
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- 🌆🍷 End of Summer Potluck Party at Buckingham Fountain 🎉🥖Buckingham Fountain East Side Landing, Closest to the Water, Chicago, IL
🌆🍷 End of Summer Potluck Party at Buckingham Fountain! 🎉🥖
✨ Water • Light Show • Wine • Food • Fun! ✨
📅 Date: Thursday, October 2, 2025
⏰ Time: 6:00 – 8:30 PM
📍 Meet: Buckingham Fountain – 301 S. Columbus Dr.
🍽️ Theme: Picnic PotluckWe’re trying something different this year—let’s have a nighttime potluck picnic by Buckingham Fountain!
We’ll set up near the fountain to enjoy the water + light show while sharing food, drinks, and conversation. Think of it like our Millennium Park picnics—just with the fountain as our backdrop.
✔️ Picnics are allowed (but be discreet with wine/beer—hide in bags or pour into thermoses).
✔️ I’ll bring tables for the food.
✔️ Restrooms are available.
✔️ Concessions may be closed this late in the season, so plan to bring your own!
✔️ Everyone brings something to drink/eat & share with the group!
***🍷 WHAT TO BRING:
✅ Wine, beer, or your favorite beverages (be discreet)
✅ Snacks & food to share—cheese, crackers, fruit, dips, baked goodies
✅ Blanket or lawn chairs (chairs are better!)
✅ Bottle opener or corkscrew
✅ Cups, napkins, plates, toothpicks (if you can)
✅ Dress for the weather (bring layers!)
***📍 WHERE TO FIND US:
✔️ We’ll set up near the fountain, in the grassy area to the side.
✔️ Easy to spot—we’ll be the big group with blankets, chairs, wine, and food!
✔️ If you arrive early, grab a bench and wait for the group.
***🏛 About Buckingham Fountain
The Clarence Buckingham Memorial Fountain (1927) is one of the largest fountains in the world, designed by architect Edward H. Bennett and French sculptor Marcel Loyau. Its hourly displays shoot water up to 150 feet, and at dusk, the light-and-music show makes it magical. The fountain runs daily May–October, 8 a.m.–11 p.m., with the final display at 10:35 p.m.Philanthropist Kate Sturges Buckingham donated the fountain in honor of her brother Clarence, a Chicago art patron. Kate worked closely with technicians to design the fountain’s colored lighting so that it would glow like “soft moonlight”.
Inspired by the Latona Fountain at Versailles, Buckingham Fountain is even larger than its French counterpart and symbolizes Lake Michigan. The four massive bronze sea horses around its base represent the four states bordering the lake.
🚗 PARKING & TRANSPORTATION:
Public Transit:
• Easy access via CTA trains & buses
• Plan your trip: CTA Trip Planner
Parking:
• Grant Park South Garage recommended
• Limited metered parking nearby—arrive early if driving
• Use SpotHero or ParkWhiz for deals
***🙌 RSVP & NO SHOW POLICY:
✅ Please update your RSVP if your plans change!
✅ The cutoff to change your RSVP is the event start time.
✅ If you’re running late, message your host directly.
❗ 3 no-shows without updating = 3-month RSVP freeze.
***✨ Let’s close out summer in style—with food, friends, wine, and one of Chicago’s most iconic landmarks as our backdrop!
- 🌆🌿 Autumn on the 606: Chicago’s Elevated Escape 🍂🚶Walsh Park, Chicago, IL
🌆🌿 Autumn on the 606: Chicago’s Elevated Escape 🍂🚶
🍁 A Fall Walk on the 606 Trail 👟
Let’s celebrate the 10th anniversary of Chicago’s famous elevated park with an official group walk! Anniversary was actually 6/6/25 so we are a little late but I still want to get this walk in while the weather is nice!
📆 Date: Friday, 10/3/25
⏰ Time: 3:15 PM – 7:30 PM (with optional dinner/drinks after)
📍 Start: Walsh Park, 1722 N. Ashland Ave.
📍 End: Ridgeway Trailhead next to McCormick YMCA, 1834 N. Lawndale Ave.
