The Holidays are Here – and You Don’t Want to Miss These Chicagoland Happenings

‘Tis the season to get out and explore. Whether you’re hunkering down in the city for the long term, plan to make a leap to suburbia in the new year, or simply want to get a sense of what’s out there, the holidays are a great time to get a feel for different communities.

Our advice? Start with some of these must-see holiday events and experiences. Scattered throughout Chicagoland, these annual go-to’s attract locals and visitors, giving you a chance to get in the mix. And when you’re done? Grab a quick bite, check out some area shops, or drive through nearby neighborhoods and get a feel for what life could be like if you made a move.


Our Favorite Holiday Happenings in Chicago

#1. Christkindlmarket (Daley Plaza)

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Also opening November 17 and running through Christmas Eve, the Christkindlmarket Chicago mirrors traditional European holiday markets – think eclectic shopping, family-friendly, and cultural activities, all infused with local charm.

While strolling the market, snag one-of-a-kind gifts, sample seasonal treats, and explore some of the most unique vendors around – and you’ll quickly see why this market is one of our holiday favorites. But we aren’t alone: last year, the Christkindlmarket Chicago was named the #3 holiday market globally and #1 outside Europe.

Bonus: Christkindlmarkets are also popping up in Aurora and Wrigleyville, ensuring everyone can indulge in the seasonal fun.

#2. Lincoln Park ZooLights (Lincoln Park)

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Be prepared to be dazzled. Launching November 17 and running through January 7, 2024, this year’s event includes new displays, festive photo ops, and tons of interactive programming, plus plenty of traditional favorites – the Light Maze, Ferris wheel, live ice carvers, and Main Mall light tunnel, for starters.

We’re especially excited about the brand-new garden-themed light show on the South Lawn. After exploring this installation, head to the Pepper Family Wildlife Center, which transforms into the North Pole – and is home to the zoo’s holiday tree and Santa himself. Then, to wrap your visit, grab a festival cocktail, cocoa, or seasonal snack from Snowy’s Spirits & S’mores. This holiday-themed pop-up bar even includes fire pits for s’more roasting.

Pro tip: While it’s $7 for general admission ZooLights tickets (and $10 on Fridays, Saturdays, and holidays), it’s FREE to visit on Mondays. Reservations, though, are still required.

#3. Light Up the Lake (Navy Pier)

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The largest indoor/outdoor holiday experience in Chicago, this seasonal event is not to be missed. From November 24th through New Year’s Eve, Navy Pier hosts a stunning lakefront light display, outdoor ice skating, holiday workshops, and more. Enjoy s’mores making, browse local vendors and artisans, and try unique activities (axe-throwing, anyone?).

Other highlights: live music each weekend, rides on the heated Centennial Ferris Wheel, and Saturday night fireworks. Plus, get free gift wrapping on your market purchases – and, during select times, grab a pic with Santa.

Tip: Bring your own skates, and it’s free to hit the rink. Tickets for axe-throwing, ice skating, and other ticketed activities can be booked online, starting now.

#4. Thanksgiving Parade (Various Locations)

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This year’s parade kicks off at 8:00am, from the corner of State Street and Ida B. Wells Drive, marching north to Randolph Street – and it will be one for the books. The big news? The beloved giant inflatable balloons are back, including Cookie Monster, Cat in the Hat, Kermit the Frog, Care Bears, and the Grinch. Other highlights: live cultural performances representing the city’s diverse population and appearances from HGTV’s Lauren Makk, Chicago’s Poet Laureate avery r. Young, plus country stars Reyna Roberts and Tayler Holder.

Expert tip: If you join in person, grab a spot underneath the “L” by the Harold Washington Library. Here, you’ll see inflatables do the “balloon limbo.”

#5. Polar Express (Union Station)

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One of the season’s most magical experiences, the Polar Express departs from Union Station for an hour-long trip to the North Pole. Once on board, travelers can sip hot cocoa and snack on shortbread, served by dancing chefs, while reading along with the classic book, The Polar Express by Chris Van Allsburg.

Before the journey ends, guests will each receive a special gift from Santa and his helpers and will have a chance to join in on caroling and other onboard entertainment, just like in the beloved film.

Insider tip: A sensory-friendly train for people with autism or sensory processing disorders will run on December 31 at 2:00pm. In addition to modifications to accommodate guests, there will be a designated quiet car on the train for those who need a break from the performance.

Our Favorite Holiday Happenings in the Suburbs

#1. Happy Holiday Railway (Union)

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Explore the winter countryside with Santa Claus on this 40-minute train ride from the Illinois Railway Museum in Union. Enjoy hot cocoa and seasonal treats, take in an all-new animated light show and holiday song performance.

