About us
๐ Welcome to & Windy City Wanderers! ๐
Weโre so glad youโre here!
Whether youโre new to Chicago or a lifelong local, these sister groups are all about being a tourist in your own cityโdiscovering hidden gems, rich history, fun facts, and unforgettable experiences across Chicagoland. ๐บ๏ธโจ
Windy City Wanderers is the sister group to 1001 Things to See in Chicago Before You Die, and we host many joint events togetherโso youโll often see crossover adventures and shared outings. ๐ค
***
๐ What to Expect
We host fun, social outings year-round (yes, even in winter โ๏ธ). Expect:
โข Walking tours & neighborhood explorations
โข Concerts, lectures & theater
โข Pop-up dinners, trivia & social nights
โข Museums, festivals & special events
Events take place throughout Chicago and nearby suburbs like Evanston, Oak Park, and Park Ridge.
๐ All events are CTA-accessible.
***
๐ฌ Why Join?
โข Discover new places all over Chicagoland
โข Meet new people and make real connections
โข Enjoy an active, well-curated event calendar
โข Try the group FREE for 90 days
***
๐ฐ Membership
โข 90-day free trial
โข Annual dues: $12/year after the trial
โข ๐ Host an event and your dues are waived!
***
๐จ RSVP / No-Show Policy (Please Read)
To keep events fair and running smoothly:
โข A no-show without updating your RSVP = 1 strike
โข 3 strikes = a 3-month pause from events
***
๐ค Stay Connected
๐ Facebook Page
https://www.facebook.com/profile.php?id=61576822533554
๐ฅ Facebook Group
https://www.facebook.com/groups/1571684466442303
๐ธ Instagram
https://www.instagram.com/1001thingstoseeinchicago/
๐ฌ๏ธ !001 Things to See in Chicago Before You Die Meetup (sister group)
https://www.meetup.com/windy-city-wanderers
***
๐ก Have an idea for an event? Want to host or co-host?
Just message meโIโd love to hear from you!
Canโt wait to explore, wander, and discover Chicago together ๐
Cheers,
Giovina Romandine
Organizer, Windy City Wanderers ๐ฌ๏ธ๐ถโโ๏ธ๐ถโโ๏ธ
Upcoming events
17

๐ค๐ฎ๐ถ Live Band Karaoke/Uno Multi-Group Meetup! ๐ถ๐ฎ๐ค
All Star Seafood and sports, 730 South Clark, Chicago, IL, US๐ค๐ฎ๐ถ Live Band Karaoke /Multi-Group Meetup! ๐ถ๐ฎ๐ค
**โญ Hosted by Deanna (**musiclovermay18) โญ
Come on out for an incredibly fun Tuesday nightโjoin multiple Meetup groups for Live Band Karaoke at All Star Seafood & Sports!
If you've never done live band karaoke before, you're in for a treat! This isn't your standard machine karaokeโthe band plays live and helps you out if you don't know all the words or need support. Whether you want to take the mic or just watch and cheer on others, it's a blast either way.
โ No experience necessary! The band will back you up and keep the energy high.
โ Or just hang out and enjoy! Watching people perform with a live band is half the fun.
โ Multi-group event: Expect a bigger, livelier crowd than the RSVP countโthese typically average 10โ12 people from our group alone, plus attendees from other groups.We want laid-back, non-judgmental, fun-loving folks who want to have a good time and support each otherโeven if someone can't carry a tune in a bucket!
๐ WHEN:
Tuesday night! Live Band Karaoke starts at 8 PM.
๐ Arrive early to get a good spot, hang out, grab food and drinks before the singing starts!๐ WHERE:
All Star Seafood & Sports
730 S. Clark St., Chicago, IL
โ Website
โ Facebook
โ Menu๐ PARKING INFO:
Street parking on Clark, Polk, and Wells Streets (watch for no parking and permit-only signsโit can be tricky).
โญ Highly recommend using SpotHero or Parking Whiz for the safest and easiest option.
๐ PUBLIC TRANSPORTATION:
Plenty of CTA optionsโplan your route here: CTA Trip Plannerโจ WHAT TO EXPECT:
โ Sing with a live band (theyโll help you!)
โ Amazing seafood and desserts
โ Drinks, friends, fun vibes
โ A supportive crowd from multiple Meetup groups
โ Outstanding food & a full bar
โ Even if you don't sing, it's a great show!โ ๏ธ OUR NO-SHOW POLICY:
โ Please update your RSVP if you canโt make it!
