Chicago events guide: things to do in Chicago in the second week of December 2025

Chicago events in December 2025 are in full holiday mode, and the second week of December 2025 is packed with things to do in Chicago for locals and visitors, from Christmas markets and light shows to big league games, concerts, theater and bar crawls. Discover the best Chicago events, concerts, holiday lights, sports and nightlife in the second week of December 2025 for locals and visitors.

Culture and holiday traditions in Chicago, December 8 to 14, 2025

Christkindlmarket Chicago and Wrigleyville

The city’s most famous holiday market stays busy all week. The Daley Plaza edition of Christkindlmarket Chicago runs daily through December 24, 2025, filling the Loop with wooden stalls, German snacks, hot spiced wine and collectible mugs. Official listings on Choose Chicago confirm daily hours from late morning into the evening, which makes it easy to visit after work or before a show.

Up in Lakeview, Christkindlmarket Wrigleyville at Gallagher Way runs on a similar schedule with an added neighborhood twist near Wrigley Field. Pair a visit with nearby holiday bars in “Wrigleyville Wonderland” for a full north side seasonal circuit.

Christmas Around the World and Holidays of Light at MSI

Hyde Park’s Museum of Science and Industry turns its central hall into a globe spanning forest of trees for the 83rd annual Christmas Around the World and Holidays of Light. For 2025 the exhibit runs from November 8, 2025 through January 5, 2026, with more than 50 decorated trees and displays curated by local communities and cultural organizations.

If you are planning things to do in Chicago in December 2025 with family, this is an ideal daytime stop on any weekday between December 8 and 14. Admission to the exhibit is included with regular MSI tickets, so you can combine it with other permanent exhibits in the same visit.

ZooLights at Lincoln Park Zoo and suburban Lightscape

For pure light overload, ZooLights at Lincoln Park Zoo runs from November 21, 2025 through January 4, 2026, with millions of LEDs, themed displays and special nights. The zoo’s ticket page notes a mix of fixed date and flexible tickets and mentions that most Monday dates are free with advance registration, which includes Monday December 8 in this second week of December 2025.

Farther north, the Lightscape trail at Chicago Botanic Garden in Glencoe continues through early January, with timed entry and special 21 plus “Cocktails Under the Lights” evenings on select dates. Both are perfect for couples looking for date night ideas in Chicago or groups wanting a slow burn night instead of a bar crawl.

Ice skating in Millennium Park and Maggie Daley Park

Outdoor skating is one of the signature things to do in Chicago in December 2025. The city lists the McCormick Tribune Ice Rink in Millennium Park as open from November 21, 2025 through February 1, 2026, with daily hours from late morning to late evening and free admission with advance reservations. An article on Choose Chicago highlights the rink as a bucket list experience thanks to skyline and Christmas tree views.

Next door, the ice ribbon at Maggie Daley Park opens in mid November 2025 and winds through a path of trees and city views. For families and visitors staying downtown, a weekday evening skate between December 8 and 14 is an easy way to feel like you are in a holiday movie without leaving the Loop.

Art fix: Yoko Ono at MCA Chicago

When you need a break from markets and lights, head to the Museum of Contemporary Art Chicago in Streeterville. The MCA is the exclusive U.S. venue for Yoko Ono: Music of the Mind, a major retrospective spanning more than 200 works from the artist’s career. The show runs from October 18, 2025 to February 22, 2026 and emphasizes audience participation and conceptual pieces.

Local coverage from outlets like Axios notes that the exhibition includes interactive installations and public art components across the city, which makes it a timely cultural highlight for anyone tracking Chicago events December 2025 beyond just holiday lights.

Theater, ballet and big stage Chicago shows in December 2025

Goodman Theatre – A Christmas Carol

The Goodman’s A Christmas Carol is one of the anchor Chicago holiday events 2025. The 48th annual production runs from November 15 through December 31, 2025 in the Goodman’s Albert Theatre and features a fresh staging directed by Malkia Stampley. Listings on Goodman’s season page confirm nightly shows and weekend matinees throughout the second week of December, making it easy to grab seats after Christkindlmarket or an early dinner in the Loop.

