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 (4+)
See all- 🍹🌆 Thursday Rooftop Vibes @ Solana (Wicker Park) ✨Cabana Club, Chicago, IL
🍹🌆 Thursday Rooftop Vibes @ Solana (Wicker Park) ✨
Let’s check out a lovely rooftop in the heart of Wicker Park with great views, good drinks, and tasty bites! Everyone loves rooftops, and we’ve still got time to enjoy the open air! 🌇
We’ve been to the Robey’s Up Room many times on the 13th floor, but this time we’re trying their other rooftop: Solana (formerly the Cabana Club) on the 6th floor. Different tower, different views, and only open in warm weather, so let’s go while we still can. Roof season isn’t over yet! 🌴☀️
📅 Date: Thursday, September 18, 2025
⏰ Time: 6:15 PM
📍 Location: Solana Rooftop (6th Floor), The Robey Hotel
🎯 Address: 2018 W North Ave, Chicago, IL 60647 → The Robey
***✨ What to Expect
- 🍸 Drinks & bites after work — no reservation, first come first served (we’ll go early to snag a spot).
- 🍴 Food available — check the Solana Menu.
- 🏊 Cute rooftop pool (for hotel guests only) adds to the vibe, especially once the sun sets.
- 🌇 180-degree skyline views: John Hancock to the east, neighborhood church steeples, even a passing L train from Damen Station.
***
💵 Payment Info
⚠️ Please bring cash!- For large groups, they often don’t split checks.
- To make it easier: pay your total + add 32% (12% Chicago tax + 20% tip).
- Bring a credit card too — policies may vary from the Up Room.
***
🙌 It’s a multi-meetup event, so expect a lively, fun-loving crowd ready to celebrate together! 🎉🏙️ About Solana & The Robey
- Location: Rear elevator to the 6th floor.
- Building: Art Deco masterpiece (Northwest Tower, 1929, designed by Perkins, Chatten & Hammond).
- Renovated by Belgian design duo Nicolas Schuybroek Architects & Marc Merckx Interiors.
- The Robey name comes from historic Robey Street (now Damen Ave).
***
🚇 Getting There
- Transit: Use CTA Trip Planner or Google Maps.
- Parking: Limited. Metered spots on Damen, Milwaukee & North. Free side-street parking a few blocks away (watch signage/permits).
***
✅ No-Show Policy- 🚫 3 no-shows (without updating RSVP) = no sign-ups for 3 months
- ✍️ Cut-off to update RSVP = event start time
- 📩 If late, message the host directly
- Not checking in = no-show
- Continual no-shows = removal from the group
***
💫 Come enjoy a stylish rooftop evening with skyline views, good company, and end-of-summer vibes! 🌆🍸
- 🌊👟 Friday Fun Lakefront Walk + Harbor Eats at Bacino’s 🍝🍷The Dock at Montrose Beach, Chicago, IL
🌊👟 Friday Fun Lakefront Walk + Harbor Eats at Bacino’s 🍝🍷
Summer is not over yet! Let’s do another late Friday afternoon walk along Chicago’s beautiful Lakefront Trail — from Montrose Beach to Diversey Harbor — followed by lunch at Bacino's Italian Grill.
📅 Date: Friday, September 19, 2025
⏰ Time: 3:45 PM
🚶 Distance: ~2.5 miles (easy pace)
🌦 Weather dependent⚠️ Important Note:
👉 We will NOT end where we start!
The walk ends about 2.5 miles from the starting point. If you drive, you’ll need to walk/bus back to your car, or plan to park in the middle or at the end.
***📍 Route & Meeting Point
- Start: The Docks at Montrose Beach (200 W Montrose Harbor Dr, Chicago, IL 60640)
- End: Bacino’s Italian Grill (248 W Diversey Pkwy, Chicago, IL 60657) — at Diversey Harbor, next to the Driving Range & Mini Golf.
