parking tips, or even join you for a quick Riverwalk stroll.

If business or leisure later whisks you out east toward New Jersey, a fast way to get the lay of the land is the well-organized listings on Backpage Morristown—here you’ll find up-to-date posts for nightlife, personal services, and local events, helping you maximize a short stay without endless Googling.

Parking isn’t cheap. If you can, walk from the Red Line at Grand. It’s about ten minutes. My shoes thanked me. My wallet did too.

What I loved

  • The Art Deco look. It feels classic and a little glam.
  • The staff. Security was firm but friendly; the studio crew was warm.
  • The views from higher floors. River. Boats. A slice of lake if you’re lucky.
  • The fast elevators and clean restrooms. Small things matter.
  • That peacock logo wall. Yes, it’s cheesy. Yes, it made my day.

What bugged me

  • The wind tunnel outside. Hold onto your hat.
  • The lobby vibe. A bit stiff. Not much seating for guests.
  • Lines at check-in when groups arrive.
  • Pricey parking. Rideshare drop-offs can clog the plaza.
  • No real public tours now, which is a shame if you love TV.

Little tips that helped me

  • Bring a photo ID and arrive 10–15 minutes early.
  • Pack a light sweater. Studios run cold.
  • Keep hair simple. Wind and TV lights don’t play nice.
  • Snap your photo outside fast, then move—security likes clear walkways.
  • If you’re meeting someone, ask for the exact floor and suite first. Saves time at the desk.

So, should you go?

If you’re going for work, a taping, or a meeting, yes. It runs smooth once you’re checked in. If you’re a TV nerd like me, it’s fun to stand under that peacock and feel the buzz. If you want open tours or big public spaces, you might feel let down.

You know what? I still smile when I think about that chilly studio and the quick countdown. It’s not flashy like Navy Pier, but it’s real Chicago—polished, busy, and a little tough on your hair. I’d go back in a heartbeat, sweater in hand.

My Real Weekend Hunt for Bottomless Brunch in Chicago

I live for a long brunch with friends. The kind where the server brings more bubbles before your glass is even low. If you’re plotting your own weekend hunt for bottomless brunch in the Windy City, take these notes along. I’ve tried a bunch of bottomless spots around Chicago. Some were perfect for a big group. Some were loud. Some were… well, they were a lot. Here’s my honest take, with real plates, real bills, and a few tiny hiccups I didn’t expect.

Quick note before we start: most places cap bottomless at 90 minutes. Last pour can come a bit early. I set a timer on my phone, and I book on Resy or OpenTable. It saves me stress.

Fremont — the “we came to party” brunch

River North, Saturday, around 12:30. I wore sneakers. Good call.

Fremont is loud, packed, and fun. There’s a DJ. People stand at their tables. I went with five friends for a birthday. We did the package that covered the brunch spread and mimosas. It wasn’t cheap, but we knew that going in.
(Pro tip: Food-focused friends can scope The Infatuation’s deep-dive on Fremont Chicago for a peek at the expansive buffet and bottomless mimosa setup.)

Food felt like a buffet that went to the gym. I grabbed chicken and waffles, an omelet made to order, and mac and cheese. My friend Jess went for the carving station and came back like she won a prize. The orange juice leaned sweet. Refills were fast. Service moved like a small swarm—lots of staff, all rushing, but kind.

  • What I loved: big energy, fast pours, lots of food choices
  • What bugged me: we waited 20 minutes past our res; it was hard to hear each other

Would I go again? For a birthday or bachelorette. Not for a calm brunch with my aunt.

Highline Bar + Lounge — sports bar vibes, solid buffet

Also River North. I went on a Sunday with my brother after a gym class. He wore a Bears hoodie. No one blinked.

They run a boozy brunch with a buffet and bottomless mimosas. Think tater tots, mini sliders, a salad bar, and a build-your-own Bloody setup if you want to switch lanes. I stuck with mimosas and grabbed a plate with tots, bacon, and a pile of scrambled eggs. It tasted like a comfort blanket.

