Live Music from The Ginger Road
Dec
19
to Dec 20

Live Music from The Ginger Road

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Regularly featured at the finest venues and festivals across Chicagoland and beyond -
from regular engagements at local high end venues like Bub City and Old Crow
Smokehouse to Festival stages and all the way to Tootsie's and Rippy's in Nashville -
Ginger Road has been Rockin' This Country since 2013 with a contagious, high energy
mix of modern and classic Country and Rock covers that will have you signing along
and dancing in your boots.

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Live Music from Dylan Raymond
Dec
20
to Dec 21

Live Music from Dylan Raymond

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Raised in Indiana, Dylan Raymond grew up on 90s country and began playing guitar at eight years old which set the stage for his musical ambitions. Known for his baritone voice and high-energy performances, Dylan is making waves in the country music industry.

Dylan's debut single, Take it Slow, released in 2016, soared to number two on the Itunes overall pre-order charts. His hit single, I Can Be That, climbed the country charts to number 35 in 2017 and currently has more than three million streams on Spotify alone without being placed on a curated playlist. His current single, Til the Cows Come Home is already on the road to being a huge hit for him and has been placed on the New Music Friday playlist by Spotify upon its release. 

"Dylan Raymond's smooth sound is exactly what country music needs. He has a way of drawing you in and keeping you wanting more through his songwriting and storytelling." – Off The Racq

Bringing his energetic, thrilling performances to any stage he steps on, Dylan has shared the stage with Trace Adkins, Gabby Barrett, Dylan Scott, Diamond Rio, Aaron Tippin, Collin Raye, Jon Langston, Jordan Davis, Chris Janson, Andy Grammer, Jake Owen, Walker Hayes, Russell Dickerson, and many more.

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Live Music from The Abby Kay Band
Dec
27
to Dec 28

Live Music from The Abby Kay Band

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The Abby Kay Band hails from Northern Illinois with strong ties and loyal followers in Lake, Cook, and McHenry counties along with southern Wisconsin. This up-and-coming band plays a wide variety of music spanning multiple decades and musical genres for an authentic midwestern rock feel that is sure to have the crowd engaged and dancing. An extensive list of covers includes the likes of artists such as Elle King, Janis Joplin, and Miranda Lambert, as well as The Black Crowes, Gretchen Wilson, Melissa Etheridge, CCR, and so much more. The Abby Kay Band also notably plays crowd-pleasing original songs that continue to develop into fan favorites. 

The Abby Kay Band plays with contagious energy and connects with any type of audience. Abby Kay provides soulful vocals with an edge and the band brings the perfect blend of searing guitar and a rockin' rhythm section that keeps the boots stomping and the crowd singing along. Rock, country, blues, and pop blend together seamlessly for a one-of-a-kind show you won't catch anywhere else. This authentic and talented band promises to keep live and original music alive.

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Eve of the Eve at Stolen Saddle, Home of Santa Baby (21+)
Dec
30
to Dec 31

Eve of the Eve at Stolen Saddle, Home of Santa Baby (21+)

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We’re hosting the party before the party! Tix include 2 drinks and express entry. Saddle up for some end-of-the-year fun at Stolen Saddle, Chicago’s newest country bar and the home of the Santa Baby pop-up.

Guests will receive drink tickets for two complimentary drinks (valid before 11pm) and express entry (before 11:30pm).

Learn more & get tickets
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Wreath Making Class with BCollevtive & Ilegal Mezcal (21+)
Dec
16
6:00 PM18:00

Wreath Making Class with BCollevtive & Ilegal Mezcal (21+)

Settle into a holiday night that feels easy, creative, and full of good energy. Our Holiday Wreath Making Workshop at Santa Baby in Wrigleyville brings together fresh greenery, hands-on fun, and cocktails that make the whole experience feel extra festive. You’ll design a 14-inch fresh wreath that’s ready to hang and enjoy all season long.

With guidance from our Chief Floral Designer, Mia and the bcollective team, you’ll work with cedar, eucalyptus, pine, and a mix of seasonal accents to build a wreath that feels personal and full of charm. Whether you’re planning a date night, a night out with friends, or simply want to do something fun this holiday season, this workshop offers a feel-good break from the holiday rush.

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What You’ll Enjoy:

  • Step-by-step support from our floral designer

  • A 14” wreath base and plenty of fresh greenery

  • Festive décor and ribbons to customize your look

  • Two holiday cocktails sponsored by Ilegal Mezcal:

    • Santa’s Spice — Ilegal Mezcal, Patrón, kiwi, grapefruit, lime, agave, club soda

    • Merry Marg — Ilegal Mezcal, agave, triple sec, fresh lime juice

You’ll head home with a wreath you’re proud of—and the feeling of a holiday night well spent in Chicago. 21+ • All tickets are non-refundable

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TBOX: Chicago's Christmas Bar Crawl (21+ Ticketed Event)
Dec
13
10:00 AM10:00

TBOX: Chicago's Christmas Bar Crawl (21+ Ticketed Event)

Santa Baby will be part of TBOX, the World’s Largest Holiday Bar Crawl, on Saturday, December 13, 2025.