โ 3 no-shows without updating = 3-month hold from events.
โ๏ธ Cut-off to update is the event start time.
โ๏ธ Message the host if youโre running late.
โ๏ธ Always check in with the host when you arrive.โจ Come sing your heart out, try some delicious tacos, cheer on your friends, and have an unforgettable Tuesday night with great people. Whether youโre the next Beyoncรฉ or just want to laugh and clap along, this event is for you.
See you there! ๐ค๐ฎ๐ป
6 attendees
๐๐ธ Fall Sunset, Sips & Skyline Views at Offshore Rooftop! ๐ ๐๏ธโจ
Offshore Rooftop, 1000 E Grand Ave, Chicago, IL, US# ๐๐ธ Fall Sunset, Sips & Skyline Views at Offshore Rooftop! ๐ ๐๏ธโจ
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! ๐
Come enjoy the changing season from high above Navy Pier with panoramic views of Lake Michigan, the Chicago skyline and the lakefront. ๐๐
๐ Thursday, October 8, 2026
โฐ 6:30 PM (Reservation time โ please arrive on time!)
๐ Offshore Rooftop 3rd Floor, Festival Hall at Navy Pier 1000 E. Grand Ave., Chicago๐ฅ GROUP DINING INFORMATION
โ ๏ธ We are seated together at ONE BIG TABLE! ๐๐ต 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:
โข 12% Chicago sales tax
โข 20% gratuity
โข 3% venue surcharge๐ WHY JOIN US?
Everyone loved this rooftop the last time we visited, so we're heading back โ this time for a beautiful fall evening! ๐We'll enjoy cocktails, appetizers, dinner, conversation and those incredible sunset and skyline views. ๐ ๐
๐ธ 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. ๐The 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 โ seafood, burgers, sandwiches, flatbreads, salads, tacos, shareable appetizers and seasonal specialties โ 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. ๐๐ธ
๐ Full Menu:
https://www.offshorerooftop.com/menu
๐ Website:
https://www.offshorerooftop.com๐ GETTING THERE
๐ 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.
๐ CTA buses serve Navy Pier.
CTA Trip Planner:
https://www.transitchicago.com/planatrip/
๐ Offshore is at Festival Hall, Entrance 2, on the 3rd floor.๐ฑ RUNNING LATE OR CAN'T FIND US?
Call or text Giovina: 312-835-4259โ ๏ธ RSVP / NO-SHOW POLICY
โ๏ธ Please keep your RSVP updated.
โ๏ธ Update your RSVP before the event if your plans change.
โ Three no-shows without updating your RSVP = 3-month RSVP restriction.๐๐ธ Come enjoy a beautiful fall evening above Navy Pier with great food, drinks, incredible views and even better company! ๐ ๐๏ธโค๏ธ
8 attendees
๐๐ Early Fall on The 606: Chicagoโs Elevated Escape! ๐ฟ๐ถโโ๏ธ
Walsh Park, 1722 N Ashland Ave, Chicago, IL, US# ๐๐ Early Fall on The 606: Chicagoโs Elevated Escape! ๐ฟ๐ถโโ๏ธ
๐๐ฟ Celebrate The 606 with an Early Fall Evening Walk!
The 606 celebrated its 11th anniversary in June 2026, so weโre a little late to the partyโbut hey, why not keep the celebration going? ๐๐
Letโs take advantage of the beautiful early-fall weather and walk the entire 2.7-mile 606 Trail, taking in gardens, public art, neighborhood views, and four Chicago neighborhoods along the way! ๐ณ๐จ๐๏ธ
๐ Friday, October 9, 2026
โฐ 5:00โ8:30 PM
๐ฝ๏ธ Optional dinner/drinks afterward
๐ Start: Walsh Park
1722 N. Ashland Ave.
๐ End: Ridgeway Trailhead
Next to McCormick YMCA
1834 N. Lawndale Ave.
๐ถ Distance: ~2.7 miles โ the full length of The 606
๐ Early fall walk | Casual pace | Rain or shine | Drop out anytime***
### โจ ITINERARY
๐ 5:00 PM โ Meet at Walsh Park entrance/trail access point
๐ถโโ๏ธ 5:00โ6:45 PM โ Walk the entire 2.7-mile 606 Trail
๐น 7:00โ8:30 PM โ Optional bites & drinks
โญ Planned stop: Wolf & Company!***
### ๐ธ OPTIONAL POST-WALK STOP
โญ Wolf & Company is right along The 606, making it an easy place to continue the evening after our walk.
