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- 🍻🎵 Jeff Fest Friday: Music, Food, Friends & Fun in Jefferson Park! 🏞️jefferson park, Chicago, IL
🍻🎵 Jeff Fest Friday: Music, Food, Friends & Fun in Jefferson Park! 🏞️
🗓️ Friday, August 1, 2025
🕕 6:00 PM – 10:00 PM
📍 Jefferson Memorial Park – 4822 N Long Ave, Chicago, IL 60630
🎟️ Official Admission: $5 (Kids 12 & under free with adult)
***
Get Ready to Celebrate at the 24th Annual Jeff Fest!Party hard—or at least kick back and enjoy amazing tunes, delicious food, family fun, and so much more at the 24th annual Jeff Fest, also known as the Jefferson Park Arts & Music Festival.
Set in the picturesque Jefferson Memorial Park, just west of Milwaukee and Lawrence Avenues, Jeff Fest is a beloved tradition in one of Chicago’s friendliest neighborhoods.
This summer celebration isn’t just about the music and food (though they’re stellar!). Families will love the vibrant Kids’ Zone, packed with fun activities and located on the north side of the park. Don’t miss the Community Stage, where local talent brings even more energy to the festival. Come join the fun and be part of a neighborhood tradition that brings people together year after year!
🎸 Main Stage Lineup
- 6:30 PM – The Gingers
🔥 Redheads that ROCK! High-energy classic rock covers—get ready to sing along! - 8:00 PM – Infinity
🎤 “Classic to Current: The Ultimate Rock Experience” with one of the Midwest’s best Journey tributes!
🎶Jefferson Park Forward Community Stage
- 6:00pm – Noiseland
- 7:15pm – Miniskirt
- 8:45pm – Josephine
- Enjoy great local talent curated by Jefferson Park Forward on the north side of the park!
***
🍔 Tentative Meetup Plan:
6:00 PM – Meet at the main fest entrance at Higgins & Long
6:00–6:30 PM – Grab food, drinks & find a good spot
6:30 PM – Rock out to The Gingers on the Main Stage
8:00 PM – Sing along with Infinity
(Or feel free to check out acts at the Community Stage!)Infinity is one of the best cover bands out there that have been playing together for over 30 years! You are in for a treat!!
🎡 Festival Highlights:
✅ Food trucks, beer tents, & craft vendors
✅ Family-friendly Kids’ Zone
✅ Art & neighborhood booths
✅ Community Stage performances
✅ All proceeds benefit the Jefferson Park Chamber & Park Advisory Council📌 More Info:
Official Fest Site
Jeff Fest Facebook Page
***
🚇 Getting There:- Close to the Jefferson Park Blue Line & Metra station
- Check CTA Trip Planner or Google Maps
- Easy driving access, but expect to walk a few blocks—street parking available on Milwaukee, Lawrence, and Higgins
- Try SpotHero or ParkWhiz for garage deals nearby
***
⚠️ RSVP & No-Show Policy:- 3 no-shows = 3-month RSVP freeze
- Cut-off to update RSVP = event start time
- Always check in with the host upon arrival
- Repeated no-shows = removal from the group
***
🎉 Bring a blanket or camp chair, grab a bite, and rock out with your Meetup friends under the stars. Come solo or bring a friend—this is one of the Northwest Side’s best summer traditions! - 6:30 PM – The Gingers
- 🏛️🕰️ Strolling Through Kenwood: Mansions, Myths & Megastars 🚶♀️🎩Blackstone Branch, Chicago Public Library, Chicago, IL
🏛️🕰️ Strolling Through Kenwood: Mansions, Myths & Megastars 🚶♀️🎩
🏠📜Kenwood Treasures: A Walk Through Chicago’s Historic South Side
Step into one of Chicago’s most elegant and storied neighborhoods! From Gilded Age mansions and Prairie School gems to Civil Rights icons and President Obama’s former home, this walking tour reveals the rich legacy of Kenwood through architecture, activism, and culture.