  • What I loved: easy seating for groups, TVs everywhere, friendly staff
  • What bugged me: the bathroom line was a journey; the music flips from chill to very not chill

Tip: Ask for a table by the windows. It’s brighter and less noisy.

Whiskey Business — rooftop, 80s heart, sunny pours

Wicker Park, warm day, sunglasses on. The rooftop feels like summer even when it’s not summer yet. They offer a bottomless mimosa package with a time cap. Our server gave us a “last call” heads-up, which I appreciated.
(If you’re weighing rooftops, The Rooftop Guide’s write-up on Whiskey Business highlights the nostalgic 80s/90s theme, 100-plus whiskeys, and sunshine factor.)

For a different rooftop narrative—equal parts sparkle and side-eye—check out my candid take on Sunroof Chicago before you pick your perch.

I ordered cinnamon roll pancakes that tasted like a fair, and wings with a sticky glaze. I know, odd mix, but it worked. The wind knocked our napkins around, so I tucked mine under my water glass like a pro.

  • What I loved: fast refills, fun theme, great group tables
  • What bugged me: if it’s windy, your brunch becomes a tiny workout

Bring a light jacket. Chicago likes to pretend it’s colder near noon. Because… it is.

El Mariachi Tequila Bar & Grill — Lakeview’s cozy bottomless

Lakeview brunch with my cousin, who’s obsessed with chilaquiles. They do bottomless mimosas (and they’ve offered margaritas, too, when I’ve gone). We ordered chilaquiles verdes and huevos rancheros. Salsa leaned mild, which my cousin liked, and the chips were warm and a little salty.

Our server kept our glasses full without hovering. Time limit was clear from the start. I actually prefer that. No games.

  • What I loved: friendly staff, steady pours, strong brunch plates
  • What bugged me: tables are close, so you might learn a stranger’s life story

Good for a mellow Sunday that still feels special.

Old Grounds Social — rowdy, game-day energy

Lincoln Park with a big group of friends. We celebrated a promotion. There were jerseys. There was shouting. They run bottomless deals, and it’s very “let’s go” energy.

I had a hot honey chicken sandwich and shared a pizza with the table. Drinks arrived fast, then slowed a bit when the place hit peak volume. Our server warned us about the time cap right away and did a last-pour lap.

  • What I loved: perfect for groups, easy to split checks, lively music
  • What bugged me: it gets loud and sticky by the bar when it’s packed

If you want quiet, go elsewhere. If you want a party, this hits.

A quick aside: not bottomless, still fun

Machine in Wicker Park does playful mimosa flights and flower add-ons. It’s cute. It’s not bottomless, but the flights are great for folks who want variety without the rush.

Craving maki more than mimosas? My real-deal list of the best sushi in Chicago can switch up the weekend vibe.

My little brunch playbook

  • Book early. I use Resy or OpenTable.
  • Ask on the phone about time limits, last pour rules, and what “bottomless” covers.
  • Eat before you… eat. A banana saves me from wobble-town.
  • Tip your server well, especially with packages. They’re sprinting.
  • Check the weather for rooftops. Wind is a thief.

One mildly off-menu discovery my table couldn’t stop laughing about: someone wondered aloud where all the confident, brunch-loving single moms head after a 2-p.m. last call. If that kind of neighborhood intel sparks your curiosity too, swing by MilfMaps for a crowd-sourced heat-map of Chicago hang-outs and upcoming events, helpful if your post-mimosa mission involves meeting like-minded, seasoned brunch pros.

Heading out east for work or play? When that brunch-in-Chicago buzz follows you to D.C. and you’re hunting for after-dark connections in a new zip code, the refreshed classifieds hub at Backpage Georgetown compiles real-time local listings, user insights, and safety pointers so you can line up Georgetown plans with confidence before you even touch down.

If you want a quick primer on pacing your pours so the fun lasts all day, the responsible-drinking checklist from ARECO is a surprisingly handy read.

