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Chicago's Ultimate 2020 Winter Bucket List

By Chicago Bucket List

Chicago winters might be icy, but the holiday season is far from frozen πŸŽΆπŸŽ„πŸ»

Published November 12, 2020

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 COVID-safe winter activities – with heated patios, snow-scapades and chocolate delights to enjoy through the end of 2020. 

Note: Beginning Monday, November 16th Chicago has ordered a stay at home advisory. To ensure safe and social distant exploring, please check with each venue to see if they are open before crossing off your bucket list. Updates to Chicago-wide COVID guidelines and restrictions can be found here.

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. This year’s reservations are required to keep skaters socially distant—but this also means no lines, wait or crowds! Sessions are $5 with your own skates, with skate rentals available for $16. 

When: Mon.– Thurs.: 12:30 – 2:00 pm, 2:45 – 4:15pm, 5:00-6:30pm, 7:15 – 8:45pm. Fri. – Sun.: 11:00am-12:30pm, 1:15-2:45pm, 3:30-5:00pm, 5:45-7:15pm, 8:00-9:30pm.
Where: 337 E Randolph St, Chicago, IL 60601

For more information. 

Jack Frost Winter Walk Pop-Up & Christmas Tree Farm

Like the rest of the world, Jack’s is reimagined for 2020, with the health and safety top of mind. Jack's Winter Walk & Christmas Tree Farm Pop-Up is 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.

Where: 1467 North Elston Avenue Chicago, IL 60642
When: Runing through January 10th

For more information.

ZooLights At Lincoln Park Zoo

The time has finally come to get in the holiday spirit by means of 2.5 million LED lights! Enjoy a stroll through the zoo with a Bing Crosby soundtrack and hot toddie in hand. We assure you, it's the hap, happiest seaaaason of all. Due to the financial hardship of the pandemic, the Zoo will be requiring $5 tickets in order to provide the show this year, but with five free nights for Chicagonians in a show of good faith. 

When: November 21–January 3, 4–10 p.m.
Where: 2001 N Clark St, Chicago, IL 60614

For more information.

Holiday Movies at Chi Town Drive In 

Drive-in theaters of the past are making a resurgence, with social distancing and safety measures at the forefront of the fun. Drive in this season to get your fix of holiday classics like Elf and the (Chicago classic) Home Alone, from the toasty comfort of your car. You can follow @ChicagoBucketList for weekly movie schedule updates. 

Where: 2343 S. Throop Street, Chicago, IL 60608

For more information.

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. You can even get BomboBar delivered this holiday season on DoorDash & Caviar. *insert whipped cream, cookie sandwiches, waffle cones, brownies* 

West Loop Window: Tues. - Fri.: 11:30am - 11pm, Sat - Sun: 10:00am - 11pm
River North Pop-Up: Fri: 12pm-10pm, Sat: 10am-10pm, Sun: 10am - 9pm

Where: West Loop Window: 832 W Randolph, Chicago IL, 60607 | River North Pop-Up: 355 N Clark St, Chicago IL, 60654

For more information.

Miracle On Madison Holiday Drive-In

Prepare your sleighs, or cars rather, because a holiday drive-in movie extravaganza is setting up shop in Santa's Village Downtown Chicago. With characters ranging from elves and the Grinch to Santa and Mrs. Claus, transport yourself to the North Pole. 

Where: 645 W Madison, Chicago, IL
When: December 3rd through December 17th.
Monday-Friday: 6PM-9:30PM
Saturday-Sunday: 4:30PM-10:30PM

For More Inforrmation.

Frosty's Christmas Hotel


Pack your finest ugly Christmas sweater because Frosty's bar is being transformed into "Frosty's A Christmas HOTEL" this year! The seasonal pop up is taking over hotel space just steps away from downtown Chicago. Reserve your room now for a suite getaway.

When: November 25th Grand Opening
Where: 809 W Evergreen Ave, Chicago, IL 60622

For more information.

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

According to Feeding America, more than 54 million people may experience food insecurity in 2020, including a potential 18 million children, due to the effects of the pandemic. 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 or volunteering at one of their various locations.

Where: 4100 W Ann Lurie Pl, Chicago, IL 60632

For more information.


Experience North Shore’s largest Drive-Thru Light Show 

Let It Shine is proud to present North Shore’s largest drive thru world of lights at Northbrook Court! Guests are invited to stay safely in their cars as they cruise through dazzling archways, sparkling candy canes, glowing snowmen and more illuminated installations.