🍝 Cute place with great food! → Bacino’s Italian Grill
🅿️ Parking:
- Big metered lot at Montrose Harbor (SP+ Parking, 601 W Montrose Ave, Chicago, IL 60640)
- Or use SpotHero / ParkWiz for parking near the end point.
🚇 Transit:
- From Montrose bus stop, take the path through the Bird Sanctuary to The Docks.
- Use CTA Trip Planner or Google Maps for public transit.
***
🚶♀️🌊 With several meetup groups coming together, it’s a fun opportunity to walk, chat, and meet new people on the lakefront path! 🌞🗺️ Stops Along the Way
We’ll enjoy scenic highlights of the Lakefront Trail:- 🏖️ Montrose Beach & Dog Beach
- 🐦 Montrose Bird Sanctuary
- ☕ Clocktower Café
- ⛳ Sydney R. Marovitz Golf Course
- 🌳 Waveland Picnic Field
- 🐦 Jarvis Bird Sanctuary & Wildlife Viewing Platform
- 🗿 Kwa-Ma-Rolas Totem Pole
- 🐕 Belmont Dog Beach
- ⚓ Belmont Harbor & Yacht Club
- 🌈 AIDS Garden
- 🌿 Diversey Natural Area
- ⚓ Diversey Harbor & Driving Range
More info on the trail: Chicago Park District – Lakefront Trail
***✅ What to Bring
- 💧 Water
- 🧴 Sunscreen & hand sanitizer
- 👟 Good walking shoes
- 👕 Dress for Chicago’s summer/fall weather
🚻 Washroom availability is limited — plan accordingly.
***
📌 No-Show Policy
- 3 no-shows (without updating RSVP) = 🚫 No sign-ups for 3 months
- Cut-off to update RSVP = event start time
- If you miss the start, message the host directly
- Not checking in with the host = counts as a no-show
***
💫 Come join us for great scenery, fresh air, and good company — and wrap up the walk with a relaxing Italian meal by the harbor!
- 🌿✨Palmer Square: Step Inside Logan Square’s Gems - House Walk 2025🌳🏡✨Old Holy Resurrection Serbian Orthodox Church, Chicago, IL
🌿✨ Palmer Square: Step Inside Logan Square’s Gems - Housewalk 2025 🌳🏡✨
🏛️ 35th Biennial Logan Square House & Garden Walk 2025 with Palmer Square Focus
📅 Saturday, September 20, 2025
⏰ 10 AM – 5 PM
📍 Kickoff: Holy Resurrection Serbian Orthodox Church
3062 W Palmer Square, Chicago, IL 60647
🎟️ Tickets required✨ Logan Square Preservation proudly presents the 35th Biennial House & Garden Walk—a rare chance to step inside some of Logan Square’s most stunning historic homes & gardens, with a special spotlight on Palmer Square.
***🌟 What’s Included
- Guided interior access to 10 sites, including:
- 7 historic homes on Palmer Square
- Holy Resurrection Serbian Orthodox Church (1910, Lowe & Bollenbacher)
- Additional unique homes, from the "Schwinn Mansion” on Humboldt Blvd to a converted church residence
- 🚗 Vintage Car Show – 50+ collectible cars lining Palmer Square’s north side
- 👩🏫 Docents provide architectural & historical insight at every stop
- 🌳 Explore beautifully kept gardens and the historic Humboldt & Palmer Square boulevards
***
🎟️ Tickets
- $35 Early Bird (thru 9/14/25)
- $50 Regular & Day-of
👉 Advance tickets recommended (may sell out!)
🔗 Buy Tickets Here
🔗 Direct Link
(Tip: The system auto-adds a donation—opt out if you wish)
🎟️ Online sales close 9/19/25; after that, purchase at the door at higher price.
