About us
🎉 Welcome to & Windy City Wanderers! 🌆
We’re so glad you’re here!
Whether you’re new to Chicago or a lifelong local, these sister groups are all about being a tourist in your own city—discovering hidden gems, rich history, fun facts, and unforgettable experiences across Chicagoland. 🗺️✨
Windy City Wanderers is the sister group to 1001 Things to See in Chicago Before You Die, and we host many joint events together—so you’ll often see crossover adventures and shared outings. 🤝
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🗓 What to Expect
We host fun, social outings year-round (yes, even in winter ❄️). Expect:
• Walking tours & neighborhood explorations
• Concerts, lectures & theater
• Pop-up dinners, trivia & social nights
• Museums, festivals & special events
Events take place throughout Chicago and nearby suburbs like Evanston, Oak Park, and Park Ridge.
🚇 All events are CTA-accessible.
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💬 Why Join?
• Discover new places all over Chicagoland
• Meet new people and make real connections
• Enjoy an active, well-curated event calendar
• Try the group FREE for 90 days
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💰 Membership
• 90-day free trial
• Annual dues: $12/year after the trial
• 🎉 Host an event and your dues are waived!
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🚨 RSVP / No-Show Policy (Please Read)
To keep events fair and running smoothly:
• A no-show without updating your RSVP = 1 strike
• 3 strikes = a 3-month pause from events
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🤝 Stay Connected
📘 Facebook Page
https://www.facebook.com/profile.php?id=61576822533554
👥 Facebook Group
https://www.facebook.com/groups/1571684466442303
📸 Instagram
https://www.instagram.com/1001thingstoseeinchicago/
🌬️ !001 Things to See in Chicago Before You Die Meetup (sister group)
https://www.meetup.com/windy-city-wanderers
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💡 Have an idea for an event? Want to host or co-host?
Just message me—I’d love to hear from you!
Can’t wait to explore, wander, and discover Chicago together 💙
Cheers,
Giovina Romandine
Organizer, Windy City Wanderers 🌬️🚶♀️🚶♂️
Upcoming events
28

🌈🎤 Queens, Cocktails & Bingo on the Beach at Aura! 🏖️🍹
Aura On the Lake, 5701 N. Lake Shore Drive, Chicago, IL, US🌈🎤 Queens, Cocktails & Bingo on the Beach at Aura! 🏖️🍹
Drag Bingo on the Beach at Aura on the Lake at Osterman Beach!
Join us for a fun summer evening of Drag Bingo on the beach at Aura on the Lake! Enjoy hilarious drag performances, bingo with prizes, tropical drinks, tasty bites, and beautiful Lake Michigan views at one of Chicago’s newest lakefront hangouts.
📅 Wednesday, August 19, 2026
⏰ Meet at 5:45 PM
🎤 Drag Bingo: 6:00–8:00 PM
📍 Aura on the Lake
5701 N. Lake Shore Dr.
Chicago, IL
🌐 Location & Menu:
https://uvaechicago.com/chicago-andersonville-uvae-kitchen-and-wine-bar-aura🍽️ Dining Information
Aura accepts cards, but for our Meetup group we are asking everyone to please bring CASH to make things easier!
💵 CASH ONLY for group dining — no separate checks.
We will likely be seated at several tables, and each table will receive one check.
Please add 32% to your total:
• 12% Chicago sales tax
• 20% gratuity
💡 Exact change is appreciated and helps the evening run smoothly.🌈 About Drag Bingo
Every Wednesday during the summer beach season, Aura on the Lake hosts Drag Bingo from 6–8 PM. Hosted by local Chicago drag personality @misswindybreeze, this lively evening combines classic bingo with comedy, music, audience participation, and plenty of laughs.🎉 Free to play bingo!
🏆 Win fun summer-themed prizes and Aura gift prizes.
