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
36
🎃👻Weeknight Spook: The Annual Rotten Rotter Halloween Party @Replay! 🕸️💀
Replay Lincoln Park, 2833 N Sheffield Ave, Chicago, IL, US🎃👻Weeknight Spook: The Annual Rotten Rotter Halloween Party @Replay! 🕸️💀
🎃👻 It’s BACK! The Annual Rotten Rotter Halloween Party @ Replay Lincoln Park**!** 🕸️💀
It’s spooky season, and that means it’s time for the Rotten Rotter Halloween Bash — a private party held in the backroom of Replay Lincoln Park to support The Night Ministry! 🎉🎃
We’ve done this the last 3 years and it’s always been a blast — a fun night for a worthy cause! ❤️
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🎤 Hosted by: Jan Rotter (our fellow Meetup member!)
👉 Note: I will not be attending this year, so please look for Jan Rotter when you arrive. It’s a friendly, welcoming crowd — you’ll have a great time! Make sure to check in with Jan so she knows you are there!
📅 Date: Thursday, October 30, 2025 (yes, a Thursday!)
💬 Normally this event is held the Friday before Halloween, but since Halloween falls on Friday this year, the party was moved up a day. Please stop by — even if just briefly — to show support and join the fun! 🎉👻
🕖 Time: 7:00 PM – 10:00 PM
📍 Location: Replay Lincoln Park
2833 N. Sheffield Ave, Chicago, IL (BACKROOM)
🔗 replaylincolnpark.com
💰 Suggested Donation: $25 (supports The Night Ministry)- Pay via Venmo: @Jan-GrossRotter
- Or at the door (cash/card)
🎭 Costume Contest @ 9 PM! 🎃👑
💀 Costumes encouraged!
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🍸 Everyone runs their own bar tab — no set drink package. Replay has great cocktails, beer, and bourbon options. 🍹🍺
(No food service — eat before you arrive. Plenty of restaurants nearby to grab a bite before or after!)🎮 About Replay:
A funky arcade bar with vintage video games, craft cocktails, and free classics like Pac-Man, pinball, and bubble hockey — guaranteed fun! 🕹️🍻
💻 Drink Menu
📘 Facebook Page***
💖 Why We Party:
Proceeds benefit The Night Ministry, a Chicago nonprofit providing housing, health care, and support to those experiencing homelessness. 🏠
Learn more or donate directly: thenightministry.org
Even if you can’t attend, please consider donating — it’s a great cause that helps Chicagoans in need. 🌙✨***
🚗 Getting There:
- CTA accessible via bus/train ➡️ Plan your trip
- Metered parking on Sheffield, Diversey & Wellington (watch for restrictions)
- Use SpotHero or Parking Whiz for best parking options
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⚠️ No-Show Policy Reminder:
Please update your RSVP if your plans change. 3 no-shows = temporary removal from future events.
If late, message the host directly.5 attendees
🌮🎃 Tacos & Tricksters! Early Dinner @Las Mañanitas Before Haunted Halsted 🍹👻
Las Mananitas, 3523 North Halsted Street, Chicago, IL, US🌮🎃 Tacos & Tricksters! Early Dinner @Las Mañanitas Before Haunted Halsted 🍹👻
Early Dinner Before Halsted Halloween Parade @Las Mananitas (Part 1 of 2)
📍 Las Mananitas Mexican Restaurant, 3523 N Halsted St, Chicago
🕕 Friday, Oct 31, 2025 | 5:00 PM – 7:00 PM (before parade)Join us for dinner before the 28th Annual Haunted Halsted Halloween Parade! Tables are first come, first served—no reservations—and each fits 4–6 people. We’ll try to grab 2–3 tables together.
💵 BRING CASH – no separate checks!
