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
24

🎃⚰️ 14th Annual Forest Park Casket Races & Costume Parade! 👻🏁
Kribi Coffee Cafe & Roastery, 7324 Madison St, Forest Park, IL 60130, USA, Forest Park, IL, US🎃⚰️ 14th Annual Forest Park Casket Races & Costume Parade! 👻🏁
💀 Caskets, Costumes & Halloween Shenanigans in the Suburbs! 🎃
Yes, you read that correctly — CASKET RACES! ⚰️😂 Get ready for one of the quirkiest Halloween traditions around as we head to nearby Forest Park for a morning of spooky fun, outrageous casket designs, costume-watching, and some seriously unusual competition!
If you’ve joined us for the Chiditarod races in West Town, you’ll love this event! Think push-cart racing, but with Halloween-themed caskets instead! 🏁💀 We checked this out last year, and it was a LOT of fun, so we’re doing it again!
🎂 AND THE BIRTHDAY CELEBRATIONS CONTINUE! 🥳
My official birthday is October 22, but why celebrate for just one day when you can celebrate ALL MONTH LONG?! 😂🎉 Come join me and my Meetup family as we keep the birthday party rolling with a little Halloween madness!📅 EVENT DETAILS
📆 Saturday, October 24, 2026
🕤 Group Meetup: 9:45 AM
🏁 Races begin: 11:00 AM
📍 Beloit Avenue between Madison Street and Adams Street, Forest Park (7500 Madison St. area)📍 OUR MEETING SPOT: NEAR MADISON & BELOIT
Because Beloit Avenue will be closed for the racecourse, we’ll meet near the north end of the event area along Madison Street, then head into the festivities together.
Look for us near Kribi Coffee Cafe & Roastery (7324 Madison St.), a recognizable landmark near the Beloit and Madison intersection.We’ll aim to meet around 9:45 AM, before the crowds get too crazy.
Please allow extra time to find us, as the area will get busy! Check back for any meeting-location updates.⚰️ WHAT ARE THE CASKET RACES?
Forest Park, nicknamed the Village of Cemeteries, hosts this delightfully bizarre annual tradition. Teams of friends, neighbors, and coworkers build and decorate elaborate Halloween caskets on wheels, complete with a helmet-wearing rider inside! 👻Then the teams race their creations down a closed section of Beloit Avenue for bragging rights and trophies. The course is about 585 feet long, and prizes recognize everything from race winners to creative decorations — even the team that finishes dead last! 💀🤣
Expect a DJ and emcee, food vendors, coffee, hot chocolate, baked treats, costumes galore, and plenty of entertaining people-watching. This is Halloween fun with a distinctly Forest Park twist! 🎃☕🍪
🎃 TENTATIVE ITINERARY
- 9:30 AM — Festival area opens, vendors set up, and caskets arrive for display.
- 9:45 AM — Meet up with Giovina near Madison & Beloit and head into the festivities.
- 10:30 AM — Parade of Caskets! A great photo opportunity as teams show off their spooky creations. ⚰️📸
- 11:00 AM — Casket races begin! 🏁💀
- Between heats — Kids’ and pets’ costume parade. 🐶👻
- 12:30–2:30 PM — Trick-or-treating along Madison Street, if we have time and interest.
- After the races — Optional lunch or coffee stop with the group! 🍕☕ See the nearby options below.
Times are tentative, so we’ll go with the flow and see how the morning unfolds!
☕🍕 RECOGNIZABLE LANDMARKS & POSSIBLE STOPS
Here are a few nearby spots to help us find our way around and possibly grab a bite or drink before or after the races:- Kribi Coffee Cafe & Roastery — 7324 Madison St. A convenient landmark near the north end of the race area and our proposed meeting point. ☕
- FatDuck Tavern & Grill — 7218 Madison St. Near the Madison and Beloit intersection.
- The Brown Cow Ice Cream Parlor — 7347 Madison St. A familiar Forest Park stop for coffee or a sweet treat. 🍦
- O’Sullivan’s Public House — 7244 Madison St. Another nearby landmark and possible place to regroup after the races. 🍻
- Francesca’s Fiore Pizzeria & Bakery — A possible post-race lunch stop for pizza and bakery treats! 🍕🥐
These are nearby options, not guaranteed reservations or designated event meeting points. Our primary meetup will be near Madison and Beloit. We’ll decide on any coffee or food stops based on timing, crowds, and group interest.
🚇 GETTING THERE — PUBLIC TRANSIT FRIENDLY!
Good news for those of us without cars! Forest Park is accessible via the CTA Blue Line to Forest Park, the last stop on the line, followed by approximately a 12-minute walk to the event area.You can also explore taking the Green Line and connecting with a PACE bus.
