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 🌬️🚶♀️🚶♂️
🕺 Harper Court Live Music & Dance | Hyde Park Steppers Contest 💃
🎶 Outdoor Music & Dancing Night at Harper Court (Hyde Park)
Bring your dancing shoes for the 2nd Annual Hyde Park Best Steppers Contest! Come watch even if you don't step (dance)
📅 Thursday, September 4, 2025
🕕 6:00–9:00 PM
📍 Harper Court, 5235 S. Harper Court, Hyde Park (53rd St. & Lake Park Ave.)
FREE – REGISTER HERE:
2nd Annual Hyde Park Best Steppers Contest Tickets
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Let’s head to Hyde Park for a lively evening of live music, dancing, and neighborhood vibes! We’ll be attending the Harper Court Summer Music Series, a free monthly outdoor concert series in the heart of Hyde Park’s 53rd Street shopping and dining district.
🎵 This Month’s Lineup:
✨ 2nd Annual Hyde Park Best Steppers Contest with DJ Eric “ET” Taylor
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🪑 Seating
Seating is not provided—please bring a folding chair if you’d like to sit. Space is limited, so we’ll leave plenty of room for dancing!
🍴 Dining
Feel free to bring your own food (liquor is technically not allowed). Or enjoy food tents and nearby restaurants, including:
- Bob’s Pizza
- Chipotle
- Daisy's Po' Boy & Tavern
- Deep Purple
- Ja’ Grill
- Roti Modern Mediterranean
- Stan’s Donuts & Coffee
- Strugglebeard Bakery
Explore more Hyde Park favorites along 53rd Street: welcometohydepark.com
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🛍 Shop Local
Check out unique shops like Recycled Modern, Suuri Design, and the iconic Silver Room, all nearby.
🚗 Transportation & Parking
- Public Transit: #6 Jackson Park Express bus or Metra Electric line (Millennium Station → 53rd Street stop). CTA Trip Planner
- Parking: Paid options in Harper Court garage (entrance on Lake Park Ave, south of McDonald’s), surface lot on Harper Ave, or metered street parking. For cheaper rates, check SpotHero or ParkWhiz.
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🌟 About the Series
The Harper Court Summer Music Series started in 2015 as a collaboration between the University of Chicago and Eric Williams of The Silver Room. Paused during 2020–2021, it’s now back as a Hyde Park summer tradition. More info: harpercourtmusic.com
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⛔ No-Show Policy
- 3 no-shows without updating your RSVP = suspension from events for 3 months.
- Please check in with the host upon arrival.
***
👉 Come enjoy a summer night of music, dancing, and Hyde Park energy!
Upcoming events (4+)
See all- 🌀🎷Brass, Beats & Breezes: Chicago’s 47th Annual Jazz Bash🎤🎺Jay Pritzker Pavilion, Millennium Park, Chicago, IL
🌀🎷Brass, Beats & Breezes: Chicago’s 47th Annual Jazz Bash🎤🎺
🎷🎶 47th Annual Chicago Jazz Festival at Millennium Park 🎶🎷
📍 Jay Pritzker Pavilion & Millennium Park, Chicago
🗓️ Sunday, August 31, 2025
🕒 We’ll be on the Great Lawn all the way in the back from ~4 PM through the evening, but feel free to arrive anytime!
***🌿 What to Expect & Where We'll Be
We'll claim a spot at the back of the Great Lawn near the sidewalk, just south of the Jay Pritzker Pavilion.🧺 Look for chairs, blankets, and a welcoming group—you can’t miss us! Bring snacks and non-alcoholic drinks. Outside alcohol is officially not allowed, but discreet wine in plastic bottles sometimes makes it through light bag checks (no guarantees). We have always been able to get stuff in. You can also buy alcohol inside from vendors.
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🧺 What to Bring (if you’re comfortable helping out!)- Blankets, lawn chairs, or a portable table (super helpful!)
- Snacks to share: cheese & crackers, fruit, baked goods, hummus + chips
- Extras: cups, napkins, plates, toothpicks, etc.
(If you’re driving or live nearby, please consider bringing extra items!)
