Your Guide to Chicago in December 2025

Yes, it’s getting colder in Chicago. (As I write this, the wind is howling outside my window.) But December is jam-packed with so many events and spectacles, it’s not time to hunker down. Not yet.

Many (Many) Pop Ups

Pop-ups just feel like a party — whether it’s a bar or an artisan market. Lucky for us, December has plenty of both.

Some Holiday Pop-Up Experiences

• 🥂 Holly Jolly Christmas Bar | Puttery | West Loop
• 🥂 Gwen's Winter Curl & Chill | Gwen Hotel | Streeterville
• 🥂 Happy's Holiday Pop-Up Bar | Chicago Athletic Association | Loop
• 🥂 Rudolph's Bar | Lost Never Found | Wrigleyville
• 🥂 Santa Baby | Stolen Saddle | Wrigleyville
• 🥂 Château Carbide’s Winter Garden | Bar Pendry | Loop
• 🥂 Sweet Home Chicago | The Shops at North Bridge | Streeterville
• 🥂 Jack Frost Christmas Holiday Pop-Up | 170 N. Green St. | Fulton Market

Stay tuned in Hey Chicago for additional pop-up bars!

Upcoming Holiday Pop-Up Markets

• 🛍️ Holiday Party and Makers Market | Lillstreet Art Center | Ravenswood | Dec. 5
• 🛍️ Western Avenue Holiday Road + Trolley | Western Avenue between 99th to 115th Streets | Morgan Park and Beverly | Dec. 6
• 🛍️ Jarvis Square 17th Annual Artisan Market | Rogers Park | Dec. 6
• 🛍️ Drie-cember Market | Driehaus Museum | Streeterville | Dec. 6
• 🛍️ Puerto Rican Artisan Market | National Museum of Puerto Rican Arts and Culture | Dec. 6-7 and 12-13
• 🛍️ Gnarly or Nice – Holiday Ceramics Market | Co-Prosperity Sphere | Bridgeport | Dec. 13

Winter Fun in the Loop

Don’t be a Scrooge — get down to the Loop this season and take in the holiday merriment.

There’s ice skating every day (weather permitting) at Millennium Park and Maggie Daley Park, but reservations are required. Reserve for Millennium Park here and Maggie Daley here.

Personally, I prefer the ribbon at Maggie Daley, although Millennium Park is home to Chicago's official Christmas tree. See it twinkling in McCormick Tribune Plaza.

Nearby, at the Macy's on State Street, catch window displays paying tribute to Marshall Field’s. Upcoming reservations to the Marshall Field’s Walnut Room (recently renamed) are full, but you can reserve a slot at the store’s Santaland here.

And, of course, there’s always the Christkindlmarket at Daley Plaza, now in its 29th season. The open-air market ends on Dec. 24. Theaters downtown are also bustling with holiday options:

• 🎭 “The Christmas Carol” | Goodman Theatre | Runs through Dec. 31
• 🎭 “The Nutcracker” | Lyric Opera House | Runs through Dec. 28
• 🎭 “Twas the Night Before…” by Cirque du Soleil | Chicago Theatre | Runs through Dec. 28

"Dick Clark's New Year's Rockin' Eve" is also adding its first-ever Central time zone show this year, live from downtown. Hosts include Chance the Rapper and Ryan Seacrest ... will you be out there with them counting down?