Chicago is stunning to visit during November and December because the city is filled with decorated Christmas trees, stunning lights, and a whole lot of Christmas Cheer! Below is my list of seasonal things to do in Chicago during the most wonderful time of the year!



1. Visit 'The Big Bean' & ice skate at Millennium Park

The McCormick Tribune ice rink is a MUST to visit in the winter. Located in the heart of downtown Chicago, the rink overlooks the downtown city skyline and has a magnificent view of "The Bean." During the holidays, The Bean reflects the holiday lights of the very large Christmas tree in the park and the rink gleams from the green and red Christmas lights!

Admission to the skate park is free and skate rentals are available for $13 on weekdays and $15 on weekends and holidays!


Traveler Tip: Every year the Ice Rink is greeted with hundreds of thousands of skaters, I would recommend going during the offseason to avoid large crowds and lines.


2. Explore Macy's

This National Historic Landmark is listed on the National Register of Historic Places and is truly a sight to see. From the ordinate Tiffany ceilings installed in 1907 to the first restaurant to ever open in a department store - The Walnut Room, Macy's State Street is a popular destination for Chicagoans and tourists alike.

During Thanksgiving, Macy's opens its doors to Black Friday shoppers quite early on Thanksgiving Day and offers deals that you just cannot beat! ( I bought one of my best winter jackets by Columbia for a steal!)

If you are interested in visiting the iconic restaurant - The Walnut Room, I recommend you make reservations prior to your visit to Chicago as it can get very busy and the wait time can span from 30 minutes to an hour and a half plus!

3. Watch a Christmas Play at the Chicago Theater

Get into the Christmas spirit by watching a Christmas Classic! Chicago is known for its plays & musicals and specifically during this festive time. Dr. Seuss' How The Grinch Stole Christmas Musical will make your heart grow a few sizes when watching this holiday tale come to life on stage! A definite show that will spark some joy and have you walking out with a bit of holiday cheer!


4. Visit the German Christmas Market - The Christkindlmarket

This German Christmas Market is a beloved Chicago tradition during this time of year! It has grown into the largest Christmas market in the U.S and is based off the Nuremberg Christmas Market in Germany (the largest in the world)!

Enjoy perusing through the market with a cup of hot chocolate or Glühwein (a German Christmas Market favorite) and stop by all the little stores filled with ornaments, crafts, food, and drinks!

This market was truly my favorite part about being in Chicago, I would definitely recommend you take a peek if given the chance!

The market runs from November 15th - December 24th.






5. Enjoy the View from the Navy Pier

The Navy Pier is one of the most visited attractions in Chicago and is located on the shoreline of Lake Michigan. This attraction is comprised of over 50 acres of parks, indoor gardens, touristic shops, cute restaurants and bars, and family attractions. Additionally, the view of the city skyline from the Navy Pier is breathtaking! The Navy Pier is open year-round however general operating hours and admission to the family attractions may vary depending on the seasons and holidays! Seeing as I visited the city during Thanksgiving week, the pier was open to the general public however the family attractions like the Centennial Wheel were not running. I would recommend checking the website beforehand if you have children or would like to take part in the attractions.


6. Magnificent Mile Lights Festival & Tree Lighting

Depending on how early you visit the city, you may be able to view the Magnificent Mile Lights Festival which is a magical event filled with Christmas music, parades, and many, many lights!


The tree-lighting parade steps off at Oak Street and North Michigan Avenue on Saturday, November 21 at 5:00 PM, heading south across the Chicago River to Wacker Drive this year.

The Magnificent Mile Lights Festival returns in 2020, starting at Lights Festival Lane at 4:00 PM on Friday, November 20, and then again at 11:00 AM on Saturday, November 21.


If you will not be able to view the parade, that is totally okay as the Magnificent Mile is lined from beginning to end with beautiful lights in the trees. Enjoy walking through the stores on the Magnificent Mile getting a head start on your Christmas list or even shopping for yourself (because you deserve it!)


7. You've Got to Try Stan's Donuts

Stan's Donuts is a Chicago delicacy! I am not much of a donut person, but I decided to give them a try after seeing so many people eating their donuts around the city... and I must say, I was not disappointed! These donuts were quite possibly the best donuts I have ever had and will definitely have them again once I am back! As first-timers, we had to try their 'Dough Boy's Best'- the Biscoff Banana Pocket (which is the donut pictured) and a couple of other seasonal favorites! I have never had such fresh and delicious flavors in a donut before in my life!!







Overall, Chicago is a beautiful city full of really awesome things to do! Although this is not an extensive list of everything there is to do in the city, these were a few of my seasonal favorites that made me get into the Christmas Spirit!


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