About us
🎉 Welcome to & Windy City Wanderers! 🌆
We’re so glad you’re here!
Whether you’re new to Chicago or a lifelong local, these sister groups are all about being a tourist in your own city—discovering hidden gems, rich history, fun facts, and unforgettable experiences across Chicagoland. 🗺️✨
Windy City Wanderers is the sister group to 1001 Things to See in Chicago Before You Die, and we host many joint events together—so you’ll often see crossover adventures and shared outings. 🤝
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🗓 What to Expect
We host fun, social outings year-round (yes, even in winter ❄️). Expect:
• Walking tours & neighborhood explorations
• Concerts, lectures & theater
• Pop-up dinners, trivia & social nights
• Museums, festivals & special events
Events take place throughout Chicago and nearby suburbs like Evanston, Oak Park, and Park Ridge.
🚇 All events are CTA-accessible.
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💬 Why Join?
• Discover new places all over Chicagoland
• Meet new people and make real connections
• Enjoy an active, well-curated event calendar
• Try the group FREE for 90 days
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💰 Membership
• 90-day free trial
• Annual dues: $12/year after the trial
• 🎉 Host an event and your dues are waived!
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🚨 RSVP / No-Show Policy (Please Read)
To keep events fair and running smoothly:
• A no-show without updating your RSVP = 1 strike
• 3 strikes = a 3-month pause from events
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🤝 Stay Connected
📘 Facebook Page
https://www.facebook.com/profile.php?id=61576822533554
👥 Facebook Group
https://www.facebook.com/groups/1571684466442303
📸 Instagram
https://www.instagram.com/1001thingstoseeinchicago/
🌬️ !001 Things to See in Chicago Before You Die Meetup (sister group)
https://www.meetup.com/windy-city-wanderers
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💡 Have an idea for an event? Want to host or co-host?
Just message me—I’d love to hear from you!
Can’t wait to explore, wander, and discover Chicago together 💙
Cheers,
Giovina Romandine
Organizer, Windy City Wanderers 🌬️🚶♀️🚶♂️
Upcoming events
23
🎸 Let The Festival Season Begin — Chicago Mayfest 2026! ☀️
Armitage @ Sheffield, 1000 W Armitage Ave, Chicago, IL, US🎸 Let The Festival Season Begin — Chicago Mayfest 2026! ☀️
The outdoor live music season is HERE and we're kicking it off right! 🙌☀️ Chicago Mayfest has been a beloved Lincoln Park staple for 28 incredible years — and this year promises to be the best one yet! We're heading out Sunday to catch some amazing bands, browse the Armitage Art Show, and soak up that festival energy. It's FREE to enter (suggested $10 donation, no obligation)! 🎶
Join us as they turn every inch of Armitage into an endless celebration showcasing all the amazing talent and businesses based in Chicago! Featuring two stages of the city's most acclaimed bands and up-and-coming talent, mouthwatering bites from your favorite local restaurants, endless paintings and sculptures in the Armitage Art Show, and unique treasures at the artisan market. 🎨🛍️
Chicago's top party bands headline the west end while the Artist's Lounge anchors the east end — plus all the delicious summertime food and libations needed to light up your weekend! 🍹📍 LOGISTICS
📅 Sunday, May 17, 2026
⏰ Meet at 2:30 PM sharp — please be on time, we go in together!
📍 Meet at 1000 W. Armitage (corner of Armitage & N. Sheffield), Chicago
🎪 Festival runs May 15–17, 2026 along Armitage Ave in Lincoln Park
💰 Free admission | $10 suggested donation (not obligated!)***
🎵 SUNDAY BAND LINEUP
🎸 Sheffield Stage- 1:00 PM — Whiskey Misfits
- 3:00 PM — Second Hand Soul Band ✅ (we will see this band!)
- 5:30 PM — Rosie & The Rivets ✅ (we will see this band!)
- 7:30 PM — The Reception (might check out!)
🎹 Racine Main Stage
- 12:30 PM — School of Rock
- 2:15 PM — One Night Band
- 4:00 PM — Matchbox 90's
- 5:30 PM — Jak Tripper
- 7:30 PM — Simply Elton (some might check out!)
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💚 Please support the RANCH Triangle Community Conservation Association with the suggested $10 donation — though you are never obligated to pay or can give a lesser amount!
🎪 WHAT TO EXPECT AT MAYFEST
- 🎶 Two stages of Chicago's most acclaimed bands & up-and-coming talent
- 🍽️ Mouthwatering bites from local Chicago restaurants
- 🎨 Armitage Art Show — paintings, sculptures & more
- 🛍️ Artisan market with unique one-of-a-kind finds
- 🍹 All the libations needed to light up your weekend!
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🚇 GETTING THERE 🚇 Brown Line — closest stop to the festival
🚌 Several CTA bus routes along Armitage
🗺️ CTA Trip Planner: https://www.transitchicago.com/planatrip/🚗 Parking is very limited during the festival — public transit strongly recommended!
🅿️ If you must drive: metered parking on Armitage & Sheffield, use SpotHero or ParkingWhiz📱 Lost or running late? Call/text 312.835.4259
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⚠️ NO-SHOW POLICY
- 😬 3 no-shows without updating your RSVP = 3-month event ban
- ⏰ Update your RSVP before the event start time; after that, message the host directly
- 👋 Check in with the host upon arrival
- 🚫 Continual no-shows = removal from the group
25 attendees
🎤🌮🎶 Live Band Karaoke/Uno Multi-Group Meetup! 🎶🌮🎤
All Star Seafood and sports, 730 South Clark, Chicago, IL, US🎤🌮🎶 Live Band Karaoke /Multi-Group Meetup! 🎶🌮🎤
**⭐ Hosted by Deanna (**musiclovermay18) ⭐
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! 🎤🌮🍻
6 attendees
Past events
932
Group links
Members
186
