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
22
🎃👻 Friday Night Frights: Rotten Rotter Halloween Party @ Replay! 🕸️💀
Replay Lincoln Park, 2833 N Sheffield Ave, Chicago, IL, US🎃👻 🎃👻 Friday Night Frights: 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 in the backroom of Replay Lincoln Park benefiting The Night Ministry! 🎉🎃❤️
We’ve been doing this for the past 4 years, and it’s always been a blast! Come enjoy a fun Halloween night with friends while supporting a worthy cause. 👻🍸
📅 EVENT DETAILS
📆 Friday, October 30, 2026
🕖 7:00–10:00 PM
📍 Replay Lincoln Park — Backroom
2833 N. Sheffield Ave., Chicago
🎤 Hosted by: Jan Rotter, our fellow Meetup member!
💰 Suggested Donation: $25 — proceeds support The Night Ministry.- Venmo: @Jan-GrossRotter
- Or donate at the door (cash/card accepted)
🎭 COSTUME CONTEST AT 9 PM! 👑🎃
Costumes are encouraged, so bring your Halloween spirit! Whether you go all out or keep it simple, come ready for a fun night. 💀🕸️🙌 YES, I’LL BE THERE THIS YEAR!
I’ll be attending, so come hang out with me and our Meetup friends! Even if you can only stop by for a little while, it’s a great opportunity to catch up, enjoy the Halloween festivities, and support a wonderful cause. ❤️🍸 DRINKS & ENTERTAINMENT
Everyone runs their own bar tab — there’s no set drink package. Replay has a great selection of cocktails, beer, and bourbon. 🍹🍺🎮 ABOUT REPLAY
Replay is a funky arcade bar featuring vintage video games, craft cocktails, and free classic games like Pac-Man, pinball, and bubble hockey. 🕹️🍻
🔗 Website: https://www.replaylincolnpark.com
🍸 Drink menu: https://www.replaylincolnpark.com/menu
📘 Facebook: https://www.facebook.com/replaylincolnpark🍔 FOOD: Replay does not offer food service, so eat beforehand! There are plenty of restaurants nearby if you want to grab a bite before or after the party. They do not allow outside food either but snacks will be available!
💖 WHY WE PARTY
This event supports The Night Ministry, a Chicago nonprofit providing housing, health care, and support to people experiencing homelessness. 🏠🌙Learn more or donate directly:
https://www.thenightministry.org
Even if you can’t make it, consider donating to this wonderful organization helping Chicagoans in need. ❤️✨🚇 GETTING THERE
- CTA buses and trains serve the area. Plan your trip: https://www.transitchicago.com/planatrip/
- Metered parking may be available on Sheffield, Diversey, and Wellington. Check posted restrictions.
- Driving? Check SpotHero or ParkWhiz for nearby parking options.
🚨 NO-SHOW POLICY REMINDER
Please update your RSVP if your plans change. Three no-shows may result in a temporary freeze on signing up for future events. Running late? Message the host directly.🎃🍸 LET’S GET OUR SPOOK ON! 👻
Come celebrate Halloween with great company, arcade games, cocktails, costumes, and a chance to give back to our Chicago community. I’m looking forward to seeing everyone and keeping this fun tradition going! 🕸️💀❤️Hope to see you there! 🎃🙌
11 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 🍹👻
Part 1 of 2 — Dinner before the Haunted Halsted Halloween Parade!
📅 Saturday, October 31, 2026
🕓 4:00–6:00 PM
📍 Las Mañanitas Mexican Restaurant
3523 N. Halsted St., Chicago🌮 LET’S EAT BEFORE THE HALLOWEEN FUN!
Join us for an early Mexican dinner before Chicago’s fabulous Haunted Halsted Halloween Parade! We’ll enjoy some food, drinks and conversation before heading out to catch the Halloween spectacle.
🍽️ IMPORTANT DINING DETAILS
Tables are first come, first served — no reservations accepted. Tables seat 4–6 people, and we’ll try to snag 2–3 tables together. Seating together isn’t guaranteed, so please arrive on time!💵 BRING CASH — NO SEPARATE CHECKS!
Please calculate your own total and add 32% for tax and tip (12% tax + 20% tip). Servers are limiting card transactions for large groups, so please come prepared with cash and enough small bills.🌮 ABOUT LAS MAÑANITAS
A lively Northalsted favorite serving Mexican dishes and margaritas! Think nachos, quesadillas, fajitas, burritos, seafood specialties and more. Come hungry!
🌐 Website: https://lasmananitas.business.site/website/lasmananitas/
📘 Facebook: https://www.facebook.com/pages/Las%20Mananitas%20Mexican%20Restaurant/120642407947004/🎭 AFTER DINNER: HAUNTED HALSTED PARADE!
After dinner, we’ll head toward our viewing spot near Halsted and Brompton. Please plan to meet outside at approximately 6:15 PM so we can get situated before the parade begins.👉 The parade is a SEPARATE Meetup event — RSVP there, too!
https://www.meetup.com/windy-city-wanderers/events/317068978/🚆 PUBLIC TRANSPORTATION
Belmont station serves the Red, Brown and Purple lines. The Addison Red Line station is another option, depending on your route.
