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 🌬️🚶♀️🚶♂️
Upcoming events
39
🍳🥂 Sunday Brunch at Uncle Mike’s Place – Filipino Breakfast Favorite! 🇵🇭✨
Uncle Mike's Place, 1700 West Grand Avenue, Chicago, IL, US🍳🥂 Sunday Brunch at Uncle Mike’s Place – Filipino Breakfast Favorite! 🇵🇭✨
Sunday Brunch before Holidays on Grand Vintage Shopping Walk!
📅 Sunday, November 8, 2025 – 9:45 AM (Part 1 of 2)
📍 Uncle Mike’s Place – 1700 W Grand Ave, Chicago, IL 60622
📍 Located in Chicago’s vibrant West Town neighborhood!
🔗 Website: https://www.unclemikesplace.com
🔗 Facebook: https://www.facebook.com/unclemikesplace
🔗 Menu: https://www.unclemikesplace.com/#menu-wrapper🛍️ Part 2: Holidays on Grand – Vintage Holiday Shopping Event 🎄
After brunch, we’ll stroll the festive Holidays on Grand market for vintage finds, gifts, and local treasures.
🎁 RSVP separately here:
👉https://www.meetup.com/windy-city-wanderers/events/311902900/***
👥 Seating Details:
This is a small venue that does not take reservations, so we’ll be seated in small groups of 4–6 people per table. Please RSVP only if you are 95% sure to attend! 🙏💵 CASH ONLY for groups!
They cannot do separate checks. To make things simple:
➡️ Add 32% to your total (12% Chicago tax + 20% tip).
Please bring cash — it makes checkout smooth for everyone! 💸🥞 About the Venue:
Tucked in the heart of West Town, Uncle Mike’s Place is home to Chicago’s most beloved Filipino breakfast! 🇵🇭🍚This cozy neighborhood diner has been a local favorite since 1991, serving up comforting lugaw (a savory chicken rice porridge similar to congee) and hearty Filipino breakfast platters with your choice of protein — from longanisa sausage to tapa beef. 🥩🍳
> “My mother-in-law lived with me for 25 years, cooking every day — eventually, we added her recipes to the menu.” – Owner Michael Grajewski
Come hungry and ready for warm hospitality — Uncle Mike’s is a true Chicago comfort food institution. ❤️
***
🚗 Parking & Transit:
- Metered parking on Grand or Ashland
- Free side-street parking nearby (watch for permit/no-parking signs)
- CTA trip planner: https://www.transitchicago.com/planatrip
***
🚫 No-Show Policy Reminder:
We love having you, but please respect the group and venue:
❌ 3 no-shows (without updating RSVP) = 3-month freeze from events
⏰ RSVP changes must be made by the event start time
📩 Running late? Message the host directly
🚶 Not checking in or repeated no-shows may result in removal***
✨ Let’s kick off our Sunday with great food, warm friends, and a true West Town gem before our holiday shopping adventure! 🎁☕
2 attendees
🎁🛍️ Holidays on Grand Vintage Shopping Walk–West Town Edition! 🎄✨
Uncle Mike's Place, 1700 West Grand Avenue, Chicago, IL, US🎁🛍️ Holidays on Grand Vintage Shopping Walk–West Town Edition! 🎄✨
🎄✨ Back by Popular Demand! Holidays on Grand Vintage Shopping Walk 2025 🛍️🎁
### 🏙️ Event Details
📅 Sunday, November 9, 2025 (Part 2 of 2)
🕛 12:00 PM – 3:00 PM
📍 Start: Uncle Mike’s Place – 1700 W Grand Ave, Chicago, IL 60622
🍳 Meet here first for brunch before shopping!
🏁 We end about 6 blocks west at 2246 W Grand Ave
🚗 Plan your parking accordingly!Let’s do some sweets, festive holiday décor, fresh inventory, and much more! 🍪🎅🎁
We’ll enjoy holiday shopping vintage style at some of the coolest stores along Grand Avenue in Chicago’s West Town. Expect one-of-a-kind finds, great company, and tons of fun — all while getting some steps in! 🚶♀️💃
We loved this event last year, so let’s go again! It’s a bit earlier this time and caught me by surprise — sorry for the late posting! 😉
***
🕐 Brunch before the walk (separate event) at📎Uncle Mike’s Place
🍳🥂 Brunch will be a separate event to keep numbers easy to manage.
If you want to join for brunch
👉 RSVP for brunch here:
🔗 https://www.meetup.com/windy-city-wanderers/events/311902884/***
### 🏬 Shopping Stops Along Grand Avenue (West Town)
🖼️ MAK Chicago – 1716 W Grand Ave (not an official stop, but worth a peek!)