๐ธ Wolf & Company
๐ 1752 N. Western Ave., Chicago, IL 60647
๐ https://wolfandcompanychicago.com/If you don't want to walk the entire trail, you can drop out along the route and meet us at Wolf & Company around 7:00 PM. You can also drive and meet us there for drinksโjust use the address above to look for nearby street parking.
Depending on the group's mood, we may also consider:
๐ท Outside Voices
๐ 3204 W. Armitage Ave.
https://www.outsidevoiceswine.com/
๐ The Moonlighter
๐ 3204 W. Armitage Ave.
http://www.themoonlighterchicago.com/***
### ๐ฟ ABOUT THE 606
The 606 is Chicago's 2.7-mile elevated trail and park, connecting Wicker Park, Bucktown, Humboldt Park and Logan Square.
Built on the former Bloomingdale Line railroad, the trail opened in June 2015 after decades of planning and community advocacy.Today, The 606 combines walking and biking trails with gardens, public art, neighborhood views and access to some of Chicago's most vibrant communities. ๐ณ๐จ๐๏ธ
More than a decade after opening, it's become one of Chicago's most recognizable urban green spacesโand there's no better way to experience it than on foot! ๐โจ
***
### ๐ก GOOD TO KNOW
โ ๏ธ This is a one-way walk. We won't finish where we started.
๐ If driving, consider parking near the middle/end of the route or plan how you'll return to your car.
๐ Public transportation is a great option.
๐ถโโ๏ธ You can drop out at several points along the route if you don't want to complete the entire walk.
๐ฝ๏ธ Our optional food/drink stop is near the trail, but you can also exit to the street whenever you'd like.
๐ Comfortable walking shoes recommended!
๐ง Bring water.
๐งด Sunscreen & sunglasses are still a good idea.
๐งฅ Bring a light layerโSeptember evenings can get cool!***
### ๐ GETTING THERE
๐ CTA service is available near multiple points along The 606.
๐บ๏ธ CTA Trip Planner:
https://www.transitchicago.com/planatrip/
๐ Street parking is available but limited. Read all signs carefully for meters, permit parking and restrictions.***
### ๐ LEARN MORE
๐ฟ The 606 โ Official Website:
https://www.the606.org/***
๐ฑ LOST OR RUNNING LATE?
Call or text Giovina at 312-835-4259.
๐ Please check in with Giovina when you arrive!***
### โ ๏ธ RSVP REMINDER
โ๏ธ Please update your RSVP if your plans change.
โ๏ธ RSVP changes should be made before the event begins.
โ Three no-shows without updating your RSVP = 3-month event restriction.***
๐๐ Come walk The 606 with usโelevated views, neighborhood history, public art, early-fall scenery and good company! ๐ฟ๐จ๐ถโโ๏ธโจ
๐ธโจ See you on the trail!
2 attendees
๐โจ Fall Fun Alert: 40th Annual St. Charles Scarecrow Festival! ๐๐
Hotel Baker, 100 West Main Street, St. Charles, IL, US***
๐โจ Fall Fun Alert: 40th Annual St. Charles Scarecrow Festival! ๐๐
๐พ๐ Scarecrows, Crafts & Fall Vibes โ St. Charles Festival! ๐๐
๐ Sunday, Oct 12, 2025
๐ 10:30 AM โ 5:00 PM
๐ Downtown St. Charles, IL + Pottawatomie Park
๐ Meetup Spot: Over by Hotel Baker, 100 W. Main Street โ ๐ https://maps.app.goo.gl/Htz4YeLDmtsoPLkq5๐ Whatโs Happening:
๐พ 110+ handmade scarecrows โ vote for your faves!
๐ถ Live music + Family Zone shows ๐ญ๐ค
๐ธ Festive photo ops + Scarecrow-to-Go crafts
๐๏ธ Autumn on the Fox Art & Craft Show (100+ artists: jewelry, glass, photography & more)
๐ด Food vendors galore + cozy sit-down restaurants
๐ป Donโt miss all the local shops, boutiques, bars & cafes downtown great for browsing and grabbing a bite or drink between activities๐ Festival Info & Schedule: https://www.stcscarecrowfest.com
๐ Parking & Carpooling
โ Free Street parking & large lots (weโll go early to snag spots)
๐ค Carpool encouraged โ post in comments if you:- ๐ Have extra seats
- ๐ช Need a ride
- ๐ Are coming late / leaving early
- ๐ Share your pickup area
- ๐ Last time we had 3โ4 carsโletโs keep it rolling!
