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

✨ Beyond Six Corners: Theatres, Bungalows & Portage Park Walking Tour 🎭
✨ Beyond Six Corners: Theatres, Bungalows & Portage Park Walking Tour 🎭
✨ “Discover the history, homes, and hidden gems of Portage Park’s east side!” ✨
🌳 Step into one of Chicago’s most charming and overlooked neighborhoods on this guided walking tour through East Portage Park! Beginning at the historic Six Corners intersection, we’ll wander past beautiful vintage theatres, lush parks, beloved local businesses, and block after block of classic early 20th-century bungalows. 🏡
Along the way, you’ll uncover stories of immigrant communities, neighborhood transformation, iconic local landmarks, and the rich history behind Chicago’s beloved Bungalow Belt — all right here in my own backyard! 💫
Come walk, learn, and enjoy a beautiful spring morning — the perfect way to explore the city, connect with fellow curious Chicagoans, and experience the Northwest Side through fresh eyes. 🌇
🎤 Led by your passionate, ever-curious guide (that’s me!) — perfect for architecture lovers, local history buffs, urban explorers, and anyone who enjoys being a tourist in their own city 😊
***
📍 LOGISTICS
🗓 Saturday, May 23, 2026
⏰ 11:00 AM – 1:30 PM (approx.)
☕ Start: City News Café 4018 N. Cicero Ave
🏁 End: Biagio Banquets 4242 N. Central Ave
👟 Distance: Approx. 2 miles
⚠️ Tour ends approximately 1.2 miles from the starting point — please plan parking accordingly!
***
✨ ABOUT THE TOUR
Join us for a special public walking tour of one of Chicago’s most underappreciated neighborhoods — Portage Park! This is Part 1 of a two-part series of Portage Park with this walk focusing on the East Side of the Portage Park neighborhood.
Presented in collaboration with Chicago for Chicagoans, a local nonprofit dedicated to educating residents about their own communities, this walk is open to the public — Meetup members, friends, and newcomers are all welcome!
💸 Pay-What-You-Can (donations collected at the end per nonprofit policy)
🎟️ Registration required to attend:
👉 https://www.eventbrite.com/e/east-portage-park-walking-tour-registration-1987362136649
***
🌿 TOUR HIGHLIGHTS
🏡 Bungalow-lined streets in Chicago’s famous “Bungalow Belt”
🎭 Historic movie palaces & classic shopping corridors
⛪ Historic churches and longtime neighborhood institutions
🌳 Peaceful parks, green spaces & community gathering spots
📎 Fascinating local trivia and lesser-known hidden gems
📸 Plenty of Insta-worthy architecture and vintage Chicago charm
👥 Meet fellow Chicagoans, history lovers, and curious explorers along the way!
***
🗺️ ROUTE HIGHLIGHTS (stops subject to change)
☕ City News Café
🗿 Portage Indian Sculpture
🎭 Portage Theater
🎎 Fantasy Costumes
🏦 National Veterans Art Museum
🎭 Filament Theater
🏢 Former Klee Building
🏬 Former Sears Building (now Six Corners Lofts)
🏦 Former Inland Bank Building (now Clarendale Senior Living)
🌭 Jeff’s Red Hots
🎭 Former Grayland Theatre (now Rasenick’s)
💡 Former People’s Gas Site (now Lydia Home offices)
🏦 Historic neighborhood bank buildings (now Binny’s)
🌳 Dickinson Park
⛪ Cornerstone Anglican Church
🏡 Bungalow Belt architectural exploration
🌳 Portage Park Field House & Senior Center
🏊♀️ Historic Portage Park Pool
⛪ St. Mary’s Romanian Orthodox Church
🍽️ Biagio Banquets & Suparossa
✨ Plus plenty of unexpected stories, neighborhood lore, architectural details, and hidden gems tucked between the stops!
***
📜 WHY PORTAGE PARK?
Named for the ancient “portage” route linking the Des Plaines and Chicago Rivers, Portage Park has long been a crossroads of cultures, transportation, and community life. Annexed into Chicago in 1889, the neighborhood rapidly developed during the early 20th century as streetcar lines — and later the Kennedy Expressway — made the Northwest Side increasingly accessible to working- and middle-class families.
Today, Portage Park remains one of Chicago’s most architecturally distinctive neighborhoods, famous for its beautifully preserved brick bungalows, classic commercial strips, and strong neighborhood identity. Walking these streets offers a fascinating glimpse into Chicago’s immigrant history, postwar growth, and enduring community spirit. 🏡🌳
The neighborhood is also home to several iconic landmarks, including the historic Portage Park Pool 🏊♀️ — host of the 1959 Pan-American Games and the 1972 U.S. Olympic Swim Trials — along with the legendary Portage Theater, Patio Theater, Six Corners, and Merrimac Park.
