Chicago's Ultimate 2021 Winter Bucket List
Chicago's Ultimate 2021 Winter Bucket List

Chicago's Ultimate 2021 Winter Bucket List

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.

 

Visit Frosty's Christmas Bar

Frosty’s Bar is back for the 2021 Holiday season better than ever! They have decked the halls across 4 Bar, 3 Levels & 2 Dance Floors + Dancing Elves, Singing Santa, Live Nutcrackers & the party doesn’t end until 4AM! Add in Sensational Seasonal Cocktails, Wonderfully interactive Holiday Photo Experiences, Lights & Music and you have a Holiday Bar experience that will knock your Christmas stockings off.

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Watch Holiday Movies at Chi Town Drive In

Watch Holiday Movies at Chi Town Drive In

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

location_on ChiTown Futbol, CHI

ChiTown Drive-In New Movies Announced

$33 $25 24% OFF
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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

Venture to this Alice In Wonderland Themed Bar

Venture to this Alice In Wonderland Themed Bar
You don't want to be late to this epic Alice In Wonderland themed cocktail adventure! Come along on a 90 minute topsy-turvy journey into the magical realm of Wonderland. For those both curious and curiouser – this will be the tea party to end all tea parties.
 
When: Opening January 2022
You don't want to be late to this epic Alice In Wonderland themed cocktail adventure! Come along on a 90 minute topsy-turvy journey into the magical realm of Wonderland. For those both curious and curiouser – this will be the tea party to end all tea parties.
 
When: Opening January 2022

Watch Drunk Shakespeare

Watch Drunk Shakespeare

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.

 

location_on The Lion Theatre, CHI

Drunk Shakespeare Experience

From$39 $25 36% off
book

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.

 

Escape The Cold At Chicago's First Ever Beer Spa

Escape The Cold At Chicago's First Ever Beer Spa

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.

 

location_on Piva Beer Spa, CHI

Piva Beer Spa

From$155 $135 13% off
book

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.

 

Take a Chicago Snow Tubing & Brewery Day Trip

Take a Chicago Snow Tubing & Brewery Day Trip

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 

location_on Wilmot Mountain, CHI

Chicago Snow Tubing & Brewery

$149
Get tickets now

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 

Head to the Let It Shine Drive-Thru Light Shows

Head to the Let It Shine Drive-Thru Light Shows

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 

click here for more information

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 

click here for more information

Take a stroll around Lightscape At Chicago Botanic Garden

Take a stroll around Lightscape At Chicago Botanic Garden

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

click here for more information

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

click here for more information

Après All Day At Paradise Park

Après All Day At Paradise Park

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

click here for more information

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

click here for more information

Ride the CTA Holiday Train

Ride the CTA Holiday Train

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...

  • Friday, November 26: Green Line and Orange Line from about 3pm to about 7 pm
  • Saturday, November 27Green Line from about 2pm to about 4:30pm
  • Tuesday, November 30: Orange Line and Green Line from about 4pm to about 8:30pm
  • Wednesday, December 1: Orange Line and Brown Line from about 3pm to about 6pm
  • Thursday, December 2: Orange Line and Brown Line from about 3:45pm to about 6:45pm
  • Friday, December 3: Orange Line and Brown Line from about 3pm to about 6pm
  • Saturday, December 4: Orange Line and Brown Line from about 12:45pm to about 5pm
  • Sunday, December 5: special Loop run from 11am to 2pm
  • Tuesday, December 7: Red Line from about 2:30pm to about 5:30pm
  • Wednesday, December 8:  Purple Line from about 3pm to about 6:15pm
  • Thursday, December 9: Red Line from about 3pm to about 6pm
  • Friday, December 10: Purple Line from about 3:45pm to about 6:45pm
  • Saturday, December 11:  Red Line and Purple Line from about 4pm to about 7pm
  • Sunday, December 12: a special Loop run from 11am to 2pm
  • Tuesday, December 14: Pink Line from about 2:30pm to about 5:30pm
  • Wednesday, December 15: Pink Line from about 3pm to about 6pm
  • Thursday, December 16: Blue Line from about 3pm to about 6:15pm
  • Friday, December 17: Blue Line from about 4pm to about 7:15pm
  • Saturday, December 18: Blue Line from about 4pm to about 6:45pm
  • Wednesday, December 22Yellow Line from about 3pm to about 7pm
click here for more information

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...

  • Friday, November 26: Green Line and Orange Line from about 3pm to about 7 pm
  • Saturday, November 27Green Line from about 2pm to about 4:30pm
  • Tuesday, November 30: Orange Line and Green Line from about 4pm to about 8:30pm
  • Wednesday, December 1: Orange Line and Brown Line from about 3pm to about 6pm
  • Thursday, December 2: Orange Line and Brown Line from about 3:45pm to about 6:45pm
  • Friday, December 3: Orange Line and Brown Line from about 3pm to about 6pm
  • Saturday, December 4: Orange Line and Brown Line from about 12:45pm to about 5pm
  • Sunday, December 5: special Loop run from 11am to 2pm
  • Tuesday, December 7: Red Line from about 2:30pm to about 5:30pm
  • Wednesday, December 8:  Purple Line from about 3pm to about 6:15pm
  • Thursday, December 9: Red Line from about 3pm to about 6pm
  • Friday, December 10: Purple Line from about 3:45pm to about 6:45pm
  • Saturday, December 11:  Red Line and Purple Line from about 4pm to about 7pm
  • Sunday, December 12: a special Loop run from 11am to 2pm
  • Tuesday, December 14: Pink Line from about 2:30pm to about 5:30pm
  • Wednesday, December 15: Pink Line from about 3pm to about 6pm
  • Thursday, December 16: Blue Line from about 3pm to about 6:15pm
  • Friday, December 17: Blue Line from about 4pm to about 7:15pm
  • Saturday, December 18: Blue Line from about 4pm to about 6:45pm
  • Wednesday, December 22Yellow Line from about 3pm to about 7pm
click here for more information

Chop your own Christmas Tree at a farm like Ben’s Christmas Tree Farm

Chop your own Christmas Tree at a farm like Ben’s Christmas Tree 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)

click here for more information

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)

click here for more information

Sip A Cocktail With Sweeping Views Of Chicago At J.Parker

Sip A Cocktail With Sweeping Views Of Chicago At J.Parker

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

click here for more information

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

click here for more information

Volunteer Or Donate To The Greater Chicago Food Depository's Food Drive

Volunteer Or Donate To The Greater Chicago Food Depository's Food Drive

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

click here for more information

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

click here for more information

Sip Hot Chocolate From BomboBar

Sip Hot Chocolate From BomboBar

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

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

click here for more information

See the Magnificent Mile Lights Festival

See the Magnificent Mile Lights Festival

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

Explore Amaze Light Festival

Explore Amaze Light Festival

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

click here for more information

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

click here for more information

Shop The Christkindlmarket In Daley Plaza

Shop The Christkindlmarket In Daley Plaza

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

click here for more information

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

click here for more information

Go to Jack Frost Winter Walk Pop-Up

Go to Jack Frost Winter Walk Pop-Up

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

click here for more information

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

click here for more information

Go Ice Skating At Maggie Daley Skating Ribbon

Go Ice Skating At Maggie Daley Skating Ribbon

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

click here for more information

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

click here for more information

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