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The Ultimate Guide to Holiday Fun in Chicago – 2019 Edition

Published on Nov 20, 2019 at 12:04 pm in Fun Stuff.

The Ultimate Guide for Holiday Fun in Chicago 2019 Edition

Winter in Chicago may be cold, but with all there is to do in the city, it’s time to bundle up! Chicago loves to celebrate, so November, December, and January are filled with traditions, festivals, and shows. There’s always something to do with family and friends.

To take advantage of everything, we’ve created a holiday guide for all there is to do in the city. Below you’ll find the best events, restaurants, shopping, and Christmas tree spots to make the most of this year’s holiday season.

Shows & Events

Holiday Festivities in Chicago

You’ll find holiday attractions, festivals, lights shows, and more all around the city this year. Deciding which events to attend can seem challenging with so much going on, so we’ve compiled a list of the most festive happenings.

  • Christmas Around the World at the Museum of Science and Industry. Explore rich holiday traditions from all over the globe at this massive display. Not only are there over 50 decorated trees to represent different cultures and celebrations, but you can attend performances on the weekends.
  • Brookfield Zoo’s Holiday Magic. Now in its 38th year, this light festival features millions of lights, a 41-foot-tall-talking tree, skating rink, ice carvers, and more. The festival runs on weekends in December.
  • Ice Skating at Millennium Park. Ice skating is provided at the McCormick Tribune Plaza Ice Rink from November through March. Free ice skating is offered each weekend.
  • Holiday Lights, City Lights. Hop aboard Big Bus Chicago to hear stores of great architects and leaders who shaped the city. There’s the added bonus of taking in the twinkling holiday lights as you ride.
  • Illumination: Tree Lights at Morton Arboretum. As you walk around this one-mile paved path, you can experience interactive lighting effects that highlight the beauty of trees in winter. Seasonal music, warm drinks, and roasted marshmallows accompany the event.
  • ZooLights at Lincoln Park Zoo. Celebrate 25 years of ZooLights at this one-of-a-kind holiday experience. Guests can enjoy seasonal activities under the glow of 2.5 million lights. This event takes place on dates throughout November, December, and January.
  • Christkindlemarket. This holiday tradition in the city offers vendors’ products from all over the world. You’ll also find German foods and beverages and performances at this outdoor market from November 15-December 24.
  • A Christmas Carol. Take part in the holiday tradition of seeing a Christmas Carol performed at Albert Theatre. Performances run November 16-December 39.
  • Magnificent Mile Lights Festival. On November 22-23, enjoy a family-friendly festival that leads up to the famous tree-lighting parade to kick off the holiday season.
  • Lightscape. From November 22-January 5, enjoy this enchanting, after-dark, illuminated trail at the Chicago Botanical Garden.
  • Krampus Fest. The 4th annual Krampus Fest takes place on December 3. Local artists, makers, bakers, and more will be featured. German-style street food and beverages will be available for sale. You can even get your picture taken with Krampus.
  • Lambs Farm Holiday Lights Gift & Craft Fair. From December 5-8, visit this annual craft show. You’ll find a variety of gifts for everyone on your list.
  • Winter WonderFest at Navy Pier. The 19th annual Winter WonderFest features 170,000 square feet of attractions, including ice skating, a carousel, inflatable rides, food, and more. This event runs from December 6-January 12, 2020.

Holiday Gifts

Best Shops for Unique Gifts in Chicago

Finding the perfect holiday gift isn’t always easy, especially for the pickier people on your list. Fortunately, there are a number of locally-owned shops all over the city selling a variety of goods and services. Our city also has multiple holiday markets you can check out for the most festive gifts.

