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Chicago winters might be icy, but the holiday season is far from frozen. With so much to do, here's what not to miss. 🎶🎄🍻
Published November 10, 2021
Chicago winters are the stuff of legends, which guarantees the holiday attractions are equally impressive to match. Check our list below for some of our favorite winter activities – with heated patios, snow-scapades and chocolate delights to enjoy through the end of 2021 and into 2022.
The enclosed heated rooftop is the perfect space for the winter. Get a good laugh at the cold, cocktail-less, people below as you take in the soaring sights of the city.
Where: 1816 N Clark St, Chicago, IL 60614
The enclosed heated rooftop is the perfect space for the winter. Get a good laugh at the cold, cocktail-less, people below as you take in the soaring sights of the city.
Where: 1816 N Clark St, Chicago, IL 60614
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Located on over 2 acres of land in the historic Goose Island. Pick a perfect Christmas Tree, grab a memorable Instagrammable moment, or just get out of the house and get some fresh air on a perfect midwinter evening, as you get lost in the largest, and only, evergreen forest in downtown Chicago.
When: Opening November 26th, 2021
Where: 1465 North Elston Avenue Chicago, IL 60642
Located on over 2 acres of land in the historic Goose Island. Pick a perfect Christmas Tree, grab a memorable Instagrammable moment, or just get out of the house and get some fresh air on a perfect midwinter evening, as you get lost in the largest, and only, evergreen forest in downtown Chicago.
When: Opening November 26th, 2021
Where: 1465 North Elston Avenue Chicago, IL 60642
Christkindlmarket is back for 2021! This iconic Chicago activtity should be on everyones winter bucket list. From holiday treats, to shopping, and so much more.
When: November 19 – December 24, 2021
- Sundays – Thursdays: 11am – 8pm
- Fridays – Saturdays: 11am – 10pm
Where: Daley Plaza, 50 W Washington St, Chicago, IL 60602
Christkindlmarket is back for 2021! This iconic Chicago activtity should be on everyones winter bucket list. From holiday treats, to shopping, and so much more.
When: November 19 – December 24, 2021
- Sundays – Thursdays: 11am – 8pm
- Fridays – Saturdays: 11am – 10pm
Where: Daley Plaza, 50 W Washington St, Chicago, IL 60602
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Prepare to be AMAZED this holiday season while wandering through seven magical worlds of light. Located in Rosemont, this year's event will feature over one million lights, a tubing hill, holiday market and more.
When: Opening November 19th
Where: 9850 Balmoral Avenue, Rosemont, Illinois 60018
Prepare to be AMAZED this holiday season while wandering through seven magical worlds of light. Located in Rosemont, this year's event will feature over one million lights, a tubing hill, holiday market and more.
When: Opening November 19th
Where: 9850 Balmoral Avenue, Rosemont, Illinois 60018
Nothing say holidays like watching someone drink a little too much. The stage is set in a hidden venue where five classically-trained actors meet as members of "The Drunk Shakespeare Society". After one performer downs 5 shots of liquor, they attempt to perform a major role in a Shakespearean play.
But you can check this event instead:
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Nothing say holidays like watching someone drink a little too much. The stage is set in a hidden venue where five classically-trained actors meet as members of "The Drunk Shakespeare Society". After one performer downs 5 shots of liquor, they attempt to perform a major role in a Shakespearean play.
Explore the Mag Mile this holiday for shopping and holiday cheer! The official lighting will take place Friday, November 19, to kick-off the season.
click here for more information
Explore the Mag Mile this holiday for shopping and holiday cheer! The official lighting will take place Friday, November 19, to kick-off the season.
click here for more information
We've discovered that overindulgence and the holiday season go hand in hand – especially with a cup of hot cocoa in hand. To celebrate this finding, make your way to BomboBar for a salted caramel bomboloni and rotating hot chocolate, you never know what you're gonna get.
Where: West Loop Window: 832 W Randolph, Chicago IL, 60607
We've discovered that overindulgence and the holiday season go hand in hand – especially with a cup of hot cocoa in hand. To celebrate this finding, make your way to BomboBar for a salted caramel bomboloni and rotating hot chocolate, you never know what you're gonna get.
Where: West Loop Window: 832 W Randolph, Chicago IL, 60607
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Looking for an escape from the Chicago cold? Experience the rejuvenating powers of beer! PIVA Beer Spa offers an incredible assortment of spa treatments including beer soaks, massages, and a relaxation room + we have a special discount for the Bucket Listers community.
But you can check this event instead:
Looking for an escape from the Chicago cold? Experience the rejuvenating powers of beer! PIVA Beer Spa offers an incredible assortment of spa treatments including beer soaks, massages, and a relaxation room + we have a special discount for the Bucket Listers community.
Go on a whirl through the park with views of the Chicago skyline lighting the path in front of you. Great for family fun or a date night!
When: Opens Friday Novemeber 19th
Where: 337 E Randolph St, Chicago, IL 60601
Go on a whirl through the park with views of the Chicago skyline lighting the path in front of you. Great for family fun or a date night!