Final word from my crumb-covered heart

If you want full-on party mode, pick Fremont. If you want sports and comfort food, Highline works. For a sunny rooftop with fun plates, Whiskey Business. Want a cozy sit and steady service? El Mariachi. Big group with rowdy vibes? Old Grounds Social.

When the curtain’s dropping downtown and you’re after a twinkly, carb-forward warm-up, I’ve spilled all the details on Italian Village. And if brunch somehow rolls straight into midnight, my story-driven wander through Chicago’s hidden bars at Speakeasy Chicago has you covered for the after-hours plot twist.

You know what? Chicago brunch is a mood. Pick the one that matches yours, set a timer, and let the bubbles do their thing.

Gold Coast, Chicago: My Week Living Fancy (and a Little Loud)

I spent a week in the Gold Coast. I stayed in a tiny studio near State and Elm. Think old brick, creaky floors, and a view of trees and taxis. It felt safe, busy, and a little glossy. Like the city put on a nice coat. Need a more detailed orientation? I used ARECO’s week-long Gold Coast playbook to frame my days. For an official snapshot of the neighborhood’s history, dining, and things to do, the Choose Chicago Gold Coast guide is a handy starting point.

First Impressions: Pretty and polished

The streets felt clean. The doormen waved. I saw tiny dogs in sweaters. I also saw dads in suits grabbing late coffee. Oak Street Beach was a few blocks away, and that blue water looked like a postcard. I took a slow walk on the Lakefront Trail at sunrise. The waves slapped the wall, and the wind tried to take my hat. It won once. I chased it. People laughed. I laughed too.

At night, Rush Street glowed. Music. Heels. Valet stands. The vibe changed fast—calm side streets one block over, then party-ville on Division. It’s a mix. Old money houses on Astor. Tall glass towers near the lake. I liked both. Craving something off-menu, I followed the hushed-password trail in ARECO’s speakeasy night-out narrative and ended up sipping gin in a low-lit basement that still smelled like history.

Where I actually ate and drank

  • Breakfast at Goddess and the Grocer on State: I grabbed a bacon, egg, and cheddar croissant and a cold brew. About $14 total. Fresh, fast, friendly. I sat by the window and people-watched. A tiny dog judged my sandwich. Fair.

  • Coffee at Dollop on Walton: I got a flat white and a banana bread slice. Warm, sweet, no fuss. The barista slid me an extra napkin like she knew I’m a crumb person.

  • Lunch by the water: I took a turkey wrap from Potash Market on State over to Oak Street Beach. Wrapped in foil, still warm. Sand in my shoes, not in my food. Win.

  • Big dinner at Gibsons on Rush: Yes, I did the thing. I split a bone-in ribeye and mashed potatoes with a friend. My martini was around $20 and hit clean and cold. The room buzzed—old-school energy. The steak? Charred edge, juicy middle. We had to wait 25 minutes past our time. Not great. But the service was smooth once we sat.

  • Date-night fancy at Maple & Ash: I saved this for a birthday. We shared wood-fired oysters and a wedge salad. Pricey. I won’t lie. But the booth felt like a hug, and the steak came with a crust that cracked just right. Would I do it every week? No. For a splurge? Yep.

  • Late-night on Division: I walked into The Lodge Tavern for a beer. Good jukebox. Sticky floor. No one cares who you are. That’s kind of nice.

  • Sweet treat: A pistachio gelato on Rush. I ate it too fast. Brain freeze. Worth it.

  • Sushi moment: When the steak overload hit, I bookmarked ARECO’s real picks for Chicago’s best sushi and flagged three spots for my next visit.

Daily life bits that mattered

  • Groceries: Potash Market had what I needed, and the deli was solid. The Jewel-Osco on Clark was bigger but a longer walk with bags.

  • Gym and steps: I used the Lakefront Trail as my gym. Run out, walk back. The breeze off the lake kept me from making excuses.

  • Work time: I posted up at a cafe window with Wi-Fi and knocked out emails. Background noise helped. That’s weird, I know.

