What we’re about
Welcome to our fun and active group!
Whether you're new to Chicago or have lived here for a while, becoming a member of this group allows you to explore the Chicago area in ways that most residents may never experience. It’s like being a tourist in your own city as we uncover hidden gems and unique experiences.
This group is a sister to the original, "1001 Things to See in Chicago Before You Die," and we will be hosting many joint events together.
Our goal is to create a club filled with enjoyable events, giving you the chance to meet new people while participating in unique and diverse outings throughout Chicagoland. This is a year-round group, and winter won't slow us down!
The annual dues are $12 per member, but you get a 90-day free trial to see if you enjoy the group! If you choose to host an event, your annual dues will be waived. We are a highly active and social group with a wide range of activities throughout Chicago.
Most of our events take place in Chicago or nearby suburbs like Evanston, Oak Park, and Park Ridge. All events are accessible via public transportation, which is why we primarily focus on Chicago.
Please note that we have a firm "three strikes" policy regarding no-shows. If you don't attend an event without updating your RSVP, you will receive a strike. After accumulating three strikes, you will be suspended from the group for three months. We aim to maintain fairness and fun for all our members.
If you have any questions about the group, suggestions for events, or would like to lead an outing, please let me know. Hosting an event allows you to waive your annual dues!
Please also check out & join our Facebook group page: https://www.facebook.com/groups/1571684466442303
We also have an Instagram page: https://www.instagram.com/1001thingstoseeinchicago/
Giovina Romandine
Organizer for Windy City Wanderers!
Upcoming events (4+)
See all- Brunch at Gemini BEFORE Old Town Art Fair (Part 1 of 3)GEMINI, Chicago, IL
Yes, I know there is a lot of events scheduled for Sat 6/14/25
Part 1 of 3 BREAKFAST/BRUNCH only 4 - 6 people per table. I have three reservations, so will have to have 4 small tables (6 + 6 + 6 + 6 = 24 ppl). We may not be able to sit near each other. You will need to be patient and follow all the rules the restaurant has in place. BRING CASH!
PLEASE ONLY RSVP IF YOU ARE 95% SURE TO ATTEND! I HAVE TO KEEP DINING EVENTS SMALL, AS SEATING IS VERY LIMITED!
I am being adventurous & want to do all 3 events on Saturday with Brunch & BOTH ART Fairs - Old Town & Wells Street - so it will be a FULL DAY. Please come for 1 portion or all 3! (yes, it is a full day!)
Tentative Itinerary:
9:30 am - 11:00 am - Breakfast at Gemini (Part 1)
11:15 AM - NORTH GATE, located at the corner of Lincoln Avenue at Wisconsin (this is the MAIN GATE). If the line is too long, we will go to the West Gate
11:15 - 1:30 pm - Check the Old Art Fair Vendors & Garden Walk (Part 2)
1:30 -1:45 pm walk over to Wells Street Art Fair
1:45 - 4 pm - check out Wells Street Art & see several live bands! (Part 3)If you are joining us for brunch BEFORE the art fair, then PLEASE BRING CASH, AS THEY CANNOT DO SEPARATE CHECKS FOR GROUPS. I kindly ask that everyone take what you ordered (the total dollar amount) & add 32% to that amount, which includes 12% for Chicago taxes and 20% for tip. CASH IS EASIER & QUICKER FOR BIG GROUPS!
I am scheduling the Old Town Art Fair AFTER as a separate event from brunch, to make it easier for all & since numbers are limited. If you want to join the art fair portion as well, please sign up for that https://www.meetup.com/windy-city-wanderers/events/307409604/
I am scheduling the Wells Street Art Fair AFTER as a separate event from brunch & Old Town Art Fair, to make it easier for all & since numbers are limited. If you want to join the art fair portion as well, please sign up for that here: https://www.meetup.com/windy-city-wanderers/events/307409625/
Located in the heart of Lincoln Park, Gemini has become everyone’s neighborhood restaurant even if they don’t live around the corner. A made-from-scratch mentality can be found throughout the dinner and brunch menus with dishes that have roots in classic American cuisine but with Midwest seasonality and sensibility. The expansive u-shaped bar serves as a focal point in the 92-seat space designed by 555 International both physically and spiritually, providing a welcoming gathering spot for its many regulars. In warmer months, the pergola-topped sidewalk patio provides a perfect escape for diners as well as their furry four-legged friends. Gemini is from partner Pauly Graves and Ballyhoo Hospitality, the Chicago restaurant group behind Coda di Volpe, Old Pueblo Cantina, Sophia Steak and Andros Taverna
http://www.geminichicago.com/
https://www.facebook.com/Geminichicago1
BRUNCH MENU:
https://geminichicago.com/menu/
BOTTOMLESS BRUNCH:
https://geminichicago.com/menu/If you are taking public transportation, please check Google Maps for directions or use CTA trip planner. https://www.transitchicago.com/planatrip/
Note that parking can be difficult during the art fair or in Old Town in general so it is best to use public transportation. brown line trains run near the restaurant & several CTA bus routes. Use SpotHero or Parking Whiz for cheapest & safest options. Metered parking on Lincoln, Clark & other streets but can be a challenge if not familiar with the area
PLEASE NOTE OUR CURRENT NO-SHOW POLICY:
- 3 no-shows without updating your rsvp, and you will not be able to sign up for future events for 3 months
- cut-off time to update your rsvp is the start time of the event. If you miss the start time, then message the event host directly
- not checking in with the event host to notify them you have arrived (for walks, tours or festival-type events)
- Continual no-shows will result in removal from the group!
