Midnight Fever
Time Out
Time Out

The best things to do in Chicago this week

Find the very best things to do in Chicago this week, including cultural events, festivals and shows.

Shannon Shreibak
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Last updated December 29, 2025: From world-class New Year's Eve events to exciting local happenings, there is no shortage of ways to celebrate the final days of 2025 in Chicago. Even if you’re sticking to a budget, the city offers a wealth of free seasonal activities to keep your spirits high. Read on for our curated guide to the best events happening around town this week.

RECOMMENDED: Discover the best things to do in Chicago in January 2026

Time Out Market Chicago

Best events in Chicago this week

  • Things to do
  • Loop

For the first time in its history, "Dick Clark’s New Year’s Rockin’ Eve," America’s most-watched New Year’s celebration, will broadcast live from Chicago, featuring the program's inaugural Central Time zone midnight countdown. Chicago native Chance the Rapper will host the live festivities and perform the countdown, joined by sets from other Chicago acts throughout the night, including Shemekia Copeland and J. Ivy. The celebration will take place along the Chicago Riverwalk at Wacker Drive (from Wells Street to Lake Street) and will include programming from ART on THE MART, a fireworks show and more.

  • Things to do
  • Streeterville

Spend the last hours of the year getting high when you party on the 94th floor of one of Chicago's tallest buildings. 360 Chicago's New Year's Eve party allows you to gaze at the skyline from above all night long while enjoying a complimentary glass of sparkling wine, light bites and access to cash/credit bars at CloudBar. Your ticket also includes unlimited rides on the observatory's TILT attraction, though you might want to take advantage of this perk before you begin buying drinks. At midnight, you'll have an amazing view of the various New Year's Eve fireworks displays bursting in the sky around you. 

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  • Things to do
  • Concerts

Midnight Fever returns for Time Out Market Chicago's best New Year's Eve experience yet by transforming the market into a three-story celebration. Chicago house music legend, Derrick Carter, takes over the decks for a special disco-infused set to ring in the new year.

  • Music
  • River West/West Town

Get ready to groove! The Salt Shed is hosting an epic disco dance party to ring in 2026, and we're spinning the best from ABBA, Donna Summer, Cher and all your favorite legends. Calling all dance queens, kings and regents to the floor! On-theme attire is highly encouraged—let's be honest, you need one last reason to rock those hot pants before the new year.

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  • Nightlife
  • Loop

Drink and dance among 2,000 guests spread throughout eight rooms at the Congress Plaza Hotel's New Year's Eve Party, featuring DJ Maximo, DJ Commando, DJ LG and a host of other entertainers, plus a buffet and multiple bars. General admission gets you in the room with all the action, but VIP ticketholders are granted additional perks, like early entry and access to balconies. Make sure you have a drink in your hand for the balloon drop at midnight.

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  • Things to do
  • Streeterville

Navy Pier's Latin-inspired restaurant, Bar Sol, will host an extravagant celebration featuring multiple levels of dynamic live entertainment, delectable gourmet appetizers, a premium drink package and unparalleled front-row views of the spectacular fireworks display at midnight. Elevate your experience with VIP admission, granting access to exclusive rooms and additional seating, or secure a table reservation for optimal views.

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  • Things to do
  • River North

Lettuce Entertain You's riverfront Italian restaurant is throwing a party that will offer guests close-up views of the fireworks along the water. Enjoy passed apps, pizza stations, a midnight toast, signature cocktails, a live DJ and more. Looking for a more private experience? Book a table or booth for up to 10 people.

  • Things to do
  • River North

Lettuce Entertain You’s popular tropical bar is transforming from a sandy paradise to a snowy winter escape for the season. Sip on special holiday cocktails, like the Cranberry Mai Tai, Hot Buttered Rum and Eggnog Grasshopper, served in charming and festive vessels and glassware. Guests can even pick up their own mugs to take home or gift from the bar’s retail shop.

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  • Nightlife
  • Late-night bars
  • Logan Square

For those hoping to close out the year in the epicenter of Logan Square, The Owl has you covered. For the beloved late night bar's New Year's Eve shindig, a DJ will be spinning all night long while guests enjoy an all-inclusive drink and buffet package. Arrive bright-eyed and ready to party into the wee hours: This event spans from 8pm to 1am.

