
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
64

🎸🎷 Golden Hour @Epiphany Center: FREE Blues, DJ Grooves & Art Adventures! 🎨
Epiphany Center for the Arts, 201 South Ashland Avenue,, Chicago, IL, US🎶🎷 Golden Hour @Epiphany Center: FREE Blues, DJ Grooves & Art Adventures! 🎨
🎶 Free Blues Friday @ Epiphany Center for the Arts in the West Loop! 🎸
We had such a great time last year, we’re heading back for more! Let’s enjoy a relaxed Friday evening at the Epiphany Center for the Arts, exploring live music, art exhibits, and their cozy café bar.
📅 Friday, November 14, 2025
🕕 6:00–10:00 PM
📍 Epiphany Center for the Arts, 201 S. Ashland Ave
🎟️ Free Admission — Registration Required
👉 Register here for DJ & Golden Hour: https://epiphanychi.com/events/golden-hour-featuring-julio-bishop-11-14/
👉 Register here for Free Friday Blues show: https://epiphanychi.com/events/live-on-the-lawn-featuring-smiley-tillmon-band-with-kate-moss-11-14/***
✨ Event Lineup:
🎧 Live DJ Sets from Julio Bishop — 5 PM–8 PM (FREE!)
🎸 Free Blues Friday featuring Smiley Tillmon Band with Kate Moss — 7:30 PM
(Performance will be outside in the Courtyard or in the spacious Epiphany Hall — weather dependent.)***
🍷 Golden Hour Happy Hour Specials (5–7 PM)
- SELECT ½-price bottles of house wine
- SELECT $4 craft beers
- SOME 2-for-1 “Lite Bites”
(Outside in the courtyard or inside café/Sanctuary if it’s too cold)
If you can’t arrive until after 6 PM, no problem — we’ll grab tables early and hang out in the bar/café area to enjoy the DJ, then pop into the galleries to check out the art before heading over to the great hall at 7:30 PM for the blues show! 🎶
***
🎧 About Julio Bishop (DJ):
If you were around during Chicago’s underground House Music movement or rave scene in the late ’80s and early ’90s, then you’ll know the name Julio Bishop. Whether from his legendary mix tape “Love Nation” or his iconic Midwest party sets, Bishop has been rocking dance floors since 1987.Starting as a dancer and DJ in Chicago’s clubs and warehouses, he quickly expanded his influence to NYC, LA, Miami, Puerto Rico, Mexico, Germany, and Sicily — bringing deep, soulful grooves wherever he spins.
Known for his mastery of Afro-Latin, Jazz, Disco, Electronica, Club & Deep House, Bishop’s sets transport listeners beyond the ordinary. In the 2000s, he co-founded RealDEEP Recordings with Brian Cullen (aka Bjak), producing on labels like Deep Explorer Music (Madrid) and Eargasmic Recordings (Chicago).With upcoming gigs across the U.S. and abroad, Julio Bishop remains a true house music veteran — a Chicago original still setting the vibe three decades strong.
https://www.instagram.com/badmixxbishop/
***
🎸 About the Smiley Tillmon Band (with Kate Moss):
One of the busiest and most beloved blues bands in Chicagoland, the Smiley Tillmon Band is pure joy on stage. Led by veteran guitarist Smiley Tillmon, the band serves up high-energy blues and soul classics that keep crowds smiling from ear to ear.Born Moses Tillmon in rural Georgia, Smiley’s musical journey began with gospel and country, later infused with Caribbean rhythms after moving to Florida. By the early 1960s, he was performing with Miami R&B acts before moving to Chicago, where he became a fixture on the South Side blues scene, playing with greats like Billy “The Kid” Emerson and Denise LaSalle.
After retiring from his day job in 2007, Smiley returned full time to the stage — teaming up with bassist Tom Rezetko, drummer George Baumann, and guitarist Kate Moss (whose powerful, Freddie King–inspired style and collaborations with Buddy Guy and Nick Moss make her a standout performer). Together, they form one of Chicago’s toughest blues combos.
