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
Featured event

๐๐ก From Railroad Stop to Hidden Gem โ Old Irving Park Walk! ๐ณ๐
๐๐ก From Railroad Stop to Hidden Gem โ Old Irving Park Walk! ๐ณ๐
Walking Chicago's Historic Old Irving Park
Looking for something different to do on a Sunday morning? Join us for a leisurely stroll through one of Chicago's most charming and least-explored historic neighborhoods! Explore the beautiful tree-lined streets of Old Irving Park, where Victorian-era mansions, early suburban architecture, immigrant history, and hidden architectural gems come together to tell the story of one of Chicago's most distinctive
communities.
โจ Step into Old Irving Park and discover a neighborhood built by affluent families, railroad entrepreneurs, and community visionaries during Chicago's boom years. Stroll past grand Victorian homes, historic churches, neighborhood landmarks, and hidden gems while hearing the stories of the immigrants, pioneers, and business leaders who transformed this once-quiet commuter suburb into one of Chicago's most treasured historic enclaves. ๐ซ
Come walk, learn, and enjoy a beautiful summer Sunday with us โ it's a wonderful way to experience Chicago and meet fellow history lovers! ๐
๐ค Led by your passionate, ever-curious guide (that's me!) โ perfect for architecture lovers, history buffs, photographers, and anyone who enjoys being a tourist in their own city! ๐
***
๐ LOGISTICS
๐๏ธ Sunday, July 12, 2026
โฐ 10:45 AM โ ~1:15 PM (~2.2 miles walking)
๐ Start: Kumon Center (old Whistle Stop Inn) โ 4200 W Irving Park Rd
๐ End: Eris Brewery and Cider House โ 4240 W Irving Park Rd
๐ฐ $20 per person โ due at start of tour
๐ต Cash preferred (exact change appreciated) | PayPal, Zelle & Venmo also accepted
๐ฆ๏ธ Casual pace | Outdoors | Rain or shine
***
Tour Highlights:
๐๏ธ Beautiful Victorian-era homes & early suburban architecture
๐ Stories of Chicago's earliest commuter railroad suburb
โช Historic churches & beautifully preserved streetscapes
๐ Immigrant history & neighborhood evolution
๐ณ Rare small-town feel within the heart of Chicago
๐ Hidden gems you've probably passed โ but never noticed!
โ ๏ธ IMPORTANT PARKING NOTE
The walk ends approximately 2 blocks from the starting point โ plan your parking accordingly! ๐
***
๐บ๏ธ Route Highlights (stops subject to change):
๐บ Whistle Stop Inn
๐ Charles Loucks House
๐ก C.O. Loucks House
๐ The Race House
๐ Nuveen House
โช Mt. Olive Church
โช Irving Park Methodist Church
๐ซ Carl Schurz High School
๐๏ธ John Gray Mansion
๐ John & Clara Merchant House
โช St. John's Episcopal Church
๐ Emeril Jensen House
๐๏ธ Irving Park YMCA
๐บ Eris Brewery and Cider House
๐บ๏ธ Route Map: https://tinyurl.com/3vu9f24r
๐บ๏ธ Route Map Part 2: https://tinyurl.com/4s4aczrh
***
๐ WHY OLD IRVING PARK?
Old Irving Park is often described as a "suburb within the city" โ a peaceful, tree-lined enclave just seven miles from downtown that blends historic elegance with everyday livability.
The neighborhood began in the early 1870s when real estate developers laid out a planned community centered around a stop on the Chicago & North Western Railway. Designed to attract affluent residents seeking cleaner air and more space, it quickly became one of Chicago's earliest commuter suburbs. Grand homes lined Irving Park Boulevard, many built by prominent families who helped shape the area's early identity.
Originally named "Irvington" after author Washington Irving, the name was later changed to avoid confusion with another Illinois town.