CTA Trip Planner:
https://www.transitchicago.com/planatrip/🚗 PARKING
Halloween parade street closures and parking restrictions will affect the area. Don’t count on finding a spot directly on Halsted or Belmont. Check posted signs carefully and consider reserving parking in advance through SpotHero or ParkWhiz. Public transportation is likely your easiest option!📌 PLEASE UPDATE YOUR RSVP!
⚠️ Three no-shows without updating your RSVP = a three-month freeze from future events.- RSVP updates close at the event start time.
- Running late or unable to attend? Update your RSVP and message the host.
- Please check in with the host when you arrive!
🌮👻 Come for the tacos, stay for the tricksters, and let’s kick off Halloween night with good food and great company! 🎃🍹
26 attendees
🎃👻 HAUNTED HALSTED 2026 — COSTUMES, QUEENS & HALLOWEEN DREAMS! 🌈🎭
Las Mananitas, 3523 North Halsted Street, Chicago, IL, US🎃👻 HAUNTED HALSTED 2026 — COSTUMES, QUEENS & HALLOWEEN DREAMS! 🌈🎭
🎃 Chicago’s legendary LGBTQ+ Halloween celebration is back!
Get ready for outrageous costumes, fabulous performances, spooky surprises and plenty of Halloween fun in the heart of Northalsted, Chicago’s historic LGBTQ+ neighborhood!
📅 Saturday, October 31, 2026
📍 North Halsted Street — Belmont Avenue to Brompton Avenue
🕖 Parade kicks off at 7:00 PM - we meet outside about 6:15 pm👻 LET’S CELEBRATE HALLOWEEN CHICAGO-STYLE!
The Haunted Halsted Halloween Parade returns for its 30th anniversary, bringing hundreds of creative costumes, colorful characters and over-the-top Halloween spirit to the streets. The parade is free to watch, so come enjoy the show!
🍽️ PRE-PARADE DINNER — SEPARATE MEETUP RSVP REQUIRED!
We’ll have dinner beforehand at Las Mañanitas, 3523 N. Halsted Street, but seating is limited, so dinner is a separate Meetup event.👉 RSVP for dinner here:
https://www.meetup.com/windy-city-wanderers/events/317068971/
Please RSVP separately for dinner if you plan to join us. Attending the parade does not automatically reserve you a seat at the restaurant.🎭 THE PARADE — WHAT TO EXPECT
We’re watching toward the end of the parade route this year, near Halsted and Brompton, for a chance to catch the festivities as they come through!Look for some spectacular sights, including:
🔥 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
And, of course, the main attraction: fabulous, outrageous, creative and sometimes downright terrifying costumes!🏆 COSTUME CONTEST — $4,000 IN CASH PRIZES!
Feeling creative? The contest features five categories:
👑 Character: Media, pop culture, celebrities and historical figures
🎨 Creative: Originality, materials and wow factor
👻 Scary: Spooky and horror-inspired creations
👯 Group: Two or more people; one shared prize
🧒 Youth: Under 13, accompanied by an adultEach category awards $500 for first place, $200 for second and $100 for third.
Contest participation is $5 according to the official event information. Spectators can watch for free.📍 Parade begins at Halsted & Belmont at 7:00 PM and ends near Halsted & Brompton around 8:00 PM.
🏅 The costume contest and post-parade party follow at 3514 N. Halsted, with the official event scheduled to wrap up at 10:00 PM.
🚆 GETTING THERE — PUBLIC TRANSPORTATION
CTA is your best bet for avoiding Halloween traffic and street closures.
🚇 Belmont station serves the Red, Brown and Purple lines.
🚇 Addison station serves the Red Line.
Plan your trip:
https://www.transitchicago.com/planatrip/🚗 DRIVING & PARKING
Please plan ahead if you’re driving. Several streets around the parade route will have parking restrictions and vehicle closures on Halloween, including portions of Halsted, Brompton, Cornelia, Aldine and nearby streets.Check all posted signs and consider reserving a spot through SpotHero or ParkWhiz. Public transportation is likely the less stressful option!
🐾 BRINGING A PET?
Pets are welcome to watch or participate in the parade, but must be leashed or carried. Consider your pet’s comfort with large crowds, loud music and Halloween costumes before bringing them along.🌧️ RAIN OR SHINE — OR EVEN SNOW!
The official event information says the parade goes on despite rain or snow, so dress for the weather and wear comfortable shoes.🎃👠 COSTUMES ARE ENCOURAGED!
We’ve done this for several years, and it’s always a blast! Come dressed up, come ready to people-watch, or simply enjoy the parade and all the Halloween creativity.📌 PLEASE UPDATE YOUR RSVP!
If your plans change, update your RSVP by the event start time so someone else can take your spot.⚠️ NO-SHOW POLICY
- Three no-shows without updating your RSVP = a three-month suspension from future events.
- RSVP updates close at 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 and festivals.
- Continued no-shows may result in removal from the group.
🌈🎃 Let’s make Halloween unforgettable in Boystown/Northalsted, with great company, outrageous costumes and one of Chicago’s most entertaining Halloween traditions!
I hope you’ll join us for a little spooky fun! 👻🥂🎉
17 attendees
Past events
1087