This 21+ all-day event begins at 10 AM, and entry will be exclusive to TBOX ticket holders. Most bars on Clark Street participate, and the atmosphere is festive and energetic, with large crowds throughout the day.

Please note that only a limited menu will be available on this date. If you’d prefer a more traditional Santa Baby experience, we recommend visiting us on another day.

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Live Music from The Ryan Craig Band
Dec
6
to Dec 7

Live Music from The Ryan Craig Band

The Ryan Craig Band formed in 2023. The band performs all over the Chicagoland area and Nashville's Music Row! Last year, they released two of their hit singles "Drink Your Memory Away" & "Summertime Feeling"! The two songs landed on Local Radio Stations 98.3 WCCQ & 100.7 The River! The boys are known for taking requests and connecting with their audience. The band is most know for their variety in music and play your favorite covers, from Joe Diffie to Metallica! The Ryan Craig band is a Country Rock Band with a touch of Nashville. Read on to find out more about the members of the band and come out and join as part of our "rowdy crowd family.”

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Live Music from The BirkenRocks
Dec
5
to Dec 6

Live Music from The BirkenRocks

The Birkenrocks, a beloved Rock Cover Band, is made up of a talented team of creative musicians who have been performing together since 2019. They pride themselves on their technical abilities and musical versatility, breaking boundaries with their unique sound. Their high energy and showmanship will keep you singing and dancing all night long! And if you're wondering, yes they do wear Birkenstocks on stage!

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Live Music from Tim Swann
Nov
28
to Nov 29

Live Music from Tim Swann

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Tim Swann has had many musical influences throughout the years, from country to rock to folk & gospel. Raised in a Pentecostal home, music was a part of everyday life & he spent 30 years playing and singing in churches, and just recently connected with several friends to work on polishing some original music & doing covers ranging from Johnny Cash to The Jackson 5 to Adele.

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Nov 23 - Bears Watch Party with Wrigleyville Sports | 12 PM
Nov
23
12:00 PM12:00

Nov 23 - Bears Watch Party with Wrigleyville Sports | 12 PM

We’re teaming up with Wrigleyville Sports for game day at Santa Baby Bar on Sunday, November 23:

  • $25 Michelob Ultra Buckets

  • Shop select Bears gear from Wrigleyville Sports — 15% off during the game

  • FREE can koozies (while supplies last)

  • Prizes after each quarter + halftime games

  • Exclusive Wrigleyville Sports coupons

make a reservation
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Live Music from Dylan Raymond
Nov
22
to Nov 23

Live Music from Dylan Raymond

  • Google Calendar ICS

Raised in Indiana, Dylan Raymond grew up on 90s country and began playing guitar at eight years old which set the stage for his musical ambitions. Known for his baritone voice and high-energy performances, Dylan is making waves in the country music industry.

Dylan's debut single, Take it Slow, released in 2016, soared to number two on the Itunes overall pre-order charts. His hit single, I Can Be That, climbed the country charts to number 35 in 2017 and currently has more than three million streams on Spotify alone without being placed on a curated playlist. His current single, Til the Cows Come Home is already on the road to being a huge hit for him and has been placed on the New Music Friday playlist by Spotify upon its release. 

"Dylan Raymond's smooth sound is exactly what country music needs. He has a way of drawing you in and keeping you wanting more through his songwriting and storytelling." – Off The Racq

Bringing his energetic, thrilling performances to any stage he steps on, Dylan has shared the stage with Trace Adkins, Gabby Barrett, Dylan Scott, Diamond Rio, Aaron Tippin, Collin Raye, Jon Langston, Jordan Davis, Chris Janson, Andy Grammer, Jake Owen, Walker Hayes, Russell Dickerson, and many more.

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Live Music from Andru Jamison
Nov
21
to Nov 22

Live Music from Andru Jamison

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Andru Jamison is a 29-year-old American Singer/Songwriter living outside Chattanooga, TN. Within a year of his career launch in February 2023, Andru won "Song of the Year: Country" for his solo-written song "Empty Bottle" at the 2024 JMA's under The Grand Ole Opry. He has been nominated for several other awards including, Songwriter of the Year. Working with ACMA Producer of the Year, Andy Wallis, a total of 26 songs have been recorded in studio, including a 19 track acoustic album "Heart Echoes". The former Combat Medic Veteran writes all of his own lyrics from experience and melodies to his music, making him a multi-talented "unicorn" in the industry. His songwriting and voice landed him a distribution deal with Virgin Music Group. Now with over 76,000 fans, he is making a name for himself with every performance he plays. From sold out shows at the Nashville Palace or ranking #11 on UKs Country charts to opening up for artists such as Struggle Jennings, Demun Jones, Jesse James, Sam Grow and Tyler Rich, Andru emotionally captivates crowds unlike anything you see in the industry today. This upcoming artist is building his career and quickly gaining traction across the country

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Champagne Bottle Paint & Sip
Jan
1
6:00 PM18:00

Champagne Bottle Paint & Sip

Celebrate the holidays with friends at Santa Baby's Champagne Bottle Paint & Sip!

