What we’re about
🍷 Welcome to Windy City Wine+!
We’re a social crew of wine, food, and spirits lovers exploring Chicago’s best sips and bites—plus fun excursions to new venues and festivals around the city (and sometimes beyond 🍇).
I’m Giovina, your organizer as of 9/10/23, taking over from Tom Besore. We'll keep our beloved Millennium Park summer wine nights and add year-round events like wine dinners, classes, tastings, festivals, and vineyard trips.
I also run 1001 Things to See in Chicago Before You Die—an active sister group with 4–5 events weekly. Check it out!
Questions or ideas? Message me anytime on Meetup!
– Giovina Romandine, Organizer 🍷
👉 Join here
Upcoming events
4
🎄✨ Jingle & Glow: South Loop to Riverwalk Holiday Lobby Stroll ❄️🏨
Hilton Chicago, 720 South Michigan Avenue, Chicago, IL, US🎄✨ Jingle & Glow: South Loop to Riverwalk Holiday Lobby Stroll ❄️🏨
🌆 A Sparkling South Loop–to–Riverwalk Holiday Adventure ✨
✨ Christmas isn’t over just yet! If you missed my walk last Sunday, we’re doing it again — and this time with a brand-new route showcasing the festive beauty of the South Loop, Grant Park, the Cultural Center, Millennium Park, and the Chicago Riverfront 🎄🌊
If you joined the Magnificent Mile version, expect a completely different experience. This edition highlights the historic South Loop hotel corridor, where early-20th-century architectural gems glow with vintage holiday charm, then leads north through Chicago’s cultural heart before ending among the modern glass towers of the Riverwalk, glittering with seasonal lights. ✨
Expect twinkling lobby trees, elegant historic décor, grand architecture, creative seasonal displays, and waterfront holiday ambiance — all wrapped into one joyful winter stroll 🎁✨
This is a fresh route, new lineup of hotels, and a whole new festive vibe, but with the same beloved holiday spirit that makes this one of my most popular annual traditions.
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### 🕰️ Schedule, Meeting Info & Cost
📅 Saturday, December 27, 2025
🕥 11:00 AM – 2:30 PM
📍 Start: Hilton Chicago — 720 S Michigan Ave
🏁 End: Sheraton Grand Chicago Riverwalk — 301 E North Water St
🚶♀️ Distance: ~2.4 miles | Easy pace | Indoor + outdoor | Rain or shine
💰 Cost: $20 (cash preferred; Zelle/Venmo/PayPal accepted)
⚠️ Important: This walk does not end where it starts — please plan transportation accordingly.
This tour runs a bit longer than my usual walks because we stop inside many hotels, warm up between lobbies, enjoy festive cocktails, take group photos, and soak up as much décor as possible 🎄✨
📸 Not a dedicated photo walk — but you’ll definitely want your camera.
🎤 Led by your ever-curious, history-loving, architecture-obsessed Chicago guide.
👢 Dress warm, festive, and comfy for a leisurely downtown stroll.
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🌟 Route & Highlights
(Stops may shift slightly depending on timing or group size)
- 🏨 Hilton Chicago — Towering trees, nutcrackers, and the famous giant gingerbread hotel
- 🖼️ The Blackstone — Boutique elegance with chic wreaths and warm lighting
- 🏛️ Congress Plaza Hotel — Classic red-and-gold décor and old-world holiday vibes
- 🎨 Fine Arts Building — Artistic seasonal touches and handmade ornaments
- 🏨 Palmer House — Massive tree beneath the iconic painted ceiling
- 🎄 Chicago Athletic Association Hotel — Cozy lodge-style holiday décor
- ❄️ Cloud Gate (The Bean) — Holiday reflections and skyline sparkle
- 🏛️ Chicago Cultural Center — Tiffany domes dressed in elegant seasonal décor
- 🏨 Fairmont Chicago — Rustic winter-lodge warmth
- 🌊 Radisson Blu Aqua Hotel — Modern holiday installations
- 🇨🇭 Swissôtel Chicago — Bright, festive displays with river views
- 🏨 Hyatt Regency Chicago — Oversized trees and dramatic garlands
- 🚤 Sheraton Grand Chicago Riverwalk — Riverfront glow and seasonal Sleigh Bar
End time: approx. 2:30 PM at the Sheraton Grand.
