All through December we'll be showcasing the best of the holiday season in cities around the world. Today it's Christmastime in Chicago, and we've asked local experts for the essential ways to enjoy the winter's best. Visitors and locals alike come together to celebrate the holidays and the New Year, and we encourage you to share your own favorites with us in the comments below.
Sylvia Rollins, Chief Concierge,
Kimpton's Hotel Monaco Chicago
- The Annual Reindog Parade at the Chicago Botanic Gardens. A dog is a Chicagoan's best friend--and it's never more evident than at the Reindog Parade. Dress up your pet in holiday style for the costume contest and canine parade through twelve gardens. Prizes are awarded for best overall costume, best puppy costume, and best owner/dog look-alike.
- The Christmas Day Bagel Ride. Starts at 10 a.m. Thursday, Dec. 25. The locals love biking--and bagels--and all the merrier when joined together. This social and leisurely paced 12-mile bike ride begins at Chicago's Waveland Clock Tower, 3700 North Recreation Drive, and ends at the Bagel Restaurant & Deli located at 3107 North Broadway.
- 25th Annual Christmas Sing-Along and Double Feature. From December 19-24, locals will make the late Gene Siskel proud by watching screenings of White Christmas and It's a Wonderful Life at the the Music Box Theatre, 3733 N. Southport Avenue. Christmas carols with Santa are sung in between the films.
- Celebrate Kwanzaa with "Raven Black" (4 p.m. Sunday, Dec. 28) at Chicago's heralded DuSable Museum of African American History. This fascinating musical production, set during the Great Migration, features the People's Jazz Theatre and music of the African Diaspora.
- The Annual "12 Bars of Christmas" Pub Crawl. Starts at 3 p.m., Saturday, Dec. 6. This walking pub tour comes complete with drink specials and is held at more a dozen bars in Chicago's Wrigleyville (where you'll find plenty of avid Cubs fans).
- Symphony in Lights. Families bring little ones to this spectacle of lights featuring a football field-sized display of 250,000 LED bulbs synchronized to the music of the Trans-Siberian Orchestra. The show is held every hour on the hour between 5 and 9 p.m., through December 31, at the Promenade in suburban Bolingbrook. Carriage rides, ice sculptures, carolers, storytelling and an appearance by Santa Claus occur nightly.
Rick Segal, General Manager,
Park Hyatt Chicago
Jon Winke, Chief Concierge (for 33 years),
The Ritz-Carlton Chicago
Kristen Klus, Concierge
Four Seasons Hotel Chicago
Photo of the Christkindlmarket in Chicago by Nora Burns Warens
Park Hyatt Chicago
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Visit Sweet Mandy B's in Lincoln Park, where you can indulge in delicious homemade treats, including decorated cut-out cookies and traditional puddings. These are great for an afternoon snack with some Intelligentsia coffee or to take to a holiday party.
- Every Friday at 6 p.m. during the holiday season, visitors can enjoy caroling in front of Cloud Gate, more commonly known as the "bean", in Millennium Park. Carolers include the Wooten
Choral Ensemble (gospel) and the Chicago Children's Choir.
- I have to include lunch or dinner at NoMI in the Park Hyatt Chicago. The French-inspired restaurant with a global flair overlooks Michigan Avenue with magnificent views of the twinkling lights and the excitement of the city as well as the historic Water Tower.
- Butch McGuire's is a local Irish pub that gets
all dolled up for the holidays. Two train sets, one stacked on top of the other, run the length of the bar and in the antique room. Extensive holiday decorations fill the establishment.
- Enjoy a romantic carriage ride around the Gold Coast and Michigan Ave. under a warm cozy blanket.
- Take a break from holiday shopping and visit the seasonal La Boule de Noel at Park Hyatt Chicago. This seasonal French macaron boutique features the delicate cookies in a variety of delicious flavors, including cranberry pecan, white chocolate cherry, and dark chocolate raspberry. The shop will be open every Tuesday-Saturday from 4:30 - 6:30 p.m. in the Library at Park Hyatt Chicago. Guests may enjoy their macarons in the comfort of the Library with an espresso or tea or they may purchase macaron gift sets to take home.
Jon Winke, Chief Concierge (for 33 years),
The Ritz-Carlton Chicago
- Over 30 years ago when Charles Dickens' A Christmas Carol premiered at the Goodman Theatre, the Chicago Tribune wrote, "Magic took over the show." The marvelous acting and stagecraft have made A Christmas Carol a beloved Chicago tradition.
