Top picks of Things To Do In Chicago for the 2019 Holiday Season!  

1. Christkindlmarket

Photo via facebook.com/christkindlmarket

Sipping hot mulled wine out of a boot-shaped mug is a Chicago tradition if there ever was one. This German-inspired open-air market has been bringing holiday joy to locals since 1996. Its flagship location sets up shop in Daley Plaza every winter and runs through December 24. Even if you’ve already wrapped up your holiday shopping for the season, Christkindlmarket’s food and drink options still make it a fun place to wander with someone you’re sweet on. From November 15th -December 24th.

Address: 50 W Washington St, Chicago, IL 60602, USA

Market Map

 

2. Walk The Magnificent Mile & Check Out The Macy’s Window Displays

Photo courtesy of The BMO Harris Bank Magnificent Mile Lights Festival

Chicago’s Magnificent Mile—the stretch of Michigan Avenue between
Oak Street and the Chicago River—always looks especially stunning during the holidays, with tons of lights, store window displays and carriages lining the streets. It makes for a beautiful nighttime stroll. Don’t forget to make a stop to visit the city of Chicago’s official tree—a 60-foot spruce decorated and on display.

Free, family fun culminates in the grand Tree-Lighting Parade down North Michigan Avenue with grand marshals Mickey Mouse and Minnie Mouse from Walt Disney World® 

Friday, November 22
4:00 – 8:00PM: Lights Festival Lane in Pioneer Court (401 N. Michigan Avenue) opens the evening before the parade with more than a dozen family-friendly activities from Chicago favorites and popular brands—plus live music and a visit with Santa Claus! Explore an interactive wonderland of holiday-themed activities, and sample treats from crowd favorites Garrett Popcorn, Frango, The Eli’s Cheesecake Company, and more.

Saturday, November 23

11:00AM – 4:00PM: Explore an interactive wonderland of holiday-themed activities at Lights Festival Lane in Pioneer Court (401 N. Michigan Avenue), including the BMO Harris Kid’s Zone. Santa Claus is always ready to greet guests, alongside more than a dozen holiday-themed activities.

Tree-Lighting Parade
North Michigan Avenue, from Oak Street to Wacker Drive.

The tree-lighting parade stepped off at Oak Street on Saturday, November 23, heading south on Michigan Avenue to Wacker Drive.

 Address: N Michigan Ave

 

3. Experience Holiday Lights from the sky with VertiPort.

Image via Instagram @zackkravits

For the best Chicago Holiday Experience make sure you book your helicopter tour and capture the entire view of the holiday lights that decorate the entire city.  From The Lincoln Park Zoo Lights, Navy Pier, and downtown buildings and more, you will have front seat to admire Chicago’s architecture as no other season.

Use promo code “thingstodochicago” for a discount when booking your tour.

TICKETS: BOOK YOUR FLIGHT

 

4. Attend the Thanksgiving Parade

Image via Instagram @chiparade

 

Enjoy gigantic balloons, the nation’s finest marching bands, majestic horses, festive floats, incredible performance groups, celebrities, and an appearance from Santa Claus! The parade starts at 8:00am Thanksgiving morning, Thursday, November 28 on State Street in downtown Chicago. Individual Sponsorships for the VIP Experience are available at www.chicagothanksgivingparade. Can’t make it down to State Street? Enjoy #ChiParade at home by watching the live broadcast on WGN 9 Chicago or WGN America.

5. Enjoy Christmas Carol at the Goodman Theater.

Photo Via Facebook.com/goodmantheatre

The story of A Christmas Carol is a classic in any city, but the Goodman’s production is a longstanding favorite and 41 years into its annual run.

 

Address From: 170 N Dearborn St, Chicago, IL 60601, USA

From Nov 16 to Dec 29

Click to Buy Tickets

 

6. ZooLightsAt The Lincoln Park Zoo

Photo Via Facebook.com/lincolnparkzoo

We’re always down to hit up Lincoln Park Zoo and hang with snow monkeys and sloths and penguins, but what about when they’re illuminated by 2.5 million holiday lights?! It’s even better. Plus, there are family-friendly activities scheduled throughout the month (and adult beverages for sale, too).

