Calendar

Holiday Gift Card Promo event photo

Holiday Gift Card Promo

Thursday December 12th

Runs until Tuesday, December 24th, 2024

10:00 AM - 10:00 PM

2024-12-12 10:00:002024-12-12 22:00:00America/ChicagoHoliday Gift Card PromoJen's GuesthouseJen's Guesthouseevents@jensguesthouse.com
Ollie Bolds Christmas Show event photo

Ollie Bolds Christmas Show

Thursday December 12th

Come enjoy dinner & live Christmas music with Ollie!

05:00 PM - 08:00 PM

2024-12-12 17:00:002024-12-12 20:00:00America/ChicagoOllie Bolds Christmas ShowCome enjoy dinner & live Christmas music with Ollie!Jen's GuesthouseJen's Guesthouseevents@jensguesthouse.com
Karaoke Night event photo

Karaoke Night

Thursday December 12th

Every Thursday

Join us late night for Karaoke every Thursday in the bar! 

09:00 PM - 12:00 AM

2024-12-12 21:00:002024-12-12 00:00:00America/ChicagoKaraoke NightJoin us late night for Karaoke every Thursday in the bar! Jen's GuesthouseJen's Guesthouseevents@jensguesthouse.com
Closed for private event event photo

Closed for private event

Friday December 13th

10:00 AM - 10:00 PM

2024-12-13 10:00:002024-12-13 22:00:00America/ChicagoClosed for private eventJen's GuesthouseJen's Guesthouseevents@jensguesthouse.com
Brunch with Santa event photo

Brunch with Santa

Sunday December 15th

Santa will be here with his Elf Balloonist! Indulge in the ice cream station, & delicious brunch options! 

10:00 AM - 03:00 PM

2024-12-15 10:00:002024-12-15 15:00:00America/ChicagoBrunch with SantaSanta will be here with his Elf Balloonist! Indulge in the ice cream station, & delicious brunch options! Jen's GuesthouseJen's Guesthouseevents@jensguesthouse.com
Craft & Sip Night event photo

Craft & Sip Night

Tuesday December 17th

Ask about the seasonal crafts!

06:00 PM - 08:00 PM

2024-12-17 18:00:002024-12-17 20:00:00America/ChicagoCraft & Sip NightAsk about the seasonal crafts!Jen's GuesthouseJen's Guesthouseevents@jensguesthouse.com
Ross Failla Christmas Show event photo

Ross Failla Christmas Show

Thursday December 19th

Christmas music & dinner with Ross!

05:00 PM - 08:00 PM

2024-12-19 17:00:002024-12-19 20:00:00America/ChicagoRoss Failla Christmas ShowChristmas music & dinner with Ross!Jen's GuesthouseJen's Guesthouseevents@jensguesthouse.com
Christmas Eve Catering event photo

Christmas Eve Catering

Tuesday December 24th

Pick up warm & ready to enjoy between 12-2 pm! 

12:00 PM - 02:00 PM

2024-12-24 12:00:002024-12-24 14:00:00America/ChicagoChristmas Eve CateringPick up warm & ready to enjoy between 12-2 pm! Jen's GuesthouseJen's Guesthouseevents@jensguesthouse.com
Christmas Eve Menu event photo

Christmas Eve Menu

Tuesday December 24th

Special Christmas Eve Menu, open from 2-7 pm. 

02:00 PM - 07:00 PM

2024-12-24 14:00:002024-12-24 19:00:00America/ChicagoChristmas Eve MenuSpecial Christmas Eve Menu, open from 2-7 pm. Jen's GuesthouseJen's Guesthouseevents@jensguesthouse.com
New Year's Eve Menu event photo

New Year's Eve Menu

Tuesday December 31st

Serving dinner from 4-11 pm. Make a later reservation & stay to enjoy Ral Donner from 8 pm-12 am & a fireworks show! 