Post-trip, check out the holiday lights display surrounding the museum, including a spectacular animated snow plow display, historic trains and streets, and the Model Railroad Exhibit – heated, indoors, and perfect for a quick warm-up.

The fun kicks off November 24 and runs through December 23 – be sure to check the website, though, since rides don’t happen daily.

Pro tip: This event features animated lights. For those travelers averse to bright or strobing lights, head to car #7658 for all the entertainment with more traditional lights and decorations.

#2. NaperLights (Naperville)

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Stroll through downtown Naperville for a free winter wonderland, running daily from Thanksgiving through New Year’s Day. Each day will feature stunning light displays, festive music, and a drive-through experience for people wishing to stay in their cars. No matter how you experience NaperLights, you’ll enjoy more than 150,000 lights, giant holiday figures, carolers, ice dancers, and a flying reindeer or two taking off from the Marquette building.

Expert tip: Be sure to snag your 3D viewing glasses at the event – and check the calendar for live performances and other special events throughout the season.

#3. Warm Bevy Walk & Open House & Window Decorating (Evanston)

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Holiday shopping just got a whole lot better. On December 14 from 4:00pm-7:00pm, head to downtown Evanston and explore dozens of shops, restaurants, and other businesses offering warm beverages and shopping or dining deals. Tickets are $10 per person, and a portion of ticket sales will be donated to a local nonprofit.

Also happening in downtown Evanston? The 9th Annual Holiday Window Decorating Contest. Kicking off Small Business Saturday (November 25), Evanston businesses will decorate their windows with a “Glitter & Glow” theme. Check out all the windows, then vote for your favorite on the Evanston Holiday Window Contest Facebook page. Winners will be announced December 23.

#4. Carriage Rides & Caroling (Long Grove)

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Every winter, historic downtown Long Grove transforms into a vintage holiday wonderland with old-world charm, quaint shops, and more. Starting November 17, hop into a horse-drawn carriage for a ride around downtown (kids under 5 are free). Another favorite? Starting December 2, enjoy local holiday carolers from Buffalo Grove High School, Stevenson High School, Long Grove Community Church, and more. Check the website for schedules and additional information.

Pro tip: Be sure to pre-register for the 10-seater carriages and, to save time, print and complete your waiver before arriving.

#5. Holiday Magic @ the Zoo (Brookfield)

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Starting November 24, the Brookfield Zoo will be illuminated with more than two million twinkling LED lights, a 41’-tall tree and  animated displays, choreographed to seasonal tunes.

Chicagoland’s longest-running lights festival features plenty of Instagram-worthy backdrops, including a 20’ orb and 3D gingerbread house, plus a 600’-long Tunnel of Lights. In addition to the light displays, many of the zoo’s animal buildings will be open, as well as the onsite restaurants and gift shops. Advanced reservations are not required but are strongly encouraged. Doors open at 3:00pm each day.

#6. Lightscape at the Chicago Botanical Garden (Glencoe)

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Running November 10 through January 7, 2024, this after-dark experience is about holiday cheer. Stunning light installations take over the Garden every season, including Evening Island. This year features classics like the Winter Cathedral, several first-time displays, music, festive snacks and drinks, and many interactive experiences.

Pro tip: Get in the Lightscape spirit. Download the 2023-2024 playlist on Spotify, perfect for playing on your drive to the Garden.

#7. It’s a Wonderful Life Pop-Up Bar (Brookfield)

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A twist on a classic: on Saturday, December 9, Joe’s Saloon in Brookfield hosts its 3rd Annual “It’s a Wonderful Life” pop-up bar. Join George Bailey and get your wings, all to support BEDS Plus, a nonprofit working to end homelessness in the local community.

Starting at 7:00pm and running til 11:00pm, this popular event brings all the feels from this iconic film to life. Step into the world of Bedford Falls, experience re-enactments from the movie and grab a drink in the meticulously designed space built to mirror Martini’s.

Tickets include an open bar with movie-inspired cocktails and snacks, including Clarence’s flaming rum punch, then test your knowledge with “It’s a Wonderful Life” trivia — bonus points for dressing like your favorite character.

This is just a taste of the holidays in Chicagoland. We want to know: what’s your can’t-miss seasonal event? Comment below. 

Written by @properties
@properties Christie’s International Real Estate is Chicagoland’s #1 brokerage. Through our affiliation with Christie’s International Real Estate, our network spans nearly 50 countries. No matter your real estate needs, we’ve got you covered.