  • Attractions
  • Parks and gardens
  • East Garfield Park

Feeling stressed by winter's cold weather and lack of leaves on the trees? Take a calming walk through hyacinth, zinnias, salvias, cosmos and other flowering blooms at Garfield Park Conservatory's annual winter flower show (which is titled "Merry & Bright" this year for ultimate festiveness). Like the rest of the Conservatory, access to the show is free—just be sure to make an online reservation ahead of your visit. 

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  • Things to do
  • Ice skating
  • Millennium Park
  • Recommended

Situated in the heart of downtown Chicago with the city's sweeping skyline as a backdrop, the Skating Ribbon at Maggie Daley Park is a winter attraction unlike any other. Skaters can lace up and wind around a winding ice-covered path that's twice the length of a lap around a traditional rink. Reservations for the popular ice rink should be made in advance, as they tend to fill up quickly.

  • Things to do
  • Exhibitions
  • Hyde Park

Every year, the Griffin Museum of Science and Industry puts up its four-story Grand Tree and surrounds the towering pine with more than 50 trees that represent Chicago's various communities and their respective holiday celebrations. Visitors will be able to take in even more seasonal cheer at the accompanying Holidays of Light exhibit, which recognizes the traditions of Chinese New Year, Diwali, Kwanzaa, Ramadan, Hanukkah, Visakha Puja Day and St. Lucia Day. 

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  • Things to do
  • Late openings
  • Lincoln Park

To see one of the largest displays of holiday lights within city limits, you need to head to Lincoln Park Zoo, where the annual ZooLights display strings up millions of LED blubs. While most of the animals will be keeping warm inside, visitors are welcome to wander through the park, snapping photos of the various displays and taking part in a variety of activities throughout the holiday season.

  • Musicals
  • Loop

Andrew Lloyd Webber's bombastic megamusical haunts the Cadillac Palace for a spectacular eight-week run. The age-old tale of love, loss and revenge unfolds against the Baroque interior of the Cadillac Palace Theatre—transporting you straight to late 19th-century Paris. 

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  • Kids
  • Streeterville

Relive cherished holiday memories—and make plenty of new ones—at Navy Pier's Winter WonderFest. Admire twinkling light displays bedecking Navy Pier's Festive Hall and prepare to be awed by a 42-foot holiday tree. Plus, there's no shortage of activities—for both kids and adults—at Winter WonderFest: Enjoy live music and special performances at the Winter Wonder Stage, lace up for a round of ice skating, enjoy tasty treats and sips and much more.

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  • Lake View

Experience the holiday classic, It's a Wonderful Life, as a 1940s-style live radio play this holiday season at The Athenaeum Center. Set in the venue's Paradiso space, every seat guarantees an intimate experience of George Bailey's renewal of faith in himself, his family and his community. Whether you're returning as part of a cherished holiday tradition or discovering the story's magic for the first time, this production is sure to lift your spirits.

  • Nightlife
  • Pop-ups and food events
  • Wrigleyville

This immersive, multi-level Christmas pop-up bar boasting wall-to-wall holiday decor returns to Wrigleyville, taking over Stolen Saddle during the most festive time of the year. You'll find photo ops galore as well as drinks decked out with decorative garnishes and garlands, including large-format cocktails. Feeling hungry? Feast upon festive options like Santa's Smash Burger, Festive Fry Flight and Grinch Shake. Don't forget to snag a reservation before you head to Santa Baby—families are welcome to stop by during the day, but after 8pm it's 21+. For full holiday hours, check Santa Baby's website.

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  • Things to do
  • Millennium Park
  • Recommended

Every year, Millennium Park is adorned with an epic Christmas tree that remains on display until the beginning of the new year. The larger-than-life attraction is festooned with twinkling lights and crowned with an illuminated star. Spectators can check out the festive tree near Washington Street and Michigan Avenue through early January. 

