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 🌬️🚶♀️🚶♂️
Featured event
🎤😂 Heaven, Hell & Hilarity: Amy Armstrong Live at Hydrate! 🎶✨
🎤😂 Heaven, Hell & Hilarity: Amy Armstrong Live at Hydrate! 🎶✨
Get ready for an unforgettable night with one of Chicago's most entertaining performers! Join us for Amy Armstrong: Heaven, Hell & Back Again Tour—a hilarious and heartfelt evening filled with powerhouse vocals, outrageous comedy, and unforgettable stories.
A two-time cancer survivor, Amy transforms life's biggest challenges into laughter, inspiration, and incredible music. One minute she'll have you wiping away tears of laughter, the next she'll leave you speechless with her amazing voice. She's witty, warm, fearless...and yes, she swears like a sailor! 😄 If you're easily offended by adult humor or racy stories, this may not be the show for you. Otherwise, you're in for a fantastic evening!
📅 Saturday, August 15, 2026
🕕 Meet: 6:00 PM (doors open)
🎤 Show: 7:00–9:00 PM
📍 Hydrate Nightclub 3458 N. Halsted St. Chicago, IL 60657
🎟️ Tickets Required
General Admission: $33.85 (includes fees)
Purchase tickets here:
https://www.eventbrite.com/e/amy-armstrong-heaven-hell-back-again-tour-tickets-1991424647729
❤️ A Personal Recommendation from Giovina: I've been going to Amy Armstrong's shows since the mid-1990s, back when she lived in Chicago and frequently performed with the legendary Freddy Allen. Although she now calls Mexico home, she still tours the U.S. and always makes a stop in Chicago. I can honestly say her shows are consistently hilarious, heartfelt, and packed with incredible vocals. Every time she comes back to town, I make it a point to see her—and she never disappoints!
### 🌟 About Amy Armstrong
Known as the "Diva of Song and Fun," Amy Armstrong combines an extraordinary voice with razor-sharp comedy and heartfelt storytelling. Whether she's belting out Broadway favorites, pop classics, or sharing hilarious tales from life on the road, Amy creates an evening that's uplifting, funny, and unforgettable.
🌐 Website:
https://amythedivaarmstrong.com/
### 🌈 About Hydrate
Hydrate has been one of Chicago's most popular LGBTQ+ nightlife destinations since 2003. Located in the heart of Northalsted, the club features live entertainment several nights a week before transforming into a high-energy dance club with nationally known DJs later in the evening.
We'll meet at 6:00 PM so we can grab seats together before the show begins.
🍹 Everyone orders drinks individually and keeps their own tab at the bar.
https://hydratechicago.com/
⚠️ RSVP Reminder
Please update your RSVP if your plans change.
If you're running late or can't find the group, call or text Giovina at 312-835-4259.
Come enjoy an evening of incredible music, outrageous laughs, and one of Chicago's most beloved entertainers. It's guaranteed to be a night you won't forget! 🎤😂🎶
Upcoming events
43
🧘♀️ Mat & Morning Magic: Free Yoga in the Park! 🌞
Millennium Park, 201 E Randolph St, Chicago, IL, US🧘♀️ Mat & Morning Magic: Free Yoga in the Park! 🌞
🌞 Millennium Park Outdoor Yoga – Hosted by Carol
Stretch, smile, and salute the sun with your fellow yogis on the Great Lawn — Carol's got her purple mat and good vibes ready!
🧘♀️ FREE Summer Workout Series
📍 Millennium Park – Great Lawn (Behind Harris Theater)
📅 Saturday, August 1, 8 & 15, 2026
🕘 Yoga: 9:00 AM – 9:45 AM | Meet at 8:40 AM!Join your event host Carol for the kickoff to the Millennium Park Summer Workouts! She'll be at the front of the lawn area near the stage with her purple yoga mat so you can easily find her. Enter the park from Michigan Ave at Washington or Madison.
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💧 Bring:
🧘♀️ Yoga mat
💦 Water bottle
☀️ Sunscreen
👗 Comfortable clothes for movement***
🗓️ Full Workout Schedule:
8:00–8:45 AM — Pilates (Carol won't be here for this, but you can join!)
9:00–9:45 AM — Yoga *(Our group joins here!)*⭐
10:00–10:45 AM — Cardio Kickboxing
11:00–11:45 AM — Zumba***
🟢 Weather Note: Event will be canceled if it rains.
⚠️ Check back weekly — Carol decides week-to-week whether she's hosting, so RSVP accordingly!
