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 🌬️🚶♀️🚶♂️
Featured event
🎄✨ Broadway Barbara’s Holiday Spectacular – Live at The Den Theatre! 🎶💃
🎄✨ Broadway Barbara’s Holiday Spectacular – Live at The Den Theatre! 🎶💃
✨ A Holiday Tradition – Broadway Barbara Returns!
Behold — it’s a Christmas miracle! Broadway Barbara, legendary performer and social media sensation (@BroadwayBarbaraOfficial), returns to The Den Theatre for a festive, high-energy holiday spectacular. Celebrate the release of her new holiday album We Need a Little Barbara with a show packed with:
🎤 Classic holiday tunes
💃 All-singing, all-dancing fun
🎁 Christmas surprises & holiday cheer
This is a true gift to yourself — Broadway Barbara live onstage in Chicago!
📅 Monday, December 15, 2025
⏰ Showtime: 7:15 PM (we meet at 7 pm)
📍 The Den Theatre – 1333 N Milwaukee Ave, Chicago
🎟️ Tickets: $35 + fees | Must buy in advance — assigned seating
My seat: M3 | Seats still open in Rows M, N & O
👉 Buy tickets here: https://tickets.thedentheatre.com/event/broadway-barbaras-holiday-spectacular-rlnjrj
🎟️ More info: https://tickets.thedentheatre.com/
🍽️ Two-Item Minimum
Plan ahead to enjoy drinks or bites at The Den — it’s required for all guests.
🍽️ Pre-Show Dinner (Optional)
Some of us may arrive early around 5:30 PM to grab a bite before the show at Falafel & Grill, Antique Taco Wicker Park, or CAVA. All are welcome to join! Check back closer to the event date for updates and to finalize dinner plans.
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✨ Behold – it’s a Christmas miracle!
Broadway Barbara – legendary performer, social media sensation (@BroadwayBarbaraOfficial), and unstoppable force of pure entertainment – makes her triumphant return to The Den Theatre!
And this year, Barbara’s giving the season a real kick in the Santa pants! To celebrate the release of her new holiday album – We Need A Little Barbara (available this fall from Razzmatazz Records) – she’s bringing along a sack packed with classic holiday tunes, a sleigh full of slay, and at least two stockings piled full of Christmas surprises.
This all-singing, all-dancing, all-Barbara evening is the perfect holiday treat. Give yourself the gift that keeps on giving: Broadway Barbara, live onstage in Chicago!
💃 A Holiday Show with Camp, Parody, & Old Broadway Glamour! 🎶
Think campy, over-the-top parody, silly humor, and classic Broadway flair — if you love singing, dancing, and old-school theater glitz, you will love this show. Broadway Barbara, the faux Broadway diva with 400,000 social media followers, is back to dazzle Chicago with a holiday spectacular full of laughs, glitz, and glitter. 🎤💃
Read more about her: https://playbill.com/article/meet-broadway-barbara-the-faux-broadway-diva-who-has-300-000-followers-on-social-media
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🌟 What to Expect:
🎄 Classic holiday tunes
🎁 Silly surprises & outrageous fun
💃 All-singing, all-dancing, all-Barbara energy
🍽️ Two-Item Minimum – plan ahead for drinks or bites.
🌟 About Broadway Barbara
Barbara Dixon is a living legend: singer, dancer, and unstoppable entertainer. With decades of experience from Broadway to near-Hollywood, Barbara brings boundless energy, unforgettable tunes, and incredible stories to every performance. Fans and critics alike agree — every room becomes her stage!
Follow Barbara online:
🌐 https://www.broadwaybarbara.com/
📸 https://www.instagram.com/broadwaybarbaraofficial/
📺 https://www.youtube.com/broadwaybarbara
🏛️ About The Den Theatre
Located at 1331 N. Milwaukee Ave in Wicker Park, The Den Theatre opened in 2010 and has grown into a vibrant, multi-level live-entertainment venue. It houses five intimate performance spaces (from 50–300 seats) — perfect for theater, comedy, improv, musicals, and more. On the first floor, you’ll find The Den Bar & Lounge, where audiences gather before and after shows to socialize and enjoy craft cocktails The Den is home to several resident theatre companies (like About Face Theatre and First Floor Theater), and consistently features national comedians, local stars, and original productions. Their mission centers on connection, accessibility, and artistic diversity — creating a welcoming space for audiences and performing artists alike. Parking note: There’s no on-site parking — use SpotHero, ParkWhiz, or meter parking on Milwaukee Ave & side street
🚆 Transit & Parking:
CTA Trip Planner: https://www.transitchicago.com/planatrip/
Street parking available (metered & nearby side streets). Watch for signage.