Please total your order + add 32% (12% tax + 20% tip). Servers are limiting card transactions for large groups.🎭 Parade After Dinner: Sign up separately here → https://www.meetup.com/windy-city-wanderers/events/311410550/
🍽️ About Las Mananitas:
A lively Northalsted favorite known for its delicious Mexican dishes & margaritas! From nachos and quesadillas to fajitas, burritos, and seafood specialties, there’s something for everyone.🌐 Website: https://lasmananitas.business.site/website/lasmananitas/
📘 Facebook: https://www.facebook.com/pages/Las%20Mananitas%20Mexican%20Restaurant/120642407947004/🚊 CTA Trip Planner: https://www.transitchicago.com/planatrip/
🚗 Street parking on Halsted, Belmont & side streets (use SpotHero or ParkWhiz).⚠️ No-Show Policy:
– 3 no-shows = 3-month freeze
– Cutoff to update RSVP = event start time
– Always check in with the host on arrival11 attendees
🎃👻 Haunted Halsted 2025 – Costumes, Queens & Halloween Dreams! 🌈🎭
Las Mananitas, 3523 North Halsted Street, Chicago, IL, US🎃👻 Haunted Halsted 2025 – Costumes, Queens & Halloween Dreams! 🌈🎭
Chicago’s legendary LGBTQ+ Halloween celebration returns! in Chicago’s landmark LGBTQ+ Northalsted neighborhood
📅 Friday, October 31, 2025
📍 Halsted St from Belmont Ave to Cornelia Ave
🕢 Parade Kickoff: 7:30 PM at Halsted & Belmont***
Dinner before the parade will be hosted as a separate Meetup event (due to limited spots) at Las Mananitas .
👉 RSVP here for dinner: https://www.meetup.com/windy-city-wanderers/events/311410480🎭 About the Parade:
The Haunted Halsted Halloween Parade is back for its 28th year — and it’s one of the top ten Halloween parades in the U.S. (Fodor’s Travel)! This is a free-to-watch event filled with jaw-dropping costumes, high-energy performances, and tons of spooky fun.💰 The spectacular Costume Contest features hundreds of entrants competing for $4,000 in cash prizes, concluding with an awards presentation.
🎤 The 2025 Parade Grand Marshals will be announced soon!
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🔥 Parade Highlights:
- Chicago Full Moon Jam fire performers
- Windy City Jeep Club
- Chicago Thriller dance troupe
- Lakeside Pride Marching Band
- Windy City Rollers
- Chicago Spirit Brigade pep squad
If you’ve never seen this parade, you’re in for a show! The costumes are always fantastic — it’s one of the 10 Best Halloweens in the U.S. (Fodor’s Travel Guide) and ranked #3 Best City for Halloween by Redfin.
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🏆 Costume Contest Details:
$4,000 in total prizes!
Each of the five categories awards:
🥇 $500 (1st Place) 🥈 $200 (2nd Place) 🥉 $100 (3rd Place)
Categories:- Character: Media, pop culture, celebrity, history
- Creative: Originality, materials, wow factor
- Scary: Spooky, horror-inspired
- Group: Two or more people (one shared prize)
- Youth (<13): Must be accompanied by an adult
🎟 Contest Registration: 6:30 PM – Halsted & Belmont
🎉 Parade Kickoff: 7:30 PM – Halsted & Belmont
🎭 Parade Ends: 8:00 PM – Halsted & Cornelia
🏅 Awards Show: 8:30 PM – Halsted & Brompton (3514 N. Halsted; parking lot)
🍸 Afterparty: 10:00 PM – End of event (optional bar hopping!)***
🍽️ Pre-Parade Dinner (Separate RSVP):
We’ll meet at Halsted & Brompton near Las Mananitas (3523 N. Halsted).
We’re viewing the parade this year toward the end of the route for the best view of the festivities!🚆 Public Transportation:
A short walk from the CTA Belmont Red/Brown/Purple Line Station or Addison Red Line Station
Plan your trip: CTA Trip Planner
🚗 Driving/Parking:
Street parking available on Halsted, Belmont, or Addison, plus side streets.
Watch for no parking and permit-only signs — some areas will be blocked off for the parade.
Use SpotHero or Parking Whiz for best options.🐾 Pets: All pets are welcome to march or watch!
🌧️ Weather: The parade goes on rain or snow!***
🚫 No-Show Policy:
Please respect our group’s attendance policy:- 3 no-shows without updating your RSVP = suspension from future events for 3 months
- Cut-off time to update RSVP is the event start time
- If you miss the start, message the event host directly
- Not checking in with the host counts as a no-show (for walks, tours, or festivals)
- Continued no-shows may result in removal from the group
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🎃👠 Come in costume for even more fun — we’ve done this for several years and it’s always a blast!
Let’s make this Halloween unforgettable in Boystown/Northalsted!
21 attendees
Past events
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