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 🌬️🚶♀️🚶♂️
🌆🌿 Step Into The Villa: Prairie Homes & A Century of Stories 🏠🌸
Let's explore Irving Park’s Hidden Prairie-Style Treasure on the northwest side on a lovely fall Sunday afternoon!
📆 Sunday, September 28, 2025
⏰ 12:00 PM – 2:00 PM
👣 Approx. 2 hours of walking 1.5 miles
💵 Cost: $20 per person | Venmo, PayPal, or Zelle accepted (pay at start)
🌦️ Outdoors | Casual pace | Rain or shine
✨ Come explore a hidden treasure on Chicago’s Northwest Side! 🌆 The Villa neighborhood is a landmarked district and a true Prairie-Style gem. I’ve arranged a private architectural walking tour so you can discover one of the city’s most picturesque areas—filled with early 20th-century Craftsman & Prairie-style homes, leafy parkways, and charming stone planters. We’ll even step inside a house or two to see the interiors! 🏠🌸 Perfect for architecture lovers, history buffs, and anyone curious about a part of the city few ever see.
✨ The tour is led by Villa residents trained as Chicago Architecture Center docents. Our walk will be led by long-time Villa resident, Ruth Mugalian. Along the way, you’ll hear about the district’s 1902 origins, its connection to Frank Lloyd Wright’s Prairie Style, and the work of architect Clarence Hatzfeld (who later designed the Portage Park fieldhouse & natatorium).
✅ Tour Highlights
· 🏡 Craftsman & Prairie style homes (inside views of 1–2!)
· 🌳 Parkway streets with distinctive stone planters
· 📖 Stories of The Villa’s development as the “Villa addition to Irving Park”
· 🏘️ Homes by Hatzfeld & Knox, and other Wright-influenced architects
· 🎉 A neighborhood featured in books, tours, and even its own centennial festival
📍 Tour Route & Logistics
· Start: NE Corner of Addison & Pulaski — 3950 W. Addison, Chicago
· End: About 2 blocks from where we started
· Length: ~2 hours, outdoors, 1.5 miles 🌞
🎒 What to Bring
· Water 💧
· Comfy walking shoes 👟
· $20 tour fee 💵 (Venmo, PayPal, or Zelle)
· Umbrella/rain jacket just in case ☔
🍽️ After the Tour
After the walk, join us for a late lunch nearby! Options include 🔥🍗 Brasa Roja Pulaski, 🍻🏈 Brudder’s Sports Bar, or 🍕❤️ La Villa Pizzeria—a local favorite since 1972.
🌟 About The Villa
A century-old neighborhood on Chicago's Northwest Side, The Villa is characterized by parkway streets, stone planters, and distinctive examples of early 20th-century residential architecture. The district was built in 1902 by several architects, many visibly influenced by Frank Lloyd Wright’s Prairie Style. Most notable are the bungalows by Hatzfeld & Knox, whose partner Clarence Hatzfeld went on to design the Portage Park fieldhouse and natatorium. Originally developed as the “Villa addition to Irving Park,” it showcases unique Craftsman and Prairie-style homes fronting on picturesque boulevard-style streets.
The Villa has been featured in magazines and books, and is a regular stop on Chicago Architecture Foundation tours. In 2007, the neighborhood celebrated its 100th anniversary with period costumes, horse-and-carriage rides, and recorded oral histories. 🎉📖
🚇 Transportation & Parking
CTA Trip Planner: https://www.transitchicago.com/planatrip/
🚇 Street parking available on Addison, Pulaski & side streets (watch for permit parking signs). 🅿️
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📸 While not a strict photo walk, there will be plenty of opportunities to capture homes, gardens & historic streets! 🌆
🙌 It’s a multi-meetup group event—please keep your RSVP updated and don’t be a no-show!
❗ No-Show Policy:
3 no-shows without updating your RSVP = 3-month freeze from future events. Please update RSVP by start time or message host if late.
Upcoming events (4+)
See all- 🎤🌮🎶 Live Band Karaoke + Taco Tuesday! Multi-Group Meetup! 🎶🌮🎤All Star Seafood and sports, Chicago, IL
🎤🌮🎶 Live Band Karaoke + Taco Tuesday! Multi-Group Meetup! 🎶🌮🎤
⭐ Hosted by Deanna ⭐
Come on out for an incredibly fun Tuesday night—join multiple Meetup groups for Live Band Karaoke at All Star Seafood & Sports!
