December doesn’t tiptoe into Chicago. It pulls up with a Christmas market in one hand, a Bulls game in the other, and a sparkly outfit ready for a night at the theater.

The first week of December 2025 (Monday, December 1 – Sunday, December 7) is stacked with culture, sports, fashion, music, nightlife, and social events all over the city and nearby suburbs. Use this ChiVibe guide to plan your week by vibe, neighborhood, and budget.

Culture & Classic Chicago Holiday Traditions

Christkindlmarket & the downtown holiday core

If you want peak “holiday-in-the-city” energy, start at Christkindlmarket Chicago. The German-style market is back across multiple locations (Daley Plaza in the Loop, Gallagher Way in Wrigleyville, and Aurora), running through Christmas Eve. Expect steaming mugs of glühwein, bratwurst, raclette, strudel, imported ornaments, and endless souvenir mugs.

Pro tip: the Daley Plaza market is adding themed experiences again this year (like Krampus nights and “Culture & Cheer” tours), so the first week of December is a sweet spot—full atmosphere, slightly less week-before-Christmas chaos.

While you’re downtown, build yourself a holiday trifecta:

• Ice skating at Millennium Park – Lace up at the
  McCormick Tribune Ice Rink, open from November 21, 2025 through early February 2026 (weather permitting). Skating is free, but advance reservations are required.
• City of Chicago Christmas Tree – Wander over to the official tree in Millennium Park; details about this year’s towering Norway spruce are on the city’s
  Christmas Tree page. It’s lit nightly through early January.
• CTA Holiday Train & Bus – Santa rides the rails on the Allstate CTA Holiday Train while a fully decked-out Holiday Bus hits routes across the city. Schedules live on the
  CTA Holiday Fleet page, with service running from late November into late December.

Big museum energy: MSI & the MCA

When the lakefront wind gets too real, head indoors:

Christmas Around the World & Holidays of Light
Hyde Park’s Museum of Science and Industry transforms its central hall into a forest of decorated trees and lighted displays for Christmas Around the World & Holidays of Light. The exhibit runs through January 5, 2026, so it’s fully in swing this first week. Expect a four-story “Grand Tree,” dozens of trees representing different cultures, and displays highlighting winter traditions from Diwali to Lunar New Year.

Yoko Ono: Music of the Mind at MCA Chicago
In Streeterville, the Museum of Contemporary Art Chicago is hosting Yoko Ono: Music of the Mind(October 18, 2025 – February 22, 2026), a major retrospective spanning more than 70 years of Ono’s work. It mixes films, scores, participatory pieces, and archival materials.

The MCA’s current exhibitions also include projects like Edie Fake’s large-scale atrium work and “City in a Garden: Queer Art and Activism in Chicago”, so you can easily make a half-day out of it before dinner and a show.

Theater, Ballet & Musicals

Goodman Theatre – A Christmas Carol

For many locals, it’s not December until they see Scrooge in the Loop. The Goodman’s long-running A Christmas Carol runs from November 15 through December 31, 2025, with nightly options all through the first week of December.

This year’s production marks the 48th outing of the show, with a fresh adaptation by Tom Creamer and direction by Malkia Stampley—still faithful to Dickens, but with new energy and updated staging.

Joffrey Ballet – World’s Fair Nutcracker

Starting Friday, December 5, the Joffrey Ballet brings back its Chicago-centric take on the classic at the Lyric Opera House. The Nutcracker (December 5–28, 2025) is set against the 1893 World’s Columbian Exposition, with lavish sets and kid-heavy casting that makes opening weekend ideal for families and date nights alike.

Broadway in Chicago – Elf & SIX

If your holiday vibes lean more Broadway than ballet, you’ve got options:

• Elf The Musical – Buddy the elf lands at the Auditorium Theatre December 2–14. Full details and tickets live on the Auditorium Theatre’s event page.
• SIX – The pop-concert-style retelling of Henry VIII’s wives runs December 2–14 at the CIBC Theatre. Check Broadway in Chicago’s listing for SIX
  for showtimes and tickets.
  
  

Stack it: do A Christmas Carol earlier in the week, then mix in Elf, SIX, or The Nutcracker over the weekend for a mini holiday-theater marathon.

Live Music: From Arenas to Intimate Rooms

Chicago’s concert calendar is loaded in early December, and the first week packs a punch across genres.

Monday, December 1 – Indie & Afrobeats (plus one major cancellation)

• Of Monsters and Men – The Salt Shed (Indoors)
  Icelandic indie-folk band Of Monsters and Men brings their 2025 tour to the indoor stage at the Salt Shed on Monday night. Ticket details are on Ticketmaster’s event page.
• Burna Boy – United Center (Canceled)
  The Chicago stop of Burna Boy’s No Sign of Weakness tour was originally scheduled for December 1 at the United Center, but the event is now marked as canceled on the official Ticketmaster listing. If you bought tickets, check your point of purchase for refund information and keep an eye on the venue and artist channels for any updates.

