Travel Magazine

Chicago’s Ultimate Christmas Guide

By Urbanmatter Chicago @UMatterChicago

Everything you need to celebrate the season we’ve all been waiting for

Christmas in Chicago is nothing short of magical. With holiday cheer spread across every street, every neighborhood, and every building, it’s pretty hard not to be excited.

There are so many things to do in the city during the holidays, it’s almost impossible to keep up. Everyone knows that when you’re in full holiday zone, you make it your mission to do every single thing.

For those of you holiday-holics that are trying to jam-pack the next few weeks with non-stop activities, we’ve got you covered! Here’s our ultimate guide to Christmas in Chicago.

Markets and Shopping


Photo Credit: Christkindlmarket Chicago

  • Christkindlmarket – Visit the most popular outdoor holiday market around and enjoy food, drinks, crafts, and more. The market runs through December 24.
  • Randolph Street Holiday Market – Voted one of the best for holiday shopping, get antiques, jewelry, clothes, and houseware. Visit on November 26 – 27 and December 10 – 11.
  • Irish Christmas Market – Celebrate the holidays with Irish tradition at this festive event in Northcenter, running December 9 – 11.

Music Festivals


Photo Credit: WKQX

  • B96 Pepsi Jingle Bash – Britney Spears, Fifth Harmony, Shawn Mendes, Alessia Cara, and more ring in the season with chart-topping music at Allstate Arena on December 10.
  • iHeartRadio Jingle Ball – Ariana Grande, Ellie Goulding, Tove Lo, and more hit Allstate Arena with a pop music holiday bash on December 14.
  • The Nights We Stole Christmas – This holiday fest brings you three nights of rock, alternative, and indie at the Aragon Ballroom from December 1 – 3.
  • Miracle on State Street – See Charlie Puth, James Bay, and JoJo perform live at The Chicago Theatre on December 3.



  • A Christmas Carol – Watch the classic Dickens story of Ebenezer Scrooge unfold at the Goodman Theatre through December 31.
  • A Charlie Brown Christmas – All of our favorite characters from the Peanut gang will entertain families at the Broadway Playhouse through January 8.
  • The Nutcracker – See award-winning choreography from the Joffrey Ballet tell the tale of the Nutcracker from December 10 – 30.

Holiday Light Displays


Photo Credit: Todd Rosenberg for Lincoln Park Zoo

  • ZooLights – Head to Lincoln Park Zoo for a magnificent light display that the whole family can enjoy on select dates in November and December, ending January 1.
  • BrewLights – Kind of like ZooLights, but for adults only. Sample delicious beers and wines under twinkling lights on December 1.
  • Brookfield Zoo’s Holiday Magic – Stroll through over one million LED lights, train displays, ice carvers, and more at Brookfield Zoo on Saturdays and Sundays in December.
  • Illumination – Walk through a winter woods of illuminated trees at the Morton Arboretum through January 2, closed on select dates.

Bar Crawls


Photo Credit: Chicago SantaCon

  • TBOX – The most popular bar crawl in town returns to Wrigleyville. Dress up in your Christmas gear for Twelve Bars of Xmas on December 10.
  • Chicago Christmas Crawl – Hop around bars and pubs in Old Town on this Christmas-themed crawl on December 10.
  • SantaCon – Join hundreds of other Santas in Logan Square for an all-day holiday bar crawl on December 10.
  • Running of the Santas – Race your way from bar to bar downtown with a massive gathering of Santas on December 3.

Runs and Races


Photo Credit: Santa Hustle

  • Santa Hustle – Hop on this 5k that starts at Soldier Field and benefits the American Cancer Society on December 3.
  • Ugly Sweater Run – Also at Soldier Field, wear your favorite ugly Christmas sweater and join others in a 5k race that benefits One Warm Coat on December 10.
  • Santa Speedo Run – Strip down to your skivvies in the lovely Chicago cold on December 3 for a run that benefits the Chicago Diabetes Project.
  • Rudolph Ramble – Head to Diversey Harbor on December 11 for a 5k that benefits Lurie Children’s Hospital.
  • Jingle Bell Run – Raise awareness for the Arthritis Foundation at this 5k race at Soldier Field on December 17.

Food, Beer and Wine Tastings


  • Christmas & Winter Beer Tasting – For just $20, enjoy samples of local and national seasonal beers at Delilah’s on December 3.
  • Winter Solstice Craft Beer Fest – Spend an afternoon at Blarney Stone Pub on December 10 to sample seasonal beers from some of the best breweries in the world.
  • Cookies & Cheer Exchange – Hang out at the Fairmont Millennium Park for all-you-can-eat cookies, wine tastings, and socializing on December 1.
  • Holiday Cheers – Enjoy a scenic view at the Chicago Botanic Garden while tasting local beers, wines, and spirits on December 7.



  • Winter WonderFest – An amazing indoor winter wonderland with rides and activities awaits you at Navy Pier through January 8.
  • Holiday Treasure Hunt and Tea Party – Spend an afternoon on an art scavenger hunt at the Art Institute and drinking tea with Artie the Lion on December 11.
  • Wonderland Express – See an extravagant model train display and listen to carolers at the Chicago Botanic Garden through January 2.
  • Polar Express Train Ride – Experience the Polar Express on Amtrak with cookies, beverages, and visits from Santa at Union Station through January 1.
  • Breakfast with Santa – Feast on a Christmas breakfast, take pictures with Santa, and participate in an ornament contest at Soldier Field on December 10.
  • Christmas Around the World & Holidays of Light – Check out this exhibit at the Museum of Science & Industry by learning about holiday traditions from across the globe through December 26.

Anything we missed? Got a tip on an awesome holiday event in the city? Let us know!

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