If you've never done live band karaoke before, you're in for a treat! This isn't your standard machine karaoke—the band plays live and helps you out if you don't know all the words or need support. Whether you want to take the mic or just watch and cheer on others, it's a blast either way.
✅ No experience necessary! The band will back you up and keep the energy high.
✅ Or just hang out and enjoy! Watching people perform with a live band is half the fun.
✅ Multi-group event: Expect a bigger, livelier crowd than the RSVP count—these typically average 10–12 people from our group alone, plus attendees from other groups.We want laid-back, non-judgmental, fun-loving folks who want to have a good time and support each other—even if someone can't carry a tune in a bucket!
🎉 TACO TUESDAY SPECIAL!
Come hungry and enjoy their awesome Tuesday Taco specials. Pair your food with drinks from their full bar.***
📅 WHEN:
Tuesday night! Live Band Karaoke starts at 8 PM.
🕗 Arrive early to get a good spot, hang out, grab food and drinks before the singing starts!***
📍 WHERE:
All Star Seafood & Sports
730 S. Clark St., Chicago, IL
✅ Website
✅ Facebook
✅ Menu***
🚗 PARKING INFO:
Street parking on Clark, Polk, and Wells Streets (watch for no parking and permit-only signs—it can be tricky).
⭐ Highly recommend using SpotHero or Parking Whiz for the safest and easiest option.
🚇 PUBLIC TRANSPORTATION:
Plenty of CTA options—plan your route here: CTA Trip Planner***
✨ WHAT TO EXPECT:
✅ Sing with a live band (they’ll help you!)
✅ Amazing taco specials
✅ Drinks, friends, fun vibes
✅ A supportive crowd from multiple Meetup groups
✅ Outstanding food & a full bar
✅ Even if you don't sing, it's a great show!***
⚠️ OUR NO-SHOW POLICY:
✅ Please update your RSVP if you can’t make it!
❗ 3 no-shows without updating = 3-month hold from events.
✔️ Cut-off to update is the event start time.
✔️ Message the host if you’re running late.
✔️ Always check in with the host when you arrive.***
✨ Come sing your heart out, try some delicious tacos, cheer on your friends, and have an unforgettable Tuesday night with great people. Whether you’re the next Beyoncé or just want to laugh and clap along, this event is for you.
See you there! 🎤🌮🍻
- 🥢🍰 Bites of Uptown: A Global Food Adventure! 🍜🍷Uptown Business Center, Chicago, IL
🥢🍰 Bites of Uptown: A Global Food Adventure! 🍜🍷
🌮🥟9th Annual Taste of Uptown 🍴🌍
We did this last year and it was FABULOUS 🙌 — well worth the ticket price, especially if you are a foodie! We’ve done this for the past few years and everyone loved it.
👉 This year, we’re doing the BOWL Route — it has more vegetarian & vegan options! 🥦✨
🎟️ TICKETS (This is a TICKETED EVENT!)
You MUST purchase tickets online ahead of time — this WILL sell out (it did last year!).
👉 🎟️ Buy Tickets Here- $30 – Early bird (through Sunday, Aug 31)
- $40 – Regular (Sept 1 – Sept 21)
- $45 – Last minute (Sept 22 – Sept 23)
- $55 – Walk-in (if available)
⚠️ Make sure to choose THE BOWL ROUTE (there are two routes this year)!
🍴 What is Taste of Uptown?
The 9th Annual Taste of Uptown celebrates Uptown’s amazing cultural & culinary diversity. 🌏🥘It’s a restaurant crawl featuring small bites & samples from 24 Uptown eateries (some include liquor 🍷). You’ll receive a passport at check-in and stroll from spot to spot, trying signature dishes.
This is a foodie’s dream — a great way to explore new restaurants while supporting local businesses!