No bingo experience is needed — just bring your sense of humor and get ready for a fun night by the lake!🏖️ Beachside Atmosphere
Drag Bingo takes place right on the sand at Kathy Osterman (Hollywood) Beach, creating the perfect Chicago summer vibe. Seating is limited, so bringing a beach blanket or lawn chair is highly recommended if you don’t grab one of the patio tables early.Enjoy:
🌊 Lake Michigan views
🎤 Live drag entertainment
🍹 Frozen cocktails and refreshing drinks
🍔 Beach bites and snacks
🔥 Tabletop s’mores kits
☀️ A relaxed summer beach atmosphere🍹 About Aura on the Lake
Located steps from Kathy Osterman Beach, Aura on the Lake is Uvae Kitchen & Wine Bar’s seasonal lakefront café and patio.Menu favorites include:
🍔 Burgers & sandwiches
🥗 Fresh salads
🌮 Tacos & shareable appetizers
🍟 Snacks and light bites
🍺 Local craft beer
🍷 Wine
🍹 Frozen cocktails and specialty drinks
🍦 Sweet treats
🌐 Menu & Info:
https://uvaechicago.com/chicago-andersonville-uvae-kitchen-and-wine-bar-aura🏖️ About Kathy Osterman (Hollywood) Beach
One of Chicago’s favorite North Side beaches, Kathy Osterman Beach offers a wide sandy shoreline, lakefront trails, volleyball courts, swimming, sunsets, and some of the best summer people-watching in the city.🚇 Transportation
CTA Trip Planner:
https://www.transitchicago.com/planatrip/
🚗 Parking:
Metered parking is available on Granville Avenue and nearby streets. Watch carefully for permit restrictions.
🅿️ SpotHero or ParkWhiz are recommended for easier parking.🦟 Pro Tip:
Bring bug spray — beachside patios can get buggy after sunset!📱 Running late or can’t find us?
Call or text Giovina at 312-835-4259.⚠️ RSVP Reminder
✔️ Please update your RSVP if your plans change.
✔️ RSVP changes must be made before the event begins.
❌ Three no-shows without updating your RSVP will result in a 3-month RSVP restriction.🌊🌈 Grab a drink, cheer on the queens, play some bingo, and enjoy a perfect Chicago summer evening on the lakefront! 🎤🍹🏖️
19 attendees
🎶🌴 Ricky Martin Live at Ravinia — A Night of Global Hits & Latin Energy! 💃🍷
Ravinia Festival, 200 Ravinia Park Rd, Highland Park, IL, US🎶🌴 Ricky Martin Live at Ravinia — A Night of Global Hits & Latin Energy! 💃🍷
Get ready for an electrifying summer night with international superstar Ricky Martin at Ravinia Festival! Bring those dancing shoes!
From “Livin’ la Vida Loca” to “She Bangs” and “La Copa de la Vida,” this is a full-scale celebration of rhythm, energy, and nonstop dancing under the stars. 🌙🔥
We’ll be relaxing on the lawn—blankets, chairs, food, wine, and great company—for one of the most fun, high-energy nights of the entire summer season. 💃✨
⚠️ These shows sell out FAST—grab your tickets ASAP!
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🎟️ TICKETS + SEATING
🎫 $88 — General Admission Lawn (fees included!)
👉 Direct tickets:
https://www.ravinia.org/events/detail/ricky-martin-260820#showing_699💺 Optional rentals (HIGHLY recommended!):
• Chair — $10
• Table — $12
⚠️ Add chairs/tables before checkout so you don’t have to carry them on the train!
🪑 I’ve already rented one table—we may want another!
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📍 EVENT DETAILS
📅 Thursday, August 20, 2026
⏰ Gates open at 5:00 PM (arrive early so we can sit together!)
📍 Ravinia Festival
🏠 200 Ravinia Park Rd, Highland Park, IL 60035
📱 I’ll post my exact lawn location once I arrive!🍷🍴 FOOD & DRINK (POTLUCK STYLE!)
🥗 Bring food or drinks to share—this is a picnic-style lawn experience!