The aftermath of the Great Chicago Fire accelerated the neighborhood's growth, as displaced families moved northwest in search of stability and opportunity. When the area was annexed into Chicago in 1889, new infrastructure โ including paved streets, streetcar lines, water service, and fire protection โ transformed it from a quiet suburb into a fully integrated urban neighborhood.
Today, Old Irving Park stands out for its remarkable preservation. Walking its streets feels like stepping through a timeline of Chicago architecture โ from ornate Victorian mansions and Queen Anne homes to Craftsman residences and early 20th-century bungalows. Combined with its strong community spirit and leafy streetscapes, it remains one of the city's most distinctive and livable historic neighborhoods. ๐ก๐ณ
***
๐ธ Not a dedicated photo walk, but you'll definitely want your camera!
***
๐ WHAT TO BRING
๐ Comfortable walking shoes
๐ง Water bottle
๐ค๏ธ Weather-appropriate attire
๐ฐ $20 tour fee (exact change appreciated; cash preferred but Zelle, Venmo & PayPal accepted)
***
๐ฝ๏ธ OPTIONAL POST-WALK HANGOUT
Stick around after the tour and join us for a drink or bite at:
๐บ Eris Brewery and Cider House โ right where the tour ends!
***
๐ GETTING THERE
๐ CTA Blue Line & multiple bus routes nearby โ use the CTA Trip Planner or Google Maps
๐ Metered parking on Irving Park Rd, Keeler & Pulaski
โ ๏ธ Watch for permit parking on side streets
***
๐ฑ LOST OR RUNNING LATE?
Call or text (312) 835-4259 and I'll point you in the right direction!
***
โ ๏ธ NO-SHOW POLICY
๐ฌ 3 no-shows without updating your RSVP = 3-month event ban
โฐ Update your RSVP before the event starts; after that, message the host directly
๐ซ Continual no-shows = removal from the group
***
๐งญ Come discover where grand Victorian mansions, railroad history, hidden gems, and Chicago's immigrant heritage come together โ and experience Old Irving Park in a whole new way! ๐ก๐๐ณ
Upcoming events
49

๐ถ๐ด Eat, Drink & Rock Out at Taste of Park Ridge! ๐๐ธ
Taste of Park Ridge, 43 S Prospect Ave, Park Ridge, IL, US๐ถ๐ด Eat, Drink & Rock Out at Taste of Park Ridge! ๐๐ธ
Let's head to the northwest suburbs for one of the area's signature summer festivals โ the Taste of Park Ridge! ๐
๐ Thursday, July 9, 2026
โฐ 5:45 โ 10:00 PM
๐ Uptown Park Ridge โ booths line Summit Avenue between Touhy & Prospect, stage at the Touhy Triangle lot
๐ WHERE TO FIND US:
โ๏ธ Meet at the corner of S. Prospect Ave & Summit Ave, Park Ridge at 5:45 PM
โ๏ธ Lost or running late? Call 312-835-4259!
๐ฐ Admission: FREE entrance. Food & drink require ticket purchase. They take credit cards & cash for food tickets
https://tasteofparkridge.com/***
๐ถ Thursday Headliner Lineup (Main Stage):
๐ต 6:00 PM โ Serendipity โญ WE WILL SEE THIS!
๐ฅ 7:30 PM โ Opening Ceremony โ a toast to the volunteers and sponsors who make it all happen
๐ธ 8:30 PM โ 7th Heaven โญ WE WILL SEE THIS!If you can't come at 5:45 pm, just meet us later as we will be there until 10 pm!
***
๐ About the Bands
๐ต Serendipity
A Chicago-area pop/rock band known for blending beloved 60s, 70s, and 80s covers with current pop hits. They've been featured on live television, radio, and commercials โ known for their high energy and sharp musicianship.
