Holiday Rex: The Ultimate Chicago Holiday Bucket List
Updated February 4, 2020
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Let it Snow
The Holiday season is a festive (and for many, a favorite) time of year. People are instantly in more cheerful moods when they get to enjoy the winter festivities and events with their friends. Lucky for us, Chicago doesn’t take Christmas lightly and goes all out decorating the city with lights, reindeer, hot cocoa, and showing holiday movies for all to enjoy.
Chicago Rex has compiled a list of Holiday Rex with 20 activities and events that you can do with friends and/or family!
For Friends and Family
We want to make sure everyone in your family can have a good time getting into the holiday spirit despite their age. Here are 10 recommendations we have for you to start planning your holiday season.
Date: Thursday, November 14th at 9:30 am
Location: 5700 S Lake Shore Dr.
Chicago, IL 60637
Held at the Museum of Science and Industry started in 1942, has 50 trees that are decorated to represent different cultures around the world.
Date: Begins Friday, November 15th at 12:00pm through March 8th, 2020 with weather permitting.
Location: 11 Michigan Ave
Chicago, IL 60602
Skate by the Bean in the heart of the city! Admission is free for all skaters. If you don’t have skates, you can rent them for $13 during the week and $15 on the weekend.
Date: Begins November 15th at 10:00 am
Location: 337 E Randolph
Chicago, IL 60601
The skating ribbon at Maggie Daley has one of the most scenic views because you can see the skyline while skating. Admission is free for all skaters. If you don’t have skates, you can rent them for $13 during the week and $15 on the weekend. Be sure to grab a cup of hot chocolate too!
Date: Open November 15th at 11:00 am through December 24th at 4:00 pm.
Location: 50 W Washington St
Chicago, IL 60602
Attracting 1 million people per year is an admission-free, German-style experience that hosts vendors’ from across the world. Enjoy amazing food, drinks, and outdoor performances. It’s everyone’s favorite holiday tradition in Chicago.
Date: Friday, November 22nd at 6:00 pm.
Location: 201 E Randolph St
Chicago, IL 60602
There’s no better way to kick off the Christmas season than by watching the lighting of the Chicago Christmas tree. Get the whole family in the holiday sprit by joining other Chicagoans!
Date: Friday, November 22nd at 11:00 am to December 31st at 9:00 pm.
Location: 3635 N Clark St.
Chicago, IL 60613
The second location in the city is in Christkindlmarket is located in Wrigley at Gallagher Way. This is an admission-free, German-style experience that hosts vendors’ from across the world. Enjoy amazing food, drinks, and outdoor performances. It’s everyone’s favorite holiday tradition in Chicago.
Dates: The lights will begin running Friday’s-Sunday’s from 4:30 pm-9:00 pm starting November 25th-27th and December 2nd-4th. Then, December 9th-January 1st (excluding the 24th and 25th).
Location: 2001 N Clark St
Chicago, IL 60614
One of the best and most favorite holiday lights display is located at the Lincoln Park Zoo. Also, on Sunday from 9:00 am-noon on December 15th, kids can eat breakfast with Santa and do holiday cookie decorating!
Date: Monday, December 2nd at 6:00 pm
Location: 3635 N Clark St.
Chicago, IL 60613
Another beautiful tree lighting ceremony hosted in Wrigley that can bring the whole family together to get into the Christmas spirit!
Date: Saturday, November 23rd from 2:00pm-7:00pm
Location: 401 N Wabash Ave
Chicago, IL 60611
Calling Dasher and Dancer and Prancer! A fun holiday event for families to play games, reindeer, music, prizes, cider, cocoa, and sweet treats!
Date: Opens Friday, December 6th at 10:00 am
Location: 600 E Grand Ave
Chicago, IL 60611
170,000 square feet of holiday festivities that include indoor ice skating, a carousel, inflatable rides, and special performances for everyone!
For Adults 21+
At Chicago Rex, we also understand the importance of having an adult night out so we’ve come up with a list of 10 boozy things for you to do to relieve all the stresses of the holidays! Whether you want to watch seasonal movies, drink some festive and Instagram worthy hot chocolate or specialty drinks, you’ve got unlimited options this season!
Dates: Open all year, Sunday through Friday from 9:00 am to 11:00 pm.
Location: 832 W Randolph St.
Chicago, IL 60607
Open all year long, BomboBar has the most exotic and prettiest hot chocolate and donuts, which is perfect to try for the colder weather.
Date: Opens Wednesday, November 20th at 9:00 am
Location: 3505 N Clark St
Chicago, IL 60657
DJ’s on the main and top floor, Christmas cocktails, and holiday decorations like you've never seen before! Santa Baby Bar has free admission before 11:00 pm, after that you’ll have to pay a cover. Frozen shots and shotskis, mistletoe margarita, jingle juice, colossal cocoa? I think, yes!
Date: Begins Friday, November 22nd at 5:00 pm.
Location: 1535 N Wells St.
Chicago, IL 60610
Get in the Christmas sprit with cocktails and food menu curated to the holiday spirit!
Date: Opens Monday, November 23rd at 11:00 am
Location:127 W Huron at LaSalle
Chicago, IL 60654
Enjoy Godfrey’s year-long rooftop with their heated domes and fire pits and to stay extra warm, order a hot cocktail and s’ mores to roast over your fire pit yourself!
Date: Saturday, November 30th from 4:30 pm-9:30 pm
Pickup Location: 546 N Wells St
Chicago, IL 60654
Before the bus takes off, you can enjoy complimentary apps and drink deals that are between $4 and $6 at the Ironside. Then, get on the party bus and rock out to some music and your BYOB while you drive by some of Chicago’s best Christmas light displays on the Magnificent Mile, Millennium Park, and Macy’s on State street.
Dates: Wednesdays starting December 4th from 7:00 pm to 10:00 pm until December 18th.
Location: 1367 N Milwaukee Ave
Chicago, IL 60622
Whiskey Business is playing some of everyone’s favorite Christmas movies this year!
12/4: Nightmare Before Christmas
12/11: Elf
12/25: Four Christmases
Date: Thursday, December 5th from 6:30 pm-10:00 pm
Location: 2001 N Clark St
Chicago, IL 60614
Who wouldn’t want to take a walk and enjoy the animals and the lights with wine and beer?
Date: Thursday’s starting December 5th through December 26th from 6:00-9:00 pm
3635 N Clark St.
Chicago, IL 60613
A perfect date night spot for cuffing season! Snuggle up with blankets and stay warm while watching a Christmas movie with a little booze and you guys are set.
TBOX Bar Crawls (12 Bars of Christmas)
Date: Saturday, December 14th from 9:00am-7:00pm
Location: 3647 N Clark St
Chicago, IL 60657
If you’re looking to get sloshed one day this winter in Wrigley, this bar crawl is exactly what you’re looking for. Put your best holiday pajamas or ugly sweater on for a good cause because some of the proceeds are donated to local communities in the city.
Date: Opening mid-November.
Location: 3845 N Clark St
Chicago, IL 60657
If you haven’t seen the movie Elf at least half a dozen times, you aren’t doing Christmas right! This Elf themed, a pop-up bar, has Buddy’s specialty breakfast and Christmas cocktails to help spread holiday cheer!