
What we’re about
🎉 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 🌬️🚶♀️🚶♂️
Featured event

🎟️ 🎶Theater Week Stop 3: $30 tix-Trial in the Delta: Murder of Emmett Till🎭
🎟️ 🎶Theater Week Stop 3: $30 tix-Trial in the Delta: Murder of Emmett Till🎭
Chicago Theater Week 2026 Play #3 - $30 Tix- Trial in the Delta: The Murder of Emmett Till @Kimball Arts Center
Chicago Theater Week Play #3
🎶 Trial in the Delta: the Murder of Emmett Till
📅 Saturday Feb 14, 2025
⏰ 7:30 PM
📍 The Kimball Arts Center | 1757 N. Kimball Ave, Chicago,
🎟️ General Admission Seating
Our 3rd & final stop for Chicago Theater Week is Trial in the Delta: The Murder of Emmett Till, a powerful, award-winning live docu-drama presented by Collaboraction in their brand-new House of Belonging in Humboldt Park.
This immersive production brings the 1955 murder trial of Emmett Till to life using the recently unearthed trial transcript, placing audiences inside the courtroom for a deeply human, radically honest examination of a case that changed America forever.
Actors sit among the audience, taking the stand as witnesses for both the defense and prosecution — including Mamie Till-Bradley — creating a stunning, immediate, and unforgettable experience.
New this year! Tickets are available on Hottix, no special codes needed!
🎟 Theater Week Deal via Hot Tix
• $30 tickets + fees (normally $55.00) — no special code
• Limited quantity — WILL sell out
👉 Buy here: https://hottix.org/shows/collaboraction-in-the-kimball-arts-center/trial-in-the-delta-the-murder-of-emmett-till/
✔️ Select 2/14/25 General Admission – 7:30 PM | The Kimball Arts Center
-reg price $55.00 for $30! so $25.00 savings!
Any issues calls Hot tix helpdesk at Phone: (312) 977-9483 or Email: help@chicagoplays.com
⚠️ Important Ticket Rules
· You must buy your own ticket
· DO NOT RSVP YES until ticket is purchased
· GA seating — we’ll meet in the bar & sit together
· High probability of value-priced tickets selling out!! - buy asap!
I’ll arrive around 7:00 PM to grab seats as general admission. I may grab a meal nearby earlier & I will post a comment of where I will go for those who wish to meet & grab a bite. Check back for updates
🍷 Food & Drinks
• No food served and no outside food allowed
• Full bar available (wine, spirits, non-alcoholic drinks allowed in theaters)
• If you want to eat, plan to do so before the show — many nearby options
• Some of us may grab a bite. I’ll post updates closer to the date
Trial in the Delta: the Murder of Emmett Till
🎶 About the Production
On September 20, 1955, testimony began in the murder trial of two members of Emmett Till’s lynch mob. What happened during that trial — and in the weeks and months surrounding it — would help ignite the Civil Rights Movement.
Written by Willie Round & G. Riley Mills, directed by Anthony Moseley & Dana Anderson, this production is drawn directly from The State of Mississippi vs. Roy Bryant and J.W. Milam trial transcript. It plays as a live courtroom reenactment, featuring top Chicago actors seated among the audience.
Join us as we witness this vital story — and stay to discuss its impact and legacy.
🏛️ About Collaboraction & the Kimball Arts Center
Collaboraction celebrates 30 years of innovative, socially conscious theater and opens its new House of Belonging in Humboldt Park.
The space includes:
• 🎭 99-seat flexible studio theater
• 🍷 50-seat cabaret with café/bar
• 🏙️ Located next to the 606 Trail, where Logan Square meets Humboldt Park
Collaboraction’s work is grounded in KEDA — Knowledge, Empathy, Dialogue, and Action — theater for social change.
Kimball Arts Center
Kimball Arts Center is a hub of Chicago creativity located next to the 606 Trail, where Logan Square meets Humboldt Park. Home to a collection of independent businesses for over 15 years. Always inclusive. Always open-minded.
🚗 Parking: Metered street parking nearby; SpotHero/ParkWhiz recommended
🚇 CTA accessible https://www.transitchicago.com/planatrip/
❗ No-Show Policy
3 no-shows without RSVP updates = 3-month event freeze.
🎭✨ This is a true Theater Week steal — grab your ticket before it’s gone!