๐ต Serendipity โ https://serendipityband.com/๐ธ 7th Heaven
A true festival legend โ 39 years in the business! 7th Heaven has charted #1 on the Midwest Billboard Charts three separate times and racked up 7 major radio hits. They've toured the U.K., Ireland, Greece, Amsterdam, Panama, Mexico, and across the U.S. Famous for their unforgettable "30 Songs in 30 Minutes" medley spanning the 70s and 80s โ a can't-miss closer to the night!
๐ธ 7th Heaven โ https://www.7thheavenband.com/***
๐๏ธ A Brief History of the Taste
The Taste of Park Ridge has deep community roots. It was founded in 2000 by the late Harry O'Brien (former Park Ridge Chamber of Commerce Executive Director), Dave Iglow (owner of Pine's Menswear), and noted restaurateur Dean Patras โ evolving from an earlier event called the "Taste of Uptown," originally created to enhance the neighborhood's traditional Summer Sidewalk Sale.By 2005, the festival had grown popular with residents but was struggling to sustain itself financially and nearly folded. Newly elected Mayor Howard Frimark secured seed funding and asked founder Dave Iglow to assemble a volunteer management committee. In just seven weeks, that committee pulled off a fantastic civic celebration โ and the Taste has thrived ever since, entirely run by non-compensated civic-minded volunteers from the Park Ridge community.
***
What started as a sidewalk sale boost in the early 2000s has grown into one of the northwest suburbs' premier summer festivals โ all powered by volunteers giving their time for free, year after year. That's a pretty great Chicagoland story. ๐๐ด
๐ฑ Lost or late? Call 312-835-4259
***
๐ Getting There:
๐ Transit (recommended โ the festival is RIGHT at the Metra station!):
๐ Metra UP-NW Line โ Park Ridge Station, 100 S. Summit Ave. The festival booths line Summit Ave directly north of the station!
๐ CTA Blue Line options:- Jefferson Park stop โ hop on CTA #68 Northwest Hwy bus toward Park Ridge
- Harlem stop โ connect to Pace bus service into Park Ridge
- Cumberland stop โ connect via Pace Routes 209 or 290
๐ Pace Routes 209, 241, 290 and CTA Route 68 all serve the Park Ridge Metra station directly
๐ Plan your trip: https://www.transitchicago.com/planatrip/ or https://metra.com/๐ Driving & Parking:
๐ ฟ๏ธ On-street parking available along Summit Avenue and Busse Highway on the north side of the tracks
๐ ฟ๏ธ Parking lot at the southwest corner of Summit & Touhy Avenues
๐ฑ Some lots use the PassportParking app โ pay by phone instead of searching for a meter!
โ ๏ธ Expect heavy congestion and limited parking near the festival itself โ taking the train in is genuinely the easiest option for this one!***
๐ NO-SHOW POLICY:
โ 3 no-shows without updating RSVP = 3-month freeze
โฐ Update RSVP by event start time โ after that, message host directly
โ Check in with the host upon arrival10 attendees
๐ท 26 Years of Bloom: Bowmanville Garden Walk! ๐ผ๐ฟ
Gateway Garden, 5346 N Ravenswood Ave, Chicago, IL, US๐ท 26 Years of Bloom: Bowmanville Garden Walk! ๐ผ๐ฟ
26th Annual Garden Walk | ๐ผ 30+ Gardens | ๐จ Local Artists | ๐ถ Live Music | ๐น Food & Drink Stops
We had a blast doing this last few years โ don't miss it for its milestone 26th year! Let's explore Bowmanville's charming neighborhood with a self-guided garden walk through hidden gems, community gardens, and neighborhood green spaces. Every garden had snacks & cocktails available to visitors!
๐ Saturday, July 11, 2026
๐ต $10 donation for guidebook & map (not required โ but if you want a map, a donation is needed)
๐ Meet at the Gateway Garden entrance, 5346 N. Ravenswood Ave.***
๐ Tentative Itinerary
10:30 AM โ Meet & greet at Bowmanville's Gateway Garden entrance. Pick up your guidebook for a $10 donation (supports the BCO).