🚶 Distance: 2.7 miles (full length of the trail)
🌦️ Rain or shine | Casual pace | Drop out anytime along the way✨ Itinerary:
- 3:15 PM – Meet at Walsh Park entrance (trail access point)
- 3:15–5:00 PM – Walk the entire 2.7-mile 606 Trail
- 5:15–7:30 PM – Optional bites & drinks:
- 🍷 Outside Voices – 3204 W Armitage Ave, Chicago, IL 60647 – https://www.outsidevoiceswine.com
- 🍔 The Moonlighter – 3204 W Armitage Ave, Chicago, IL 60647 – http://www.themoonlighterchicago.com
- 🍸 Wolf & Company – 1752 N. Western Ave, Chicago, IL 60647 – https://wolfandcompanychicago.com
💡 Important Notes:
- This is a one-way walk — we won’t end where we started. If driving, consider parking near the halfway point or plan how you’ll return.
- Street parking is available but limited; check signage for meters or permit-only spots.
- Public transit is a great option (see CTA Trip Planner: https://www.transitchicago.com/planatrip).
🌟 About the 606
The 606 is Chicago’s 2.7-mile elevated park and trail system, connecting four vibrant neighborhoods: Wicker Park, Bucktown, Humboldt Park, and Logan Square. Once an abandoned rail line, it was reimagined into green space, art, and community trails after decades of planning. Today it’s a hub for walking, biking, history, and local culture.🔗 Learn more:
👉 The 606 on Facebook
👉 The 606 Official Website🙌 Come explore this Chicago icon with us—walk the neighborhoods, enjoy the fall scenery, and celebrate a decade of The 606!
📸✨ See you on the trail!
- Italian grocery/deli @ Freddy's Pizzeria (Cicero, IL) & Houby FestFreddy's Pizza, Cicero, IL
NOTE: This meetup will be done in conjunction with The International Supper Club of Chicago & 1001 Things to See in Chicago Before You Die - the lunch at Freddy's will start at 12:30 PM, and then we will head to Houby Fest (located at Laramie Ave & 34th St) around 2:00 PM for live music and entertainment.
The festival is accessible from Freddy's by public transportation (a 10 minute walk from the #315 Pace bus stop at Central & 34th St), but carpools are appreciated!
Menu for Freddy's: https://www.freddyspizza.com/pdf/FreddysPickup032625.pdf
Meetup for 16 at Freddy's Pizzeria, a corner Italian restaurant and grocery store/deli in Cicero, IL. The restaurant has been around since the 1960s, and has been featured on "Check, Please", ABC's "Hungry Hound", "Chicago's Best", the Chicago Tribune, and the Wednesday Journal (local Oak Park newspaper).
From the Wednesday Journal,
"I’d forgotten that to walk into Freddy’s Pizza at lunchtime is to be momentarily and delightfully bewildered. There are people standing around, and some are paying for food, and others are giving orders, which they then pick up at various locations along the front deli counter. There are a two lines of people winding around the grocery shelves, butting up against each other all across the front of the hot table, two throngs of people who, despite the lack of a clear queue, seem to politely know when it’s their turn to order, and then after a respectful pause, take their food and pay.
This hungry mass of humanity is ordering things like involtini (slices of eggplant rolled around veal with peas), pizza topped with the usual cheese/sauce/sausage accoutrements as well as a few odd options (e.g., fried calamari), porchetta sandwiches (thin sliced pork on bread), sautéed rapini (Italian broccoli), batter-fried artichoke hearts, salads of beans and tomato mozzarella, seafood and many, many other good-looking edibles.
Along the far wall is a mound of many different but all beautiful Italian breads, some of which are sliced for sandwiches, others of which go home whole with many of the hundreds of people who pass through the doors of this place every day: old Italian grannies, cops, construction workers, neighborhood guys, wise guys, moms with kids, random visitors like me and, the day I was there, a film crew from New York that was there to document what is likely a disappearing breed: the neighborhood Italian-American grocery/deli/hot table.
Freddy’s is a good place to visit any time of year, but there’s something about it that I find especially Christmas-appropriate. Maybe it’s all the deep red colors (sausage, sauce, etc.) and greens (rapini, salad, etc.), though there’s also the extremely homey and welcoming nature of all who work there.
Visiting Freddy’s last week, I had the involtini and a slice of sopressata pizza, and while we sat in the little enclosed eating structure (constructed maybe 8 or so years ago to accommodate dining in), at least three employees, including both the husband and wife who own the place, came by to ask if everything was okay, how’s the food, can I get you anything, how about more napkins? Nice.