***
💟 WHAT TO BRING
👟 Comfortable walking shoes
💧 Water bottle
🧥 Weather-appropriate attire
***
🍽️ OPTIONAL POST-WALK MEETUP
Join us afterward for a casual bite at Legno by Suparossa — all are welcome! 🍕😊
🌐 https://www.legnochicago.com
***
🤝 ABOUT CHICAGO FOR CHICAGOANS
Founded in 2016 by Patti Swanson, Chicago for Chicagoans is a 501(c)(3) nonprofit using pay-what-you-can tours to connect residents to their city.
🌐 https://www.chicagoforchicagoans.org/
💖 Donations help support accessible, community-based learning experiences.
***
🚇 GETTING THERE
🚇 CTA Trip Planner: https://www.transitchicago.com/planatrip/
🚗 Metered parking available on Cicero, Irving Park & Milwaukee
⚠️ Free side-street parking nearby — watch for permit signs!
⚠️ Remember: the tour ends approximately 1.2 miles from the starting point, so plan accordingly.
***
📌 RSVP & ATTENDANCE POLICY
✅ Keep your RSVP up to date
⏰ Update before the event start time if plans change
🚫 Repeated no-shows may result in removal from the group
***
Can’t wait to walk with you through my neighborhood where I will share some of the stories, architecture, and hidden history that make Portage Park so special! ✨🏡🌳
—Giovina
Upcoming events
21

🍽️ BYOB Dinner at Lao Der with Yumi 🌿
Lao Der, 3922 N Elston Ave,, Chicago, IL, US🍽️ BYOB Dinner at Lao Der with Yumi 🌿
📅 Thursday, May 21
🕖 7:00 PM
📍 Lao Der (Laotian) 3922 N. Elston Ave, Chicago
📞 (872) 241-4879
👩🍳 Host: Yumi
🤝 Multi-Meetup Group Event!
Reservation under Yumi for 12 people🔗 Lao Der Website
https://www.laoderchicago.com/
🔗 Yelp
https://www.yelp.com/biz/lao-der-chicago🍷 BYOB
✅ Bring wine or beer to share with the group
✅ Don’t forget a corkscrew just in case
✅ As this is a large group dinner, please be patient with ordering & wait times
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💵 CASH ONLY for Group Checks
✅ No separate checks
✅ Please bring CASH
✅ Add 32% to your total (12% tax + 20% tip)
❌ Credit cards are too complicated for large groups — thank you for helping keep things smooth!
***
🚫 NO-SHOW POLICY
• Please RSVP or update your status by event start time
• 3 no-shows = 3-month RSVP restriction
• Always check in with the host — especially for large group events✨ Hope to see you then!
Thanks,
Yumi14 attendees
✨ Beyond Six Corners: Theatres, Bungalows & Portage Park Walking Tour 🎭
City News Cafe, 4018 N Cicero Ave, Chicago, IL, US✨ Beyond Six Corners: Theatres, Bungalows & Portage Park Walking Tour 🎭
✨ “Discover the history, homes, and hidden gems of Portage Park’s east side!” ✨
🌳 Step into one of Chicago’s most charming and overlooked neighborhoods on this guided walking tour through East Portage Park! Beginning at the historic Six Corners intersection, we’ll wander past beautiful vintage theatres, lush parks, beloved local businesses, and block after block of classic early 20th-century bungalows. 🏡
Along the way, you’ll uncover stories of immigrant communities, neighborhood transformation, iconic local landmarks, and the rich history behind Chicago’s beloved Bungalow Belt — all right here in my own backyard! 💫
Come walk, learn, and enjoy a beautiful spring morning — the perfect way to explore the city, connect with fellow curious Chicagoans, and experience the Northwest Side through fresh eyes. 🌇
🎤 Led by your passionate, ever-curious guide (that’s me!) — perfect for architecture lovers, local history buffs, urban explorers, and anyone who enjoys being a tourist in their own city 😊
***
📍 LOGISTICS
🗓 Saturday, May 23, 2026
⏰ 11:00 AM – 1:30 PM (approx.)
☕ Start: City News Café 4018 N. Cicero Ave
🏁 End: Biagio Banquets 4242 N. Central Ave
👟 Distance: Approx. 2 miles
⚠️ Tour ends approximately 1.2 miles from the starting point — please plan parking accordingly!***
✨ ABOUT THE TOUR
Join us for a special public walking tour of one of Chicago’s most underappreciated neighborhoods — Portage Park! This is Part 1 of a two-part series of Portage Park with this walk focusing on the East Side of the Portage Park neighborhood.