✔️ Snacks, meals, wine, beer, desserts welcome
✔️ Please comment what you’re bringing
🪑 I’ll bring a table—extra tables welcome!
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🚇 TRAIN (BEST OPTION!)
🚆 Union Pacific North Line (Metra)
Board at: Ogilvie / Clybourn / Ravenswood
🎯 Stop: Ravinia Park (direct entrance) or Braeside (short walk)
👉 https://www.ravinia.org/visit/getting-here#train
👉 https://ridertools.metrarail.com/maps-schedules/train-lines/UP-N
I will post exact train schedule closer to the date so check back!
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🚗 PARKING INFO
🚘 $25 on-site parking
⚠️ Big shows may redirect to remote lots + shuttle buses
💡 Tip: Arrive early or take Metra to avoid delays
🆓 Highland Park Metra parking after 4 PM + shuttle option
***🎶 OTHER RAVINIA SHOWS THIS SEASON (join 1 or all 5 shows)
📅 7/12 — Billy Idol
📅 8/20 — Ricky Martin
📅 8/22 — Bonnie Raitt
📅 8/27 — Kool & the Gang + Morris Day & The Time + Con Funk Shun
📅 9/5 — Rod Stewart + Richard Marx
👉 Meetup event list (FOR ALL SHOWS):
https://www.meetup.com/windy-city-wanderers/events/🎶 ABOUT THE ARTIST
Ricky Martin is a Puerto Rican singer, songwriter, and actor known for his explosive stage presence and global influence on Latin pop music.He began performing at age 9 in TV commercials and joined the legendary boy band Menudo at just 12 years old, launching his career across Latin America.
In the 1990s, he rose to international fame with Spanish-language albums Ricky Martin (1991) and Me Amaras (1993), followed by his breakthrough A Medio Vivir (1995), featuring the hit “María.”
His 1998 album Vuelve earned him his first Grammy Award and included “La Copa de la Vida,” which became a defining global anthem after his iconic performance at the 1999 Grammy Awards.
His crossover into English-language music came with the 1999 album Ricky Martin, led by the worldwide smash “Livin’ la Vida Loca,” which helped ignite the “Latin explosion” in mainstream U.S. pop culture.
Since then, he has released major hits including:
• “She Bangs”
• “Nobody Wants to Be Lonely”
• “La Mordidita”
• “Vente Pa’ Ca”He has sold over 70 million records worldwide and earned multiple Grammy, Latin Grammy, Billboard, and MTV awards, along with a star on the Hollywood Walk of Fame.
Beyond music, Ricky Martin is also an actor (including General Hospital and The Assassination of Gianni Versace) and a dedicated humanitarian. Through the Ricky Martin Foundation, he advocates against human trafficking and supports children’s rights globally.
He remains one of the most influential Latin artists in the world, known for his dynamic stage presence, fusion of pop and Latin rhythms, and continued global touring and performances. 💃
Today, he continues to perform internationally, blending classic hits with newer material while remaining a major cultural icon in Latin pop music. 🌎🎤
🌐 https://www.rickymartinmusic.com/
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🎼 ABOUT RAVINIA
Ravinia Festival is North America’s oldest outdoor music festival and summer home of the Chicago Symphony Orchestra. It offers a unique picnic-style concert experience under the stars. It hosts a series of outdoor concerts and performances every summer from June to September. The first orchestra to perform at Ravinia Festival was the New York Philharmonic under Walter Damrosch on June 17, 1905. It has been the summer home of the Chicago Symphony Orchestra (CSO) since 1936. Located in the Ravinia neighborhood, the venue operates on the grounds of the 36-acre (15 ha) Ravinia Park, with a variety of outdoor and indoor performing arts facilities, including the architectural prairie style Martin Theater. The Ravinia Festival attracts about 600,000 listeners to some 120 to 150 events that span all genres from classical music to jazz to music theater over each three-month summer season.