  • Errands: Dry cleaner on Dearborn was fast. Not cheap, but fast.

    Speaking of Dearborn, if your travels ever stretch to the Michigan namesake city and you want a no-nonsense place to scout local classifieds for gigs, dating, or nightlife, the modern Backpage alternative over at Backpage Dearborn lays out current listings with built-in safety guidelines so you can plan an evening—or a side hustle—without wading through sketchy forums.

Getting around without losing your cool

  • Walking is king here. Most blocks felt safe, even at night, but I still stayed on lit streets.

  • CTA Red Line: Clark/Division had steady crowds. Chicago/State too. Trains were frequent during rush hours. Late-night rides felt fine with a buddy.

  • Buses: The 151 got me to Lincoln Park Zoo in minutes. The 22 on Clark was slow at rush hour. That’s just how it is.

  • Parking: Pain. Street spots were rare. Garages were pricey. If you’re driving, plan ahead or you’ll loop forever.

The stuff I loved

  • Oak Street Beach mornings. Calm water. Soft light. The city looked gentle.

  • Architecture on Astor Street. Old stone, tall trees, quiet gates. I took too many photos of doors.

  • A quick flip from fancy to casual. I could get a martini in a glass with a stem, then a beer in a plastic cup two blocks later.

  • Window shopping on Oak Street. Prada and Chanel stared me down. I waved back with my $12 sandwich.

The stuff that bugged me

  • Price creep. A salad hits $18 fast. Cocktails start around $16. You feel it.

  • Noise on weekends near Rush and Division. It’s fun until you’re tired. Bring earplugs if your window faces the action.

  • Lines. Dinner waits were real, even with a booking. I learned to grab early tables or late ones.

  • Wind. The lake wind cuts in winter. Even in spring it can slap. A light jacket turns out not so light.

  • Petty stuff. I saw two phone snatches on a busy corner. I kept my bag in front and stayed alert. Most folks did.

For travelers who find the Gold Coast’s price tags more jaw-dropping than the skyline, you might be curious how some residents offset costs—one avenue is the sugar-dating scene. Before you decide if that path fits your comfort zone, check out this straightforward primer on Seeking Arrangement for an inside look at the platform’s expectations, safety tips, and potential perks that could sponsor your next round of $20 martinis.

Who this place fits

  • You like the mix: beach, fancy dinners, low-key bars, all within a mile.

  • You want the lake right there. Runs, swims, or just thinking time on a bench.

  • You don’t mind paying for the polish. Because you will.

  • You sleep fine with city noise, or you have a sound machine that means business.

Little moments that made it real

One morning, a doorman handed me a forgotten scarf from the lobby lost-and-found. He called me “kiddo,” and I’m not a kid. I smiled anyway. Another day, a server at Carmine’s slid over an extra basket of bread after I joked I could live on carbs. I almost did. And on my last night, I watched a couple take wedding photos by The Drake Hotel while a bus hissed and a siren blipped and lake mist floated in. It felt very Chicago—pretty, loud, and kind, all at once.

Quick tips I wish I knew

  • Book dinner early or super late to skip the worst waits.

  • Bring a windproof layer, even on “nice” days.

  • For a budget bite, hit deli counters or happy hours.

  • If you need quiet, stay two blocks off Rush or Division.

  • Sunrise at Oak Street Beach beats sunset crowds.

Want to dive deeper into Chicago’s other corners? The straightforward neighborhood primers on ARECO offer transit, dining, and safety snapshots for every pocket of the city. If you’re curious about real-estate vibes and where each block shifts from vintage walk-ups to sleek high-rises, Compass’s Gold Coast neighborhood guide breaks it down in plain language.

Final take

I liked living here for a week. I liked the ease, the water, the old bones of the buildings. I didn’t love the prices or the wait times, but I knew what I was signing up for. Gold Coast feels special without trying too hard. It wears its polish, sure—but it also laughs at a sandy sandwich and a windy bad hair day. And you know what? That balance stuck with me. I’d go back, scarf and all.