Presented in collaboration with Chicago for Chicagoans, a local nonprofit dedicated to educating residents about their own communities, this walk is open to the public — Meetup members, friends, and newcomers are all welcome!💸 Pay-What-You-Can (donations collected at the end per nonprofit policy)
🎟️ Registration required to attend:
👉 https://www.eventbrite.com/e/east-portage-park-walking-tour-registration-1987362136649***
🌿 TOUR HIGHLIGHTS
🏡 Bungalow-lined streets in Chicago’s famous “Bungalow Belt”
🎭 Historic movie palaces & classic shopping corridors
⛪ Historic churches and longtime neighborhood institutions
🌳 Peaceful parks, green spaces & community gathering spots
📎 Fascinating local trivia and lesser-known hidden gems
📸 Plenty of Insta-worthy architecture and vintage Chicago charm
👥 Meet fellow Chicagoans, history lovers, and curious explorers along the way!***
🗺️ ROUTE HIGHLIGHTS (stops subject to change)
☕ City News Café
🗿 Portage Indian Sculpture
🎭 Portage Theater
🎎 Fantasy Costumes
🏦 National Veterans Art Museum
🎭 Filament Theater
🏢 Former Klee Building
🏬 Former Sears Building (now Six Corners Lofts)
🏦 Former Inland Bank Building (now Clarendale Senior Living)
🌭 Jeff’s Red Hots
🎭 Former Grayland Theatre (now Rasenick’s)
💡 Former People’s Gas Site (now Lydia Home offices)
🏦 Historic neighborhood bank buildings (now Binny’s)
🌳 Dickinson Park
⛪ Cornerstone Anglican Church
🏡 Bungalow Belt architectural exploration
🌳 Portage Park Field House & Senior Center
🏊♀️ Historic Portage Park Pool
⛪ St. Mary’s Romanian Orthodox Church
🍽️ Biagio Banquets & Suparossa✨ Plus plenty of unexpected stories, neighborhood lore, architectural details, and hidden gems tucked between the stops!
***
📜 WHY PORTAGE PARK?
Named for the ancient “portage” route linking the Des Plaines and Chicago Rivers, Portage Park has long been a crossroads of cultures, transportation, and community life. Annexed into Chicago in 1889, the neighborhood rapidly developed during the early 20th century as streetcar lines — and later the Kennedy Expressway — made the Northwest Side increasingly accessible to working- and middle-class families.Today, Portage Park remains one of Chicago’s most architecturally distinctive neighborhoods, famous for its beautifully preserved brick bungalows, classic commercial strips, and strong neighborhood identity. Walking these streets offers a fascinating glimpse into Chicago’s immigrant history, postwar growth, and enduring community spirit. 🏡🌳
The neighborhood is also home to several iconic landmarks, including the historic Portage Park Pool 🏊♀️ — host of the 1959 Pan-American Games and the 1972 U.S. Olympic Swim Trials — along with the legendary Portage Theater, Patio Theater, Six Corners, and Merrimac Park.
***
💟 WHAT TO BRING
👟 Comfortable walking shoes
💧 Water bottle
🧥 Weather-appropriate attire***
🍽️ OPTIONAL POST-WALK MEETUP
Join us afterward for a casual bite at Legno by Suparossa — all are welcome! 🍕😊
🌐 https://www.legnochicago.com***
🤝 ABOUT CHICAGO FOR CHICAGOANS
Founded in 2016 by Patti Swanson, Chicago for Chicagoans is a 501(c)(3) nonprofit using pay-what-you-can tours to connect residents to their city.
🌐 https://www.chicagoforchicagoans.org/
💖 Donations help support accessible, community-based learning experiences.***
🚇 GETTING THERE
🚇 CTA Trip Planner: https://www.transitchicago.com/planatrip/
🚗 Metered parking available on Cicero, Irving Park & Milwaukee
⚠️ Free side-street parking nearby — watch for permit signs!
⚠️ Remember: the tour ends approximately 1.2 miles from the starting point, so plan accordingly.***
📌 RSVP & ATTENDANCE POLICY
✅ Keep your RSVP up to date
⏰ Update before the event start time if plans change
🚫 Repeated no-shows may result in removal from the group***
Can’t wait to walk with you through my neighborhood where I will share some of the stories, architecture, and hidden history that make Portage Park so special! ✨🏡🌳
—Giovina2 attendees
🎸☀️ 41st Annual Belmont-Sheffield Music Fest: Kick Off Summer! 🎪🍹
3200 N Sheffield Ave, 3200 North Sheffield Avenue, Chicago, IL, US🎸☀️ 41st Annual Belmont-Sheffield Music Fest: Kick Off Summer! 🎪🍹
Belmont-Sheffield Music Fest: Live Bands, Food & Summer Vibes
The outdoor festival season is officially HERE—and we’re starting strong for our 2nd festival of the season! 🙌☀️Plus it is Memorial Day Weekend, so we are off on Monday!