Address: 2001 N Clark St, Chicago, IL 60614, USA

4:30–9 p.m.
November: 29, 30
December: 1, 6, 7, 8, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 26, 27, 28, 29, 30, 31*
January: 1, 2, 3, 4, 5
(Early closure of 8 p.m. on December 31 for Zoo Year’s Eve)

7. Experience The Tree Lights at The Morton Arboretum

Photo Via Facebook.com/mortonarboretum

The Morton Arboretum’s annual tree lighting display, “Illumination,” projects beautiful hues onto the mile-long walking stretch through January 1st. Wintry activities like marshmallow roasting also abound here.

Address: 4100 IL-53, Lisle, IL 60532, EE. UU.

Admission

  • Happy Thanksgiving – Free Admission.
  • Adults ages 18–64, $15 ($10 Wednesdays*)
  • Seniors 65, +$13 ($9 Wednesdays*)
  • Children ages 2–17, $10 ($7 Wednesdays*)
  • Children 1 and younger are free

*Wednesdays are discount admission!

Admission includes FREE parking. Members always enter for free with valid membership credentials.

Upcoming  Events and Tickets

8. Take a Trolley Tour

Photo Via Facebook.com/chicagotrolley

Walking is great and all, but let’s not forget that December is kind of cold. Stay warm(er) with the Chicago Trolley & Double Decker Co.’s holiday lights tours—bussing you to all of the best displays.

Tours start 11/29/2018. Private rentals are also available. Pre-sale tickets are available only at www.ChicagoTrolley.com. Limited tickets will be available on the day of the tour.

9. Go Ice Skating At Millennium Park

Photo via instagram.com/barrybutler9

The McCormick Tribune Ice Rink is one of the most picturesque rinks in the city, surrounded by twinkling skyscrapers and nestled under The Bean. Let’s not forget that admission is also free! (However, skate rentals do cost between $13 and $15.) Thanks to the Maggie Daley Park Skating Ribbon, you now have another ice skating option nearby if your tradition needs a slight changeup.

November 15, 2019—March 8, 2020

Address:201 E Randolph St, Chicago, IL 60602, EE. UU.

Admission: Skating is FREE and open to the public

Skate Rentals & Sharpening:

Toddler 8 to Adult 13 available

  • $13 Skate Rental Monday–Thursday
  • $15 Skate Rental Friday–Sunday and Holidays listed below
  • $10 Skate Aid Rental (for new skaters under 42 inches tall)
  • $9 Skate Sharpening

Coin-operated locker rentals are available for $1 (4 quarters).

Regular Hours (weather permitting):

  • Mondays–Thursdays, noon–8pm
  • Fridays, noon–10pm (ice skating lesson at 11am)
  • Saturdays & Sundays, 10am–9pm (ice skating lesson at 9am)

Free Ice Skating Lessons:

The Winter Workouts program will offer free skating lessons for all ages and skill levels, one hour before the rink opens, on

  • Fridays, 11am
  • Saturdays & Sundays, 9am
  • Chicago Public School’s Winter Break (December 23—January 3, except December 25 and January 1), 9am
  • Martin Luther King Jr. Day (January 20), 9am
  • Presidents’ Day (February 17), 9am

10. Watch The Joffrey Ballet’s Performance Of ‘The Nutcracker’ 

Photo Via Facebook.com/thejoffeyballet

We’ve come to expect a fresh take on old classics from the Joffrey Ballet and they continue to prove us right with the company’s production of The Nutcracker, retold with a Chicago twist.  

Journey to Chicago’s 1893 World’s Fair with Wheeldon’s holiday masterpiece. Magic is on the horizon for young Marie and her mother, a sculptress creating the iconic Statue of the Republic. As they prepare for their annual holiday celebration, a visit from the charming but mysterious Great Impresario sets off a Christmas Eve dream of whirlwind romance and adventure. Wheeldon’s Nutcracker is a must-see tradition boldly reimagined for a new generation.

November 30 – December 29, 2018

Click To Buy Tickets

11. Caroling At Cloud Gate

Photo via cityofchicago.org

Bundle up and belt out some holiday classics as local Chicago choral groups lead hundreds of celebrants in song.

Schedule: 

Fridays, November 29, December 6, 13, 20
Free Admission • 6–7pm

    • November 29 – Sounds Good! Choir
    • December 6 – Mark Hubbard and The Voices
    • December 13 – Chicago Children’s Choir
    • December 20 – Wicker Park Choral Singers

Address: 201 E Randolph St, Chicago, IL 60602, EE. UU.

12. Catch the Holiday CTA Train & Bus

Image via Instagram @thelensoftruth

It’s the only time of year you’ll race to catch a certain train for reasons other than running late to work. The Chicago Transit Authority’s holiday train and bus are backed and more decked out than ever.