Joffrey Ballet – The Nutcracker at Lyric Opera House

Joffrey Ballet’s Chicago World’s Fair inspired The Nutcracker runs from December 5 to December 28, 2025 at the Lyric Opera House. Ticketing pages show multiple performances during the second week of December, including evening shows on Thursday December 11 and Friday December 12 and matinee plus evening performances on Saturday December 13 and Sunday December 14.

If you are looking for things to do in Chicago with kids in December 2025, a weekend matinee paired with a visit to Christkindlmarket or Maggie Daley Park is a perfect one day itinerary.

Elf The Musical at Auditorium Theatre

Elf The Musical brings Buddy’s sugar fueled chaos to the Auditorium Theatre from December 2 through December 14, 2025. The theater’s event listing notes multiple shows in this second week, with evening performances and some earlier matinees. It is a great pick for families staying in the South Loop or anyone who wants something lighter than a two hour ballet.

SIX at CIBC Theatre

Broadway in Chicago has SIX at the CIBC Theatre from December 2 to December 14, 2025. The Tony winning pop concert style musical gives the six wives of Henry VIII a chance to retell their stories in an 80 minute show with no intermission. Ticketing on Broadway in Chicago and Ticketmaster shows weekday and weekend performances across the second week, including a daytime show on Wednesday December 10 that is ideal if you want to catch a matinee before ZooLights or dinner.

The Phantom of the Opera at Cadillac Palace Theatre

A touring production of The Phantom of the Opera opens at Cadillac Palace Theatre on December 11, 2025 and runs through February 1, 2026. Tour information and ticket pages list performances on Friday December 12 and Saturday December 13 in this second week of December, with a matinee on Sunday December 14. This is a strong choice for date night in the Loop, especially if you combine it with Christkindlmarket and a late drink in River North.

Live music and concerts in Chicago, second week of December 2025

103.5 KISS FM Jingle Ball at Allstate Arena

On Monday December 8, 2025, 103.5 KISS FM’s Jingle Ball Presented by Capital One returns to Allstate Arena in Rosemont with a 7:30 pm start. The station’s event page lists a multi artist lineup that includes Teddy Swims, Nelly, Jessie Murph, Ravyn Lenae, Shinedown, Zara Larsson, Audrey Hobart, Jackson Wang and Renee Rapp, plus a special sing along moment tied to the “KPOP Demon Hunters” film.

If you are searching for “Chicago concerts December 2025” and want a one stop holiday pop show, this is the obvious pick for the start of the week.

Holiday Rhythms at Jazz Showcase

For a smaller and more Chicago centric concert, the Chicago Human Rhythm Project brings back Holiday Rhythms to Jazz Showcase in the South Loop. Event listings on Jazz Showcase and Time Out show a Monday December 8, 2025 performance from about 6:30 pm to 9:00 pm featuring jazz vocalist Dee Alexander and tap artist Jumaane Taylor. It is a strong option for music fans who want something local and live instead of a huge arena show.

Dijon at the Salt Shed and more concerts

Indie R and B singer Dijon plays a headlining show at the indoor stage at The Salt Shed on Monday December 8, 2025, with ticket listings on platforms like SeatGeek showing a 7:30 pm start time. This is one of many mid size concerts in the city that week, alongside a long list of club shows listed on Songkick’s December 2025 Chicago concerts page.

Checking aggregate listings is a smart move if you want to pair your holiday plans with music but care more about genre than a specific artist. Whether you want jazz, metal, house, indie rock or classical, you will find something on at least one night between December 8 and 14.

Sports: Bulls, Bears and Blackhawks in mid December 2025

Chicago Bulls: home game vs New Orleans Pelicans

According to the NBA schedule feed, the Chicago Bulls head to Charlotte to face the Hornets on Friday December 12, 2025, then host the New Orleans Pelicans at the United Center on Sunday December 14. The listing shows an afternoon West Coast timestamp, which translates to an early evening tipoff in Chicago.

If you are planning a Sunday in the West Loop, this Pelicans at Bulls game is a perfect anchor, especially if you combine it with brunch or dinner in Fulton Market before or after the game.

Chicago Blackhawks: midweek and Saturday at the United Center

On the ice, the Chicago Blackhawks 2025-26 schedule lists a home game against New York on Wednesday December 10 at 7:30 pm, followed by a road game at St. Louis on Friday December 12 and a home matchup against Detroit on Saturday December 13 at 8:00 pm. The Wednesday and Saturday home dates give fans two chances to see Connor Bedard and company in person during this second week of December.