***
🎄 Holiday Magic in the South Loop, Grant Park & the Chicago River District ✨
South Loop Historic Hotel Corridor
South Michigan Avenue, part of Chicago’s historic Central Business District expansion in the early 1900s, became home to grand hotels catering to travelers, socialites, and performers visiting nearby theaters. During the holidays, these hotels have long competed to dazzle guests with lavish Christmas trees, twinkling lights, and festive displays, creating a tradition that stretches back nearly a century. Many buildings retain their original Beaux-Arts and Renaissance Revival architecture, making the holiday décor even more striking against their historic facades.
Cultural & Civic Chicago
As we move north, we pass through Chicago’s cultural heart — the Fine Arts Building, the Chicago Cultural Center, and Millennium Park. These areas have historically been centerpieces of the city’s civic and artistic life, and during the holiday season, the combination of public art, illuminated fountains, and seasonal décor transforms them into magical winter wonderlands.
Chicago Riverfront
The Riverwalk, a relatively modern addition completed in the 2010s, connects historic commercial architecture with contemporary urban design. During the holidays, the riverfront glows with festive lights, tree-lined promenades, and seasonal installations, creating a reflective, sparkling scene that perfectly complements the grand hotel lobbies along our route. The Riverwalk has become a holiday destination in its own right, drawing locals and visitors to stroll along the water, sip warm drinks, and admire the city’s winter magic.
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🚇 Getting There
Public transit highly recommended.
CTA Trip Planner: https://www.transitchicago.com/planatrip/
🚗 Parking
Limited and can be expensive.
SpotHero / ParkWhiz recommended.
Street parking varies — always check signs carefully.
***
📝 RSVP & No-Show Policy
✔️ Please keep your RSVP updated
✔️ Cancel if you can’t attend
❌ Repeat no-shows may be removed from future events
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🎄✨ Join us for a heartwarming stroll through the South Loop, Grant Park, Millennium Park & the Chicago River — filled with stories, architecture, history, and magical holiday sparkle! ✨
***17 attendees
🎄🍸 After-Work Cocktails @ the Sheraton Sleigh Bar ❄️✨
Shula’s Steak House, 301 E North Water St ·, Chicago, IL, US🎄🍸 After-Work Cocktails @ the Sheraton Sleigh Bar ❄️✨
Holiday Drinks at Shula’s Steak House | Riverwalk Magic
✨ We’re not done with the holidays yet! ✨
Let’s squeeze in one more festive night out with cocktails at one of downtown Chicago’s most polished seasonal pop-ups — the Sheraton Sleigh Bar inside Shula’s Steak House at the Sheraton Grand Chicago Riverwalk. Cozy, classic, and very Chicago. 🛷🥂
📅 Monday, 12/29/25 @ 6:15 PM
👥 Group Size: 24 people
📍 Shula’s Steak House
Inside the Sheraton Grand Chicago Riverwalk
301 E North Water St · Chicago, IL 60611
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🍸 The Sleigh Bar Experience
Each holiday season, Shula’s transforms into the Sheraton Sleigh Bar — a warm, festive escape from the cold featuring:
🎄 Elegant Christmas décor (classy cabin vibes — not kitsch)
🍹 Seasonal cocktails & classic favorites
🪵 Cozy lounge atmosphere perfect for after-work unwinding
🌊 Steps from the Chicago Riverwalk with twinkling winter views
Festive, relaxed, and perfect for lingering conversations — because December isn’t over yet. 😉
***
🍽️ MEAL & DRINKS (PLEASE READ)
✅ Reservations confirmed for 4 tables of 6
📋 Tables are booked under the following names:
Giovina Romandine, Rose Lucian, Laura Bandas & Ashley Marie
- Seating will be split among the four reserved tables
- Cocktails, wine, beer, and light bites available
💵 PLEASE BRING CASH!
- They cannot do separate checks for groups
- Please add 32% to your total (12% tax + 20% tip)
- 💡 Cash makes everything easier for large groups!
***
🏨 A Little History: Sheraton Grand Chicago Riverwalk
• Opened: 1992
• Architect: Perkins & Will
• One of Chicago’s largest riverfront hotels
• A major anchor of the Chicago Riverwalk, helping redefine downtown’s relationship with the river 🌊
• Longtime host to conventions, galas, and visiting celebrities
Its scale, river orientation, and interior spaces make it a standout example of late-20th-century Chicago hospitality architecture.