🚶 Our Walking BOWL Route (~2 miles total)
📍 Start: Uptown Chamber of Commerce – 4619 N. Broadway (near Wilson Red Line)
1️⃣ Demera Ethiopian Restaurant (4801 N Broadway)
2️⃣ Fat Cat (4840 N Broadway)
3️⃣ Nabala Café (4660 N Broadway)
4️⃣ Uptown Deli (4759 N Sheridan Rd)
5️⃣ RAKKAN Ramen (4926 N Broadway)
6️⃣ Rupee Wine & Spirits (4812 N Broadway – 21+)
7️⃣ Sun Wah BBQ (5039 N Broadway) 🦆
8️⃣ Hon Kee BBQ & Seafood (5009 N Winthrop Ave)
9️⃣ Kie-Gol-Lanee Oaxacan (5004 N Sheridan Rd) 🌮
🔟 La Patisserie P (1050 W Argyle St) 🥐
1️⃣1️⃣ Uni Uni Boba (1130 W Argyle St) 🧋
✅ End: Near Argyle Red Line station👉 Expect ~35–40 minutes of walking (not counting food stops).
👉 Wear good walking shoes 👟 and dress for outdoor weather ☀️☔.
🗓️ Event Details
📅 Date: Wednesday, September 24, 2025
🕕 Time: 6:00 PM
🌧️ Rain or shine event (no refunds, but you can resell tickets)🚗 Transportation & Parking
🚇 CTA Red Line: Wilson (start) / Argyle (end)
🚌 Multiple bus routes nearby
🚘 Metered Street parking (Broadway, Lawrence, Sheridan, Argyle) + free side streets (watch signs).
💡 Try SpotHero or ParkingWhiz for garages.
CTA Trip Planner: https://www.transitchicago.com/planatrip/📌 Meetup Notes
We’ll meet at check-in (4619 N Broadway) and start together.
We’ll walk as a group, but if one spot is too crowded, we can skip & move on.
Remember: we finish about 1 mile from where we start, so plan parking accordingly!🍽️ Food + drinks + community = guaranteed good time!
✨ Last year sold out — don’t wait. Grab your ticket and join us for this multicultural Uptown feast!
👉 🎟️ Buy Your Ticket Now (BOWL ROUTE!)
✨ RSVP / No-Show Policy
- Please RSVP only if you are certain you can attend — tickets are limited and the event usually sells out.
- If you cannot attend after RSVPing, please notify the group or transfer your ticket to another participant.
- No-shows without notice may affect future event invitations.
- 🍷🎞️ Lights, Camera, Sip! Coppola Wine Tasting at Buzzed by ZEA w/Michael 🍇🥂Buzzed By ZEA - Salon & Bar, Chicago, IL
🍷🎞️ Lights, Camera, Sip! Coppola Wine Tasting at Buzzed by ZEA w/Michael 🍇🥂
The Director’s Cut-Francis Coppola Wine tasting at buzzed Zea
Join us for an elevated wine experience with renowned Sommelier & Chocolatier Michael Roberts at Buzzed by ZEA Salon & Bar! ✨
We’ve loved doing these wine classes with Michael in the past at The Reveler and Francesca’s—and now he’s expanded to venues all over Chicago! These are always a blast, with great food, expert wine knowledge (no snobbery!), and a super social vibe.
This time, we’re diving into The Director’s Cut—featuring 4 wines from the Francis Ford Coppola winery! Join us for a captivating evening celebrating the artistry of wine making, inspired by the Oscar-winning director, Francis Ford Coppola. paired with small bites and Michael’s exquisite homemade chocolates.
NOTE: This is a pre-paid event. You MUST purchase a ticket via Eventbrite to attend. Space is limited and these tastings always sell out—so don’t wait!
👉 🎟️ $65 + fees (includes wine, food pairings, chocolates, taxes & service fees)
✅ https://www.eventbrite.com/e/the-directors-cut-tickets-1658188710069
***
📅 Event Details
🗓️ Date: 9/24/25
🕰️ Time: 6:30–8:30 PM Structured Class + Open Social Hour After
📍 Venue: Buzzed by ZEA Salon & Bar, 3344 N Halsted St, Chicago, IL
Host for this Meetup: Susie Brodie
***
🌟 What to Expect
✅ 4 expertly selected Francis Coppola wines 🍇
✅ Small bites thoughtfully paired with each wine
✅ Homemade chocolates crafted by Michael himself
✅ An approachable, fun, non-snobby class led by a true expert
✅ Post-class social hour to mix and mingleMichael Roberts is both a certified sommelier and chocolatier, with a deep love of all things food, wine, and chocolate. If you haven’t taken one of his classes before, you’re in for a treat! He makes wine approachable, educational, and fun.
Bonus: All wines and chocolates are available for purchase at discounted prices after the class!
