What we’re about
This group is for people who want to get out and explore Chicago and beyond. If you don't want to wait on their friends to finally say “yes” to get out to enjoy all that Chicago has to offer and to see the world. Life is too short and the world is too big!
The local events in this group are member-driven so if you’d like to host a Meetup in your area (i.e. walk, museum, coffee, play pickleball, concerts, etc), feel free to let me know and I'll help you get it set up in the group!
The trips in this group are usually 90% solo travelers but everyone is welcome, female/male, solo/couple/friends, straight/LGBTQIA+! So let’s travel together with fun, like-minded travelers! If you have an open mind and are kind to fellow travelers, you will fit in perfectly on these trips!
NOTE: The people on these trips are from all over the States but you’ll always be connected with people from the same city on a trip so you can meet up face to face and get to know your future travel buddies prior to the trip. You’ll also be connected to the whole group via email prior to the trip so you can virtually get to know those that are from different areas. On average, the people on each trip are 90% solo travelers but it’s hard to predict the exact demographic for each trip so please keep this in mind.
Feel free to join the Facebook group to connect with past travelers on these trips, see pictures, ask questions, funny travel memes, travel-related articles, etc: https://www.facebook.com/groups/613025845523107
The trips in this group are put on by a tour company called Globe Drifters and they focus on small group trips geared towards solo travelers with the mission of giving new meaning to travel by putting the human experience at the heart of their trips. The groups are small, usually with 12 people maximum per trip and about 90% of everyone on each trip are solo travelers so you’re not stuck being the odd man out on trips with mostly couples. You’ll have the best of both worlds, solo travel with the security of a small group of other solo travelers for some company on your adventure! To contact Globe Drifters directly, you can email [info@globe-drifters.com](mailto:info@globe-drifters.com).
Upcoming events (4+)
See all- 🏛️🕰️ 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
***🔎 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! 🏛️🌳👟
- 🏙️🛤️ 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.
- Karaoke at Randall's Pub!Randall's Pub, CHICAGO, IL
Join your host Lisa Lenny on the edge of Roger's Park and Edgewater for karaoke at Randall's Pub! The temperature is rising, but it is COOL at Randall's 😎
Randall's is a fun and friendly environment where you can be comfortable to sing your heart out to a supportive crowd. Lisa Lenny runs a good vibes only room with a 2-drink minimum to participate in karaoke (drinks include non-alcoholic beverages).
If you'd like to check out our karaoke song list ahead of time, follow the link below:
https://www.karafun.com/karaoke-song-list.htmlSee you at Randall's!