Chicago Bears vs Cleveland Browns at Soldier Field

The Chicago Bears 2025 schedule shows a Week 15 home game against the Cleveland Browns at Soldier Field on Sunday December 14, with a 1:00 pm kickoff on FOX. With the team sitting at 9-3 going into December in ESPN’s standings snapshot, this matchup is likely to carry playoff implications.

For many fans, spending Sunday afternoon tailgating or watching the game from a neighborhood bar counts as one of the essential things to do in Chicago in December 2025.

Fashion, shopping and Chicago holiday markets, December 8 to 14

Randolph Street Holiday Market in the West Loop

If you want to combine holiday shopping with vintage treasure hunting, the Randolph Street Holiday Market returns on Saturday December 13 and Sunday December 14, 2025, at 1341 W Randolph St inside Plumbers Union Hall in the West Loop. Event listings highlight more than 100 vendors, from vintage furniture and fashion to art, holiday decor, gourmet treats and seasonal cocktails, all under one roof from 10:00 am to 5:00 pm both days.

This is ideal for design minded shoppers, couples and friend groups who want a more curated experience than a big box store but still like the energy of a busy market.

Ongoing markets and gift stops

Even outside of Randolph Street, you can treat the entire city like a holiday mall. Christkindlmarket’s downtown and Wrigleyville locations are packed with artisans from Germany and beyond selling ornaments, textiles and specialty foods. The One of a Kind Holiday Show at The Mart concludes on December 7, but many of the designers represented there also maintain online shops or Chicago studio spaces you can follow up with later in the week.

For a more conventional outlet style spree, the Fashion Outlets of Chicago Holiday HQ programming in Rosemont continues all month, which pairs nicely with Jingle Ball at Allstate Arena at the start of the week.

Nightlife and social events: bar crawls, pop ups and indoor playgrounds

Navy Pier Winter WonderFest

For a climate controlled dose of chaos, Winter WonderFest at Navy Pier runs from December 5, 2025 to January 4, 2026 inside Festival Hall. The event description highlights rides, slides, an indoor ice rink, bumper cars, kiddie attractions and dense holiday decor, all under one roof. If you have kids or simply want to avoid the wind off the lake, this is one of the most reliable things to do in Chicago in December 2025 regardless of weather.

Jack Frost Christmas Pop Up in Fulton Market

In Fulton Market, the Jack Frost Christmas Pop Up transforms roughly two acres at 170 N Green St into an outdoor holiday playground from late November through early January. Ticketing pages for 2025 show multiple time slots on Wednesday December 10, Friday December 12, Saturday December 13 and Sunday December 14, with afternoon to late evening sessions featuring a Christmas market, full sized ice rink, bumper cars, axe throwing and many photo heavy installations.

Santa Baby Bar and Wrigleyville Wonderland

If your idea of Chicago events December 2025 involves more cocktails than cocoa, head to Wrigleyville. The neighborhood wide Wrigleyville Wonderland promotion describes more than 25 heavily decorated holiday themed bars, including the popular Santa Baby Bar, which offers reservations, standing room tickets and holiday party bookings for the 2025 season. Their reservation page notes 21 plus rules after 8:00 pm and pre sold drink ticket packages, which makes it easier to plan a structured night out.

TBOX 12 Bars of Xmas and Official Ugly Sweater Bar Crawl

Saturday December 13, 2025 is stacked for bar crawl fans. The long running TBOX 12 Bars of Xmas returns for its 29th year, with opening ceremonies at Cubby Bear in Wrigleyville at 10:00 am and access to 20 plus neighborhood bars throughout the day. The organizer site notes ticket tiers that include gift cards, breakfast buffets and other perks.

On the same day downtown, the 2025 Official Ugly Sweater Bar Crawl Chicago runs from 2:00 pm to 9:00 pm, starting at PB and J: Pizza Beer and Jukebox in the West Loop. Event listings on Eventbrite and Facebook describe ticket packages, drink specials and a dress code heavy on loud sweaters.

