Windy City Wanderers!

4.7•435 ratings

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

7 seats left

🎤😂 Heaven, Hell & Hilarity: Amy Armstrong Live at Hydrate! 🎶✨

Sat, Aug 15 · 6:00 PM CDT

hydrate nightclub, 3458 n halstead street, Chicago, IL, US

🎤😂 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! 🎤😂🎶