👉 Plan your trip here:
https://www.transitchicago.com/planatrip/🚗 DRIVING & PARKING
Street parking may be available along Madison Avenue and nearby streets, but pay attention to posted parking signs. Forest Park also has municipal parking lots in the area, so check local parking information before heading out.🤝 CARPOOLING: If you’re unfamiliar with the area or would rather not travel alone, consider coordinating a carpool or riding the Blue Line together with other members!
👻 A FEW THINGS TO KNOW
- This is an outdoor event, so dress for the weather.
- Costumes are encouraged, but definitely not required!
- Bring your camera — the caskets and costumes make for some memorable photos. 📸
- Arriving early is your best bet for finding a good viewing spot before the 11 AM crowds.
- Lunch and any additional stops are optional and depend on timing and group interest.
🔗 MORE EVENT INFORMATION
🎃 Official Forest Park event page — 14th Annual Casket Races:
https://www.exploreforestpark.com/event/14th-annual-forest-park-casket-races/
📘 Facebook event:
https://www.facebook.com/events/forest-park-illinois/forest-park-casket-races/968288799621583/
ABC7 coverage of the Casket Races:
https://abc7.com/forest-park-il-news-casket-race/12390925/🚨 OUR USUAL RSVP POLICY — PLEASE READ!
• Please update your RSVP if your plans change.
• Running late? Message the host directly.
• Check in with Giovina when you arrive — failure to check in counts as a no-show.
• Three no-shows without updating your RSVP = a three-month event RSVP freeze.
• RSVP changes close at event start time. Continued no-shows may result in removal from the group.🎃⚰️ LET’S GET IN THE ‘SPIRIT’! 👻
Come enjoy a wonderfully weird Chicago-area Halloween tradition with us! Between the outrageous caskets, creative costumes, racing teams, and all the Halloween festivities, this is definitely NOT your average Saturday morning! 😂And remember, the birthday celebrations are still going strong! 🥳🎂 Come celebrate with me, enjoy the madness, and let’s make another fun memory together!
Hope to see you there! 🎃🙌14 attendees
🎃🎭 Puppets, Pageantry & Nighttime Magic! Arts in the Dark Parade 🎃✨
Balbo and Columbus, Chicago, IL, US🎃🎭 Puppets, Pageantry & Nighttime Magic! Arts in the Dark Parade 🎃✨
Chicago’s Spectacular Halloween Parade Returns to Columbus Drive**!** 🏙️👻
Get ready for a night of Halloween magic! 🎃 We’re heading downtown to experience Arts in the Dark, Chicago’s spectacular nighttime Halloween parade featuring giant puppets, glowing floats, incredible costumes, marching bands, and amazing performers! 🎭✨
This uniquely Chicago celebration transforms the streets into a dazzling outdoor spectacle, with artists and cultural organizations bringing Halloween to life. And this year, the parade is returning to Columbus Drive, with Buckingham Fountain and the Chicago skyline providing a fabulous backdrop! 🌃🎃
📅 EVENT DETAILS
📆 Saturday, October 24, 2026
🕔 Meet at 5:00 PM | Parade: 6:00–8:00 PM
📍 Meeting Point: Corner of Balbo & Columbus Drive, near Buckingham Fountain
👀 Viewing Area: West side of Columbus Drive, facing east toward the fountain👉 THE PLAN: We’ll meet around 5:00 PM and head toward our viewing spot to claim a good place before the parade begins at 6:00 PM. We’ll hang out, chat, and enjoy the Halloween atmosphere while we wait! 🎃👻
Please be flexible! This is a popular event, and crowds may affect exactly where we can stand. Check back for updates on our meeting location.🎭 WHAT TO EXPECT
- Giant, spectacular puppets and illuminated floats 🎃
- Creative costumes and glowing performers ✨
- Performing arts groups, marching bands, and plenty of Halloween spirit 🥁
- A nighttime parade with the Chicago skyline as its backdrop 🌃
- Lots of photo opportunities and festive fall fun! 📸🍂
👻 COSTUMES ENCOURAGED! Break out your Halloween gear, spooky accessories, or anything that glows! Not into dressing up? No worries — come as you are!
🧥 WHAT TO BRING
- Dress in layers! It can get chilly near the lake after dark.
- A small folding chair or blanket is optional, but space may be limited.
- Your camera or phone for photos!
- Your patience — crowds are part of the experience!
🎃 A LITTLE CHICAGO CULTURE
Arts in the Dark celebrates Halloween as an artist’s holiday, showcasing Chicago’s vibrant creative community. Expect imaginative, larger-than-life art, theatrical performances, and a parade that’s anything but ordinary! 🎨🎭THIS IS NOT YOUR FATHER’S PARADE! This is not a parade for dignitaries, politicians or sponsorship floats. This is a celebration of cultural organizations and artists of every sort – all of whom bring passion and creative problem solving to the challenge of parading. It is “parade as art” as our contingents combine costumes, spectacle, music, movement, audience engagement, and lighting elements.
https://artsinthedark.com/
📍 IMPORTANT: The parade route and event logistics can change, so check back before heading downtown. We’ll do our best to find a good viewing spot, but arriving early doesn’t guarantee a front-row view.