Sample itineraries for the second week of December 2025

Monday December 8 – Pop party or jazz night

Start your week by choosing between the Jingle Ball arena spectacle or a club sized jazz show. In the northwest suburbs, pre game at a Rosemont restaurant then head into Allstate Arena for Jingle Ball. In the city, grab dinner in Printer’s Row and walk to Jazz Showcase for Holiday Rhythms.

Wednesday December 10 – Museum, skating and Blackhawks

Spend the afternoon at the MCA Yoko Ono exhibit, then skate the McCormick Tribune Ice Rink as the city lights come on. Wrap up at the United Center for the Blackhawks vs New York game or catch it at a West Loop sports bar if tickets are tight.

Saturday December 13 – Holiday market plus bar crawl

Start with the Randolph Street Holiday Market from late morning through early afternoon, then decide whether your night looks like the Official Ugly Sweater Bar Crawl in the West Loop or TBOX in Wrigleyville. Night owls can end at Jack Frost or Santa Baby Bar for one last round of photos.

Sunday December 14 – Bears, Bulls and ballet

Build a full sports and arts crossover day. Start with the Bears vs Browns game at Soldier Field at 1:00 pm. From there you can head to the United Center for the Pelicans at Bulls game, or change into something dressier and go to a Sunday evening performance of The Nutcracker or The Phantom of the Opera.

FAQ about Chicago events in December 2025

What are the best things to do in Chicago in December 2025?

Some of the best Chicago events December 2025 include Christkindlmarket in the Loop and Wrigleyville, ZooLights at Lincoln Park Zoo, the McCormick Tribune Ice Rink and Maggie Daley ribbon, A Christmas Carol at Goodman Theatre, Joffrey Ballet’s Nutcracker at Lyric Opera House, the Jingle Ball concert at Allstate Arena, Winter WonderFest at Navy Pier and big sports matchups for the Bears, Bulls and Blackhawks. Add in special markets like Randolph Street Holiday Market and bar crawls like TBOX and the Official Ugly Sweater Bar Crawl and you can fill every day and night between December 8 and 14.

Is December a good time to visit Chicago?

December is cold, but it is one of the most atmospheric times to visit Chicago. Lights, markets, theater, concerts and pop up bars are in full swing, hotels often offer seasonal packages and indoor attractions like museums and Winter WonderFest help you avoid the worst of the weather. If you pack warm layers and plan your days so that outdoor time is grouped around indoor stops, December can be one of the most memorable times to explore the city.

What holiday events are happening in Chicago the second week of December?

Between December 8 and 14, 2025 you can visit Christkindlmarket, Christmas Around the World and Holidays of Light at MSI, ZooLights at Lincoln Park Zoo, Lightscape at Chicago Botanic Garden, skating at Millennium Park and Maggie Daley Park, Winter WonderFest at Navy Pier and Jack Frost Christmas Pop Up in Fulton Market. Stage wise you have A Christmas Carol, The Nutcracker, Elf The Musical, SIX and the opening of Phantom of the Opera. On top of that are big nights like Jingle Ball, Holiday Rhythms at Jazz Showcase, the Bears vs Browns game, a Bulls home game against the Pelicans, Blackhawks games at the United Center, Randolph Street Holiday Market and multiple bar crawls.

How far ahead should I book tickets for December events in Chicago?

For popular shows like The Nutcracker, Phantom of the Opera, Elf, SIX and Jingle Ball, as well as high demand time slots at ZooLights, Lightscape and Jack Frost, it is smart to book several weeks in advance. Big sports games, Randolph Street Holiday Market tickets and bar crawl passes also benefit from early purchase, since prices often rise closer to the date. If you are reading this in early December 2025 and planning for the second week, you should prioritize ticketed events first, then layer in free or flexible activities like Christkindlmarket and outdoor skating.

Plan your second week of December 2025 with ChiVibe

The second week of December 2025 is one of those classic Chicago windows where everything happens at once. You can spend your days drifting between markets, museums and ice rinks, then your nights bouncing from arenas and theaters to club shows, bar crawls and late night pop ups. To keep it all straight, use ChiVibe.com as your command center: track dates, favorite events, compare options by neighborhood and build custom itineraries for each day between December 8 and 14. Check back often as new Chicago events December 2025 are added, and share your own finds so the whole city can vibe with you.