❗ No-Show Policy:
3 no-shows without updating RSVP = 3-month restriction
Update RSVP before start time; message host if late
Check in with host upon arrival
🎄✨ Join us for a silly, glamorous, high-energy holiday evening — Broadway Barbara style!
Upcoming events
40
🎁✨ Holiday Magic After Dark-Lightscape Show at Chicago Botanic Garden!🎄🍸
Chicago Botanic Garden, 1000 Lake Cook Road, Glencoe, IL, US🎁✨ Holiday Magic After Dark-Lightscape Show at Chicago Botanic Garden! 🎄🍸
🎄✨ Lightscape at the Chicago Botanic Garden – Adults Only Night! 🍸🌟
📅 Thursday, December 4, 2025 | ⏰ 7:00–9:00 PM
📌 Hosted by: Mary Kinas
Join us for one of the most magical holiday experiences in Chicagoland — Lightscape at the Chicago Botanic Garden! We’ve chosen Adults Only Night (21+) for an evening filled with breathtaking lights, music, and special handcrafted drinks just for the grown-ups.
Please buy your ticket very soon because these nights and time slots sell out! I would hate for you to miss it!
🥂 Pre-Dinner at PF Chang’s (Northbrook)
- We’ll meet at 5:15 PM at PF Chang’s, 1819 Lake Cook Rd., Northbrook (near Northbrook Court Mall).
- If you can’t make it right at 5:15, just join when you can!
- After dinner, we’ll carpool to the Garden for our 7:00 PM entry to Lightscape.
🌟 How to Get Your Ticket (PLEASE READ ALL THE WAY THRU):
1️⃣ Go to the Chicago Botanic Garden Lightscape page
2️⃣ Choose “Lightscape 21 and Over Only.”
3️⃣ Select Thursday, Dec 4 – 7:00 PM entry time
4️⃣ Tickets: $36 (nonmembers)
5️⃣ Parking: $18 per car (members park free)
Here is the direct ticket link for Adults Night on 12/4/25 Make sure to hit Lightscape 21 and Over Only:
https://secure.chicagobotanic.org/webstore/shop/viewItems.aspx?cg=2050&c=12165
🚗 Transportation:
If you have a car and can offer a ride, please comment below!
Some members will carpool from the city, while others will meet at PF Chang’s to carpool from there and split parking costs at the Garden.
🚗 Carpooling Info
Need a ride? 🚘 Got a car with extra seats? 🪑 Drop a comment here so we can match people up!
👉 When posting, please include:
- 🚀 If you’re coming early for dinner or just for the light show portion at the Botanical Gardens
- 🕒 If you’ll stay for the whole event
- 📍 What part of the city are you located in / pickup area
✔️ RSVP only after you’ve purchased your ticket
🚫 Please update your RSVP if plans change
👯♀️ Guests are welcome — bring a friend and let’s make it a magical night!
🎉 With multiple Meetup groups joining in, it’s the perfect chance to mingle, make new friends, and enjoy some holiday magic together!
✨ Don’t miss this festive adults-only Lightscape adventure!12 attendees
✨🎁 5TH ANNUAL HOLIDAY PARTY @ DAD'S PLACE IN WRIGLEYVILLE! (w/KARAOKE!)🎁🎅⛄🤶
Dad's Place, 3369 N Clark St, Chicago, IL, US🎉🎄🎅 ANNUAL MULTI-MEETUP HOLIDAY PARTY! 🎅🎄🎉
📍 Dad's Place – Wrigleyville
🗓️ Starts at 7:00 PM — Please be on time to grab tables!! ⏰✨
Get ready for the MOST ✨🎁 FESTIVE 🎁✨ night of the year — our Annual Holiday Party is back and bigger than ever at Dad’s Place in Wrigleyville! 🍻🎉
Expect food 🍔, drinks 🍹, holiday cheer 🎄✨, and karaoke 🎤😄 all night long!
And YES — karaoke is TOTALLY optional 😉🙌 (sing, cheer, vibe — it’s all good!)
we'll be partying with multiple Meetup groups, so get ready to meet new people 🤝✨, make holiday memories 📸🎁, and celebrate the season together!
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🍔🍕🌭 DELICIOUS MENU ALERT! 🤤🎉
Come hungry — we’ve got all the goodies!
🍔 Burgers
🧀 Quesadillas
🌭 Brats & Chips
🍕 Pizza
🥑 Guac & Chips
YUM. 😋❤️
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🎤🎶🎄 ABOUT DAD’S PLACE
Wrigleyville’s coziest, friendliest, karaoke-loving holiday spot!