📅 Saturday, August 2, 2025
🕛 12:00 PM – approx. 2:00 PM
📍 Start: Blackstone Branch Library, 4904 S. Lake Park Ave
🎯 End: Isidore Heller House, 5132 S. Woodlawn Ave (approx. 6 blocks from start)
💰 Cost: $20 (cash preferred; Zelle, Venmo, PayPal accepted)
🚶♀️ Distance: About 2.5 miles outdoors
⚠️ Tip: Walk Ends about 6 blocks from the start — if driving, consider parking midway point
***
🔎 What You’ll See & Learn:
✅ Stately Gilded Age homes & early Prairie-style architecture
✅ Sites tied to Barack Obama, Muhammad Ali, and Julius Rosenwald
✅ Hidden gems by Frank Lloyd Wright, Shaw, and other local legends
✅ Historic houses of worship, activists, educators & entrepreneurs
✅ Insightful storytelling and great company across multiple meetup groups!📸 It’s not a photo walk but trust us—you’ll want your camera!
🎤 Led by a passionate, knowledgeable guide (that’s me!), this walk is perfect for architecture buffs, history lovers, and curious Chicagoans.
***🏛️ Featured Stops & Highlights Include:
🏛️ Blackstone Branch Library
🧱 George Blossom House (FLW)
🧱 Warren McArthur House (FLW)
🏠 Former Elijah Muhammad House
🏡 Howard Van Doren Shaw House
🥊 Former Muhammad Ali Residence
🏠 Charles Adams Goodyear House
🏠 Ezra S. Brainerd House
🏢 Rainbow PUSH Coalition HQ
🏛️ Julius Rosenwald House
🧱 Gustavus F. Swift Mansion
🧱 Moses Born Residence
🏛️ Martin A. Ryerson House
🧱 McGill House
🦅🏛️Former Obama Family Home
🕍 KAM Isaiah Israel Congregation
🏠 Isidore Heller House (FLW)
***🍽️ Optional Lunch After the Tour
Stick around and grab a bite at one of these local favorites:- 🥗 Can’t Believe It’s Not Meat (vegan)
- 🥪 Cafe 53
- 🍕 The Sit-Down Cafe
💵 Bring cash for lunch—some spots don’t split checks!
***👟 What to Bring:
• Comfortable walking shoes
• Water bottle
• Weather-appropriate attire
• $20 tour fee (exact change appreciated; cash preferred but Zelle, Venmo, PayPal accepted)🚗 Transit & Parking Tips:
• Free & metered street parking available on Lake Park, Woodlawn & side streets—watch signs
• Park midway if you’d like to be close to both start & end
• CTA-accessible – use the CTA Trip Planner for the best route
***📌 RSVP & No-Show Policy
✔️ Please keep your RSVP current
🚫 No-shows make future planning tough
🕛 RSVP updates close at the tour start time
***✨ Discover Kenwood — where elegance, activism, and architectural beauty converge. Come explore the stories behind the stones on this engaging neighborhood walk! 🏛️🌳👟
- 🍽️ BYOB Dinner at Antepli with Yumi (Turkish Food) 🌿Antepli Mediterranean Grill,Baklava&Kunafa, Chicago, IL
## Details
🍽️ BYOB Dinner at Antepli with Yumi 🌿
Turkish Food📅 Saturday, Aug 2, 2025
🕕 7:30 PM📍 Antepli – 4849 N Kedzie Ave, Chicago
Host for this Meetup: Yumi
Multi-Meetup group event!https://www.yelp.com/biz/antepli-mediterranean-grill-chicago-2
https://www.anteplichicago.com/***
🌳 Dining outdoors (weather permitting)
🌧️ If it rains, we'll move indoors
***
🍷 BYOB
✅ Bring wine or beer to share, and keep it in your bag because they're halal and accommodating us
✅ Don’t forget a corkscrew just in case!
***
💵 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—help us keep it easy!
***
🚇 GETTING THERE
🚌 Use CTA Trip Planner or Google Maps for transit
🚗 Driving? Try SpotHero or ParkWhiz for parking deals. Metered street parking is also available nearby.
***
🚫 NO-SHOW POLICY
• RSVP or update by event start time
• 3 no-shows = 3-month RSVP restriction
• Always check in with the host—especially for large groups!
***
✨ We hope to see you then!