Upcoming events
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🎲🧠 Game Night + Trivia Vibes @ Stay & Play Café 🍹🍽️
Stay And Play Game Cafe, 3932 w Irving Park road, Chicago, IL, US🎲🧠 Game Night + Trivia Vibes @ Stay & Play Café 🍹🍽️
Board Game + Trivia Night @ Stay & Play Game Café (Old Irving Park)
📅 Thursday, January 22, 2026
⏰ 6:00–9:00 PM
📍 Stay & Play Game Café 3932 W. Irving Park Rd · Chicago
Let’s plan another fun board game night at one of my favorite neighborhood spots on the Northwest Side — Stay & Play Game Café, conveniently close to my home and highly recommended for game lovers!
This welcoming, spacious café features 500+ board games, delicious food, and creative cocktails — plus Trivia Night every fourth Thursday in the back room, with a different theme each month and prizes for the winning team 🏆.
🧠 Board games take place in the front area, so you can play games, do trivia, or float between both.
This is a great chance to support a local, independent, woman- and Latino-owned business while laughing, playing, and socializing together. 💙
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🎲 Game Night Vibes
I tend to love the classics — Monopoly, Scrabble, Life, Jenga, Taboo, Boggle, Mastermind — but they also have tons of modern games.
We’ll split into smaller tables based on what people want to play… or feel free to just hang out and socialize. No pressure, no judgment!
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💵 Game Pass Options
• $5 daily gaming pass with $10 minimum food/drink purchase
• OR $15 adult game pass (no food/drink minimum)
▫️ Includes up to 2 hours of gameplay
Either option costs less than a movie ticket — and is way more interactive and fun!
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🍽️🍹 Food & Drinks
• Puerto Rican–inspired menu 🌴
• Rum-based cocktails 🍹
• Full menu available online
🔗 Food & Drink Menu:
https://stayandplaygamecafe.com/menu
🎲 Game Library:
https://stayandplaygamecafe.com/game-library
🌐 Website:
https://stayandplaygamecafe.com
📘 Facebook:
https://www.facebook.com/profile.php?id=100077988332148
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❤️ Meet the Founders
Yesenia and Jose met as college freshmen in 1991 and bonded over their love of family, Puerto Rican culture, great food, and board games. Game nights were always a staple in their lives, and they created Stay & Play as a place where friends, families, and loved ones could build memories through cooperation, friendly competition, and fun.
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🚇 Getting There
• Near the Blue Line
• CTA #80 Irving Park, #53 Pulaski buses
• CTA Trip Planner:
https://www.transitchicago.com/planatrip/
🚗 Parking
• Metered parking on Irving Park Rd
• Free side-street parking (watch signs)
• 🚙 Small parking lot in the back!
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⚠️ NO-SHOW POLICY — PLEASE READ
• 3 no-shows without RSVP updates = 3-month event freeze
• RSVP cut-off = event start time
• If late, message the host directly
• Failure to check in counts as a no-show
• Continued no-shows may result in removal from the group
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🎉 Come play, laugh, do trivia, and support a great local business — whether you’re competitive, casual, or just there for the vibes!20 attendees
✨🎷 Smooth, Soulful & Swingin’: Elaine Dame Live @ Gateway Lounge 🍸🎶
Copernicus Center, 5216 West Lawrence Avenue, Chicago, IL, US✨🎷 Smooth, Soulful & Swingin’: Elaine Dame Live @ Gateway Lounge 🍸🎶
Live Jazz with Elaine Dame @ Copernicus Center – Gateway Lounge
A Jazz Lounge Collection with Celebrated Vocalist Elaine Dame ✨🎷
🗓 Friday, January 23, 2026
⏰ Show: 7:30 PM | Doors Open: 6:30 PM
👨👩👧👦 All Ages Welcome - ticket required- can pay at the door
📍 Copernicus Center – Gateway Lounge
5216 W Lawrence Ave, Chicago (Jefferson Park)
🎟 Tickets: $25 + fees - purchase below
👉 https://www.etix.com/ticket/p/94915724/a-jazz-lounge-collection-with-celebrated-vocalist-elaine-dame-chicago-gateway-lounge
🎟️ Can also buy tickets at the door for $30
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🎶 About the Performance
Join celebrated Chicago jazz vocalist Elaine Dame for an evening of hip, soulful, and swinging jazz in the intimate Gateway Lounge at the Copernicus Center. This special Jazz Lounge Collection features fresh reimaginings of jazz classics and hidden gems, performed with warmth, sophistication, and unmistakable swing, supported by a talented jazz ensemble.