- 🎤 Karaoke & live music
- 🍺 Great drinks & tasty food
- 🎄 Cozy, festive, neighborhood vibes
🔗 Venue website: https://www.dadsplacechicago.com/
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✨💚❤️ FESTIVE ATTIRE ENCOURAGED! ❤️💚✨
Bring the HOLIDAY SPIRIT — any holiday you celebrate! 🎅🕎🎄🌟
🎉💫 Classic Holiday Festive Ideas:
- 🤶 Ugly sweaters (the uglier, the better!)
- ✨ Sparkles, sequins, glitter — SHINE!
- ❤️💚 Holiday colors galore
- 🎅 Santa hats • 🦌 Reindeer antlers • 🧝 Elf gear
- 🔔 Fun jewelry, scarves, socks — GO BIG!
The more festive, the more fun. 🔥🎄
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🚇🚗 GETTING THERE
- 🚆 Public Transit: CTA Trip Planner / Google Maps
🔗 transitchicago.com/planatrip
- 🚗 Driving: SpotHero or Parking Whiz recommended
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❗🚫 NO-SHOW POLICY
Help keep our events amazing! 🌟
- ❌ 3 no-shows = 3-month RSVP freeze
- 🕢 Update your RSVP before the event starts
- 📩 Late? Message the host!
- ✔️ Check in with the host at certain events
21 attendees
NEW DATE!🎄After-Work Drinks @Butch McGuire’s: Chicago’s Wildest Holiday Decor🍸
Butch McGuire's Tavern, 20 West Division Street, Chicago, IL, US***RESCEDULED TO MONDAY 12/8/25 @ 6 pm!***
🎄 After-Work Drinks @ Butch McGuire’s: Chicago’s Wildest Holiday Decor! 🍸
Holiday Cocktails & Bites in the Gold Coast
Let’s check out a true Gold Coast institution and one of Chicago’s most outrageously decorated holiday bars! 🎅✨ During the season, Butch McGuire’s transforms into a full-blown winter fever dream — lights, garland, giant ornaments, and not one but two double-decker trains chugging through the bar and antique room.
(Even Santa thinks it’s too much… which means it’s perfect for us!) 🎁🤣
📅 Monday 12/8/25 @ 6 PM
📍 Butch McGuire’s Tavern
20 W Division St · Chicago, IL
MEAL & DRINKS
Tables seat 4–6 and the bar does not take reservations, so we’ll be in small groups.
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💵 PLEASE BRING CASH!
They cannot do separate checks for groups.
Please add 32% (12% tax + 20% tip) to your total.
Cash makes everything easier for large groups!
This place gets crowded during the holidays so we will go on a Monday evening early in the season to beat the crowds!
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## 🍸 A Little Butch McGuire’s History (It’s Wild.)
In 1961, Butch McGuire borrowed money from his mother and opened his “world famous” saloon — sparking the legendary Rush & Division nightlife corridor.
The place quickly became Chicago’s first singles bar, and legend has it that 5,000–10,000 marriages began here over cocktails and chaos! ✨💍
Butch was famous for:
• Sending drivers to bring “stewardesses” from Sandburg Village
• Insisting men give up bar seats for women (or get thrown out!)
• Hiring female bartenders & managers before anyone else
• Inventing the Harvey Wallbanger & Skip and Go Naked
• Perfecting a Bloody Mary garnished with celery (still iconic)
And of course…
🎄 Turning Christmas at Butch McGuire’s into a Chicago tradition — complete with trains that raise money for the Boys & Girls of Mercy Home.
This man was camp before camp existed.
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## 📜 Links
Website: https://butchmcguires.com/
Facebook: https://www.facebook.com/ButchMcGuires/
Menu: https://butchmcguires.com/menu/#lunchdinner
Drinks: https://butchmcguires.com/menu/#beer
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## 🚇 Getting There
Use CTA Trip Planner: https://www.transitchicago.com/planatrip/
Easily accessible by bus & train.
## 🚗 Parking
Metered street parking on Division, Rush & side streets (watch signs!).
SpotHero & ParkWhiz strongly recommended.
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## 🚫 No-Show Policy
• 3 no-shows without updating RSVP = 3-month freeze
• Update RSVP before event start
• Message host if late
• Not checking in counts as a no-show
• Repeat offenders may be removed from the group
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🍸🎄 Join us for cocktails, comfort food, and the most gloriously over-the-top holiday decor in Chicago.
If you love glitter, lights, and pure holiday camp — this is the night out for you!18 attendees
Past events
793
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