🌐 https://ravinia.org/
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📌 IMPORTANT REMINDERS
⚠️ Arrive early so we can sit together
⚠️ Bring food/drinks to share
⚠️ Add chair/table rentals before checkout
⚠️ Keep RSVP updated—no-shows impact the group
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Get ready for a high-energy night of dancing, Latin pop classics, and summer magic at Ravinia! 💃🌴🎶9 attendees
🌊☀️ Northside Beach Hopping: Mahony Griffin to Berger Park Lakefront Walk! 🍹
Jarvis Beach & Park, 1208 W Jarvis Ave, Chicago, IL, US🌊☀️ Northside Beach Hopping: Mahony Griffin to Berger Park Lakefront Walk! 🍹🚶♀️
Part 1 of 2 — North Side Beaches, Parks & Lake Views
Join us for a beautiful Friday afternoon walk along one of Chicago’s most scenic stretches of lakefront! We’ll explore the far north end of the Lakefront Trail, starting at Mahony Griffin (Marion) Beach Park near Loyola and making our way south through beaches, parks, and hidden lakefront gems before ending at Berger Park and The Waterfront Café.
📅 Friday, August 21, 2026
⏰ 3:00–5:45 PM
📍 Start: Jarvis Beach & Park
1208 W. Jarvis Ave.
Chicago, IL
🏁 End Point: The Waterfront Café
6219 N. Sheridan Rd.🚶 About the Walk
✅ Distance: Approximately 3.2 miles
✅ One-way walk
✅ Easy/moderate pace with lake views and photo stops
Our route includes:
🌊 Mahony Griffin (Marion) Beach Park
🌊 Sherwin on the Lake
🌊 Leone Beach Park
🌊 Loyola Beach
🌳 Loyola Park Natural Area
🌊 Tobey Prinz Beach Park
🌊 Columbia (Helen Doria) Beach
🌊 North Shore Beach Park
🌊 Hartigan Beach
🌊 Rosemont Avenue / Edgewater Beach
🍹 The Waterfront Café⚠️ The Lakefront Trail does not fully connect through this section, so we’ll zig-zag along Sheridan Road and neighborhood streets while walking along the beach whenever possible.
🍹 Part 2: Dinner & Live Music at The Waterfront Café
After the walk, many of us will continue with dinner, drinks, and live music at The Waterfront Café!⚠️ Dinner is a separate Meetup event due to limited space.
If you want to join us for dinner and music, RSVP here:
https://www.meetup.com/windy-city-wanderers/events/315748432/🍴 The Waterfront Café is a casual, family-friendly lakeside restaurant and performance venue with beautiful lake views.
Menu:
http://waterfrontcafechicago.com/fooddrink📌 What to Bring
✅ Water
✅ Sunscreen
✅ Comfortable walking shoes
✅ Summer clothing
✅ Camera — lots of great photo opportunities!
🚻 Public restrooms may be limited depending on beach facilities, so plan ahead.🚇 Transportation & Parking
🚗 Limited street parking near the starting point.
🅿️ Consider parking closer to the end point since this is a one-way walk.🚇 Easy CTA access:
- Red Line nearby
- CTA buses #146, #147, #151
Use CTA Trip Planner:
https://www.transitchicago.com/planatrip/
🅿️ Parking apps:
SpotHero or ParkWhiz🌤️ Weather Note:
This is a weather-dependent outdoor event. We’ll monitor the forecast and update if needed.⚠️ RSVP Reminder
✅ Please update your RSVP if your plans change.
✅ RSVP changes must be made before the event begins.
📱 Running late? Message the host directly.
❌ Three no-shows without updating your RSVP = 3-month signup freeze.🌊☀️ Come enjoy lake breezes, beautiful beaches, Chicago history, and a perfect summer Friday along the North Side lakefront. Let’s walk, explore, and end the day with great food and music! 🍹🎶
12 attendees
🌊🎷 Lake Views, Live Jazz & Dinner at Waterfront Café! 🍽️
The Waterfront Cafe, 6219 N Sheridan Rd, Chicago, IL, US🌊🎷 Lake Views, Live Jazz & Dinner at Waterfront Café! 🍽️
Part 2 of 2 — Dinner, Drinks & Live Jazz at Berger Park
🌴 Let’s head back to one of our favorite Chicago summer spots — Waterfront Café! It feels like a little Miami escape right here on the North Side with beautiful lake views, a relaxed beach café atmosphere, great food, drinks, and live music on the patio.