***
🍸💇♀️About the Venue
Buzzed by ZEA is a unique, stylish neighborhood spot that’s half hair salon, half craft cocktail bar. During the day, you can sip a Manhattan during your haircut. At night, the lights go down and it transforms into a cozy, intimate lounge.
✅ Buzzed by ZEA Website
✅ Buzzed by ZEA Facebook Page
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🚗 Transportation & Parking- CTA-friendly! Plan your trip: CTA Trip Planner
- Metered parking on Halsted + limited free side-street parking (watch for permit-only signs!)
- Highly recommended: SpotHero or ParkWhiz for stress-free garage options
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⚠️ RSVP & No-Show Policy
✅ RSVP here on Meetup so the host knows you’re attending!
✅ But you MUST buy your ticket via Eventbrite to hold your spot.
✅ Please update your RSVP if you can’t make it.
✅ 3 no-shows without updating your RSVP = 3-month freeze from events.
***
Come raise a glass with us and enjoy a relaxed, delicious evening of wine, food, chocolate, and great company. Perfect for wine newbies and enthusiasts alike.🥂 Cheers to love, laughter, and delightful discoveries!
***
🎟️ Buy Your Ticket Now:
👉 https://www.eventbrite.com/e/the-directors-cut-tickets-1658188710069 - 🍏🥂 Sip, Savor & Celebrate – Cider Fest 2025! 🍎🍂Architectural Artifacts Inc, Chicago, IL
🍏🥂 Sip, Savor & Celebrate – Cider Fest 2025! 🍎🍂
🍎✨ Cider Fest 2025 – Unlimited Tastings! ✨🍎📅 Thursday, September 25, 2025
⏰ 6:30–9:30 PM
📍 Artifact Events, Ravenswood
Dogs allowed!We had such a blast last year that we’re going back for the third-annual Cider Fest — a celebration of all things cider! 🥂
🎟️ Tickets Required: $35 + fees → includes 3 hours of unlimited tastings + commemorative tasting glass
👉 BUY TICKETS NOW (It WILL sell out — don’t wait!)
***🍏 What to Expect
- 🍻 Unlimited Tastings from local + regional cider brands
- 🍎 6 classifications of cider (modern, heritage, traditional, and more!)
- 🍸 Special cocktail collabs from cideries & distilleries
- 🍔 Food vendors on site (savory, sweet, and GF options)
- 🐾 Dog-friendly event (furry friends welcome!)
- 🎉 21+ only — sip, mingle, and celebrate cider season
***
🍎 With several groups coming together, you’ll have the chance to mingle, laugh, and make new friends while exploring unique ciders! 🍏🍺 Cideries & Beverage Vendors
- 1911 Established
- 2 Towns Cider House
- 375 Park Avenue Spirits
- Angry Orchard
- AVAL Cider
- Crispin Cider
- Eris Brewery & Cider House
- JK's Farmhouse Ciders
- Journeyman Distillery
- Misbeehavin' Meads & Bad Humor Cider Co.
- Original Sin
- Right Bee Cider
- Schilling Cider
- Seattle Cider Co.
- Uncle John’s Hard Cider
- Vander Mill Cider
- Shacksbury Cider
- Strongbow Cider
- Heaven's Door Whiskey
- Koval Distillery
- Maplewood Brewery & Distillery
- Play Hard Seltzers
- …and more announced soon! 🍾
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🍸 Cocktail Collab Pairings- 🍏 Eris Brewery & Cider House × Koval Distillery
- 🍯 Right Bee Cider × Heaven’s Door
- 🌳 Uncle John’s Hard Cider × Maplewood Brewery & Distillery
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🍔 Food Vendors (for purchase)- Irene’s Chicago
- Rojo Gusano 🌮
- Mindful Baking 🧁
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🚇 Getting There- 🚆 Public Transit: Montrose Brown Line nearby — CTA Trip Planner recommended
- 🚗 Driving/Parking: Metered parking on Ravenswood & Montrose; limited free street parking (watch signs). For less stress → SpotHero or Parking Whiz.
***
⚠️ No-Show Policy
🚫 3 no-shows without updating RSVP = 3-month freeze from future events.
✍️ RSVP cut-off = event start time.
📩 Running late? Message the host directly.
***✨🍏 Come thirsty, leave happy — join us for cider season’s best night out! 🍻🎶