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Dublin Carol at Steppenwolf Theater is about a man
holding down a steady job at a Dublin undertaker's office, after his drinking problem nearly destroyed his life. When his estranged
daughter appears on Christmas Eve with disturbing news, it sets off a
series of painful confessions that ultimately offer him a chance to escape the burdens of his past.
- Macy's On State Street. For generations Chicagoans have brought their families to see Macy's (formerly Marshall Fields) decked out for the holidays. Marvel at the 45-foot Great Tree decorated with over 1,200 themed ornaments and 25,000 dazzling lights in the Walnut Room. Experience animated window displays on State Street and enjoy elaborate decorations suspended from the ten-story atrium.
- Take a two-hour lightly narrated tour aboard a warmly decorated Chicago Trolley. You'll travel among the festive lights and holiday sights of downtown Chicago including the Magnificent Mile, State Street windows, Daley Plaza's 40-foot tree, and Navy Pier.
- Take a shopping break and enjoy a York Peppermint Brownie and hot cocoa at the Hershey's Store on Michigan Avenue.
Kristen Klus, Concierge
Four Seasons Hotel Chicago
- For 13 years, the open-air German-style Christkindlmarket market in Daley Plaza has been one of the city's seasonal highlights. The market showcases handmade glass ornaments, accessories, homemade food, clothing, and gifts. Visitors also can sip beer and hot-spiced wine and feast on German delicacies such as potato pancakes, bratwurst, schnitzel, strudel and more.
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Dine in the legendary Walnut Room under the Great Christmas Tree decorated with vintage ornaments at Macy's. It's
well worth the wait for this taste of nostalgia and menu items such as
Mrs. Hering's Famous Chicken Pot Pie and the Field's Special sandwich.
Fairies sprinkle fairy dust and ask for your holiday wishes. Kids have
a special menu.
- Perhaps there's no better place to truly absorb the holiday spirit than skating among the city's skyscrapers at the ice rink at Millennium Park. Just off Michigan Avenue, the ice rink is a magical setting to skate while enjoying the views of city lights. Once you've hung up your skates, warm up inside the Park Grill with hot chocolate as you watch others take to the ice.
- The Do It Yourself Messiah is a tradition at the Civic Opera House where you can be a participating chorus member of Handel's Messiah. Although tickets are sold out for the 3 p.m. performance on Dec. 21 and the 7 p.m. performance on Dec. 22, visit the Ticket Return Table in the lobby of the Civic Opera House before the performances. Unused tickets will be collected and re-districuted.
- If you are dreaming of a 'Green Christmas' then the Gifting Green Activity Room at the Peggy Notebaert Nature Museum is the perfect holiday activity. You'll learn to make eco-friendly gifts such as ornaments, mosaic birdhouses, pots, papier-mâché bowls and more.
- Chestnuts roast on an open fire every evening from 5 pm to 7 p.m. at the Seasons Lounge and Conservatory in the Four Seasons Hotel. Enjoy complimentary roasted chestnuts prepared by servers who roast them right before your eyes in a cast iron pan over a roaring fire. Pair with a holiday cocktail such as the Jack Frost Martini or Ebenezer's Egg Nog.
- The Museum of Science and Industry features an annual display with more than 50 trees decorated to represent holiday traditions around the world. You'll feel like you are in a winter wonderland as you walk among the trees and enjoy intermittent falling snow.
- Kids of all ages love Zoo Lights at Lincoln Park Zoo where the zoo is illuminated with more than one million lights. Also, children can visit with Santa, watch ice-carving demonstrations, enjoy a music light show extravaganza, ride the carousel and more.
Photo of the Christkindlmarket in Chicago by Nora Burns Warens











Wow, thanks for putting this all in one place. Looks like there's a lot to do in my new hometown!
I recently came across your blog and have been reading along. I thought I would leave my first comment. I don't know what to say except that I have enjoyed reading. Nice blog. I will keep visiting this blog very often.
Sarah
http://www.thetreadmillguide.com
The first recorded Christmas wreaths were made by a German man named Johann Hinrich Wichern, of Hamburg. He studied theology, and was also a highly-regarded teacher in the town of Hamburg.
Rose.
There really is a great deal to do in Chicago. But I'm not sure how, "The first recorded Christmas wreaths were made by a German man named Johann Hinrich Wichern, of Hamburg. He studied theology, and was also a highly-regarded teacher in the town of Hamburg." applies...?
I was on my annual California Vacations during Christmas and it was definitely nothing like the winter season in Chicago! I wish I could be in Chicago every winter, but I just can't stomach the cold. Kudos to those brave hearted that can take advantage of this wonderful city!