When: Open Nov 15th - Jan 9th; on weekdays from 4:30 PM -10 PM and 4:30 - 11:00 PM on weekends.
Where: 1515 Lake Cook Road Northbrook, IL 60062
GA: Enter on the south west side of the mall (adjacent to Corner Bakery and AMC Theatres).
Fast Pass will enter on the north side of the mall (directly across from Crate & Barrel).

For more information.

Lightscape At Chicago Botanic Garden

Returning for a second year, Lightscape is the Chicago Botanic Garden's winter wonderland. Though the event is now sold out, if you were one of the lucky few to snag tickets, you’ll be able to explore the tunnel of light and avenues of luminous trees.

When: November 13, 2020 – January 3, 2021 (select dates) & 4:30 – 10 p.m. / 4:30 – 11 p.m. select Fridays & Saturdays
Where: 1000 Lake Cook Rd, Glencoe, IL 60022

For more information.

Cozy Up Outside At The Violet Hour 


Hidden behind a mural in Wicker Park, The Violet Hour will place you into an Alice in Wonderland dream. In the style of New Orleans “Coffee Houses” from the 19th Century, the concealed bar has moved out from their cozy salons to the outdoors. Cozy up with a cocktail made by some of the best mixologists in the city. With COVID-19 restrictions in place, you’ll need to make patio reservations in advance. Plus, they’re now offering virtual mixology classes and signature cocktails to go!

Be sure to bookmark our favorite speakeasies for when indoor dining reopens!

Where: 1520 N Damen Ave, Chicago, IL 60622

For more information. 

Après All Day At Paradise Park Patio

The ghost of breadsticks past, pizza present, and of brunching future are all at Paradise Park - and they're asking for you. Our favorite restaurant is getting all dressed up in holiday cheer. Throw on your ski gear and come party with them every Sunday from 10:30am-1:30pm! $25 Bottomless Mimosas when you wear your best Après Ski attire.

When: Open daily from 10:30 AM to 10 PM
Where: 1913 W North Ave, Chicago, IL 60622

For more information.

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

For more information.

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

Chicago has a plethora of tree farms nearby to make a short day trip out 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. Unfortunately though, wagon rides will not be offered for the 2020 season.

When: Open Friday-Sun 9:00 AM - 4:30 PM 
Where: 7719 Ryan Road, Harvard, IL 60033 (Ben's flagship farm)

For more information. 


Magnificent Mile Lights Festival

Although there will not be a live parade this year, ABC 7 is still turning on the Christmas lights! Tune in for an hour of exciting performances, Disney surprises, and magical moments capped off with the thrilling illumination of trees that line Chicago’s Magnificent Mile. 

Where: ABC 7 
When: Sunday, November 22, 6-7 PM

For more information.

Christmas Around the World at the Museum of Science & Industry

[11/23/20 Update: The Museum is currently closed.] As it has since 1942, MSI is bringing a world of holiday displays to one immersive space with Christmas Around the World + Holidays of Light! The annual celebration features a four-story, floor-to-dome Grand Tree, surrounded by a dazzling forest of 40 trees and displays based on holiday traditions around the globe. 

Additionally, this year you can enjoy the spectacle with the hygienic space you need. Expect daily attendance limits and timed tickets for fast, contactless entry and reduced crowds. 

Where: 5700 S Lake Shore Drive Chicago IL 
When: November 13, 2020 - January 3, 2021.

For more information.

Go Ice Skating & Find the Perfect Gift at the Fashion Outlets of Chicago

Fashion Outlets of Chicago transformed once again into a winter wonderland for the holiday season. With 130+ designer outlets up to 75% off, you can cross everyone from your brother and your boss to your dog and dog...walker(?) off your shopping list. Remember to wear your mask and maintain 6 feet of distance from other shoppers! (Or, enjoy they’re newly provided contactless shopping options)

Across the street lies Rosemont’s Parkway Bank Park Entertainment District, with excellent dining options—including the reopened King’s Dining & Entertainment. Fingers crossed we’ll also see the return of the NHL sized ice rink for “Skating in the Park.”

Where: 5220 Fashion Outlets Way Rosemont, IL 60018
When: Open Mon-Sat from 10 AM - 9 PM; and Sundays until 7 PM

For more information.


Shop The Christkindlmarket In Daley Plaza from Home

We wish we could enjoy the german market in its usual snowy, crowded glory—but this year for the first time ever you’ll be able to shop the 47 Christkindlmarket vendors all online! Surf the authentic german gems with a cup of hot mulled wine and warm pretzels to complete the experience. 

When: November 1st – December 31st

For more information.


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