#Chicagowinter
December 14, 2025 at 3:50 AM
First Snow of season in Season. #chicago #chicagowinter #snow #coldasf
November 10, 2025 at 10:34 PM
It has begun. #chicagowinter #6pm
December 20, 2024 at 12:27 AM
Puppy Wants Summer Beach Times again… #chicagowinter #hollywoodbeach #pup #coldAF
January 30, 2026 at 2:28 AM
January 18, 2026 at 4:22 PM
Tonight’s Get up at Work, cause it’s Fucking Cold… #Unionsuit #Pup #musclepup #puphood #winter #chicagowinter #mo #mustache #hairy #fuzzy #Hairychest #VPL
February 14, 2025 at 7:38 AM
It’s important to stay moisturized in winter. #ChicagoWinter
January 11, 2026 at 11:18 PM
If you needed confirmation that it’s winter in Chicago…here you go. ❄️ 🥶
📸: @waywelling via Instagram
#Chicago #architecture #Chicagowinter #allfortheloveofChicago
December 15, 2025 at 11:46 PM
Bundle up, yall! It's getting real outside! 🥶🫣 #chicagowinter
January 5, 2025 at 5:25 PM
First Snow of the Season so means Pup is Layering clothing and sweeper off the GTi. Still Loving Hot Hatch life, Takes the snow like a champ. #chicagowinter #Winter #chicago #snow #mustache #Mo #stache #vwgti #VW #GTi #MK7 #golf #golfgti
November 22, 2024 at 4:26 AM
Presence means being fully conscious of what is right here, right now.
This week that has meant unusually beautiful winter weather — and the small pleasure of wearing lighter layers by the lake. #FullyPresent #ChicagoWinter
February 10, 2026 at 11:30 PM
🕳️ Can’t be mad at a longer winter when it looks like this. ❄️💙
📸: @waywelling via Instagram
#Chicago #architecture #allfortheloveofchicago #chicagowinter #groundhogday
February 2, 2026 at 8:32 PM
Friendly Reminder: Do the little things to keep you young and happy.

Ex: Build a 6ft igloo with family! #chicago #chicagowinter #snowstorm #fun #vacation #guncle #blackgaysky #addblackgaysky #blacksky
December 1, 2025 at 11:40 PM
February 15, 2025 at 4:55 PM
Cold? It's not cold. #cats #Chicagowinter
December 14, 2025 at 4:13 PM
We’ve hit double digits! Might be a shorts day. #Chicagowinter #navypier
January 22, 2025 at 3:41 PM
Did I mention it’s cold? 😝 Y’all stay warm out there now #belowfreezing #polarvortex #chicagowinter #coldgay
January 19, 2025 at 8:24 PM
At Navy Pier, winter doesn’t just bite; it devours. Caught this guy just soaking in the chill, probably thinking about the warmer days. That’s Chicago, beautiful but doesn’t give a damn if you’re cold. #ChicagoWinter #NavyPier #StreetPhotography
February 8, 2024 at 3:17 PM
It’s amazing how good 20 degrees can feel when you’ve been in single digits for a few days.
#chicagowinter #warmup #chicagoskyline #northavenue #landscape #chicago #lakemichigan
February 21, 2025 at 4:00 AM
Our building is old so #chicagowinter gets inside too. Gotta keep those ears cozy
November 22, 2024 at 5:09 PM
I miss tanning. Fucking Chicago winter. #chicago #chicagowinter #chicagogays #gay #brownboy #latino #latinogays
December 21, 2024 at 10:40 PM
Tried to outrun my fear of the future yesterday. All I got were ice eyelashes (it was 5 degrees). #chicagowinter
January 21, 2025 at 11:25 PM