🪶 “Smiley knows how to have a good time — and makes sure his audience does too.” — Bill Dahl
https://www.smileytillmonband.com/
***
🎨 Current Art Exhibits:
- Melissa Weber – Ode to Common Things (Barcelona Room)
- Laurie LeBreton – Insisting and Maintaining (Slemmons Gallery)
- Margot McMahon – Ring of Fire: Friends, Reefs, and Bouncing Back (Guild Room)
- Laurie Buman – Santos y Milagros (Saints & Miracles)
- The Light Within the Darkness Series (Sacristy Gallery)
- Marianne Lovink – Counterweight (Catacombs Gallery)
🖼️ More info: https://epiphanychi.com
☕ Café Bar & Menu: https://epiphanychi.com/cafe-bar-menu/***
🏛️ About the Venue:
The historic Church of the Epiphany has been beautifully preserved and transformed into a 42,000 sq. ft. arts campus dedicated “For the Good of Art, Entertainment, and Events.”Conceived with the vision of returning Epiphany to a gathering place for the community, the once-shuttered church has been thoughtfully adapted into an iconic cultural hub in the West Loop. The campus features three distinct venues, multiple art studios, classrooms, exhibit and gallery spaces, a café, commercial and catering kitchen, VIP suite, and a collection of artistically designed outdoor spaces — including a charming quarter-acre courtyard, spacious terrace, and stunning patio.
The property was acquired and lovingly restored by David Chase and Kimberly Rachal, who were married at the Church of the Epiphany 23 years ago. Together, they’ve invested $15 million to preserve its architectural legacy and reimagine it as a vibrant destination for art, culture, and community in Chicago’s West Loop.
***
🚗 Getting There:
- CTA Trip Planner: https://www.transitchicago.com/planatrip/
- Parking: Metered street parking on Ashland & Adams + limited free spots on side streets (watch for signs).
***
⚠️ Please keep your RSVP up to date and don’t be a no-show!
8 attendees
🏙️🛤️ Milwaukee Ave Uncovered: Trails, Towers & Treasures 🚶♂️🌆
Germain House, 729 Sagamon, Chicago, IL, US🏙️🛤️ Milwaukee Ave Uncovered: Trails, Towers & Treasures 🚶♂️🌆
A Saturday fall stroll through River West, Noble Square & Wicker Park
☀️ I know we just had some snow, but it’ll be MUCH warmer this weekend — and it is still good walking weather, so let’s make the most of it! 🚶♀️🌆 We’re ending the season with another great neighborhood adventure!
Take a historical stroll down one of Chicago’s oldest streets — while the weather’s still walking-worthy!
Walk the old Native path, check out iconic Polish churches, and uncover stories of long-gone shops that made this street famous.
Ready to step off the grid and onto one of Chicago’s oldest, boldest streets? Join us for a guided walk down Milwaukee Avenue — a diagonal slice of city life with layers of history. From Indigenous trails and Polish cathedrals to vanished department stores and reborn landmarks, we’ll explore how this vibrant corridor keeps reinventing itself.
***
🗓️ Saturday, November 15, 2025
🕚 12:00 PM – 2:20 PM
📍 Start: Germain House, 729 N. Sangamon St.
🎯 End: The Robey Hotel, 2018 W. North Ave. (~2.5 miles total)
💰 Cost: $20 (cash preferred; Zelle, Venmo, PayPal accepted)
🚶♀️ Casual pace | Entirely outdoors⚠️ Note: Walk ends 2.5 miles from the start — if driving, consider parking near the midpoint! Or hop the L or a bus back.
☀️ A casual, curiosity-filled outing for lovers of Chicago stories, old and new.
***
🔍 What You’ll See & Learn:
✅ One of Chicago’s oldest trails — from Native path to Polish main street
✅ Grand churches, vanished businesses, reborn banks, and funky artist spaces
✅ Architectural eye candy paired with deep neighborhood stories
✅ The ever-evolving tale of immigrant hustle, urban reinvention, and civic pride📸 Not a photo walk, but you’ll want your camera!
🎤 Led by your passionate, ever-curious guide (that’s me!) — perfect for architecture buffs, history lovers, and anyone who wants to be a tourist in their own city.