  • Things to do
  • Exhibitions
  • Suburbs

The Chicago Botanic Garden hosts this annual (and quick to sell out) display of festive lights, giving guests a host of shimmering reasons to visit the forest preserve during the holiday season. Set along an illuminated path, the after-dark experience features a series of installations to explore, including a 110-foot tunnel made up of 100,000 lights and a group of trees festooned in bulbs that “sing” holiday songs. 

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  • Things to do
  • River West/West Town

If you're jonesing for an outdoor Christmas adventure this year, the folks behind Jack's Pumpkin Pop-Up are bringing back its winter sibling in Fulton Market. The sprawling two-acre attraction boasts a Christmas market, photo opportunities and a variety of activties like ice skating, bumper cars, axe throwing, curling and more. You'll also have the opportunity to sip on boozy hot cocoa and other holiday cocktails while wandering through a light-filled Christmas tree walk.

  • Things to do
  • Festivals
  • Suburbs

More than two million lights cover the trees, fences and structures in the Brookfield Zoo at this annual holiday event, which is now in its fourth decade. Guests can walk through a 300-foot-long tunnel featuring colored lights synchronized to music, spot larger-than-life illuminated animal sculptures, gaze up at a 41-foot-tall lit tree and warm up with concessions such as funnel cakes, pizza, spiced wine and hot cocoa. 

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  • Things to do
  • Festivals
  • Wrigleyville
  • Recommended

The Cubs may be hibernating for the winter, but Gallagher Way provides some excellent reasons to hang out in Wrigleyville during baseball's offseason. The Wrigley Field-adjacent space hosts a variety of seasonal activities, including photos with Santa, a winter market, carnival rides and holiday movie screenings. Opening on November 23, you'll be able to shop for gifts, sip a hot beverage and enjoy delicious treats through December 31. Visit the Winterland website for hours and additional information about programming.

  • Nightlife
  • Pop-ups and food events
  • Lake View

Chicago's only Hanukkah-themed pop-up takes over The Graystone Tavern in Wrigleyville for another year, filling the bar and weatherproof patio with more than 30,000 blue-and-white lights, dreidel ornaments, lighted menorah and a Hanukkah sweater wall (among other festive bits of decor). Dine on Hanukkah classics like latkes and matzo ball soup alongside not-so-classic options like boozy jelly donuts. 

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  • Nightlife
  • Pop-ups and food events
  • Loop

Happy’s is back for its farewell season, and they're closing out a holly, jolly run in full holiday spirit. Situated on the ground floor of the Chicago Athletic Association, Happy's transforms the hotel's Tank space into a holly, jolly wood-paneled dive bar serving cocktails and bar bites. Admission is free, and the pop-up is just a short walk from the Millennium Park ice skating rink.

  • Nightlife
  • Pop-ups and food events
  • River North

Frosty's Christmas Bar near Goose Island brings three levels of festive fun, four bars, two dance floors, life-size toy soldiers and a themed soundtrack that keeps the crowd bumping well past midnight every night of the week. Don your favorite holiday attire and enjoy a glass of something boozy and marshmallow-topped while eating Christmas cookies amidst the twinkling lights, tinsel and over-the-top decorations.

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  • Things to do
  • Ice skating
  • Millennium Park
  • Recommended

Skate under the Chicago skyline and within eyeshot of the Chicago Christmas Tree at the McCormick Tribune Ice Rink in Millennium Park. Plus, take advantage of free skating lessons on most Saturdays and Sundays, where you can learn both beginner- and intermediate-level skills. Note that you'll need to make a free online reservation for both regular skating and lessons, and if it seems too warm to skate, call ahead.

  • Things to do
  • Streeterville

Located on the terrace of The Peninsula Chicago, the 2,100-square-foot Sky Rink offers ice skating in the shadows of the city's tallest buildings, all while overlooking Michigan Avenue. Show off your skills in a winter wonderland featuring snowflake lighting and festive music, and when you need to warm up, grab a hot drink and snack at the Chalet.