📌 CHECK IN WITH CAROL upon arrival so she knows you're there! She'll post what she's wearing — look for the purple yoga mat up front! 💜
Leave comment if cannot find the group!***
🔗 More Info: 🌐 https://www.chicago.gov/city/en/depts/dca/supp_info/millennium_park4.html
🌐 https://millenniumparkfoundation.org/programs/summer-workouts/***
📌 NO-SHOW POLICY:
❗ 3 no-shows without updating your RSVP = 3-month pause from signing up
⏰ Update your RSVP before event start time
✅ Must check in with host upon arrival — failure to do so counts as a no-show
🚫 Repeated no-shows = removal from the groupCome move, stretch & soak up summer in the city with us! 🌿🌞
2 attendees
🌊🎷 Lake Views, Live Jazz & Dinner at Waterfront Café! 🍽️
The Waterfront Cafe, 6219 N Sheridan Rd, Chicago, IL, US🌊🎷 Lake Views, Live Jazz & Dinner at Waterfront Café! 🍽️
Part 2 of 2 — Dinner, Drinks & Live Jazz at Berger Park
🌴 Let’s head back to one of our favorite Chicago summer spots — Waterfront Café! It feels like a little Miami escape right here on the North Side with beautiful lake views, a relaxed beach café atmosphere, great food, drinks, and live music on the patio.
Join us for a fun Friday night of dinner, conversation, and jazz overlooking Lake Michigan!
📅 Friday, August 21, 2026
⏰ Meet: 6:00 PM
🎶 Live Music: 7:00–9:00 PM
📍 Waterfront Café
Berger Park
6219 N. Sheridan Rd.
Chicago, IL🎷 Featured Performance:
Allan Laskey Trio
The Allan Laskey Trio brings a cool, sophisticated jazz sound featuring:
🎵 Traditional jazz & swing
🎵 Classic jazz standards
🎵 Great American Songbook favorites
🎵 Jazz blues influences inspired by artists like Charlie Parker
Perfect music for a relaxing summer evening by the lake!⚠️ IMPORTANT:
This Meetup is ONLY for the dinner and music portion.
Earlier that afternoon, we are hosting:
🌊☀️ Northside Beach Hopping: Mahony Griffin to Berger Park Lakefront Walk! 3-5:30 pm
The walk is a separate Meetup event, and space is limited for each.
If you want to do the WALK TOO please RSVP separately here:
https://www.meetup.com/windy-city-wanderers/events/315748420/🌞 The Plan
🍽️ Meet at Waterfront Café at 6 PM.
We’ll arrive early to grab tables since seating is first-come, first-served and reservations are not available.
✅ Tables are usually limited to 4–6 people
✅ We’ll try to grab a cluster of tables together
✅ If you arrive later, message me and we’ll try to save space (no guarantees)
🎶 Music starts at 7 PM, but tables can fill up well before then!🍔 About Waterfront Café
Located in historic Berger Park, Waterfront Café is a unique lakefront dining spot housed in a historic landmark coach house connected to one of Chicago’s last remaining lakefront mansions.
Enjoy:
🌊 Amazing Lake Michigan views
🎶 Outdoor patio music
🍔 Casual beach café food
🍹 Full bar and summer drinks
🌅 One of Chicago’s best sunset settings
🌐 Website:
http://waterfrontcafechicago.com/🍽️ Dining Information
Counter-service restaurant — everyone orders separately.
💳 CREDIT/DEBIT ONLY — NO CASH
For our group, please plan to add approximately 32% to your order:
• 12% Chicago sales tax
• 20% gratuity
🦟 Pro Tip:
Bring bug spray! Beachside patios can get buggy after sunset.🎷 Featured Performance:
Second City Jazz
Second City Jazz is a talented Chicago-based ensemble performing everything from swing, Big Band, and Dixieland to jazz standards,Latin jazz, and contemporary favorites. Known for their outstanding musicianship and energetic performances, they're a favorite at festivals, parks, and community events throughout the Chicago area.
Whether you're a longtime jazz fan or simply enjoy great live music, you're in for a wonderful evening!
🌐 Website: https://www.secondcityjazz.com/
📘 Facebook: https://www.facebook.com/SecondCityJazz/🚇 Transportation
CTA Trip Planner:
https://www.transitchicago.com/planatrip/
🚗 Parking:- Metered parking available on Granville Avenue
- Limited free street parking nearby (watch permit signs!)
- SpotHero or ParkWhiz recommended
⚠️ RSVP Reminder
✅ Please only RSVP if you are 95% sure you can attend.
✅ Seating is limited, so accurate headcounts are important.
✅ Update your RSVP before the event begins if plans change.
❌ Three no-shows without updating your RSVP = 3-month RSVP pause.🌴🍹 Come enjoy a little Chicago beach magic — great friends, lake views, delicious food, and live jazz under the summer sky. It’s the perfect way to end a summer Friday! 🎶🌊
2 attendees
Past events
1003
Group links
Members
197