Elaine Dame sings — and people stop and listen.
Since 1996, the woman Time Out Chicago calls “a jazz dynamo” and “a gem in the city’s vocal jazz scene” has captivated audiences coast to coast. Drawing on her background in Chicago’s theater scene, Elaine brings storytelling, nuance, and emotional depth to every performance.
The Chicago Reader praised her “winning stage presence and chameleon-like vocal flexibility,” while Grammy Award–winning jazz critic Neil Tesser wrote:
“Dame has risen to the top ranks of Chicago jazz singers… centered intonation, enviable rhythm, and a translucent but powerful instrument.”
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🏛 About the Venue: Copernicus Center
The Copernicus Center is one of Chicago’s true hidden gems — a premier cultural and event center serving the city since 1971. Operated by the nonprofit Copernicus Foundation, the Center hosts concerts, theater, community events, workshops, and multicultural programming year-round and is home to the Taste of Polonia Festival, the largest Polish music festival in the U.S.
Located in the heart of Jefferson Park, the venue offers excellent acoustics, historic charm, and easy accessibility from anywhere in the city.
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🚗 Parking & Transit
✔ Free parking lots + free street parking (watch for permit-only signs; arrive early)
✔ CTA accessible via Jefferson Park Blue Line & multiple bus routes
✔ CTA Trip Planner: https://www.transitchicago.com/planatrip/
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⚠️ NO-SHOW POLICY (PLEASE READ)
• 3 no-shows without updating RSVP = 3-month suspension from events
• RSVP cut-off = event start time
• If late, message the host directly
• Failure to check in counts as a no-show
• Continued no-shows may result in removal from the group
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🎷✨ Come early, grab a drink, and enjoy a night of world-class Chicago jazz in an intimate lounge setting! 🎶💙10 attendees
✨⛪ Guided Church Tour: Faith, Art & Architecture @ Holy Trinity Cathedral🏛️
Holy Trinity Russian Orthodox Cathedral, 1121 N Leavitt St, Chicago, IL, US✨⛪ Guided Church Tour: Faith, Art & Architecture @Holy Trinity Cathedral 🏛️
🌿 An Inspiring Afternoon Inside a Louis Sullivan–Designed Chicago Landmark ✨
Join us for a special guided visit to Holy Trinity Russian Orthodox Cathedral, a designated Chicago Landmark and one of the city’s most extraordinary sacred spaces. Designed by legendary architect Louis Sullivan — often called the “father of skyscrapers” — this church is one of his few religious commissions and a true architectural treasure.
This immersive experience explores Orthodox faith, symbolism, immigrant history, and Sullivan’s architectural vision, all within a richly decorated, awe-inspiring interior.
This is a stationary guided church visit — no walking route or neighborhood stroll — allowing us to slow down and truly absorb the art, architecture, iconography, and spiritual atmosphere of this remarkable landmark.
Expect vivid murals, traditional Orthodox icons, gold accents, incense, and powerful stories of faith and immigration — all shared in a respectful and informative setting. ✨
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🕰️ Schedule, Meeting Info & Cost
📅 Saturday, January 24, 2026
⏰ 1:00 PM – 3 PM
📍 Holy Trinity Russian Orthodox Cathedral 1121 N. Leavitt St.,
⏱️ Visit length: ~90 minutes
💰 Cost: $15 per person
💵 Cash strongly preferred
(Zelle / Venmo / PayPal accepted if needed so I can submit one group donation)
⚠️ All attendees must check in with me at the start of the tour and submit payment directly to me so I can give to the church
📸 Photography is typically allowed — please be respectful of the sacred space and follow any onsite guidance.
🎤 Private guided experience arranged for our group.
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🌟 What We’ll Experience
⛪ The stunning sanctuary designed by Louis Sullivan
🎨 Traditional Orthodox iconography and hand-painted murals
🕯️ Candles, incense, and sacred ritual elements
📜 The history of the parish and its immigrant roots
🏛️ Architectural details that blend Orthodox tradition with Sullivan’s design philosophy
This visit takes place entirely inside the church and its immediate grounds.