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  • Things to do
  • Festivals
  • Suburbs

Ready to get into the holiday spirit? The Morton Arboretum's annual holiday light show returns for its 13th anniversary as a mile-long, walk-through spectacle of LED lights and music, featuring a blend of new and returning light displays set amid 50 acres of trees. Back again this year is "Electric Illumination," a series of late-night parties with DJ-curated playlists that will synchronize progressive house and '80s dance beats with the light shows, as well as "IllumiBrew," a special evening where guests can sample beers and ciders from local breweries. 

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  • Things to do
  • Armour Square

See Christmas lights while staying warm at this pandemic-era innovation that allows visitors to drive through a gleaming tunnel of more than one million LED lights synchronized with holiday music. Plus, the show takes place in Bridgeport at Rate Field, home of the Chicago White Sox.

  • Drama
  • Loop
  • Recommended

The Goodman Theatre’s annual holiday production of the Charles Dickens classic returns to the stage, with Christopher Donahue and Austin Tichenor taking on the role of Ebenezer Scrooge. The play has been a staple of the Goodman's calendar for more than 40 years, allowing returning attendees and new generations to see the quintessential Christmas story unfold before their eyes. Prepare to be visited by three spirits—and don't be suprised if A Christmas Carol's touching tale of redemption makes you shed a few tears.

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  • Things to do
  • River North

Lettuce Entertain You’s popular tropical bar is transforming from a sandy paradise to a snowy winter escape for the season. Sip on special holiday cocktails, like the Cranberry Mai Tai, Hot Buttered Rum and Eggnog Grasshopper, served in charming and festive vessels and glassware. Guests can even pick up their own mugs to take home or gift from the bar’s retail shop.

  • Nightlife
  • Pop-ups and food events
  • Lake View

The 2003 holiday movie Elf takes center stage at this Wrigleyville pop-up located inside of Stretch Bar & Grill, which gets dressed up with more than 1,000 decorative elves, Christmas trees and plenty of festive Christmas lights. Want to catch a glimpse of Buddy the elf himself? Visit the pop-up between Thursday and Sunday, when he's known to make appearances from time to time. 

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  • Sports and fitness
  • Yoga & Pilates
  • Streeterville
  • Recommended

Head to 360 Chicago on Saturdays for yoga with a killer view. Instructor Britta Eumann will lead an hour-long class on the 94th floor of 875 North Michigan Avenue (formerly the John Hancock Center) that’s suitable for all ages and skill levelsyou just need to bring your own mat and arrived properly dressed. Registration is $55 and includes a cocktail or coffee, plus admission to the observation deck so you can stick around and snap some photos after you're done striking poses on the mat.

  • Kids
  • Exhibitions
  • Streeterville

“Take Care with Peanuts: The Exhibit” is an immersive fan experience inspired by a global initiative of the same name. Based on the captivating world depicted in Charles M. Schulz’s iconic comic strip, the exhibit brings the beloved Peanuts gang to life through interactive displays and hands-on activities promoting self-care, empathy and environmental stewardship. 

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  • Things to do
  • Festivals
  • Recommended

Every two years, Chicago becomes a global hub of architecture and design during the Chicago Architecture Biennial. This edition’s theme is SHIFT: Architecture in Times of Radical Change, bringing together over 100 projects by architects, artists and designers from 30 countries—each piece engaging with the cultural, social and environmental fluxes transforming our world.

Not sure where to start? Check out our first-timer's guide to the exhibition. Stay up-to-date by visiting the Chicago Architecture Biennial website.

  • Things to do
  • Exhibitions
  • Avondale

With soundstage-sized pieces like horned sculptures emitting soap bubbles, inflated spheres bedecked in abstract squiggles and surreal faceless figures hovering in space, “EmotionAir” reimagines the humble balloon as any other artistic medium—a conduit for creativity and emotion. 

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  • Drama
  • Lincoln Park
  • 5 out of 5 stars
  • Recommended

In Peter Shaffer’s Amadeus, genius is not just a blessing: It’s a declaration of war. Composer Antonio Salieri sees himself as one of its principal casualties. Once the darling of the 18th-century Viennese court, he watches in mounting horror as “the creature”—his term for the rising musical prodigy Wolfgang Amadeus Mozart—launches an artistic takeover that endangers not just Salieri’s career but his very conception of himself.

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