Train schedule

The train will travel all ‘L’ lines in late November and December as part of regular rail service. Normal CTA fares apply.

The train generally operates from about 1pm to 8pm on weekends and 3pm to 7pm on select weekdays (schedules for each rail line will vary), and will make stops at all stations along the respective routes. And every Saturday the Holiday Train is in service, the Elves’ Workshop Train will follow to allow more riders to enjoy this one of a kind holiday experience.

Here’s a look at the full schedules:

BUS:

NOTE: Schedule times are approximate

Tue 11/26

#56 Milwaukee

12:28p

NB from Madison/Wabash

Wed 11/27

#56 Milwaukee

1:15

SB from Jefferson Park Blue Line

Photo session:

Jefferson Park Blue Line

approx. 4:20p-5:20p

Fri 11/29

#22 Clark/#97 Skokie

12:38p

WB as #97 from Howard Terminal to Old Orchard

Photo session:

Old Orchard

approx: 1:35p-2:30p

2:46p

EB from Old Orchard

3:55p

SB as #22 from Howard Terminal to Harrison/Clark

Sat 11/30

#22 Clark

12:30p

SB from Howard Terminal (Red/Purple/Yellow lines)

Photo session:

Howard Terminal

approx: 4:10p-5:05p

Sun 12/1

#92 Foster and #91 Austin

12:13p

WB as #92 from Berwyn Red Line to Jefferson Park Blue line

1:05p

SB as #91 from Jefferson Park Blue Line

5:40p

EB as #92 from Jefferson Park Blue Line to Berwyn Red Line

Tue 12/3

#66 Chicago

12:04p

EB from Chicago/Austin

Photo session:

Navy Pier

approx. 4:15p-5:15p

Wed 12/4

#66 Chicago

12:24p

EB from Chicago/Austin

Thu 12/5

#126 Jackson

1:00p

EB from Jackson/Austin

Fri 12/6

#12 Roosevelt

1:40p

EB from Harrison/Central

Photo session:

Harrison/Central

approx. 4:10p-5:10p

Sat 12/7

#12 Roosevelt

1:10p

EB from Harrison/Central

Wed 12/11

#62 Archer

12:40p

SB from Kinzie/Sate

Thu 12/12

#62 Archer

1:10p

NB from Midway Orange Line

Photo session:

Midway Orange Line

approx. 4:05p-5:05p

Fri 12/13

#49 Western and #X49 Western Exp.

12:39p

NB as #49 from 79th/Western

2:30p

SB as #X49 from Berwyn/Western

5:50p

NB as #X49 from 79th/Western

7:40p

SB as #49 from Berwyn/Western

Photo session:

79th/Western

approx. 4:25p-5:40p

Sat 12/14

#79 79th

12:44p

EB from 79th/Western

1:55p

WB from 79th/Lake Front

to Ford City Mall

Photo session:

Ford City Mall

approx. 3:25p-4:25p

Wed 12/18

#3 King Drive

1:35p

SB from Ontario/Fairbanks

Photo session:

@ 95th/Chicago State U.

approx. 3:20p-4:20p

Thu 12/19

#3 King Drive

12:20p

NB from 95th/Chicago State U.

Fri 12/20

#28 Stony Island

1:10p

NB from Olive Harvey College

to 47th/Lake Park

3:08p

NB from Olive Harvey College

to Union Station

Photo session:

Union Station

approx. 4:45p-5:45p

Sat 12/21

#29 State

12:03p

NB from 95th Red Line

Photo session:

Navy Pier

approx. 4:15p-5:15p

Sun 12/22

#29 State

12:30p

NB from 95th Red Line

Mon 12/23

#J14 Jeffrey Jump

11:17a

NB from 103rd/Stony Island

TRAIN:

* = Elves’ Workshop Train to follow

Green Line & Orange Line Fri 11/29

Green Line Sat 11/30*

Green Line & Orange Line Tue 12/3

Orange Line & Brown Line Wed 12/4

Orange Line & Brown Line Thu 12/5

Orange Line & Brown Line Fri 12/6

Orange Line & Brown Line Sat 12/7*

Pink Line Tue 12/10

Pink Line Wed 12/11

Blue Line Thu 12/12

Blue Line Fri 12/13

Blue Line (+ photo-only stop on Pink Line) Sat 12/14*

Red Line Tue 12/17

Purple Line Wed 12/18

Red Line Thu 12/19

Purple Line Fri 12/20

Red Line & Purple Line Sat 12/21*

Yellow Line Skokie Swift Bird Fri 12/23

View CTA Website

 

13. Navy Pier’s Winter WonderFest

Photo via navypier.com

Navy Pier’s Festival Hall gets decked out in holiday spirit again this year. Hundreds of trees, thousands of ornaments and a full-sized ice skating rink make up this family fun zone. You can also fill the day with activities like cookie decorating, cliff hanger ride, a festive carousel, and inflatable rides.. Who knows? You might even spot Santa!

