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The Ultimate Chicago Holiday Bucket List
Lakeshore Blog

The Ultimate Chicago Holiday Bucket List

If there’s a few things that come to mind when you think of the Windy City; jazz, deep dish, and Christmas. The holiday season in Chicago is a magical time in which the city erupts in cheer and goodwill. With so many festive activities to choose from in Chicago this winter, it may be difficult to prioritize for your trip. With you in mind, our team has consolidated them into an unofficial bucket list that will ensure you experience the best Christmas in Chicago has to offer.

Image Courtesy of Choose Chicago

Take a Picture with the Millennium Park Tree

The starting gun to the holiday season in Chicago is the Tree Lighting Ceremony in Millennium Park. A tradition that spans centuries, the ceremonial lighting kicks off the cheer the Saturday before Thanksgiving. The Tree Lighting Ceremony is accompanied by the Lights Festival, a parade that treks the length of the historic Magnificent Mile.

Millennium Park is Chicago’s municipal backyard with over 300 acres of public space. During the holiday season, the Park embodies the infectious Christmas cheer of the city. Ice skate in Millennium Park or take in the city’s extravagant official Christmas tree which rivals any other US city in both size and stature.

Drink Hot Cocoa at Christkindlmarket

Christkindlmarket is a season-long, open-air daily Barvarian market. Every year, over one million visitors flock to this market to celebrate Christmas traditions from around the world. International vendors showcase holiday wares from handmade ornaments to paper lanterns.

After strolling the market and peaking at all of the unique wares, warm up with a hot beverage, served in a signature collectible market mug.

The original market located downtown at Daley Plaza is where it all began, but their multiple locations have also popped up in the Chicagoland area at Wrigley Field and in Napervile.

Take in the Zoo Lights at Lincoln Park

Lincoln Park Zoo’s animals may be in hibernation, but the Zoo is most certainly not. Throughout winter, the Lincoln Park Zoo puts on an epic lights display nightly. The Lincoln Park Zoo Lights is not only a festive display of neon and decorations.

During Zoo Lights, the Lincoln Park Zoo comes alive with ice sculpture, carolers, and more! Bring the whole family every night of the holiday season.

Say Cheers at a Christmas Pop-Up

Parents, we haven’t forgotten about you. While there is a lot of family fun to be had in Chicago during the holiday season, the adult fun also gets into the whimsy of the season.  

Some bars and restaurants take their cheer to the next level and allow the holiday spirit to transform their space.

Frosty’s Christmas Bar is returning for another season of holiday shenanigans. The space is almost as expansive as the North Pole, featuring four bars and three floors of over the top décor guaranteed to shake off the humbug.

National Lampoon’s fans can raise a reindeer glass at The Griswold’s, a pop-up bar tribute to the cult classic, Christmas Vacation. The pop=up bar will even feature a full-size replica of the family living room.

Graystone Tavern’s 8 Crazy Nights Hanukkah Pop-Up Bar where they toast to the Jewish holiday with a booze-infused jelly donut.

Find the Perfect Present on Michigan Avenue

Michigan Avenue is the shopping mecca of the Midwest, a stretch of retail spaces that have earned the namesake “The Magnificent Mile”. From the Water Tower Place mall to the dozens of flagship stores, Michigan Avenue is the destination for unique gifts that will truly delight.

Already got your Christmas list taken care of? The Avenue is still worth a stroll just to see the elaborate window displays that adorn the storefronts.

Feeling depleted from Christmas shopping? Stop in the world’s largest Starbucks, the flagship store that just opened on Michigan Avenue November 2019. The Chicago Roastery embodies the brand in a multi-floor concept space.

Tiled dome ceiling of the Historic Macy's on State Street in Chicago.
Image Courtesy of Macy’s

Dine at the Walnut Room in Macy’s on State


The Macy’s on State Street has a heritage that spans the city’s history. The epic flagship retail space is opulent, featuring Tiffany vaulted ceilings and thirteen floors of retails space. While the festive window displays and expansive retail selection are more than enough reason to stop by this historic building, the Macy’s on State Street is a holiday attraction for more than just Christmas shopping.

On the top floor, the Walnut Room was the first restaurant ever to open in the retail space in 1907. Every year, the space is adorned with elaborate holiday décor and a 45 foot Christmas tree. There’s not many ways that you can go wrong on the Walnut Room menu, but the pot pie is a mainstay. While reservations at the Walnut Room are hard to come by, you can always arrive early and browse for gifts as you wait to be seated.

When you’re looking to get into the holiday spirit, look no further than Chicago. The city that never hibernates takes seasonal celebrations up a notch. However you celebrate, there’s something for you this season in downtown Chicago.  While it’s impossible to do it all in Chicago this holiday season, this bucket list is a sure-fire way to get into the spirit. To learn more about our holiday offers at the Fairmont Chicago, click here.

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