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
12
🎉🌅 Sunset Soirée & Birthday Bash at Offshore Rooftop! 🍸🎂✨
Offshore Rooftop, 1000 E Grand Ave, Chicago , IL, US🎉🌅 Sunset Soirée & Birthday Bash at Offshore Rooftop! 🍸🎂✨
Let’s keep the party going! 🎊 Join us on Friday, October 17, 2025, to end the week right and celebrate my birthday in style. My official birthday is 10/22/25, but I love to celebrate all October long with my friends & meetup family. 🥳 Come raise a glass with me as we catch the sunset from the world’s largest rooftop bar — Offshore Rooftop on Navy Pier! 🌊🏙️
✨ Event Details ✨
📅 Date: Friday, October 17, 2025
🕕 Time: 6:15 PM (reservation time – please be on time!)
📍 Location: Offshore Rooftop, Navy Pier – 3rd Floor of Festival Hall
🌅 Highlights: 180° lake + skyline views, cocktails, bites, birthday fun***
🍹 Why Join Us?
Everyone loved this rooftop last time — it’s a Chicago must-do! We’ll have reserved tables (two groups of 10). It’s the perfect spot for after-work drinks, birthday toasts, and soaking up the last bit of good rooftop weather.🥂 Group Dining Rules (Important!):
- Tables are limited to 10 people each – we may not all sit together
- CASH ONLY for groups – no separate checks
- Please calculate your bill by adding +32% (12% tax + 20% tip) to your total
***
🍴 About Offshore Rooftop
- Guinness World Record: World’s Largest Rooftop Venue 🌍
- Coastal-inspired New American menu (light bites & shareables)
- Indoor/outdoor with retractable walls for all-weather comfort
- Incredible panoramic views of Lake Michigan & Chicago’s skyline
📜 Menu: Offshore Rooftop Menu
🌐 Website: offshorerooftop.com***
🚗 Getting There
- Parking: Valet at Navy Pier, East/West garages, or use SpotHero/ParkWhiz
- 🚇 CTA: Use CTA Trip Planner or Google Maps
- Note: Limited metered street parking a few blocks away
***
⚠️ No-Show Policy Reminder
✅ 3 no-shows = 3-month RSVP freeze
✅ RSVP updates allowed until event start time
✅ Check in with host on arrival
❌ Repeated no-shows = removal from the group***
🎂✨ Come for the skyline, stay for the company — and let’s toast to birthdays, sunsets, and friendship at the top of Navy Pier! 🌆🥳
22 attendees
🚪🏙️ Behind the Doors: Open House Chicago 2025 🔎🏛️
Chicago Board of Trade, 141 W Jackson, Chicago, IL, US🚪🏙️ Behind the Doors: Open House Chicago 2025 🔎🏛️
✨ Inside Chicago: Hidden Gems & Architectural Icons ✨
📅 Sunday, 10/19/25
🕙 10:00 AM – 5:00 PM
🚶♀️ Approx. 2.5 miles walkingThere's no bigger celebration of Chicago’s architectural diversity than the annual Open House Chicago! I have not had the Chicago Open House event with the group in a while, but I am going to give it a shot on Sunday. Let’s hope the weather cooperates! This is a great way to get inside buildings not normally open to the public or those you always wished you could look inside!
There’s no bigger celebration of Chicago’s architectural diversity than the annual Open House Chicago! For one weekend only, 200+ architecturally, culturally, and historically significant sites open their doors citywide. It’s one of the largest architecture events in the world 🌍—and free!
This year, I’ve picked 15 sites—a mix of new spots and old favorites. Locations may change based on lines, logistics, or weather, so check back for updates. Expect to stand in some lines at popular spots. Dress in layers since we’ll be in and out of buildings.
📍 Start: Chicago Board of Trade, 141 W. Jackson Blvd
📍 End: Columbia Yacht Club, 111 N. Lake Shore Dr (≈1.4 miles from start—plan parking accordingly!)### 🗺️ Tentative Site List:
- Chicago Board of Trade
- Wintrust Bank
- The Central Standard Building
- Federal Reserve Bank
- Union League Club
- The Red Building (333 S Wabash)
- Auditorium Building
- Fine Arts Building
- Cliff Dwellers
- Marquette Building
- 1 N Dearborn
- Nederlander Theatre
- McCormick Bridgehouse & River Museum
- PRU Building (180 N Stetson)
- Columbia Yacht Club
🚊 Transit: Use CTA Trip Planner
🚗 Parking: Limited meter parking + garages nearby. Try SpotHero or ParkWhiz for best options.🍽️ After the tours, some of us may stop for a bite depending on time & energy!
⚠️ RSVP / No-Show Policy:
- Cutoff to update RSVP = event start time.
- 3 no-shows without updating = 3-month freeze.
- Please check in with host upon arrival.
✨ Open the door to Chicago’s architectural gems—let’s explore together!
35 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! 🎤🌮🍻
7 attendees
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