When: Opens Friday Novemeber 19th
Where: 337 E Randolph St, Chicago, IL 60601
Chicago has a plethora of tree farms outside the city if you're into making a short day trip to cut down your own tree. You and your loved ones can choose from 8 varieties of tree saplings at Ben’s Christmas Tree Farm, then retire to the Warming Barn with a cup of complimentary hot chocolate with your spoils.
Where: 7719 Ryan Road, Harvard, IL 60033 (Ben's flagship farm)
Chicago has a plethora of tree farms outside the city if you're into making a short day trip to cut down your own tree. You and your loved ones can choose from 8 varieties of tree saplings at Ben’s Christmas Tree Farm, then retire to the Warming Barn with a cup of complimentary hot chocolate with your spoils.
Where: 7719 Ryan Road, Harvard, IL 60033 (Ben's flagship farm)
One of Chicago’s most unique holiday traditions, the CTA Holiday Train and CTA Holiday Bus can be found at various times usually starting in early Decemeber.
Upcoming 2021 Train Schedule...
One of Chicago’s most unique holiday traditions, the CTA Holiday Train and CTA Holiday Bus can be found at various times usually starting in early Decemeber.
Upcoming 2021 Train Schedule...
The ghost of breadsticks past, pizza present, and of brunching future are all at Paradise Park - and they're asking for you. One of our favorite restaurants is getting all dressed up in holiday cheer.
Where: 1913 W North Ave, Chicago, IL 60622
The ghost of breadsticks past, pizza present, and of brunching future are all at Paradise Park - and they're asking for you. One of our favorite restaurants is getting all dressed up in holiday cheer.
Where: 1913 W North Ave, Chicago, IL 60622
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The enchanting, after-dark, illuminated trail created just for the Garden will include an all-new path filled with favorite artistic installations, like the Winter Cathedral, along with new and reimagined pieces. Attendees are encouraged to purchase tickets early to secure their preferred date.
When: Opening November 12th
Where: 1000 Lake Cook Rd, Glencoe, IL 60022
The enchanting, after-dark, illuminated trail created just for the Garden will include an all-new path filled with favorite artistic installations, like the Winter Cathedral, along with new and reimagined pieces. Attendees are encouraged to purchase tickets early to secure their preferred date.
When: Opening November 12th
Where: 1000 Lake Cook Rd, Glencoe, IL 60022
Back and bigger than ever for 2021, Let It Shine returns to Northbrook Court on November 5th along with two new locations at Fox Valley Mall in Aurora and at Wintrust Field in Schaumburg on November 12th.
Where:
- Northbrook Court Mall - 1515 Lake Cook Road Northbrook, IL 60062
- Fox Valley Mall - 195 Fox Valley Center Dr, Aurora, IL 60504
- Wintrust Field - 1999 S Springinsguth Rd, Schaumburg, IL 60193
When:
Northbrook: November 5th - January 9th
Aurora & Schaumburg: November 12th - January 9th
Back and bigger than ever for 2021, Let It Shine returns to Northbrook Court on November 5th along with two new locations at Fox Valley Mall in Aurora and at Wintrust Field in Schaumburg on November 12th.
Where:
- Northbrook Court Mall - 1515 Lake Cook Road Northbrook, IL 60062
- Fox Valley Mall - 195 Fox Valley Center Dr, Aurora, IL 60504
- Wintrust Field - 1999 S Springinsguth Rd, Schaumburg, IL 60193
When:
Northbrook: November 5th - January 9th
Aurora & Schaumburg: November 12th - January 9th
Volunteering is one of the most rewarding and vital things you can do during the holidays. Help the Chicago Food Bank provide meals to those in need by donating items or volunteering time at one of their various locations.
Where: 4100 W Ann Lurie Pl, Chicago, IL 60632
Volunteering is one of the most rewarding and vital things you can do during the holidays. Help the Chicago Food Bank provide meals to those in need by donating items or volunteering time at one of their various locations.
Where: 4100 W Ann Lurie Pl, Chicago, IL 60632
Looking for snow tubing near Chicago? Get ready to spend your Saturday night (or afternoon) on an adventure! Hop on the Chicago Snow Tubing & Brewery Bus and enjoy a 2-hour night snow tubing session at Wilmot Mountain followed by a visit to a local brewery with dinner and round-trip transportation from Chicago included.
When: Trips run most Saturdays all winter long starting early January
But you can check this event instead:
Looking for snow tubing near Chicago? Get ready to spend your Saturday night (or afternoon) on an adventure! Hop on the Chicago Snow Tubing & Brewery Bus and enjoy a 2-hour night snow tubing session at Wilmot Mountain followed by a visit to a local brewery with dinner and round-trip transportation from Chicago included.
When: Trips run most Saturdays all winter long starting early January
Drive-in theaters of the past are making a resurgence. Take your car to the cinema this season to get your fix of holiday classics like "Elf" and the (Chicago classic) "Home Alone", from the toasty comfort of your car.
Where: 2343 S. Throop Street, Chicago, IL 60608
Drive-in theaters of the past are making a resurgence. Take your car to the cinema this season to get your fix of holiday classics like "Elf" and the (Chicago classic) "Home Alone", from the toasty comfort of your car.
Where: 2343 S. Throop Street, Chicago, IL 60608
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