It’s the most wonderful time of the year in Chicago. Festive lights shine bright, carolers sing next to The Bean, and cozy cafes welcome guests looking to warm up inside. Even Chicago’s hotels get in on the festive spirit, with picture-perfect decorations, beloved traditions, and special holiday packages and deals.

If you’re looking to make some magical memories this winter, take advantage of all the holiday happenings with a weekend getaway in Chicago. These historic Chicago Hilton hotels promise to bring plenty of holiday spirit with exciting events and seasonal decor that might even inspire a new annual tradition. 

The Palmer House a Hilton Hotel

Palmer House
Palmer House

The Palmer House a Hilton Hotel is one of Chicago’s most historic hotels. With its prime location near Millennium Park, the Art Institute, and the Theatre District, Palmer House a Hilton Hotel has been welcoming guests (including celebrities and presidents) since 1871. During the holiday season, the hotel’s gorgeous lobby brims with holiday cheer, making it a hub of holiday activity.  

Kick off the holiday season at the Palmer House Hotel’s annual tree lighting ceremony. The annual tree lighting event on Nov. 18 invites guests to enjoy complimentary hot cocoa and Palmer House brownies to celebrate the start of the holiday season. You won’t want to miss taking photos in the stunning lobby, bedecked with bows, twinkling lights, garland, and, of course, the grand Christmas tree.

Palmer House magic show
Palmer House

Add a little magic to your holidays with a spectacular performance at The Magic Parlour. Magician extraordinaire Dennis Watkins wows audiences with his magic and mentalism in the Palmer House’s intimate, sophisticated show space. The Magic Parlour Holiday Package includes overnight accommodations and a magic performance on select dates throughout the season. The evening begins at the Lobby Bar, where festive cocktails welcome guests before they’re escorted to a secret venue within the hotel for an awe-inspiring show.   

Celebrate National Brownie Day at the hotel where the sweet treat was invented. The brownie was created in the Palmer House kitchen when Bertha Palmer, wife of hotel founder Potter Palmer, asked for a compact chocolate dessert for ladies’ lunch boxes at the 1893 World’s Fair. While you can indulge in the sweet treat on National Brownie Day (Dec. 8), the original Palmer House brownie is always on the menu at the Lockwood Restaurant and Bar, along with the Brownie Manhattan cocktail.

Insider tip: Pamper yourself post-holiday shopping at The Spa at Palmer House, a wellness oasis on the hotel’s fifth floor. Relax with the spa’s signature Chicago Fire and Ice Massage, a detoxifying treatment incorporating heated and cooled stones to reduce stress and inflammation.

Hilton Chicago

Hilton holiday cocktails
Hilton Chicago

Overlooking Grant Park, Hilton Chicago is known for its elegant atmosphere with grand columns, statement staircases, and gold crown molding — all of which are beautifully adorned in evergreen garland and bows during the holidays. Hilton Chicago kicks off the season with the grand unveiling of the gingerbread replica of the hotel, followed by the official lighting of the 24-foot tall tree, on Friday, Nov. 18.

Deck the donuts. Start your morning with sprinkles! On select dates throughout the holiday season, Herb’ N Kitchen, Hilton Chicago’s in-hotel market, will be serving up hot donuts made to order and ready to decorate with holiday-inspired edible garnishes.

Set of Christmas donuts on gray stone background. Christmas and New Year celebration concept. Top view.
Hilton Chicago

Relive the classic Home Alone experience. The Home Alone 2 Holiday Package | The Kevin recreates the classic 1992 movie by giving guests the opportunity to live the lavish Kevin McCallister life in the Conrad Suite — the exact one featured in the movie. The package also includes a cheese pizza delivered to the suite, a pool reservation so you can practice your cannonballs, and a candy surprise. 

The Home Alone 2 Holiday Package | The Silver Tuna takes the Kevin McCallister experience a step further and includes three nights in the famed Conrad Suite, which will be decked out to the max with a recreation of Duncan’s Toy Chest, a fully stocked ‘Wet Bandit Bar,’ an in-room holiday party complete with themed cocktails and passed hors d’oeuvres, a daily personal training session for ‘Battle Plan’ agility, a personal photographer, plus a VIP luxury limousine ride to and from the McCallisters’ iconic brick home, and more, making it the most over-the-top holiday hotel package in the city. 

Insider tip: Hilton Chicago’s Call Dibs on Sleigh Parking Package features overnight accommodations, self-parking, and bottomless coffee or cocoa during your stay.

The Drake Hotel

Perfectly situated on Michigan Avenue, The Drake Hotel plays a starring role in many of Chicago’s seasonal festivities. The classic hotel is decorated to the nines during the holiday season, starting with the grand tree adorned with handcrafted ornaments that welcome guests into the lobby.

You might already recognize the hotel as the elegant movie backdrop in The Blues Brothers, Risky Business, and My Best Friend’s Wedding. Designed in an Italian Renaissance style in 1920, everyone from Winston Churchill to Amelia Earhart to Princess Diana has called The Drake home for a night or two. 

Enjoy holiday tea in the historic Palm Court. Afternoon tea has been served in Palm Court for over a century, and it’s still the top spot in town for holiday tea. Palm Court Holiday Tea Service is hosted from November through Jan. 8, 2023. Holiday carolers and a live harpist will provide a musical backdrop on select dates through Christmas. Advance reservations are highly recommended for this popular annual tradition.

The Drake Hotel

Snap a selfie with Santa Claus. St. Nick himself is coming to The Drake Hotel to meet with guests and let them know if they’re on the nice or naughty list. The Photos with Santa Holiday Package includes an overnight stay on Nov. 18 or Dec. 2, plus a voucher for three digital portraits with Santa.

Ring in the New Year at the most historic party in town. Since the hotel’s opening party on New Year’s Eve in 1920, The Drake Hotel’s annual celebration remains one of the hottest tickets in town. Countdown to 2023 with a balloon drop, a champagne toast, top local DJs, and lots of Art Deco elegance. Book a general admission package for overnight accommodations for up to two adults, tickets to the party, plus complimentary hats, noisemakers, and party favors.

Insider tip: The Drake Hotel is located right on one of Chicago’s most celebrated shopping districts, The Magnificent Mile. Reserve The Drake Drive-In Package for hassle-free holiday shopping: you’ll receive deluxe accommodations plus drive-in and out privileges at the 900 N. Michigan parking garage.