Join us for a fun Friday night of dinner, conversation, and jazz overlooking Lake Michigan!
📅 Friday, August 21, 2026
⏰ Meet: 6:00 PM
🎶 Live Music: 7:00–9:00 PM
📍 Waterfront Café
Berger Park
6219 N. Sheridan Rd.
Chicago, IL🎷 Featured Performance:
Allan Laskey Trio
The Allan Laskey Trio brings a cool, sophisticated jazz sound featuring:
🎵 Traditional jazz & swing
🎵 Classic jazz standards
🎵 Great American Songbook favorites
🎵 Jazz blues influences inspired by artists like Charlie Parker
Perfect music for a relaxing summer evening by the lake!⚠️ IMPORTANT:
This Meetup is ONLY for the dinner and music portion.
Earlier that afternoon, we are hosting:
🌊☀️ Northside Beach Hopping: Mahony Griffin to Berger Park Lakefront Walk! 3-5:30 pm
The walk is a separate Meetup event, and space is limited for each.
If you want to do the WALK TOO please RSVP separately here:
https://www.meetup.com/windy-city-wanderers/events/315748420/🌞 The Plan
🍽️ Meet at Waterfront Café at 6 PM.
We’ll arrive early to grab tables since seating is first-come, first-served and reservations are not available.
✅ Tables are usually limited to 4–6 people
✅ We’ll try to grab a cluster of tables together
✅ If you arrive later, message me and we’ll try to save space (no guarantees)
🎶 Music starts at 7 PM, but tables can fill up well before then!🍔 About Waterfront Café
Located in historic Berger Park, Waterfront Café is a unique lakefront dining spot housed in a historic landmark coach house connected to one of Chicago’s last remaining lakefront mansions.
Enjoy:
🌊 Amazing Lake Michigan views
🎶 Outdoor patio music
🍔 Casual beach café food
🍹 Full bar and summer drinks
🌅 One of Chicago’s best sunset settings
🌐 Website:
http://waterfrontcafechicago.com/🍽️ Dining Information
Counter-service restaurant — everyone orders separately.
💳 CREDIT/DEBIT ONLY — NO CASH
For our group, please plan to add approximately 32% to your order:
• 12% Chicago sales tax
• 20% gratuity
🦟 Pro Tip:
Bring bug spray! Beachside patios can get buggy after sunset.🎷 Featured Performance:
Second City Jazz
Second City Jazz is a talented Chicago-based ensemble performing everything from swing, Big Band, and Dixieland to jazz standards,Latin jazz, and contemporary favorites. Known for their outstanding musicianship and energetic performances, they're a favorite at festivals, parks, and community events throughout the Chicago area.
Whether you're a longtime jazz fan or simply enjoy great live music, you're in for a wonderful evening!
🌐 Website: https://www.secondcityjazz.com/
📘 Facebook: https://www.facebook.com/SecondCityJazz/🚇 Transportation
CTA Trip Planner:
https://www.transitchicago.com/planatrip/
🚗 Parking:- Metered parking available on Granville Avenue
- Limited free street parking nearby (watch permit signs!)
- SpotHero or ParkWhiz recommended
⚠️ RSVP Reminder
✅ Please only RSVP if you are 95% sure you can attend.
✅ Seating is limited, so accurate headcounts are important.
✅ Update your RSVP before the event begins if plans change.
❌ Three no-shows without updating your RSVP = 3-month RSVP pause.🌴🍹 Come enjoy a little Chicago beach magic — great friends, lake views, delicious food, and live jazz under the summer sky. It’s the perfect way to end a summer Friday! 🎶🌊
24 attendees
Past events
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