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🥩 About Shula’s Steak House
Founded by legendary NFL coach Don Shula, this classic steakhouse is known for:
• Prime steaks & classic cocktails
• Old-school supper-club energy
• A loyal following of business travelers, locals, and celebratory diners
During the holidays, it becomes one of the coziest spots in the building thanks to the Sleigh Bar transformation.
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🎄 Why This One’s Special
🎁 Holiday pop-up inside a classic Chicago hotel
🍸 Festive but calm — no chaotic crowds
🌃 Riverwalk location adds winter sparkle
🥂 Perfect “between-the-holidays” gathering
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🔗 Links
Sheraton Grand Chicago Riverwalk
https://www.marriott.com/en-us/hotels/chigs-sheraton-grand-chicago-riverwalk/overview/
Shula’s Steak House Chicago
https://www.shulas.com/locations/chicago/
Menu & Drinks
https://www.shulas.com/locations/chicago/menu/
***
🚇 Getting There
• CTA buses along Michigan Ave & Grand
• Short walk from Grand (Red Line) or State/Lake
• Easy access from the Loop & River North
🚗 Parking
• Valet available at the hotel
• SpotHero & ParkWhiz recommended
• Limited street parking — watch posted signs
***
🚫 No-Show Policy
• 3 no-shows without updating RSVP = 3-month freeze
• Update RSVP before event start
• Message host if running late
• Not checking in counts as a no-show
• Repeat offenders may be removed from the group
***
🍸🎄 Join us for one last round of holiday cocktails, cozy vibes, and riverfront sparkle — because the season isn’t over until we say it is. 🛷✨16 attendees
🥳🍾NYE Day Drinking: Mimosas to Irish Midnight, Class, Chaos & Champagne 🍸😂
Bub City, 435 N Clark St, Chicago, IL, US🥳 🍾NYE Day Drinking: Mimosas to Irish Midnight, Class, Chaos & Champagne 🍸😂
🎉 NEW YEAR’S EVE DAY DRINKING ADVENTURE!
Wednesday, December 31, 2025 • 12:00 PM – 7:30 PM
✨ New Year, New Plan, Less Nonsense ✨
This year we're ditching the usual Weeds Midnight Party and embracing something revolutionary:
Celebrating New Year’s Eve WITHOUT dealing with drunk amateurs. 😆🍾
Let’s be honest…
Who actually wants to:
❌ Pay $150 to stand in a crowded hotel ballroom?
❌ Play surge-pricing roulette with Uber?
❌ Spend 20 minutes freezing on a curb while valet “can’t find your car”?
❌ Wear sparkly shoes that destroy your feet?
❌ Get elbowed by a 22-year-old who pregamed with Fireball at 3 PM?
Not. Us.
So instead…
We’re day drinking.
Like classy, responsible adults who know their limits and their bedtime. 🍻😇
We’ll be done before the amateurs crawl out of their caves — home in jammies, snacks in hand, and dignity intact.
***
🍔🥂 STEP 1: LUNCH — Because We’re Grownups
📍 Bub City — 12–1 PM
435 N Clark St
🔗 https://www.bub-city.com/
We begin with food.
Because if we’re going to toast 7 different midnights, we’re going to need a base.
This is science. 🔬🍔
***
🗺️ TENTATIVE ITINERARY (a.k.a. The Magical Mystery Bar Crawl)
Subject to change depending on:
• vibes
• crowds
• sudden cravings
• who gets distracted by shiny objects
1️⃣ Bub City — 12–1 PM
435 N Clark St
The pre-game feast. Carb loading = strategic brilliance.
2️⃣ Boss Bar — 1–2 PM
📍 420 N Clark St
A River North classic. Where time stands still and the people-watching is elite.
3️⃣ Rossi’s Bar — 2–3 PM
📍 412 N State St
An iconic dive. Sticky floor included at no additional cost.
4️⃣ Mother Hubbard’s — 3–4 PM
📍 5 W Hubbard St
Sports bar energy. Cold beer. TVs shouting at you. Comforting.
5️⃣ Snickers Bar & Grill — 4–5 PM
📍 448 N State St
A no-frills staple. Perfect for that “we’re still pacing ourselves, right?” drink.
6️⃣ Fadó Irish Pub — 5–7 PM
📍 100 W Grand Ave
🔗 https://fadoirishpub.com/chicago/
Champagne toast at 6 PM for Irish New Year! We WILL toast like we’ve suddenly developed an Irish accent. They actually do a real champagne toast at 6 PM for Irish New Year. We will be there — ready to shout “SLÁINTE!” like we’re on vacation in Dublin.