- 75th Annual Old Town Art Fair & Garden Walk (Part 2 of 3)North Lincoln Avenue & West Wisconsin Street, Chicago, IL
Part 2 of 3. The Old Town Art Fair takes place in the heart of the charming Old Town Triangle Historic District. There will be 200+ nationally acclaimed artists, an estimated 30,000 art lovers, a Garden Walk, Live Music, Food Court, and Children’s Corner. This is always a great art fair!
Suggested Donation is $12.00 for Entry for one person on Saturday, June 7th. Remember, this is a donation and NOT required, so you can pay less or nothing if you want!
I am being adventurous & want to do all 3 events on Saturday with Brunch & BOTH ART Fairs - Old Town & Wells Street - so it will be a FULL DAY. Please come for 1 portion or all 3! (yes, it is a full day!)
Tentative Itinerary:
9:30 am - 11:00 am - Breakfast at Gemini (Part 1)
11:15 AM - NORTH GATE, located at the corner of Lincoln Avenue at Wisconsin (this is the MAIN GATE). If the line is too long, we will go to the West Gate
11:15 - 1:30 pm - Check the Old Art Fair Vendors & Garden Walk (Part 2)
1:30 -1:45 pm walk over to Wells Street Art Fair
1:45 - 4 pm - check out Wells Street Art & see several live bands! (Part 3)-NORTH GATE located at the corner of Lincoln Avenue at Wisconsin (MAIN GATE) - this is where we will go in, so if not doing brunch, then try to meet us there (we will only wait a few minutes, so late arrivals meet inside)
-If the NORTH GATE line is too long, then we will walk over to the WEST GATE. It is located at the corner of W Wisconsin St & N Sedgwick St
- Call me 312.835.4259 if you cannot find the groupI am scheduling the BRUNCH portion BEFORE the fair as a separate event, to make it easier for all & space is limited. It'll be at Gemini. If you want to join the BRUNCH portion @Gemini before the art fair, then please sign up for that separately at this link below: https://www.meetup.com/windy-city-wanderers/events/307409598/
I am scheduling the Wells Street Art Fair AFTER as a separate event from brunch & Old Town Art Fair, to make it easier for all & & since numbers are limited. If you want to join the art fair portion as well, please sign up for that at link here: https://www.meetup.com/windy-city-wanderers/events/307409625/
Optional Garden Walk! Included in the entrance fee/donation. Take a peek into the quaint green spaces that make the Old Town Triangle on Chicago’s north side a truly charming and delightful neighborhood. Over 50 gardens will be in bloom and on display, many of them private and viewable only during the Art Fair. Descriptions of the gardens are displayed throughout the Garden Walk. You’ll also discover historical information, fun facts, and anecdotes about the homes, architecture, and past and present residents. Who knows, you may even spot a proud gardener in their natural habitat.
Your $12.00 donation to the Old Town Art Fair includes access to the Garden Walk and a map of the self-guided tour – available at any of the six entry gates to the Fair!
Voted the #1 Art Fair in America. Chicago's original art fair since 1950!
The Old Town Art Fair is a Fine Art Fair which includes 2D and 3D Mixed Media, Drawings, Paintings, Photography, Printmaking, Ceramics, Glass, Fiber, Jewelry and works in Metal, Stone and Wood. Each year, every artist is selected by an independent jury of art professionals from the Chicago area. You’ll find returning favorites along with many fresh things to explore — nearly half of the exhibiting artists will be new to the Fair.https://www.oldtownartfair.org/
https://www.facebook.com/OldTownArtFair
GETTING HERE: https://www.oldtownartfair.org/getting-hereIf you are taking public transportation please check Google Maps for directions or use CTA trip planner. https://www.transitchicago.com/planatrip/
Note that parking can be difficult during the art fair in Old Town in general, so it is best to use public transportation. brown line trains run near the restaurant & several CTA bus routes. Use SpotHero or Parking Whiz for the cheapest & safest options. Metered parking on Lincoln, Clark & other streets, but can be a challenge if not familiar with the area
PLEASE NOTE OUR CURRENT NO-SHOW POLICY:
- 3 no-shows without updating your rsvp, and you will not be able to sign up for future events for 3 months
- cut-off time to update your rsvp is the start time of the event. If you miss the start time, then message the event host directly
- not checking in with the event host to notify them you have arrived (for walks, tours or festival-type events)
- continual no-shows will result in removal from the group!