Join us for the 41st Annual Belmont-Sheffield Music Fest, one of Chicago’s most beloved early-summer street festivals, taking over Sheffield Ave in the heart of Lakeview—just steps from the Belmont “L”! 🎶
Expect a full evening of live music, great food, cold drinks, and festival vibes as we hang out, explore, and catch some fantastic bands together. This is always a fun one!
💰 Free admission (suggested $10 donation—optional!)
⚠️ Note: This year we’re attending purely for fun—I will not be volunteering. The Chicago for Chicagoans crew will instead be volunteering at Taste of Randolph in June—so we’re all just here to enjoy the fest! 😎
***
📍 LOGISTICS
📅 Sunday, May 24, 2026
⏰ 5:30 PM – 10:00 PM (arrive on time—we’ll head in together!)
📍 Meet at: 3200 N Sheffield Ave
🎪 Festival runs along Sheffield Ave (Belmont → Roscoe), Lakeview
💰 Free admission | $10 suggested donation (not obligated!)***
🎪 WHAT TO EXPECT
🎶 Two stages of live music (tribute bands + local acts)
🍔 Great eats from local vendors
🍺 Beer, wine & summer drinks
🛍️ Artisan vendors & neighborhood businesses
💃 A lively, high-energy crowd to kick off festival season!***
🎵 SUNDAY BAND LINEUP (OUR GAME PLAN)
🎸 Main Stage (Sheffield & Roscoe)
12:30 PM — Generation Band ⏭️ (skip — too early)
2:00 PM — RAVIV – Electric Cellos ⏭️ (skip — too early)
4:00 PM — Petty Union ⏭️ (skip — too early)
6:00 PM — The Divas 🤔 (maybe — depends when we arrive)
8:00 PM — Hello Weekend ✅ (WE WILL SEE!)🎤 Belmont Stage (Sheffield & Belmont)
12:30 PM — Bear & Jake Acoustic ⏭️ (skip — too early)
2:00 PM — Sucker Punch ⏭️ (skip — too early)
3:30 PM — My Weekend Crush ⏭️ (skip — too early)
5:00 PM — Rumor Hazit 🤔 (maybe — if we get there early)
6:45 PM — Chasing Rumours (Fleetwood Mac Tribute) ✅ (WE WILL SEE!)
8:30 PM — Mellencougar 🤔 (maybe — depending on energy level!)***
🎯 Game Plan for the Group
🎤 Chasing Rumours — 6:45 PM ✅
🎸 Hello Weekend — 8:00 PM ✅🌟 FEATURED BANDS
🎤 Chasing Rumours (Fleetwood Mac Tribute)
A fan-favorite tribute bringing the timeless sound of Fleetwood Mac to life—expect all the classics, rich harmonies, and that unmistakable 70s vibe!
👉 https://www.facebook.com/chasingrumourschicago/🎸 Hello Weekend
A high-energy cover band known for keeping the crowd dancing with a mix of party hits, throwbacks, and crowd favorites—perfect for closing out the night!
👉 https://www.helloweekendband.com/Belmont-Sheffield Music Fest is one of the first of scores of Windy City warm weather fests. Top local tribute bands on the main stage (near Roscoe), great eats, libations (beer and wine), artisans and a groovin’ second stage featuring local artists and entertainment are on tap for this iconic 41st annual happening. The fest’s second (aka ‘community’) stage, located on Sheffield at Belmont, will showcase an eclectic entertainment mix that includes deejay sets, cover bands, and other nifty local acts and performances.
***
🌐 FESTIVAL INFO
👉 https://chicagoevents.com/event/belmont-sheffield-music-fest/
👉 https://lakevieweast.com/2026-chamber-annual-events/
👉 https://www.facebook.com/belmontsheffieldmusicfestival/***
🚇 GETTING THERE
🚇 CTA Trip Planner: https://www.transitchicago.com/planatrip/
🚉 Just steps from the Belmont Red/Brown/Purple Line
🚗 Parking is VERY limited
🅿️ Metered parking further out + limited side streets
💡 Best bet: SpotHero or ParkingWhiz***
📱 Lost or running late? Call/text 312.835.4259
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📌 NO-SHOW POLICY
⚠️ 3 no-shows (without updating RSVP) = 3-month event ban
⏰ Update RSVP before start time
📱 Running late? Message the host
👋 Check in upon arrival***
Let’s kick off festival season with great music, good vibes, and dancing in the street! 🎶☀️💃
22 attendees
Past events
935