🌍 Cultural gifts celebrating art, community, and Ukrainian culture. 💙💛
👉 https://www.makshopchicago.com☕ The Center of Order and Experimentation (COE) – 1727 W Grand Ave
A creative coffee + retail space curating curious objects of exceptional utility while fostering community.
👉 https://www.thecoechicago.com🪑 Warehouse 55 – 1819 W Grand Ave
A stunning mix of vintage finds, repurposed furnishings, and one-of-a-kind accessories for every aesthetic.
👉 https://www.warehouse55chicago.com🏛️ Urban Remains – 1820 W Grand Ave
Specializing in reclaimed American architectural artifacts — a treasure trove of design history.
👉 https://www.urbanremainschicago.com🏠 Salvage One – 1840 W Hubbard St
A Chicago icon with 60,000 sq ft of antiques, art, and architectural salvage. Perfect for design lovers.
👉 https://www.salvageone.com🪞 Salvage Haus – 2000 W Grand Ave
A curated collection of vintage art, clothing, accessories, and home décor — each piece with a story.
👉 https://www.salvagehauschicago.com🌏 The Golden Triangle – 2035 W Grand Ave
A breathtaking 10,000 sq ft showroom featuring a global mix of antiques, art, and modern design.
👉 https://www.goldentriangle.biz🖼️ N E Y B I R – 2246 W Grand Ave
A fine art and design shop celebrating the past, present, and future through storied objects.
👉 https://www.neybir.com***
### 🚶♀️ Walking Route Info
🛍️ Start: 1700 W Grand Ave (Uncle Mike’s)
🏁 End: 2246 W Grand Ave – about 6 blocks west
🚗 Plan your parking accordingly!***
### 🚆 Transportation Tips
🚗 Metered parking on Grand & Ashland + free side-street spots (watch signs).
🚇 Public transit: https://www.transitchicago.com/planatrip/***
### 🚫 No-Show Policy Reminder
We love having you, but please respect the group and venues:
❌ 3 no-shows (without updating RSVP) = 3-month freeze from events
⏰ RSVP changes must be made by the event start time
📩 Running late? Message the host directly
🚶 Repeated no-shows or not checking in may result in removal***
✨🎁 Let’s make a day of it — brunch, browsing, and a festive stroll through West Town’s best vintage shops! Bring your holiday spirit, shopping bags, and comfy shoes — it’s going to be a merry afternoon on Grand Avenue! 🎅🛍️☕💖
4 attendees
🥪🍕 Fontano’s Feast: Quick Dinner Before Wait Wait…Don’t Tell Me! 🎙️🍽️
Fontano’s Subs & Pizzeria, 332 S Michigan Ave, Chicago, IL, US🥪🍕 Fontano’s Feast: Quick Dinner Before Wait Wait…Don’t Tell Me! 🎙️🍽️
🍽️ Part 1 of 2 – Quick Dinner Before the show!
📅 Date & Time: Thursday, November 13, 2025, 5:45 PM
📍 Location: Fontano’s Subs & Pizzeria, Chicago
🔗 Website & Menu: https://www.fontanosonmichigan.com/Important: Only 4–6 people per table. No reservations, first-come, first-served. We’ll grab several tables, but seating is limited! COUNTER SERVICE — everyone pays on their own.
💵 Payment: Please take the total of your order and add 32% (12% Chicago tax + 20% tip). Cash or credit accepted.
Why Fontano’s: Fontano’s has been a neighborhood favorite for decades, known for hearty Italian subs, thin-crust pizzas, and fresh, high-quality ingredients. Casual, welcoming vibe perfect for a quick, fun pre-show dinner!
🥗🥪 About the Spot: Cozy, casual Italian pizzeria & sub shop! Famous for hearty sandwiches, fresh ingredients, and classic pizzas 🍕🍅. Counter service—everyone pays separately 💵💳.
RSVP: Only sign up if you are 95% sure you can attend — small group size due to limited seating.
🚆 Public Transit: Easily accessible via CTA bus or train — check CTA Trip Planner
🚗 Parking: Metered spots on Michigan Ave & nearby streets; limited free spots. Use SpotHero or Parking Whiz for easiest options.Wait Wait…Don’t Tell Me Show: Sign up separately here: https://www.meetup.com/windy-city-wanderers/events/311635852/
⚠️ No-Show Policy:
- 3 no-shows without updating RSVP → 3-month sign-up restriction
- Update RSVP by event start or message host directly
- Not checking in may result in removal from future events
🎉 Quick, fun meetup before the show! Perfect for a pre-show bite 🍽️😋.
17 attendees
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