🚇 GETTING THERE
Public transportation is highly recommended due to street closures and limited parking.
CTA options:- Roosevelt: Red, Green, and Orange Lines
- Harrison: Red Line
From either station, allow time to walk to Balbo and Columbus. Check the CTA Trip Planner for your route:
https://www.transitchicago.com/planatrip/🚗 Driving & Parking: Street parking will be limited. If driving, check SpotHero or ParkWhiz in advance, and expect traffic and road closures around Grant Park.
🚨 OUR USUAL RSVP POLICY — PLEASE READ!
• Please update your RSVP if your plans change.
• Running late? Message the host directly.
• Check in with Giovina when you arrive — failure to check in counts as a no-show.
• Three no-shows without updating your RSVP = a three-month event RSVP freeze.
• RSVP changes close at event start time. Continued no-shows may result in removal from the group.🎃✨ Come celebrate Halloween, Chicago-style! Between the glowing puppets, spectacular performances, and nighttime skyline, this should be a fun way to enjoy one of the city’s most creative fall traditions. Bring your Halloween spirit, dress warmly, and let’s enjoy the show together! 👻🏙️🍂
Hope to see you there! 🎃🙌
18 attendees
🍂🍸 Fall Sunset, Sips & Skyline Views at Offshore Rooftop! 🌅🏙️✨
Offshore Rooftop, 1000 E Grand Ave, Chicago, IL, US# 🍂🍸 Fall Sunset, Sips & Skyline Views at Offshore Rooftop! 🌅🏙️✨
Celebrate fall in Chicago with an evening of cocktails, food, conversation and spectacular views at Offshore Rooftop, the Guinness World Record holder as the World's Largest Rooftop Venue! 🏆
Come enjoy the changing season from high above Navy Pier with panoramic views of Lake Michigan, the Chicago skyline and the lakefront. 🍂🌆 Plus it is my birthday 10/22/26 so we can continue to the celebrations!
📅 Wednesday, October 28, 2026
⏰ 6:00 PM (Reservation time — please arrive on time!)
📍 Offshore Rooftop 3rd Floor, Festival Hall at Navy Pier 1000 E. Grand Ave., Chicago🥂 GROUP DINING INFORMATION
⚠️ We are seated together at ONE BIG TABLE! 🙌💵 CASH ONLY for our group! The restaurant accepts credit cards, but cash makes things much easier with a large group.
There are no separate checks, so we'll divide the bill at the table.
Please add approximately 35% to your food/drink total:
• 12% Chicago sales tax
• 20% gratuity
• 3% venue surcharge🍂 WHY JOIN US?
Everyone loved this rooftop the last time we visited, so we're heading back — this time for a beautiful fall evening! 🍁 If cool out lots of indoor seating with windows all around for views!We'll enjoy cocktails, appetizers, dinner, conversation and those incredible sunset and skyline views. 🌅🍂
🍸 ABOUT OFFSHORE ROOFTOP
Located on the 3rd floor of Festival Hall at Navy Pier, Offshore Rooftop spans more than 52,000 square feet and holds the Guinness World Record as the World's Largest Rooftop Venue. 🏆The rooftop features expansive terraces, floor-to-ceiling windows and spectacular views of Lake Michigan, Navy Pier, the Chicago skyline and the harbor.
The menu includes coastal-inspired New American cuisine — seafood, burgers, sandwiches, flatbreads, salads, tacos, shareable appetizers and seasonal specialties — along with handcrafted cocktails, wine and local craft beer.
Inside you'll find stylish lounges, fire pits, landscaping and retractable glass walls, so we can still enjoy the views even if Chicago's fall weather decides not to cooperate. 🍁🍸
📜 Full Menu:
https://www.offshorerooftop.com/menu
🌐 Website:
https://www.offshorerooftop.com🚗 GETTING THERE
🚗 Navy Pier East & West Garages are available. Discounted self-parking may be available when booked ahead in the West Garage. Offshore also offers discounted valet parking.
🚇 CTA buses serve Navy Pier.
CTA Trip Planner:
https://www.transitchicago.com/planatrip/
📍 Offshore is at Festival Hall, Entrance 2, on the 3rd floor.📱 RUNNING LATE OR CAN'T FIND US?
Call or text Giovina: 312-835-4259⚠️ RSVP / NO-SHOW POLICY
✔️ Please keep your RSVP updated.
✔️ Update your RSVP before the event if your plans change.
❌ Three no-shows without updating your RSVP = 3-month RSVP restriction.🍂🍸 Come enjoy a beautiful fall evening above Navy Pier with great food, drinks, incredible views and even better company! 🌅🏙️❤️
10 attendees
Past events
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