- 50th Annual Wells Street Art Festival (Part 3 of 3)West North Avenue & North Wells Street, Chicago, IL
The Wells Street Art Festival is where art enthusiasts are guaranteed to find plenty of inspiration for this early summer showcase. Held on the eponymous strip of Wells Street between North Avenue and Division in Chicago’s historic Old Town neighborhood, it’s a treasure trove of creativity and much more. Lots of great live music at this event!
Suggested Donation is $8.00 Entry for one person on Saturday June 14th. Remember, this is a donation and NOT required, so you can pay less or nothing if you want!
I am being adventurous & want to do all 3 events on Saturday with Brunch & BOTH ART Fairs - Old Town & Wells Street - so it will be a FULL DAY. Please come for 1 portion or all 3! (yes, it is a full day!)
Tentative Itinerary:
9:30 am - 11:00 am - Breakfast at Gemini (Part 1)
11:15 AM - NORTH GATE, located at the corner of Lincoln Avenue at Wisconsin (this is the MAIN GATE). If the line is too long, we will go to the West Gate
11:15 - 1:30 pm - Check the Old Art Fair Vendors & Garden Walk (Part 2)
1:30 -1:45 pm walk over to Wells Street Art Fair
1:45 - 4 pm - check out Wells Street Art & see several live bands! (Part 3)We will ENTER the fair at the NORTH AVE & WELLS STREET ENTRANCE! If you are not doing the brunch before or the Old Art Fair before, then meet at this gate. I would suggest trying to attend at least the Old Town Art Fair as it may be difficult to find the group with the crowds at this Well Street Art fest!
I am scheduling the BRUNCH portion BEFORE the fair as a separate event, to make it easier for all & space is limited. It'll be at Gemini. If you want to join the BRUNCH portion @Gemini before the art fair, then please sign up for that separately at this link below: https://www.meetup.com/windy-city-wanderers/events/307409598/
I am scheduling the Old Town Art Fair BEFORE as a separate event from brunch & Wells Street Art Festival, to make it easier for all & since numbers are limited. If you want to join the art fair portion as well, please sign up for that at this link: https://www.meetup.com/windy-city-wanderers/events/307409604/
The Wells Street Art Festival is an annual community art event held outdoors in Chicago’s historic Old Town neighborhood. Old Town is well known throughout the United States for its historic landmarks and Victorian-era buildings. Each year, the festival’s proceeds go towards securing its continuing development and beautification. Attendees of the summer-time extravaganza are treated to an eclectic array of artwork as well as tasty local cuisine and live music performances by local musicians. Whether you’re looking for a unique painting to accentuate your home or one-of-a-kind jewelry, the festival’s 200+ artists are sure to have something that will strike your fancy.
The annual art extravaganza features the works of more than “250 juried artists with the eclectic mix running the gamut from paintings, sculptures and glasswork to photography, ceramics, woodwork and much more. It also features the tasty cuisine of Old Town restaurants, the always-hoppin music stage, and a silent auction.
The Wells Street Art Festival has a 2 dedicated music stages. The musical lineup for Saturday 6/14/25 is as follows:
Main Stage Saturday
Noon – School of Rock
1:30pm – Jesse White Tumblers
2:00pm – Super Creeps
4:00pm – Stache
6:00pm – Trippin Billies
8:00pm – 16 CandlesSide Street Stage Saturday
1:00pm – XOChI
2:00pm – RAVIV Electric Cellos
3:45pm – Pink Raspberry Cats (Jazz)
5:15pm – Sam Fazio 4
7:00pm – Rosie & The Rivetshttps://www.wellsstreetartfest.us
https://www.wellsstreetartfest.us/festival-guideIf you are taking public transportation, please check Google Maps for directions or use CTA trip planner. https://www.transitchicago.com/planatrip/ -
Note that parking can be difficult during the art fair or in Wells Street Art Fair in general, so it is best to use public transportation. brown line trains run near the fair & CTA bus routes. Use SpotHero or Parking Whiz for the cheapest & safest options. Metered parking on North Ave, LaSalle & Clark streets, but can be a challenge if not familiar with the area
PLEASE NOTE OUR CURRENT NO-SHOW POLICY:
- 3 no-shows without updating your rsvp, and you will not be able to sign up for future events for 3 months
- cut-off time to update your rsvp is the start time of the event. If you miss the start time, then message the event host directly
- not checking in with the event host to notify them you have arrived (for walks, tours or festival-type events)
- continual no-shows will result in removal from the group!
