All That Glitters is Chicago in November

Chicago in November is a movie set disguised as a city. I landed and immediately felt like Mariah Carey was going to pop out of O’Hare singing “All I Want for Christmas.” Snow flurries, department store windows exploding with tinsel, trees dripping in lights—it was Hallmark meets Gossip Girl with Chicago as the stage and me refusing to play background.

From the top floor of the Millennium Hotel, the city didn’t just sit outside my window—it performed. The Magnificent Mile stretched below, strung with Christmas lights that blinked like paparazzi. I sat with a glass of red, watching the snow blur into the skyline, and for a second it felt like Chicago was putting on the show just for me.

Book your holiday skyline moment ✨ [Expedia link]

🎄 First Night: Drunk on Lights, Not Just Wine

We dumped our bags and ran straight outside because the city was glowing like it had just gotten engaged. Every lamppost was wrapped in garlands, Michigan Avenue looked like a Pinterest board threw up on it (in the chicest way possible), and I was officially in full Christmas mode, a full month early, matching the city, sparkle for sparkle.

Also, it was cold. Not, like, “oh, sweater weather” cold. More like, “my soul just left my body and is floating over Lake Michigan” cold. Thank God for spiked hot chocolate.

*My favorite cold weather fits: cute and so cozy*Link to blog post*

🎨 The WNDR Museum (Where I Lost All Sense of Reality)

Inside The WNDR Museum was like stepping into someone’s dream that refused to wake up. There was Kusama’s “Love is Calling” infinity mirror room, tentacles of polka dots reflecting back at me, endless and soft stretching like the cave of your mind at 4 AM when you’re half awake and full of feelings. Then there was the Iris wall: they took a super close photo of your eyeball, every fold, color, fleck, and displayed it among thousands of other eyes. Huge, shimmering, weirdly intimate. I stared into someone else’s iris and felt like I was both exposed and hiding.

There was a room built with LED floors that reacted to your footsteps — every step you take sent ripples of color underfoot. If you jumped, the floor exploded in neon splashes. Kid-me would’ve screamed; adult-me stood there laughing because I couldn’t believe art could chase you like that. They had interactive projection cubes (one called Touch) where pressing into walls made the visuals swirl and rip. I pressed so hard I half-expected to melt into the art, be absorbed. Knowing it was cold outside, snow swirling, wind cutting, but in here I was burning, engulfed in light and color.

Every corner was set up to drop your jaw: giant domes of color, mirrored hallways that made you feel like you were walking through a kaleidoscope, brightness that felt holy. And though it was short — maybe an hour or so if you don’t linger — it was enough. Enough for me to be floating in memory afterwards.

Book ahead, it sells out faster than Mariah’s Christmas concert 🎬 [Expedia link].

🏙️ Touristy, Shameless, Perfect

November in Chicago = all the cliché spots, but under Christmas lights, which makes them even more iconic.

The Bean: Snow dusted on top, reflecting the city like a frosted jewel. I snapped the literal ultimate winter selfie while dodging ten other people doing the exact same pose. Honestly? Worth elbowing my way in.

Millennium Park: If you only do one thing in Chicago, let it be this. The view is non-negotiable—daytime gives you a living, breathing patchwork of the city in full color, while nighttime wraps it all in diamonds of light. Then there’s the glass box: stepping out feels like breaking a law of physics. My stomach dropped, palms sweated, and yes, I was screaming internally while serving face for the camera like it was casual. Tickets here

Willis Tower Skydeck: If you go to Chicago and do one sole activity, make it this. The ulitmate view, photo, and experience, no matter what time of day it is. It's surreal at night with the city lights sparkling, and beautifully live and colorful in the daylight. Standing on that glass box with the whole city glittering beneath me? Felt illegal. My stomach dropped, my palms sweated, and yes, I screamed internally the entire time—while smiling like it was casual. Tickets here 🪟 [Expedia link].

Navy Pier: Half carnival, half snow globe, twinkly lights stretching down the boardwalk. I bought about 10 handmade ornaments, 15 other souvenirs, and kettle corn the size of my torso because: holidays. Then immediately questioned my life choices when I had to carry it three blocks back to the Uber.

Riverwalk: Every bridge, every lamppost, drenched in Christmas, and dripping in lights rippled across the water like liquid tinsel. I wouldn’t have blinked if Mrs. Claus floated past sipping mulled wine. Chicago, you’re dramatic, and I'm obsessed.

🍝 Eating My Feelings (Warm Ones, Preferably)

Chicago knows it’s cold. Chicago feeds you accordingly.