10:40 AMโ3:30 PM โ Self-guided tour of 30+ gardens using the official map (to be released in July).
3:30โ5:00 PM โ Optional post-walk gathering at a local favorite:
๐ป Half Acre Brewery โ 2050 W. Balmoral Ave โ https://halfacrebeer.com/
๐ฝ๏ธ Lady Gregory's โ 5260 N. Clark St โ http://www.ladygregorys.com/
๐Calo Ristorante - 5343 N Clark St, - https://calorestaurant.com/***
๐ What to Expect:
โ 30+ lush residential & community gardens
๐จ Live art creation by visual artists
๐ถ Local musicians & neighborhood specials
๐ฑ Ask-the-Master-Gardener table for expert plant advice
๐ธ Amateur Photography Contest โ winning photo used in next year's promo!
๐ผ Garden Party for participating gardeners and volunteers later that evening***
๐ Note: The walk does NOT end where we begin, so if you're driving, plan accordingly and check back for the finalized garden map.
๐ ฟ๏ธ Street parking (metered + free) is available, but it can be tricky โ allow extra time. Be mindful of permit signs.
๐ Taking transit? Use CTA Trip Planner or Google Maps for the best route: https://www.transitchicago.com/planatrip/***
๐ Stay tuned for the official garden map & final list of stops:
๐ป https://bcochicago.org/garden-walk
๐ https://www.facebook.com/bcochicago***
โ ๏ธ RSVP Policy Reminder:
โ 3 no-shows without notice = 3-month RSVP restriction
โฐ Cut-off to change your RSVP = event start time
๐ฒ If you arrive late or miss check-in, message the host directlyLet's soak in the summer blooms, connect with neighbors, and celebrate 26 years of this fantastic Chicago tradition! ๐ผโจ
โ Giovina18 attendees
๐๐ก From Railroad Stop to Hidden Gem โ Old Irving Park Walk! ๐ณ๐
4200 W. Irving Park, 4200 W. Irving Park Road, Chicago, IL, US๐๐ก From Railroad Stop to Hidden Gem โ Old Irving Park Walk! ๐ณ๐
Walking Chicago's Historic Old Irving Park
Looking for something different to do on a Sunday morning? Join us for a leisurely stroll through one of Chicago's most charming and least-explored historic neighborhoods! Explore the beautiful tree-lined streets of Old Irving Park, where Victorian-era mansions, early suburban architecture, immigrant history, and hidden architectural gems come together to tell the story of one of Chicago's most distinctive
communities.โจ Step into Old Irving Park and discover a neighborhood built by affluent families, railroad entrepreneurs, and community visionaries during Chicago's boom years. Stroll past grand Victorian homes, historic churches, neighborhood landmarks, and hidden gems while hearing the stories of the immigrants, pioneers, and business leaders who transformed this once-quiet commuter suburb into one of Chicago's most treasured historic enclaves. ๐ซ
Come walk, learn, and enjoy a beautiful summer Sunday with us โ it's a wonderful way to experience Chicago and meet fellow history lovers! ๐
๐ค Led by your passionate, ever-curious guide (that's me!) โ perfect for architecture lovers, history buffs, photographers, and anyone who enjoys being a tourist in their own city! ๐
***
๐ LOGISTICS
๐๏ธ Sunday, July 12, 2026
โฐ 10:45 AM โ ~1:15 PM (~2.2 miles walking)
๐ Start: Kumon Center (old Whistle Stop Inn) โ 4200 W Irving Park Rd
๐ End: Eris Brewery and Cider House โ 4240 W Irving Park Rd
๐ฐ $20 per person โ due at start of tour
๐ต Cash preferred (exact change appreciated) | PayPal, Zelle & Venmo also accepted
๐ฆ๏ธ Casual pace | Outdoors | Rain or shine***
Tour Highlights:
๐๏ธ Beautiful Victorian-era homes & early suburban architecture
๐ Stories of Chicago's earliest commuter railroad suburb