DECEMBER 6, 2019 – JANUARY 12, 2020 / FESTIVAL HAL

Packed with indoor family fun, Fifth Third Bank Winter WonderFest is a delightful family tradition featuring 170,000 square feet of attractions, including rides, giant slides, indoor ice skating, and holiday decor that is sure to get you into the holiday spirit!

Address: 600 East Grand Avenue Chicago, IL 60611

See Details | Buy Tickets

 

14. Christmas Around The World At MSI

Photo Via Facebook / Museum of Science and Industry

The Museum Of Science and Industry’s yearly holiday celebrations “Christmas Around The World” and “Holiday Of Lights” are back through
January 5th. More than 50 holiday displays representing cultures and traditions from around the globe are on display now with special performances happening every weekend!

Opening November 14, 2019

Christmas Around the World and Holidays of Light open on Thursday, November 14 and will run through Sunday, January 5, 2020.

Also you must not miss the Science behind Pixar! 

Address: 5700 S Lake Shore Dr, Chicago, IL 60637, USA

Regular Hours

Daily from 9:30 a.m. to 4 p.m. except as noted below.

Extended Hours and Exceptions

November Thursday, November 28
CLOSED
Friday, November 29 – Saturday, November 30
9:30 a.m. – 7 p.m.
December 2019 Sunday, December 1
Saturday, December 7 – Sunday, December 8
Saturday, December 14 – Sunday, December 15

9:30 a.m. – 5:30 p.m.Saturday, December 21 – Sunday, December 22
9:30 a.m. – 7 p.m.Monday, December 23
9:30 a.m. – 5:30 p.m.Tuesday, December 24
9:30 a.m. – 4 p.m.Wednesday, December 25
CLOSED
Thursday, December 26 – Monday, December 30
9:30 a.m. – 7 p.m.Tuesday, December 31
9:30 a.m. – 4 p.m.
January 2020 Wednesday, January 1
11 a.m. – 5:30 p.m.Thursday, January 2 – Friday, January 3
9:30 a.m. – 5:30 p.m.

15. Attend the “Lightscape” Debut at the Botanic Garden

 

Image via chicagobotanic.org

Spectacular New Magic for the Holidays

Wander into a festive world of wonder and light. Along a mile-long path, the night comes alive with color, imagination, and sound, from a playful choir of singing trees to a spectacular waterfall of light. At times, you’ll find yourself in the center of it all — stepping inside a cathedral of golden light, walking down an avenue of luminous linden trees, moving through colorful ribbons of light.

Exclusive U.S. Experience

Direct from London, Lightscape is making its U.S. debut at the Garden. An enchanted after-dark illuminated trail. More than one million people in 2018 were delighted by the show across the U.K.

Hours: Friday, November 22, 2019 – Sunday, January 5, 2020
4:30 – 10 p.m. (last entry at 8 p.m.)

Value:  Price is dependent on the day you choose to attend.
Adult: $17/$20
Child 3-12: $8/$10

Standard:
Adult: $21/$23
Child 3-12: $10/$12

Peak:
Adult: $23/$25
Child 3-12: $11/$13

Child under 3: free

Tickets purchased the day of the event are an additional $2 per ticket

Parking: 

$10 per car (includes tax) One time use only, no refund.
This parking is only for Lightscape ticket purchasers.

BUY TICKETS | BUY PARKING

16. Holiday-Themed Pop-up Bars – Frosty’s A Christmas Bar

Photo Via facebook.com/frostyschristmasbar

It’s all the rage! Temporary bars themed around your favorite holiday movies, stories and traditions are sprouting up all over town. Step in for spirited food, drinks and an Instagram-worthy experience. 

Limited time, 1-of-a-kind, ultimate Christmas pop-up experience! Celebrate the season w/3 levels of festive holiday fun! Book your Holiday Party now!

Adress: 809 W Evergreen Chicago, Illinois 60642

 

 

HAPPY HOLIDAYS!

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