I went all in on deep dish (obviously). And not just anywhere, I made the pilgrimage to Lou Malnati’s, the Chicago institution. Let’s be clear: this isn’t “pizza,” it’s a commitment ceremony with cheese, buttery crust, molten center, tangy sauce piled high. By slice three you’re questioning your life choices, by slice four you’re proposing marriage to the pie. Worth every bite.

One crisp Sunday brunch had me at City Winery on the Riverwalk. Little heated domes around our table so we could enjoy the outside view without frostbite, brunch plates stacked, wine flowing, the river sparkling. Perfect midmorning indulgence.

Then there’s Goddess and the Baker the spot where I quite literally consumed 24K gold. Yes. Gold. The second I walked in, the smell hit me—sweet, warm, buttery—but with this chic twist, like if Chanel bottled croissants as perfume. I wanted to live in it. I ordered a lavender latte and the chocolate mousse cake, and when they landed on the table, both dusted in gold, I just froze. Who gets to casually drink and eat jewelry? Me, apparently. Every sip, every bite, silky, rich, decadent. Too perfect to touch, yet too good not to. I still think about it every single day.

If Chicago sells you anything, it’s an experience—and The Drifter delivered. Hidden beneath the Green Door Tavern, the speakeasy felt like stepping into another era: low ceilings, velvet booths, and cocktails that arrived looking more like artifacts than drinks. The room buzzed with that secret-club energy, and then the show began. A woman spun gracefully under the spotlight, sequins flashing, the kind of performance you expect in a tucked-away cabaret. But then—in a single blink—her costume vanished. Gone. The room froze, breath caught mid-air. Not a laugh, not a whisper, just wide eyes and stunned silence from the audience among the jazz music that played unitl her performance ended. None of us expected it, but it felt exactly like something Chicago would sneak into the script.

🍸 Nights Out: Holiday Edition

River North in November isn’t subtle, it's cinematic. Bars spill out warmth, jazz seeps into the street, and saxophones trail you like a soundtrack. Blue Chicago gave me music so raw it felt stitched into my chest, paired with cocktails that tasted like velvet, you can't help but dance the night away. Over at the House of Blues, the lights blurred, the drinks hit harder, and suddenly strangers weren’t strangers anymore, they were dance partners under a ceiling strung with stars. Let's just say there was no way we were waking up early the next morning. Chicago may not be the "City that Never Sleeps", but they're definitely sisters.

🛍️ Shopping, But Festive

The Magnificent Mile in November is retail wrapped as holiday spirit. Saks Fifth Avenue strung in garlands, the 900 North Michigan Shops glowing like a luxury snow globe, and the windows at Water Tower Place so over-the-top they deserved their own standing ovation. I swiped my card like it wasn’t real money, convincing myself leather boots counted as a “souvenir.” Not necessary in the slightest. But I strutted out like Chicago itself had styled me, and couldn't be happier.

Now, the Magnificent Mile isn’t just shopping, it’s a full excursion. Nearly a mile of Michigan Avenue transformed into a runway for the holidays, every tree wrapped in lights, every marquee glowing, every store begging you to step inside “just to look” (which, obviously, never happens). There’s Saks and Nordstrom anchoring the classics, Water Tower Place with its glittery chaos, and the flagship Apple store gleaming like it landed from the future. Luxury giants—Gucci, Louis Vuitton, Burberry—stood side by side with Chicago icons like Garrett Popcorn, perfuming the street with caramel and butter. Walking the Magnificent Mile in November feels less like shopping and more like being swept onto a holiday movie set where your credit card is the uncredited star.

🛎️ Back at the Millennium

Every night ended the same: top floor, city lit like a Christmas tree, me sprawled dramatically across the bed like a tragic movie heroine in silk pajamas. The Millennium Hotel lobby set the tone—marble columns, chandeliers sparkling like they’d been staged, and that unspoken rule of “don’t ask how much the champagne costs, just order it.” But the penthouse was the crown jewel. From our window, the view was unreal: Michigan Avenue twinkling below, the lake stretched out in silver calm, and snow tumbling past the glass like confetti tossed by the city itself. If heaven has an address in Chicago, I found it.

Book your skyline view 🏙️ [Expedia link].

🎬 Final Frame

Chicago in November surprised me at every turn. One moment I was eating gold at a bakery, the next I was holding my breath on a glass ledge 100 floors up. It was museums and music, skyline views and late-night dancing, food that felt like a hug, and a city that somehow matched my energy step for step. Cold? Absolutely. But the kind of cold you forgive when the city keeps handing you reasons to stay outside anyway.

So if you’re even half-considering it:🛫 Pack your coat, book the top floor, sip the spiked cocoa, and let Chicago own you 👉