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📖 About Holy Trinity Russian Orthodox Church
Founded in 1903, Holy Trinity Russian Orthodox Church is one of Chicago’s oldest Orthodox parishes. The building was designed by Louis Sullivan, a pioneering American architect best known for shaping modern architecture and mentoring Frank Lloyd Wright.
Unlike Sullivan’s commercial work, Holy Trinity reflects his ability to adapt architectural form to religious meaning. The church’s simple exterior contrasts dramatically with its richly ornamented interior, emphasizing spirituality over spectacle — a deliberate and powerful design choice.
Designated a Chicago Landmark, Holy Trinity stands as both a sacred space and an architectural masterpiece. It represents the perseverance of immigrant communities who preserved their faith, culture, and traditions while shaping the city’s cultural landscape.
Today, the church continues to serve a diverse Orthodox congregation and remains one of the most visually striking and historically significant religious buildings in Chicago.
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🍽️ Optional Coffee or Lunch After the Visit
Those interested are welcome to join me afterward for coffee or lunch at a nearby neighborhood spot.
🍽️ Options will be shared closer to the date.
⚠️ Please bring cash — some venues may not split checks.
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👟 What to Bring
• Camera (if permitted)
• Respectful attire
• $15 tour fee (exact change appreciated; cash preferred but Zelle, Venmo, PayPal accepted)
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🚇 Getting There
Public transportation is easy and encouraged.
Use Google Maps or CTA Trip Planner:
https://www.transitchicago.com/planatrip/
🚗 Parking
• Free and metered street parking nearby
• Generally easy to find during daytime hours
• Always check posted signs
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📝 RSVP & No-Show Policy
✔️ Please keep your RSVP updated
✔️ Cancel promptly if your plans change
❌ Repeated no-shows may result in removal from future events
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✨⛪ Join us for a rare opportunity to experience a Louis Sullivan–designed Chicago Landmark — where faith, immigration, and architecture come together in one unforgettable space. ✨23 attendees
🎸🎤Cash for Kids! 21st Annual Johnny Cash Festival-Music & Fun for a Cause🍀🎶
Irish American Heritage Center, 4626 N Knox Ave, Chicago, IL, US🎸🎤 Cash for Kids! 21st Annual Johnny Cash Festival – Music & Fun for a Cause 🍀🎶
Cash for Kids! 21st Annual Johnny Cash Festival @ Irish American Heritage Center
We’ve done this for over 6 years and it’s always a ton of fun! Great music in a variety of genres — not just tribute bands playing Johnny Cash tunes. It’s so much more! Held at a cool northwest side location, the Irish American Heritage Center, now back on its original January date. All proceeds go to a great cause — the Pediatric Brain Tumor Foundation.
📅 Date: Saturday, January 24, 2026
📍 Location: Irish American Heritage Center – 4626 N. Knox Ave, Chicago, IL
🎟️ Tickets: $25 online / $30 at the door (must have ticket)
🔗 Tickets & Info:
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🎶 About the Festival
- Chicago’s only Johnny Cash Festival, raising funds for the Pediatric Brain Tumor Foundation
- Music on 3 stages with 8+ bands
- Genres include country, folk, rockabilly, blues, and more
- Celebrate The Man in Black and the Carter Family’s contribution to American music
🎸 2026 Performers (subject to change)
- The Waco Brothers
- Iron Horse
- Alaina Stacey
- The John Allen Green Band
- Mike Gianinni & The Rhythm Rangers
- In Spite of Ourselves
- State of the City
- The Rock Islanders
- Lawrence Peters
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🏛️ About the Venue: Irish American Heritage Center
- 86,000 sq. ft. cultural center dedicated to Irish arts, culture & traditions
- Features:
- 658-seat theatre
- Library & museum
- Art gallery
- Authentic Irish pub
- Dance studios
- Meeting & banquet rooms
- Wheelchair accessible
- Multiple bars & food available (fish & chips, corned beef sandwiches, patty melts, hot dogs)
🔗 Learn more:
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🚗 Parking & Transit
- 2 free parking lots + street parking (watch for permit-only signs; arrive early!)
- CTA accessible: Montrose Blue Line + buses
- CTA Trip Planner
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⚠️ No Show Policy
- 3 no-shows without updating RSVP = 3 months ineligible for future events
- Cut-off: event start time
- Message host if late / missed check-in
- Continual no-shows may result in removal from the group
💜 All proceeds benefit the Pediatric Brain Tumor Foundation, supporting children & families battling brain tumors.
27 attendees
Past events
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