- 🤠36th Annual Broken Arrow Speed & Action Rodeo Horse Show 🐎South Shore Cultural Center, Chicago, IL
🎉 Get Ready for an Unforgettable Chicago Experience! 🎉
🎉 Father’s Day Rodeo + Potluck Picnic! 🐎
Speed & Action Rodeo Horse Show
📅 Sunday, June 15, 2025
🕒 3:00 PM (meet time 1:00 pm but rodeo starts at 3pm)
📍 South Shore Cultural Center – 7059 S. Lake Shore Dr.
🎟️ Tickets: $12–$15 → Buy Tickets HereJoin us for a thrilling Father’s Day outing with live rodeo action by the Broken Arrow Horseback Riding Club, Chicago’s oldest multicultural riding club! Skilled riders, serious cowboy flair, and good vibes guaranteed. It will be an unforgettable day of culture, competition, and community as the Broken Arrow Riding Club presents the 36th Annual Speed & Action Rodeo Horse Show — a Father’s Day tradition like no other, held at the historic South Shore Cultural Center in Chicago!
🔥 What to Expect:
- Fast-paced rodeo events featuring speed & action categories
- Horse showmanship from one of Chicago’s oldest Black riding clubs
- Family-friendly fun, vendors, food, and community pride
- A celebration of Black cowboy heritage and urban horsemanship
📞 For More Info: 773-814-0545
This is more than just a show — it’s a movement. Bring your loved ones and let’s ride into tradition, together.🍽 Potluck Picnic Style – Just Like Ravinia or Millennium Park!
Bring food to share, something to drink, your own plates, silverware & napkins. Grills are allowed if you want to get fancy! They also have food trucks, so you can purchase onsite as well🪑 What to Bring:
• Lawn chairs or picnic blanket (seating is limited!)
• Sunscreen, hat, water
• Early arrival = best spot🚗 Parking: Metered lot on-site – fills up quickly! Chicago Park District Parking Info
🚌 Transit: #J14 Jeffery Jump & #6 Jackson Park Express. CTA Trip Planner
📍 Never been to this event or location before—stay tuned for the exact meetup spot.
🚕Drop a comment if you’d like to carpool or are driving and have room!🌐 Learn more:
🔹 Broken Arrow Horseback Riding Club
🔹 Facebook GroupWe’re teaming up with several other Meetup groups for this fun event, so it’s a multi-group gathering! If you see my name with a large number next to it, that means lots of people are attending from various groups — it's going to be a great crowd!
The Broken Arrow Horseback Riding Club, established on January 15, 1989, is Chicago's first and oldest multicultural riding club. Founded by Murdock, known as "the Man with No First Name," the club aims to reintegrate horseback riding into the inner city, providing opportunities for riders of all backgrounds and abilities to engage with horsemanship.
With over 600 members, the club participates in demonstrations, community events, and philanthropy, including the annual High Noon Ride Picnic on Chicago's historic trails and the Speed & Action Rodeo Horse Show at the South Shore Cultural Center, featuring various equestrian competitions.
Committed to supporting inner-city youth, Broken Arrow seeks to establish an equestrian center in Chicago to offer lessons and broaden its outreach. For more information, visit the Broken Arrow Horseback Riding Club website.
The South Shore Cultural Center, located at 7059 S. South Shore Drive in Chicago, highlights the city’s architectural and cultural heritage. Established in 1905 as the South Shore Country Club by the architectural firm Marshall & Fox, it served as an exclusive retreat for the elite, featuring a golf course, stables, tennis courts, and a private beach along Lake Michigan.
As the neighborhood demographics shifted in the mid-20th century, membership declined due to exclusionary policies. In 1975, the Chicago Park District purchased the property, and thanks to community activists, it was transformed into the South Shore Cultural Center.
Now a community hub, it houses the South Shore Cultural Center School of the Arts, the Paul Robeson Theater, and the Parrot Cage Restaurant, operated by the Washburne Culinary Institute. The grounds feature a public golf course, beach, nature sanctuary, and butterfly garden. The center also hosted significant events, including Barack and Michelle Obama’s wedding reception in 1992. It is recognized for its historical and architectural significance and was added to the National Register of Historic Places. Register of Historic Places in 1975 and designated a Chicago Landmark in 2004. For more information, you can visit the Chicago Park District's official page for the South Shore Cultural Center.
⚠️ RSVP Policy Reminder:
❌ 3 no-shows without notice = 3-month RSVP restriction
⏰ Cut-off to change your RSVP = event start time
📲 If you arrive late or miss check-in, message the host directly