***
🎶 Full Schedule Highlights
🎤 Jay Pritzker Pavilion (Tribute Stage)
3:15–3:45 PM Windy City Ramblers (Second Line Parade)
3:45–4:00 PM Emcee Intro, National Anthem, Lift Every Voice
4:00–4:45 PM Natalie Scharf Quintet ft. Paul Asaro
5:05–6:05 PM G. Thomas Allen
6:25–7:25 PM Ari Brown Quintet
7:45–9:00 PM Eliades Ochoa🎺 Von Freeman Pavilion
3:00–4:00 PM Thadeus Tukes Sextet
1:50–2:45 PM Maison Électronique
12:40–1:35 PM Abigail Riccards Trio
11:30–12:25 PM Ben Waltzer Quartet🎧 WDCB Jazz Lounge
6:45–7:45 PM Denise Thimes Quintet
4:30–6:15 PM Kyle Swan Quartet
2:15–4:00 PM Neal Alger's Here and Now
12:00–1:45 PM Joel Paterson’s Green Mill All-Stars🌆 Harris Theater Rooftop Terrace – Next Generation of Jazz
3:00–4:00 PM FM Trio
2:00–2:45 PM .VOM
1:00–1:45 PM Aaron Kaufman-Levine Quartet
12:00–12:45 PM Kevin King Regime
11:00 AM–Noon Jack Nelson Ciavash
***🚇 Getting There
- CTA: Take the Red Line to Lake or State/Monroe. Use CTA Trip Planner
- Driving: Use Grant Park North Garage via SpotHero or ParkWhiz
(Metered parking is limited)
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❄Park Rules & Tips
- No knives or corkscrews allowed
- No outside alcohol (officially), but… be discreet if you try
- Dress for the weather – bring layers or sunscreen
- If it gets too hot/sunny, step into the shady pavilions or grab a cold drink inside the park
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### 📵 RSVP & No-Show Policy
- 3 no-shows without updated RSVP = 3-month freeze from attending
- Text/call the host if running late
- Be sure to check in with the host when you arrive
***
🎷 Come enjoy a relaxing evening of great jazz, great people, and good vibes under the Chicago skyline!
Let’s keep this Chicago tradition going strong! 🎶🌇🧺
- 🏰✨ Mansions, Mimosas & Gossip: Stroll the Glittering Gold Coast 🍾🏛️Chicago History Museum, Chicago, IL
🏰✨ Mansions, Mimosas & Gossip: Stroll the Glittering Gold Coast 🍾🏛️
Join us for a special Labor Day Walk of Chicago’s Gilded Playground on the Near North Side!
Step into Chicago’s Gilded Age and explore the Gold Coast Historic District, one of the city’s most affluent and architecturally stunning neighborhoods. Stroll past grand mansions, historic townhomes, and elegant row houses, built by industrialists, entrepreneurs, and cultural figures of the late 19th century. Hear stories of the families, immigrants, and visionaries who shaped this vibrant lakeside community.
✨ Tour Highlights:
· 🏘️ Gilded Age mansions & exquisite architecture (Queen Anne, Romanesque, and Italianate)
· ⛪ Historic churches & preserved streetscapes
· 🍺 Legendary Astor Street and iconic Gold Coast hotspots
· 🏛️ Insights into Chicago’s elite social & political historyLed by a passionate local guide, this tour brings Chicago’s rich Gold Coast past to life.