  • Roost. From home accessories to festive holiday décor, you’ll find products with moderns lines and well-crafted details at Roost.
  • Milk Handmade. This women’s boutique specializes in ethically and sustainably produced goods from independent designers.
  • Andersonville Galleria. This retail market building features over 100 vendors offering apparel, jewelry, artwork, giftware, and gourmet treats.
  • Merz Apothecary. This old world apothecary carries the finest natural health products. This store is a landmark for those looking for unique gifts.
  • Timeless Toys. As an independent toy store in the Lincoln Square neighborhood, this place is full of classic fun for children and families.
  • Randolph Street Holiday Market. This year’s holiday market happens on November 23-24. There, you’ll find a mix of vintage and modern objects, fashion, art, and food. While you’re there, enjoy cocktail samplings and free popcorn.
  • One of a Kind Holiday Show. The 19th annual One of a Kind Holiday show returns to The Mart from December 5-8. There will be over 600 talented artists and makers. Those out shopping will find ceramics, fashion, home goods, jewelry, mixed media, pet products, and more.

Dining & Spirits

Chicago’s Jolliest Holiday Dining Options

If you’re looking to grab a bite to eat while you’re out shopping, you want to enjoy a holiday dinner with friends, or you want to skip the dishes, there are dozens of restaurants all over the city to choose from. We’ve compiled our favorites below.

  • Bub City. Whether you pop in to enjoy A Very Bub City Thanksgiving or you’re heading in later in December for their festive décor, the food’s always good at Bub City.
  • Dinkel’s Bakery & Café. Dinkel’s is the perfect place to pick up dessert for the holidays. Just be sure to order ahead. You can even have their baked goods mailed.
  • Saint Lou’s Assembly. This throwback restaurant features old-school, customizable comfort-food platters. In the holiday months, you can buy a Christmas tree in the lot next door.
  • Atwood Café. This café utilizes the finest local ingredients to create seasonal American fare.
  • Blue Line. Enjoy dinner in this cozy train-car-themed pub that serves America fare and specialty martinis.
  • Bistronomic. Located in the heart of Chicago’s Gold Coast neighborhood, this stylish restaurant serves creative, modern French dishes.
  • Big Jones. At this Southern kitchen and bar, you’ll find coastal Southern cuisine and a large whiskey and bourbon menu.
  • Harry Caray’s Italian Steakhouse. A Chicago icon for over three decades, this location opened in 1987 to celebrate the Hall of Fame broadcaster and his love of sports, great food and drinks, and sports fans.
  • Lockwood Restaurant. Serving classic American fare, this restaurant features simple midwestern flavors with a sense of elegance. Seatings throughout December features Santa’s Workshop Yuletide Brunch.
  • Vermilion. This restaurant’s menu features a global melding of Indian and Latin cuisines.

Christmas Trees

Finding the Perfect Christmas Tree in Chicago

Finding the perfect Christmas tree is easier than you’d think in Chicago. With a number of retailers in the city and tree farms nearby, you’ll have many to choose from. Depending on where you purchase your tree, you can even have it delivered.

  • Chicago Christmas Tree Lots. Located in six spots throughout the city, this Christmas tree business has been in operation for over 85 years. All of their trees are grown in northern Wisconsin.
  • City Tree Delivery. This company will deliver, set up, and remove your tree. They provide award-winning Fraser Firs and donate a portion of their profits back to the community.
  • Ivy’s Christmas Trees. At Ivy’s, you’ll found tree sizes from tabletop to 12 feet tall. They can also help you choose a tree stand and they have garlands and wreaths for sale.
  • Bob’s Tree Farm. Only a half-hour outside the city, this tree farm provides fresh northern Michigan Christmas trees and wreaths.
  • Sandhill Christmas Trees. While this tree farm is located in central Wisconsin, you can visit their tree lot in Oak Park.

Season’s Greetings and Best Wishes from Thomas Law Offices

As you can see, there’s so much to do in Chicago this holiday season. We hope this guide helps you navigate the area’s best events, shopping, dining, and more.

From all of us at Thomas Law Offices, we wish you and your family a happy holiday season and a safe, healthy new year.