***
🗺️ Route Highlights (subject to change):
🏠 Germain House – Queen Anne gem
⛪ St. John Cantius – A Polish baroque beauty
⛪ St. Boniface – Towering twin-spired ghost
🌳 Eckhart Park – A community anchor
🏛️ Polish Museum of America – A cultural time capsule
🕍 Holy Trinity – Where grandeur meets grit
⛪ St. Stanislaus Kostka – The original Polish cathedral
🌿 Pulaski Park – WPA charm in a leafy square
🧠 National Alliance – Mid-century mission hub
🏦 Home Bank & Trust – Financial strength in stone
🏬 Wieboldt’s (former) – Lost department store legend
🎨 Indigo Lofts – Wallpaper meets art lofts
🎭 Flatiron Arts – Boho central
🏛️ Noel State Bank – Walgreens with a dome
🏨 The Robey – A tower of transit turned trendy hotel***
🏙️ Fun Facts Along the Way:
💬 Milwaukee Ave began as a Native trail, then became a plank-lined toll road
🚌 Streetcars once zipped through what’s now rush-hour traffic
🎨 Wicker Park’s art scene exploded here in the ’80s
🍺 Expect tales of beer barons, preservation fights, and colorful characters***
📌 Quick Logistics:
✔️ Start near Grand Blue Line
✔️ End near Damen Blue Line
✔️ Wear good walking shoes & bring water
✔️ DM or email with questions
✔️ Tour runs rain or shine! 🌦️👟 What to Bring:
• Comfortable walking shoes
• Water bottle
• Weather-appropriate attire
• $20 tour fee (exact change appreciated; cash preferred but Zelle, Venmo, PayPal accepted)***
🍽️ Optional Lunch After the Tour
Stick around and grab a bite at one of these local favorites:
• 🥗 Sultan’s Market – casual Middle Eastern eats
• 🥪 CAVA – build-your-own Mediterranean bowls
• 🍕 Paradise Park – funky patio vibes + pizza
• 🌮 Big Star – beloved taco + whiskey joint
💵 Bring cash for lunch — some spots don’t split checks!***
🧭 Come walk where the old city still hums — Milwaukee Ave is calling.
2 attendees
🎅🎄 5th Annual Holiday Dinner Under the Great Tree at the Walnut Room! 🎁🍽️
The Walnut Room, 111 N. State St., Chicago, IL, US🎅🎄 5th Annual Holiday Dinner Under the Great Tree at the Walnut Room! 🎁🍽️
🎄✨ A Chicago Holiday Tradition: Dinner Under the Great Tree at the Walnut Room! 🍽️🎁
Let’s kick off the holiday season with a Chicago classic — a traditional Christmas dinner beneath the Great Tree inside Macy’s (forever known as Marshall Field’s!) in the gorgeous Walnut Room. 🌟
For the 5th year in a row, we’re keeping this beloved 1001 tradition alive! 🎉 Normally, we dine on Black Friday, but this year the only available reservations I could get was Monday, November 17 @5pm, so we’ll be celebrating a bit early — while the Christmas décor inside and outside Macy’s will be already in full swing! 🎅🎄✨
> 💡 The Christkindlmarket opens on Nov 21, but you’ll still enjoy all the magical holiday lights, décor, and festive spirit!
I could not get my normal 40 spots, so we are limited to only 16 this year. 😢 Please only RSVP if you are 100% sure you can attend!
***
### 🍽️ DINNER & DRINKS DETAILS
📅 Date: Monday, November 17, 2025
🕔 Time: 5:00–7:00 PM (arrive on time — the restaurant will not seat us until our full group has arrived; allow extra time for traffic & parking!)
📍 Location: The Walnut Room, Macy’s (111 N State St, Chicago)
👥 Group Size: Limited to 16 guests only! (4 tables of 4 each)
⚠️ Tables are small this year and we may not sit together.
💵 Bring Cash! The Walnut Room cannot do separate checks for groups.
👉 Please total your meal cost and add 32% (12% tax + 20% tip) for simplicity.***
### 🕯️ ABOUT THE WALNUT ROOM
The world-famous Walnut Room was the first restaurant ever opened inside a department store (est. 1905). With Circassian walnut paneling imported from Russia, Austrian chandeliers, and its signature Mrs. Hering’s Chicken Pot Pie, it remains one of Chicago’s most cherished holiday dining experiences. 🍗🎁✨
📖 Learn more:
🔗 Main Site → https://macysrestaurants.com/walnut-room/
🔗 Holiday Info → http://macysrestaurants.com/walnut-room/holiday2025/
🔗 2025 Holiday Menu → http://macysrestaurants.com/walnut-room/holiday-menu-2025/***
### 🚆 GETTING THERE
🚇 Public Transit: https://www.transitchicago.com/planatrip/
🚗 Driving? Metered parking on Randolph, Monroe, and nearby streets (watch for signs).
💰 Save money: Use SpotHero or ParkWhiz for cheaper parking options.
⏰ Be on time! They will only seat us once the full party has arrived.***
### 🚫 NO-SHOW POLICY
To keep things fair for everyone:
❌ 3 no-shows = 3-month RSVP suspension
⏰ RSVP updates must be made before event start time
📲 Check in with the host upon arrival
⚠️ Repeated no-shows may result in removal from the group***
🎁✨ A little sparkle, a little nostalgia — and a whole lot of holiday cheer! 🎄🥂
17 attendees
🎤🌮🎶 Live Band Karaoke + Taco Tuesday! Multi-Group Meetup! 🎶🌮🎤
All Star Seafood and sports, 730 South Clark, Chicago, IL, US🎤🌮🎶 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! 🎤🌮🍻
1 attendee
Past events
778