📅 Date & Time:
Monday September 1, 2025
🕚 12:15 pm – 2:30 PM (~1.8 miles walking)
📍 Start: Chicago History Museum, 1601 N Clark St, Chicago, IL 60614
🎯 End: St. Chrysostom's Episcopal Church & Day School 1424 N Dearborn St
💰 Cost: $20 (cash preferred; Zelle/Venmo/PayPal accepted)
🌦️ Casual pace | Outdoors | Rain or shine⚠️ Walk ends ~3 blocks from start — plan parking accordingly
📍 Route & Highlights
· 🏛️ Chicago History Museum – 1601 N Clark St
· ⛪ Archdiocese of Chicago – Cardinal Mansion – 1555 N State Pkwy
· 🏠 John Lewis Cochran House (George Maher, architect) – 1521 N State Pkwy
· 🌳 1535 Wooden Alley
· 🏰 Madlener House – 4 W Burton Pl
· 🏡 Edward Tyler & Ruby McCormick Blair Home – 1516 N Astor St
· 🏛️ Former Home of Robert Todd Lincoln – 1525 N Astor St
· 🏰 Patterson-McCormick Mansion – 20 E Burton Pl
· 🏥 International Museum of Surgical Science – 1524 N Lake Shore Dr
· 🏠 Howard Van Doren Shaw Designed Home – 1451 N Astor St
· 🏰 Grandiose Château – 1449 N Astor St
· ⛪ Maryknoll Fathers (Catholic missionary order) – 1421 N Astor St
· 🏛️ Charnley-Persky House Museum – 1365 N Astor St
· 🏘️ Astor Court – 1355 N Astor St
· 🏨 Astor House– 1340 N Astor St
· 🏛️ John Wellborn Root House – 1310 N Astor St
· 🏨 Astor Tower Hotel - 1300 N. Astor St
· 🏨 Ambassador East Hotel – 1301 N State Parkway
· 🎉 Original Playboy Mansion – 1340 N State Pkwy
· ☕ 3 Arts Club Cafe at RH Chicago – 1300 N Dearborn St
· 🏠 Augustus Warner House – 1337 N Dearborn St
· 🏢 MCNALLY & QUINN Architects – 1366 N Dearborn Pkwy
· ⛪ St. Chrysostom's Episcopal Church & Day School – 1424 N Dearborn St🎒 Bring:
- 👟 Comfortable walking shoes
- 💧 Water bottle
- 🌦️ Weather-ready gear
- 💵 $20 tour fee
🍽️ Optional Lunch After the Tour
Grab food & drinks nearby:
☕ 3 Arts Club Cafe at RH Chicago – 1300 N Dearborn St – https://rh.com/us/en/chicago/restaurant
🍻 Woodie’s Flat – 1535 N Wells – https://woodieschicago.com/
🍝 Topo Gigio Ristorante – 1516 N Wells – https://topogigiochicago.com/
🌮 Adobe Grill – 215 W North Ave – https://www.adobochi.davinci-group.com/
🍺 Corcoran’s Pub – 1615 N Wells – https://corcoransoldtown.com/
💵 Bring cash — some restaurants don’t split checks!🚗 Getting There
🚆 CTA: Brown Line / multiple buses — plan via CTA Trip Planner
🚘 Driving: Metered Street parking along Wells, North Ave, Dearborn & LaSalle
💡 Tip: Gold Coast parking is tricky — SpotHero / ParkWhiz recommended📝 RSVP & No-Show Policy
✔️ Keep your RSVP updated — no-shows prevent others from joining
❌ Please cancel if you cannot attend🌟 Why Gold Coast?
The Gold Coast is one of Chicago’s most treasured neighborhoods—famous for quiet, tree-lined streets 🌳, stately mansions 🏰, and deep ties to the city’s history 📜.
🏠 Early Development:
Once called the Astor Street District (late 1800s), it stretched from North Ave. to Division (then Bishop St). Today, the Gold Coast runs North Ave. ➝ Oak St. and lakefront ➝ Clark St. Astor Street honors John Jacob Astor—one of America’s richest men, though he never lived in Chicago.
💼 Potter Palmer’s Vision:
After the Great Chicago Fire (1871), Palmer bought swampy land up north while others flocked to Prairie Ave. He built his Lake Shore Drive mansion 🏰 (the “goldfish bowl castle”) and developed the Palmer House Hotel for his wife, Bertha.
🌊 Lakefront Living:
When Lake Shore Drive opened (1875), the Gold Coast took off. The Palmers’ home became a hub of high society, and Bertha’s Impressionist art collection now lives at the Art Institute 🎨. Though demolished in 1950, their mansion helped define the Gold Coast’s glamorous legacy.💫Step back in time, explore stunning architecture & rich local history, and experience Chicago’s Gold Coast like never before! 💼💎