***
🚶 What to Expect
- Walk runs 10 AM – 5 PM
- We will not end where we start—plan accordingly
- Trolley may be available; otherwise, expect to walk between sites
- We’ll grab a bite nearby after the tour (optional, location TBD)
- Bring comfy shoes + water
***
🚗 Getting There & Parking
- CTA: Short walk from the California Blue Line station → CTA Trip Planner
- Street parking available on Kedzie, Fullerton, Humboldt, & side streets (watch permit signs)
- Possible special parking lot—confirmation closer to date
***
ℹ️ About the Event
- Started in the early years of Logan Square Preservation, this is the group’s longest-running education & outreach event
- Funds raised support:
- 🌳 Tree planting
- 📜 Historic archives
- 🎉 Free community events
- 🏛️ Preservation advocacy
***
🌳 Palmer Square History:
· Named for Charles Palmer, a prominent late-19th-century Chicago developer
· Central green space features a landscaped triangle & fountain, surrounded by grand Tudor Revival, Prairie, and Classical Revival homes
· Historically home to Chicago’s middle- and upper-middle-class families
· Park and homes preserved as part of Logan Square’s historic district, highlighting the neighborhood’s rich architectural heritage📌 RSVP / No-Show Policy
- Cut-off time to update RSVP = event start time
- 3 no-shows (without updating RSVP) → suspension from RSVPs for 3 months
- Must check in with host on arrival
***
👉 Don’t miss this chance to step inside 10 historic gems, see vintage cars, and experience the architecture & history of Logan & Palmer Square up close!
- 🌳🏠 Step Inside Edgewater’s Most Beautiful Homes — 34th Annual Tour! 🗝️✨Granville Ave United Methodist Church, Chicago, IL
🌳🏠 Step Inside Edgewater’s Most Beautiful Homes — 34th Annual Tour! 🗝️✨
🏡 34th Annual Edgewater Home Tour — Step Inside Historic Homes! 🏛️
Explore Edgewater North’s most stunning historic residences — beautiful interiors, lush gardens, and rich architectural history await!
📅 Date: Sunday, September 21, 2025
🕛 Time: 12:00 PM – 5:00 PM
📍 Meet/Registration: Granville Ave United Methodist Church, 1307 W. Granville Ave, Chicago, IL 60660
🎟️ Admission: $25 per person — includes a souvenir Tour Booklet with:
· 🗺️ Map of featured homes on Wayne, Lakewood, Magnolia, & Granville
· 🏠 Photos & descriptions of each home, including architectural highlights
· ✔️ Checklist of homes & tour sponsor info
· ☕ Refreshments at registrationBUY A TICKET AT THE DOOR!
✨ Tour Highlights:
· Guided access inside 10+ architecturally significant homes
· Volunteer docents share the history and unique features of each home
· Explore gardens and interiors from grand turn-of-the-century homes to charming historic residences
· Walking distance: ~1 mile💡 Neighborhood Notes: Edgewater, Chicago – Quick History
· Location: North Side of Chicago, along Lake Michigan, just north of Uptown
· Early History: Originally inhabited by the Potawatomi; settled by Europeans in the mid-1800s as part of Lake View Township
· Late 19th Century: Lakeside retreat for wealthy Chicagoans; large estates & mansions built
· Transportation Boost: Streetcars & Northwestern Elevated Railroad (now Red Line) increased accessibility & growth
· Early 20th Century: Edgewater Beach Hotel (1916) became a social hub; immigrant communities shaped the cultural fabric
· Mid-20th Century: Many mansions replaced by apartments; Edgewater Beach Hotel demolished in 1971
· Modern Edgewater: Ethnically diverse, historic architecture, lakefront parks, and active preservation of early 20th-century homes🚇 Transit: CTA Trip Planner: https://www.transitchicago.com/planatrip/
🚗 Driving/Parking: Street parking along main streets & surrounding side streets (watch permit signs). Special parking options may be available — updates to come!📌 RSVP / No-Show Policy
- Cut-off time to update RSVP = event start time
- 3 no-shows (without updating RSVP) → suspension from RSVPs for 3 months
- Must check in with host on arrival
🔗 More info: Edgewater Historical Society Home Tour Preview: https://www.edgewaterhistory.org/ehs/tours/home-tour-preview
🍴 Post-Tour Plans: Some of us may grab a bite in nearby Edgewater — location TBD on the day of the event!