Tuesday, December 2 – Holiday pop vs. neo-soul

• Pentatonix – “Christmas in the City” at Allstate Arena
  The Grammy-winning group turns Allstate Arena into a retro-glam holiday variety show on Tuesday, December 2 at 7:30 p.m. with their Christmas in the City tour. Event details and parking info are on the
  Allstate Arena event page.
• Erykah Badu – Mama’s Gun ’25: The Return of Automatic Slim at The Chicago Theatre
  Neo-soul icon Erykah Badu brings her anniversary tour for Mama’s Gun to The Chicago Theatre on December 2 and 3. See the official event page for show details and tickets.

Midweek & weekend picks

• Valeria Castro – Instituto Cervantes of Chicago (Wednesday, December 3)
  Rising Canary Islands singer-songwriter Valeria Castro plays an intimate show at Instituto Cervantes (31 W. Ohio St.) on December 3. The Songkick listing for the concert is here, if you want to track tickets and RSVP.
• Chicago Symphony Orchestra: Till Eulenspiegel & Bullock Sings Aucoin (December 4–7)
  At Symphony Center, the CSO’s program Till Eulenspiegel & Bullock Sings Aucoin runs Thursday–Sunday, December 4–7. The program pairs Strauss’ mischievous Till Eulenspiegel’s Merry Pranks, Brahms’ Symphony No. 3, and the world premiere of Matthew Aucoin’s Song of the Reappeared featuring soprano Julia Bullock.
  
  

Layer in club shows at venues like Thalia Hall, Schubas, Subterranean, Reggies, and House of Blues and you can easily do “one concert per night” this entire week.

Sports: Bulls, Blackhawks & Bears

Chicago Bulls – Games all week long

The Bulls’ early-December schedule is friendly to fans looking for an excuse to hit the United Center. According to the team’s official schedule, the first week of December includes:

• Monday, December 1 – at Orlando Magic
• Wednesday, December 3 – vs. Brooklyn Nets (United Center)
• Friday, December 5 – vs. Indiana Pacers (United Center)
• Sunday, December 7 – vs. Golden State Warriors (United Center)
  
  

Home games make for a perfect West Loop/Fulton Market combo: pregame dinner, the game, then postgame drinks.

Chicago Blackhawks – On the road, but on every TV

While the Bulls are at home, the Blackhawks are on a West Coast swing. The
team schedule shows a road-heavy first week of December:

• Tuesday, December 2 – at Vegas Golden Knights
• Thursday, December 4 – at Los Angeles Kings
• Sunday, December 7 – at Anaheim Ducks
  
  

That means lots of late-night hockey at sports bars around the city—perfect for a lower-key hang with friends after earlier holiday plans.

Chicago Bears – Rivalry Sunday at Lambeau

The Bears are having a season worth watching, and Week 14 is a big one. On Sunday, December 7, they head to Lambeau Field to face the Green Bay Packers in a late-afternoon game with major implications for the NFC North race. You can see details for the matchup on ESPN’s game page and the full season schedule on ChicagoBears.com.

Expect every TV in the city to be tuned in—book a table early if you’re planning a group watch at your favorite bar.

Fashion, Shopping & Holiday Markets

One of a Kind Holiday Show – THE MART (December 4–7)

The One of a Kind Holiday Show returns to THE MART from Thursday–Sunday, December 4–7, 2025. It’s a massive indoor market featuring 600+ artists, designers, and makers—ideal for fashion lovers, home-decor nerds, and anyone who’d rather gift something handmade.

For hours, ticket prices, and tips on navigating the show, hit the “Plan Your Visit” section on the official site here.

Jack Frost Christmas Pop-Up – Fulton Market

Fulton Market gets a full Christmas takeover at the Jack Frost Christmas Pop-Up,
an all-ages outdoor playground at 170 N Green St. Think: ice skating, curling, bumper cars, light tunnels, holiday cocktails, and a market full of seasonal vendors.

Tickets, time slots, and package options (including skating rentals) are laid out on the
Jack Frost ticketing page. This is where cozy sweaters, beanies, and statement coats go to be seen.

Fashion Outlets of Chicago – Holiday HQ

If you need a more traditional shopping fix (or a place to kill time before or after a concert), the Fashion Outlets of Chicago in Rosemont runs its Holiday HQ program through December 24, 2025.

Expect Santa photos, special events, and outlet deals under one roof—easy to pair with the Pentatonix show at nearby Allstate Arena.

More festive shopping moments

• Christkindlmarket doubles as a fashion-and-accessories hunting ground, with imported scarves, knitwear, and jewelry stalls throughout all locations.
• Jack Frost mixes vintage holiday gear and photo-ready “ugly sweater” finds alongside its rides and rink.