โช Historic churches & beautifully preserved streetscapes
๐ Immigrant history & neighborhood evolution
๐ณ Rare small-town feel within the heart of Chicago
๐ Hidden gems you've probably passed โ but never noticed!โ ๏ธ IMPORTANT PARKING NOTE
The walk ends approximately 2 blocks from the starting point โ plan your parking accordingly! ๐***
๐บ๏ธ Route Highlights (stops subject to change):
๐บ Whistle Stop Inn
๐ Charles Loucks House
๐ก C.O. Loucks House
๐ The Race House
๐ Nuveen House
โช Mt. Olive Church
โช Irving Park Methodist Church
๐ซ Carl Schurz High School
๐๏ธ John Gray Mansion
๐ John & Clara Merchant House
โช St. John's Episcopal Church
๐ Emeril Jensen House
๐๏ธ Irving Park YMCA
๐บ Eris Brewery and Cider House๐บ๏ธ Route Map: https://tinyurl.com/3vu9f24r
๐บ๏ธ Route Map Part 2: https://tinyurl.com/4s4aczrh***
๐ WHY OLD IRVING PARK?
Old Irving Park is often described as a "suburb within the city" โ a peaceful, tree-lined enclave just seven miles from downtown that blends historic elegance with everyday livability.The neighborhood began in the early 1870s when real estate developers laid out a planned community centered around a stop on the Chicago & North Western Railway. Designed to attract affluent residents seeking cleaner air and more space, it quickly became one of Chicago's earliest commuter suburbs. Grand homes lined Irving Park Boulevard, many built by prominent families who helped shape the area's early identity.
Originally named "Irvington" after author Washington Irving, the name was later changed to avoid confusion with another Illinois town.The aftermath of the Great Chicago Fire accelerated the neighborhood's growth, as displaced families moved northwest in search of stability and opportunity. When the area was annexed into Chicago in 1889, new infrastructure โ including paved streets, streetcar lines, water service, and fire protection โ transformed it from a quiet suburb into a fully integrated urban neighborhood.
Today, Old Irving Park stands out for its remarkable preservation. Walking its streets feels like stepping through a timeline of Chicago architecture โ from ornate Victorian mansions and Queen Anne homes to Craftsman residences and early 20th-century bungalows. Combined with its strong community spirit and leafy streetscapes, it remains one of the city's most distinctive and livable historic neighborhoods. ๐ก๐ณ
***
๐ธ Not a dedicated photo walk, but you'll definitely want your camera!
***
๐ WHAT TO BRING
๐ Comfortable walking shoes
๐ง Water bottle
๐ค๏ธ Weather-appropriate attire
๐ฐ $20 tour fee (exact change appreciated; cash preferred but Zelle, Venmo & PayPal accepted)***
๐ฝ๏ธ OPTIONAL POST-WALK HANGOUT
Stick around after the tour and join us for a drink or bite at:
๐บ Eris Brewery and Cider House โ right where the tour ends!***
๐ GETTING THERE
๐ CTA Blue Line & multiple bus routes nearby โ use the CTA Trip Planner or Google Maps
๐ Metered parking on Irving Park Rd, Keeler & Pulaski
โ ๏ธ Watch for permit parking on side streets***
๐ฑ LOST OR RUNNING LATE?
Call or text (312) 835-4259 and I'll point you in the right direction!***
โ ๏ธ NO-SHOW POLICY
๐ฌ 3 no-shows without updating your RSVP = 3-month event ban
โฐ Update your RSVP before the event starts; after that, message the host directly
๐ซ Continual no-shows = removal from the group***
๐งญ Come discover where grand Victorian mansions, railroad history, hidden gems, and Chicago's immigrant heritage come together โ and experience Old Irving Park in a whole new way! ๐ก๐๐ณ
1 attendee
Past events
983