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🌍✨ THE WORLD MIDNIGHT TOASTS
We are absolutely using Google World Clock to justify every drink.
It’s educational.
We’re basically scholars.
🎉 1 PM CST — UTC+5
Pakistan, Uzbekistan, Maldives, Western Kazakhstan, places we can’t pronounce but still appreciate.
🎉 2 PM CST — UTC+4
UAE, Oman, Georgia, Seychelles — lots of fancy places we probably can’t afford to visit.
🎉 3 PM CST — UTC+3
Saudi Arabia, Turkey, East Africa, Moscow.
We toast responsibly. Unlike Moscow.
🎉 4 PM CST — UTC+2
South Africa, Egypt, Greece.
Yes, we WILL yell “OPA!” at some point.
🎉 5 PM CST — UTC+1
France, Italy, Spain, Germany.
This is the chic hour. Pinkies up.
🎉 6 PM CST — UTC+0
Ireland 🇮🇪, UK, Portugal, Iceland.
🍾 Fadó champagne toast = our Super Bowl.
***
⏰ THE GRAND FINALE — 7:30 PM
And then…
We go home.
Before the amateurs come out.
Before the $75 Uber rides.
Before the sequined chaos.
We will be at home in slippers, watching the ball drop like the responsible, fabulous adults we are. 🛋️✨
🚇 Transportation Tips
Parking in the River North can be extremely challenging.
Highly recommended:
• CTA (train or bus)
• Metra
• SpotHero or ParkWhiz for better parking rates
CTA Trip Planner:
🔗 https://www.transitchicago.com/planatrip/
***
❗ No-Show Policy (Please Read!)
• Three no-shows without updating your RSVP = 3-month suspension
• Cut-off to update your RSVP = event start time
• If you arrive late, message the host directly
• Not checking in with the host at walks/tours/festival events counts as a no-show
• Repeated no-shows may result in removal from the group41 attendees
🎶🕺💃 "I Love 80's Fridays" @ Holiday Club–Dinner🍔, Drinks🍹& DANCING💃!
Holiday Club, 4000 North Sheridan Road, Chicago, IL, US🎶🕺💃 "I Love 80's Fridays" @ Holiday Club–Dinner🍔, Drinks🍹& DANCING💃!
🎶🕺💃 I Love 80’s Fridays – Holiday Edition!
Friday, January 2, 2026 • 8:30 PM – 12:00 AM
📍 Holiday Club, 4000 N Sheridan Rd, Chicago, IL
https://holidayclubchicago.com/
https://www.facebook.com/holidayclubchicago/
Since we all like to eat, drink & dance to the oldies, let's check out the Holiday Club in Buena Park! It has everything we want and more! On Friday nights at 10 PM, they play old-school 80's music with the original music videos! 🎶💿 It will be a blast from the past! Plus, they serve food, so we can grab a bite before we dance the night away! 🍔🍹💃 We have been here many times & it is always a lot of fun!
We’ll grab a bite to eat first at 8:30 PM, then head to the back room to dance! Want to skip dinner? No problem — join us at 10 PM for dancing! 💃🕺
💵 Cash Only for Groups — separate checks for the FOOD PORTION aren’t possible. Please add 32% (12% tax + 20% tip). Easier for large groups!
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### About Holiday Club
- Chicago tradition since 1993! 🏙️
- Rat Pack-inspired retro lounge & restaurant with classic cocktails, comfort food, photo booth, pool tables, karaoke, and DJs 🍸📸🎤
- Formerly a Wicker Park “Swingers Mecca,” now Uptown location with air conditioning, sidewalk café & private lounge 🌟
- A 30+ year hub for fun, music, and dancing 🕺💃
📖 Menus & Info:
- Food Menu: https://holidayclubchicago.com/eats/
- Drink Menu: https://holidayclubchicago.com/lively-libations/
🚗 Parking: Metered street spots on Montrose & Sheridan, plus free street parking nearby (watch for signs!)
🚍 Transit: Easily accessible by bus or train — CTA Trip Planner
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### ❗ RSVP / No-Show Policy
- 3 no-shows without updating RSVP = 3-month hiatus from events
- Cut-off to update RSVP: 8:30 PM start time
- Must check in with host at arrival
- Continual no-shows = removal from the group
***
🎉 Come eat, drink, dance, and celebrate the holidays 80’s-style! 🌟🎶💃🕺16 attendees
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