Nightlife & Social Events

Cheer at the Pier – Navy Pier (Thursday, December 4)

On Thursday, December 4, Navy Pier throws its annual winter fundraiser
Cheer at the Pier from 6–9 p.m. Tickets include access to Winter WonderFest attractions, skyline views, and plenty of festive photo ops. Proceeds support Navy Pier’s free programming for schools and community groups.

It’s a rare chance to ride indoor attractions, sip drinks, and feel like a kid again—all while doing something good.

Immersive light shows after dark

• Illumination: Tree Lights at The Morton Arboretum (Lisle)
  The Arboretum’s beloved Illumination: Tree Lights runs November 15, 2025 through January 3, 2026. Walk a mile-long paved trail lined with interactive light installations, with specialty “Electric Illumination” late-night sessions on select Fridays (including December 5).
• Lightscape at Chicago Botanic Garden (Glencoe)
  Up north, Lightscape turns the Chicago Botanic Garden into a glowing trail of tunnels, sculptures, and soundscapes starting mid-November and running into early January. It’s one of the most popular light shows in the region, so advance tickets are strongly recommended.

Theater-kid nightlife: The Neo-Futurists & The Paper Machete

If your ideal night out includes weirdo theater and sharp comedy:

• Best of The Infinite Wrench 2025 – From December 5–14, The Neo-Futurists remount 30 of their favorite short plays from the year in Best of The Infinite Wrench 2025, with late-night performances on December 5 & 6 and an earlier show on Sunday, December 7.
• The Paper Machete at the Green Mill – The weekly “live magazine” of comedy, storytelling, and music returns Saturdays at the historic Green Mill. Time Out’s listing for The Paper Machete includes December dates, including a Saturday, December 6 show squarely inside this week.

Build Your Own First-Week-Itinerary

Here’s how you might stitch all of this together into a very Chicago first week of December.

Monday, December 1 – Loop lights & indie anthems

• Hit Christkindlmarket at Daley Plaza after work for mulled wine and ornaments.
• Stroll through Millennium Park to see the official city Christmas tree
  and maybe squeeze in an evening skating slot at the McCormick Tribune Ice Rink.
• End the night at Of Monsters and Men at the Salt Shed (tickets here), or keep it low-key with dinner and Bulls-on-TV if you’re not traveling to Orlando.

Tuesday, December 2 – Museum + train + big show

• Spend the afternoon at the MCA exploring Yoko Ono: Music of the Mind
  and other current exhibitions. Catch a ride on the CTA Holiday Train or Bus
  on your way back toward the Loop or out to the neighborhoods.
• Pick your lane: holiday pop spectacle with Pentatonix at Allstate Arena
  (event page) or neo-soul perfection with Erykah Badu at The Chicago Theatre
  (event page).

Wednesday, December 3 – Chill midweek culture night

• Daytime: head to Hyde Park for Christmas Around the World & Holidays of Light at MSI.
• Evening: catch Valeria Castro’s intimate show at Instituto Cervantes
  (concert details) and then grab tapas or wine nearby.

Thursday, December 4 – Shop + give back + late-night drinks

• Afternoon: browse the One of a Kind Holiday Show at THE MART for gifts and new local designers.
• Evening: walk or rideshare to Navy Pier for Cheer at the Pier,
  the Pier’s winter fundraiser and Winter WonderFest preview night.
• Nightcap in Streeterville or River North, depending on your vibe.

Friday–Sunday, December 5–7 – Full holiday send

• Pick a big show: Opening weekend of The Nutcracker at Joffrey,
  A Christmas Carol, or a performance of the CSO’s December 4–7 program.
• Support the home teams: snag tickets to a Bulls home game via the Bulls schedule, or plan a watch party for the Sunday Bears–Packers showdown using the Bears’ official schedule.
• Go full cozy chaos: lock in a night at Jack Frost Christmas Pop-Up or a suburban light stroll at Illumination or Lightscape.
• Late-night theater kids’ choice: snag tickets to Best of The Infinite Wrench 2025 or dip into The Paper Machete for a free afternoon show at the Green Mill.

Make ChiVibe Your December Command Center

The first week of December is one of those times when Chicago gives you too many good options. That’s where ChiVibe comes in.

• Note the events that fit your vibe (family-friendly, date night, friend squad, or solo explorer).
• Take note of the neighborhood so you’re not zig-zagging across the city in the cold.
• Layer categories—build nights that mix culture, sports, fashion, and nightlife instead of choosing just one.

However you stack your week, tag your adventures and share them so other Chicagoans can vibe with you—and keep checking ChiVibe as new events, pop-ups, and last-minute shows get added to the calendar.