โ No-Show Policy Reminder
โข 3 no-shows = 3-month suspension
โข Cut-off to update RSVP = event start time (otherwise message host)
โข Always check in with host upon arrivalโจ Join us for a nostalgic fall traditionโscarecrows, crafts & autumn vibes! ๐๐จ๐๐โจ Fall Fun Alert: 41st Annual St. Charles Scarecrow Weekend! ๐๐
๐พ๐ Scarecrows, Crafts & Fall Vibes in St. Charles! ๐๐
Get ready for one of my favorite fall traditions! ๐ We're heading out to St. Charles for a day filled with scarecrows, handmade crafts, live music, food, shopping and plenty of autumn fun! ๐๐จ
๐ Sunday, October 11, 2026
๐ 10:30 AMโ5:30 PM
๐ Downtown St. Charles + Pottawatomie Park
๐ MEETUP SPOT: Over by Hotel Baker 100 W. Main Street, St. Charles
๐MAP LOCATION https://maps.app.goo.gl/Htz4YeLDmtsoPLkq5๐๏ธ THE FESTIVAL IS FREE!
๐ WHAT'S HAPPENING
๐พ 120+ handmade scarecrows โ wander downtown and check out all the creative entries. You can even vote for your favorites!
๐ถ Live music & entertainment throughout the festival, including performances at 1st Street Plaza.
๐ญ Family & Activity Zones with festive photo ops, pumpkin painting, magic shows, Scarecrow-to-Go and other activities.
๐๏ธ Autumn on the Fox Art & Craft Show at Pottawatomie Park features 150+ artists and crafters with jewelry, stained glass, photography, woodworking, ceramics, metal art, seasonal dรฉcor and more! Sunday hours are 10 AMโ4 PM.
๐ด Food & fall treats โ food vendors and food trucks will be scattered throughout the festival, plus plenty of restaurants and grab-and-go options downtown.๐ป EXPLORE DOWNTOWN ST. CHARLES
Don't forget about all the local shops, boutiques, bars, cafes and restaurants! We can wander around, browse the shops and stop for a bite or drink along the way.๐ SCARECROW-TO-GO
Want to make your own scarecrow? You can create one for $15, with proceeds benefiting Scouting America Troop 60.๐ OFFICIAL FESTIVAL INFO & SCHEDULE:
https://www.scarecrowfest.com/๐ AUTUMN ON THE FOX ART & CRAFT SHOW:
https://artoftheheartland.com/autumn-on-the-fox/Lots of great restaurants to grab a bite. Many with outdoor seating!
๐ PARKING & CARPOOLING
โ ๏ธ COME EARLY FOR BETTER PARKING! This is a BIG festival and downtown parking fills up, especially closer to Main Street. We'll be meeting at 10:30 AM, so I recommend arriving early if you want a better shot at parking close to downtown.๐ ฟ๏ธ PARKING GARAGES & LOTS
๐ข First Street Parking Garage / Klinkhamer Parking Deck โ A great central option near downtown. The City notes that the top two levels of the five-story garage often have spaces even when the lower levels are full.
๐ข Walnut Avenue Garage โ 200 Walnut Ave., another city public parking garage with easy access to downtown.
๐ Free public lots โ There are 1,500+ free public parking spaces throughout downtown, all within walking distance of shops, restaurants and festival activities. If the closest lots are full, don't give upโthere are additional lots a few blocks away.
๐ City Parking Information & Map:
https://www.stcharlesil.gov/Resources/Getting-Around/Parking๐ค CARPOOLING ENCOURAGED!
Post in the comments if you:
๐ Have extra seats
๐ช Need a ride
๐ Are coming late / leaving early
๐ Want to share your pickup area
Last time we had 3โ4 cars, so let's keep the carpool tradition going! ๐โ ๏ธ RSVP / NO-SHOW POLICY
โ Please only RSVP if you are 95% sure you can attend.
โ Update your RSVP if your plans change.
โฐ The cutoff to update your RSVP is the event start time. After that, message the host directly.
๐ Please check in with the host when you arrive.
โ Three no-shows without updating your RSVP = 3-month suspension from RSVPing to group events.โจ Come spend a fall day with me in St. Charles! We'll wander through the scarecrows, check out the crafts, listen to some music, grab something yummy to eat or drink and enjoy all those beautiful fall vibes. ๐๐๐
Come early, come late or stay the whole dayโjust come ready for some fall fun! ๐๐
7 attendees
Past events
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