Tickets includes a full champagne bottle for you to paint and take home. We provide allll the essential supplies such as paint, glitter, glitz, paint brushes, and aprons. Plus, enjoy a complimentary glass of champagne to get those creative juices flowing.

21+ Event
Food & drink may be purchased during the event

Get tickets here!
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Wrigleyville New Year's Eve Bar Crawl (21+)
Dec
31
7:00 PM19:00

Wrigleyville New Year's Eve Bar Crawl (21+)

Get ready to kick off the new year in style at the Chicago New Year’s Eve Bar Crawl in Wrigleyville! Crawl from bar to bar with over 15 bars to choose from!

Tickets get you admission to all bars, appetizer buffets, gift cards to use on the crawl, a champagne toast & more - all in Wrigleyville! 21+ Event.

GET TICKETS
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Champagne Bottle Paint & Sip
Dec
18
6:00 PM18:00

Champagne Bottle Paint & Sip

Celebrate the holidays with friends at Santa Baby's Champagne Bottle Paint & Sip!

Tickets includes a full champagne bottle for you to paint and take home. We provide allll the essential supplies such as paint, glitter, glitz, paint brushes, and aprons. Plus, enjoy a complimentary glass of champagne to get those creative juices flowing.

21+ Event
Food & drink may be purchased during the event

Get tickets here!
 
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Grinch Trivia Night
Dec
16
7:00 PM19:00

Grinch Trivia Night

Themed Trivia Every Monday at 7pm!

Free to Join
Up to 6 People Per Team
Prizes Awarded for 1st, 2nd, & 3rd Place!
Reservations Encouraged

Specials:

  • $5 Mistletoe Mix Cocktails

  • $7 Patron Margaritas

  • $7 Frozens

  • $5 NÜTRLs

  • $4 Michelob Ultras

reserve now
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TBOX Bar Crawl (21+ All Day Event)
Dec
14
4:30 PM16:30

TBOX Bar Crawl (21+ All Day Event)

We will be part of the TBOX, the World's Largest, Longest Running Holiday Bar Crawl, on Saturday, December 14, 2024. This is a 21+ all day event. We recommend joining us another day if you do not wish to be part of the crawl. A limited menu will be available.

GET BAR CRAWL TICKETS
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Champagne Bottle Paint & Sip
Dec
11
6:00 PM18:00

Champagne Bottle Paint & Sip

Celebrate the holidays with friends at Santa Baby's Champagne Bottle Paint & Sip!

Tickets includes a full champagne bottle for you to paint and take home. We provide allll the essential supplies such as paint, glitter, glitz, paint brushes, and aprons. Plus, enjoy a complimentary glass of champagne to get those creative juices flowing.

21+ Event
Food & drink may be purchased during the event

Get tickets here!
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Elf Trivia Night
Dec
9
7:00 PM19:00

Elf Trivia Night

Themed Trivia Every Monday at 7pm!

Free to Join
Up to 6 People Per Team
Prizes Awarded for 1st, 2nd, & 3rd Place!
Reservations Encouraged

Specials:

  • $5 Mistletoe Mix Cocktails

  • $7 Patron Margaritas

  • $7 Frozens

  • $5 NÜTRLs

  • $4 Michelob Ultras

reserve now
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Champagne Bottle Paint & Sip
Dec
4
6:00 PM18:00

Champagne Bottle Paint & Sip

Celebrate the holidays with friends at Santa Baby's Champagne Bottle Paint & Sip!

Tickets includes a full champagne bottle for you to paint and take home. We provide allll the essential supplies such as paint, glitter, glitz, paint brushes, and aprons. Plus, enjoy a complimentary glass of champagne to get those creative juices flowing.

21+ Event
Food & drink may be purchased during the event

Get tickets here!
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Music Bingo Tuesdays
Nov
26
7:00 PM19:00

Music Bingo Tuesdays

Join us every Tuesday for Music Bingo at 7pm!

Free to Join
Prizes Awarded for 1st, 2nd, & 3rd Place!
Reservations Encouraged

Specials:

  • $5 Mistletoe Mix Cocktails

  • $7 Patron Margaritas

  • $7 Frozens

  • ½ Off Pizzas

  • $5 NÜTRLs

  • $4 Michelob Ultras

Reserve now
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