04:00 PM - 10:00 PM

2024-12-31 16:00:002024-12-31 22:00:00America/ChicagoNew Year's Eve MenuServing dinner from 4-11 pm. Make a later reservation & stay to enjoy Ral Donner from 8 pm-12 am & a fireworks show! Jen's GuesthouseJen's Guesthouseevents@jensguesthouse.com
New Year's Eve event photo

New Year's Eve

Tuesday December 31st

Bring in the New Year with Ral Donner Jr. & our yearly fireworks show! Dinner from 4-11 pm. Reservations recommended!

04:00 PM - 12:00 AM

2024-12-31 16:00:002024-12-31 00:00:00America/ChicagoNew Year's EveBring in the New Year with Ral Donner Jr. & our yearly fireworks show! Dinner from 4-11 pm. Reservations recommended!Jen's GuesthouseJen's Guesthouseevents@jensguesthouse.com
HAPPY NEW YEAR! event photo

HAPPY NEW YEAR!

Wednesday January 1st

10:00 AM - 10:00 PM

2025-01-01 10:00:002025-01-01 22:00:00America/ChicagoHAPPY NEW YEAR!Jen's GuesthouseJen's Guesthouseevents@jensguesthouse.com
Hector Fernandez event photo

Hector Fernandez

Friday January 10th

Acoustic Guitarist

06:00 PM - 09:00 PM

2025-01-10 18:00:002025-01-10 21:00:00America/ChicagoHector FernandezAcoustic GuitaristJen's GuesthouseJen's Guesthouseevents@jensguesthouse.com
Psychic Night event photo

Psychic Night

Tuesday January 14th

Join us for Psychic Night! Call Maribeth for your Psychic reading & book your dinner reservations through us!

06:00 PM - 09:00 PM

2025-01-14 18:00:002025-01-14 21:00:00America/ChicagoPsychic NightJoin us for Psychic Night! Call Maribeth for your Psychic reading & book your dinner reservations through us!Jen's GuesthouseJen's Guesthouseevents@jensguesthouse.com
Ross Singing Live event photo

Ross Singing Live

Friday January 17th

06:00 PM - 09:00 PM

2025-01-17 18:00:002025-01-17 21:00:00America/ChicagoRoss Singing LiveJen's GuesthouseJen's Guesthouseevents@jensguesthouse.com

"Tour of Napa" Wine Dinner

Thursday January 23rd

06:30 PM - 09:00 PM

2025-01-23 18:30:002025-01-23 21:00:00America/Chicago"Tour of Napa" Wine DinnerJen's GuesthouseJen's Guesthouseevents@jensguesthouse.com
Winter Hours event photo

Winter Hours

Monday January 27th

Runs until Friday, February 28th, 2025

10:00 AM - 10:00 PM

2025-01-27 10:00:002025-01-27 22:00:00America/ChicagoWinter HoursJen's GuesthouseJen's Guesthouseevents@jensguesthouse.com
Superbowl Catering event photo

Superbowl Catering

Sunday February 9th

02:00 PM - 05:00 PM

2025-02-09 14:00:002025-02-09 17:00:00America/ChicagoSuperbowl CateringJen's GuesthouseJen's Guesthouseevents@jensguesthouse.com
Valentine's Weekend Entertainment event photo

Valentine's Weekend Entertainment

Thursday February 13th

Runs until Saturday, February 15th, 2025

05:00 PM - 08:00 PM

2025-02-13 17:00:002025-02-13 20:00:00America/ChicagoValentine's Weekend EntertainmentJen's GuesthouseJen's Guesthouseevents@jensguesthouse.com
Psychic Night event photo

Psychic Night

Thursday February 20th

Join us for Psychic Night! Call Maribeth for your Psychic reading & book your dinner reservations through us!

06:00 PM - 09:00 PM

2025-02-20 18:00:002025-02-20 21:00:00America/ChicagoPsychic NightJoin us for Psychic Night! Call Maribeth for your Psychic reading & book your dinner reservations through us!Jen's GuesthouseJen's Guesthouseevents@jensguesthouse.com