If you’ve never been to Freddy’s, there’s really no good reason why you haven’t. This tiny place, Cicero’s humble jewel, has been featured in the Sun-Times and Tribune, television shows like “Check, Please!” and “Chicago’s Best,” Steve Dolinksy’s ABC segment “The Hungry Hound,” and it’s been visited by Bobby Flay and other big names. None of this media attention seems to have changed the basic customer service orientation and the genuinely open and friendly attitudes of owners Joe and Anna Marie Quercia.
And that’s another one of the other things I like about this place: it’s timeless, unchanged by fame, chugging along the same as it ever was, doing what it does best. Freddy’s hasn’t bought all the spaces next door and turned itself into an Eataly-type place; it hasn’t hired a battalion of servers and set up a dining room; heck, they haven’t even upgraded the efficiency of the queuing systems, and why should they? It’s successful. It’s working. Don’t mess with it. Such quirks give the place character.
Another quirk that I find charming is that some canned goods are on shelves behind the counter, so that you have to ask for them, just as you would at an old-timey general store: very inefficient but endearing, and my guess is that the Quercia family needs the extra space to display retail products." - 🌈🍷 Taste of Northalsted: A Fall Food & Drink Adventure 🍂🍹🍴Roscoe's Tavern, Chicago, IL
🌈🍷 Taste of Northalsted: A Fall Food & Drink Adventure 🍂🍹🍴
*Food & Drink Sampling Crawl of Chicago’s Proudest Neighborhood!*🌈
Date & Time:
📅 Saturday, October 4, 2025
🕐 1:00 PM – 5:00 PM CDT
📍Location (Check-In):
Roscoe’s Tavern – 3356 N Halsted, Chicago (we will meet at Roscoe's!)
plus 5 other starting locations to choose from!
***
About the Event
Celebrate fall in Chicago’s Proudest Neighborhood with a culinary adventure through Northalsted! 🌈Stroll between 20+ participating locations, sampling signature dishes, craft beers, creative cocktails, and spirits from the area’s top restaurants, bars, and businesses. This is the perfect way to discover new favorites while enjoying the vibrant energy of Northalsted.
This year’s crawl includes an extra hour and six starting locations for smoother check-in. Grab your glass, wristband, and tasting guide at your chosen check-in spot, then head out to eat, sip, and explore!
***🎟️ Tickets
- $30 in advance (highly recommended – this event always sells out!)
- Day-of tickets may be available in limited quantities.
- Refunds available through 11:59 PM, Thursday, October 2, 2025.
👉 BUY TICKETS – Fall Taste of Northalsted: Food & Drink Sampling Crawl – Northalsted
***What’s Included
✔️ 20+ food & drink tastings (one sample per location)
✔️ A souvenir glass & tasting guide
✔️ Access to all participating businesses along the crawl
✔️ An afternoon of food, drinks, friends & fun! 🎉
Note: Tastings are sample-sized portions; some locations will offer food, others beverages.
***Participating Locations (Partial List)
- Men’s Room Chicago
- El Taco Cart 🌮
- Lark 🍕
- Sidetrack 🍸
- El Mariachi Tequila Bar & Grill
- Progress Bar
- Drew’s on Halsted
- The Villa Toscana
- Roscoe’s Tavern 🍹
- GoodTimes Brewery 🍺
- 2d Restaurant
- Out of the Closet Thrift Store
- Center on Halsted
- Elevate Coffee ☕
…plus many more to be announced!
***
Need to Know
- Must be 21+ with valid ID to participate.
- Walking event; please wear comfortable shoes. 👟
- Crawl does not end where you start; plan transportation accordingly. 🚇🚖
- Check-in to receive your glass, wristband & tasting guide.
- Coordinate with your group if you want the same starting location (tickets per site are limited).
***
Getting There
🚇 Easily accessible by CTA bus & train. Plan your trip: CTA Trip Planner
🚗 Driving? Use SpotHero or Parking Whiz for the safest & cheapest options. Metered parking and nearby lots also available.
***No-Show Policy
To keep events fair, 3 no-shows without updating your RSVP will suspend signup access for 3 months. Please update RSVP by event start time if you cannot attend.
***🍷🍂 Come hungry, come thirsty, and come ready to explore the best of Northalsted this fall!