Windy City Wanderers!

4.7•347 ratings

Chicago, IL, US

196 members · Public group

What we’re about

🎉 Welcome to Windy City Wanderers! 🌆

We’re so excited to have you here!

Whether you’re new to Chicago or a lifelong local, this group lets you explore the city in fresh, unforgettable ways. Think of it as being a tourist in your own town—discovering hidden gems, fun facts, and unique experiences across Chicagoland. 🗺️✨

This group is the sister to our original, "1001 Things to See in Chicago Before You Die," and we’ll be hosting lots of joint events together! 🤝

🎟️ Membership Info:

Enjoy a 90-day FREE trial
After that, it’s just $12/year
Want to skip the dues? Host an event, and your annual fee is waived! 🙌

🚇 Most events happen in the city or nearby suburbs like Oak Park, Evanston, and Park Ridge—and all are CTA-accessible.

❗Group Policy: We have a “3-strikes” no-show policy. Miss three events without updating your RSVP, and you'll be suspended for 3 months. This keeps things fair and respectful for everyone.

🎉 This is a year-round group—winter won’t slow us down! We’re all about meeting new people and having fun through one-of-a-kind outings all over the Chicago area.

💬 Got questions or ideas? Want to lead an outing? Message us anytime—we’d love to hear from you!

Let’s stay connected:
📘 Facebook Page
👥 Facebook Group
📸 Instagram
🌟 Sister Group on Meetup

Can’t wait to wander with you!

Giovina R.
Organizer, Windy City Wanderers 🌬️🚶‍♀️🚶‍♂️

Featured event

Wed, Dec 31 · 12:00 PM CST

🥳🍾NYE Day Drinking: Mimosas to Irish Midnight, Class, Chaos & Champagne 🍸😂

Bub City, 435 N Clark St, Chicago, IL, US

🥳 🍾NYE Day Drinking: Mimosas to Irish Midnight, Class, Chaos & Champagne 🍸😂

🎉 NEW YEAR’S EVE DAY DRINKING ADVENTURE!

Wednesday, December 31, 2025 • 12:00 PM – 7:30 PM

✨ New Year, New Plan, Less Nonsense ✨
This year we're ditching the usual Weeds Midnight Party and embracing something revolutionary:
Celebrating New Year’s Eve WITHOUT dealing with drunk amateurs. 😆🍾
Let’s be honest…
Who actually wants to:
❌ Pay $150 to stand in a crowded hotel ballroom?
❌ Play surge-pricing roulette with Uber?
❌ Spend 20 minutes freezing on a curb while valet “can’t find your car”?
❌ Wear sparkly shoes that destroy your feet?
❌ Get elbowed by a 22-year-old who pregamed with Fireball at 3 PM?
Not. Us.
So instead…
We’re day drinking.
Like classy, responsible adults who know their limits and their bedtime. 🍻😇
We’ll be done before the amateurs crawl out of their caves — home in jammies, snacks in hand, and dignity intact.

***

🍔🥂 STEP 1: LUNCH — Because We’re Grownups
📍 Bub City — 12–1 PM
435 N Clark St
🔗 https://www.bub-city.com/
We begin with food.
Because if we’re going to toast 7 different midnights, we’re going to need a base.
This is science. 🔬🍔

***

🗺️ TENTATIVE ITINERARY (a.k.a. The Magical Mystery Bar Crawl)
Subject to change depending on:
• vibes
• crowds
• sudden cravings
• who gets distracted by shiny objects
1️⃣ Bub City — 12–1 PM
435 N Clark St
The pre-game feast. Carb loading = strategic brilliance.
2️⃣ Boss Bar — 1–2 PM
📍 420 N Clark St
A River North classic. Where time stands still and the people-watching is elite.
3️⃣ Rossi’s Bar — 2–3 PM
📍 412 N State St
An iconic dive. Sticky floor included at no additional cost.
4️⃣ Mother Hubbard’s — 3–4 PM
📍 5 W Hubbard St
Sports bar energy. Cold beer. TVs shouting at you. Comforting.
5️⃣ Snickers Bar & Grill — 4–5 PM
📍 448 N State St
A no-frills staple. Perfect for that “we’re still pacing ourselves, right?” drink.
6️⃣ Fadó Irish Pub — 5–7 PM
📍 100 W Grand Ave
🔗 https://fadoirishpub.com/chicago/
Champagne toast at 6 PM for Irish New Year! We WILL toast like we’ve suddenly developed an Irish accent. They actually do a real champagne toast at 6 PM for Irish New Year. We will be there — ready to shout “SLÁINTE!” like we’re on vacation in Dublin.

***

🌍✨ THE WORLD MIDNIGHT TOASTS
We are absolutely using Google World Clock to justify every drink.
It’s educational.
We’re basically scholars.
🎉 1 PM CST — UTC+5
Pakistan, Uzbekistan, Maldives, Western Kazakhstan, places we can’t pronounce but still appreciate.
🎉 2 PM CST — UTC+4
UAE, Oman, Georgia, Seychelles — lots of fancy places we probably can’t afford to visit.
🎉 3 PM CST — UTC+3
Saudi Arabia, Turkey, East Africa, Moscow.
We toast responsibly. Unlike Moscow.
🎉 4 PM CST — UTC+2
South Africa, Egypt, Greece.
Yes, we WILL yell “OPA!” at some point.
🎉 5 PM CST — UTC+1
France, Italy, Spain, Germany.
This is the chic hour. Pinkies up.
🎉 6 PM CST — UTC+0
Ireland 🇮🇪, UK, Portugal, Iceland.
🍾 Fadó champagne toast = our Super Bowl.

***

⏰ THE GRAND FINALE — 7:30 PM
And then…
We go home.
Before the amateurs come out.
Before the $75 Uber rides.
Before the sequined chaos.
We will be at home in slippers, watching the ball drop like the responsible, fabulous adults we are. 🛋️✨
🚇 Transportation Tips
Parking in the River North can be extremely challenging.
Highly recommended:
• CTA (train or bus)
• Metra
• SpotHero or ParkWhiz for better parking rates
CTA Trip Planner:
🔗 https://www.transitchicago.com/planatrip/

***

❗ No-Show Policy (Please Read!)
• Three no-shows without updating your RSVP = 3-month suspension
• Cut-off to update your RSVP = event start time
• If you arrive late, message the host directly
• Not checking in with the host at walks/tours/festival events counts as a no-show
• Repeated no-shows may result in removal from the group