Please RSVP and come hungry. Let’s make it a fun summer dinner!Thanks,
Yumi - 🏙️🛤️ Milwaukee Ave Uncovered: Trails, Towers & Treasures 🚶♂️🌆Germain House, Chicago, IL
🏙️🛤️ Milwaukee Ave Uncovered: Trails, Towers & Treasures 🚶♂️🌆
A Sunday stroll through River West, Noble Square & Wicker Park
Walk the old Native path, check out iconic Polish churches, and discover stories of long-gone shops that made this street famous.
Ready to step off the grid and onto one of Chicago’s oldest, boldest streets? Join us for a guided walk down Milwaukee Avenue — a diagonal slice of city life with layers of history. From Indigenous trails and Polish cathedrals to long-lost department stores and reborn landmarks, we’ll explore how this vibrant corridor keeps reinventing itself.
***🗓️ Sunday, August 3, 2025
🕚 11:45 AM – ~1:45 PM
📍 Start: Germain House, 729 N. Sangamon St.
🎯 End: The Robey Hotel, 2018 W. North Ave. (~2.5 miles total)
💰 Cost: $20 (cash preferred; Zelle, Venmo, PayPal accepted)
🚶♀️ Casual pace | Outdoors |
⚠️ Note: Walk ends 2.5 miles from the starting point — if driving, consider parking near the midpoint! Or take the bus or the L train back☀️ A casual, curiosity-filled outing for lovers of Chicago stories, old and new.
***🔍 What You’ll See & Learn:
✅ One of Chicago’s oldest trails — from Native path to Polish main street
✅ Grand churches, vanished businesses, reborn banks, and funky artist spaces
✅ A mix of architectural eye candy and deep neighborhood stories
✅ The ever-evolving story of immigrant hustle, urban reinvention, and civic pride📸 Not a photo walk, but you’ll want your camera
🎤 Led by your passionate, ever-curious guide (that’s me!) — this one’s for architecture buffs, history lovers, and anyone who wants to be a tourist in their own city.
***🗺️ Route Highlights:
🏠 Germain House – Queen Anne gem
⛪ St. John Cantius – A Polish baroque beauty
⛪ St. Boniface – Towering twin-spired ghost
🌳 Eckhart Park – A community anchor
🏛️ Polish Museum of America – A cultural time capsule
🕍 Holy Trinity – Where grandeur meets grit
⛪ St. Stanislaus Kostka – The original Polish cathedral
🌿 Pulaski Park – WPA charm in a leafy square
🧠 National Alliance – Mid-century mission hub
🏦 Home Bank & Trust – Financial strength in stone
🏬 Wieboldt’s (former) – Lost department store legend
🎨 Indigo Lofts – Wallpaper meets art lofts
🎭 Flatiron Arts – Boho central
🏛️ Noel State Bank – Walgreens with a dome
🏨 The Robey – A tower of transit turned trendy hotel
***🏙️ Fun Facts Along the Way:
💬 Milwaukee Ave started as a Native trail, then a plank-lined toll road
🚌 Streetcars once zipped through what’s now rush-hour traffic
🎨 Wicker Park’s art scene exploded here in the ‘80s
🍺 Expect tales of beer barons, preservation fights, and colorful characters
***📌 Quick Logistics:
✔️ Start near Grand Blue Line
✔️ End near Damen Blue Line
✔️ Wear good walking shoes & bring water
✔️ DM or email with any questions
✔️ Tour runs rain or shine 🌦️
***👟 What to Bring:
• Comfortable walking shoes
• Water bottle
• Weather-appropriate attire
• $20 tour fee (exact change appreciated; cash preferred but Zelle, Venmo, PayPal accepted)🍽️ Optional Lunch After the Tour
Stick around and grab a bite at one of these local favorites after the walk:
• 🥗 Sultan’s Market (Wicker Park) – casual Middle Eastern eats
https://www.sultansmarket.com/
• 🥪 CAVA (Wicker Park) – build-your-own Mediterranean bowls
https://cava.com/locations/1611-n-damen-ave-chicago-il
• 🍕 Paradise Park – funky patio vibes + pizza
https://www.paradiseparkchi.com/
• 🌮 Big Star – beloved taco + whiskey joint
https://www.bigstarchicago.com/💵 Bring cash for lunch—some spots don’t split checks!
🧭 Come walk where the old city still hums — Milwaukee Ave is calling.
