Plan your Chicago getaway at these festive Hilton hotels

It’s the most wonderful time of the year in Chicago. festive Shine bright lightsand sing carols alongside The Bean and Cozy cafes We welcome guests looking to warm up inside. Even Chicago hotels are getting in the holiday spirit, with picture-perfect decorations, beloved traditions, and holiday specials and packages.

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

Palmer House

Palmer House

The Palmer House It is one of the most historic hotels in Chicago. With its prime location near Millennium Park, the Art Institute, and the Theater District, the Palmer House 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 November 18 invites guests to enjoy free hot cocoa and Palmer House Brownies to celebrate the start of the holiday season. You won’t want to miss taking pictures in the stunning foyer, decorated with arches, twinkling lights, garlands, and of course, the large Christmas tree.

View the charm of the Palmer House
Palmer House

Add a little magic to your holiday with an amazing performance at The Magic Parlor. Magician extraordinaire Dennis Watkins dazzles audiences with his charm and wit in Palmer House’s intimate and sophisticated exhibition space. The Magic Parlor Holiday Package Includes overnight stays and magic performances on select dates throughout the season. The evening begins at the Lobby Bar, where guests are greeted with festive cocktails before being taken to a secret location within the hotel for a spectacular show.

Celebrate National Brownie Day at the hotel where sweets were invented. The The brownie was created in the Palmer House kitchen When Bertha Palmer, wife of hotel founder Potter Palmer, ordered a mini chocolate treat for the ladies’ lunch boxes at the 1893 World’s Fair. While you can enjoy the sweet treat on National Brownie Day (December 8), the original Palmer House brownie is always on the menu at Lockwood Restaurant and Baralong with a Manhattan brownie cocktail.

Insider tip: Treat yourself to post-holiday shopping at The Spa at Palmer HouseWellness oasis on the fifth floor of the hotel. Unwind with the spa’s signature Chicago Fire and Ice massage, a detoxifying treatment with hot and cooling stones to reduce stress and inflammation.

Hilton Chicago

Hilton Holiday Cocktails
Hilton Chicago

overlooking Grant Park, Hilton Chicago It’s known for its elegant atmosphere, with grand columns, distinctive staircases, and golden crown molding – all beautifully decked out in evergreen wreaths and bows during the holidays. Hilton Chicago kicks off the season with the unveiling of a gingerbread replica of the hotel, followed by the official lighting of the 24-foot tree, on Friday, November 18.

Cake decorating. Start your day with sprinkles! On select dates throughout the holiday season, Herb in Kitchenthe Hilton Chicago Market within the hotel, will serve made-to-order hot cakes and Ready to decorate With sprinkles and edible holiday-inspired decorations.

Set of birthday cupcakes on gray stone background.  Concept of celebrating Christmas and New Year.  Top view.
Hilton Chicago

Take back the classic Home Alone expertise. The Home Vacation Package 2 | Kevin It recreates the 1992 classic by giving guests the chance to live Kevin McCallister’s lavish life in the Conrad Suite – exactly the one featured in the movie. The package also includes a cheese pizza delivered to the suite and a pool reservation so you can practice cannon balls and surprise candy.

Home Alone Holiday Package 2 | Silver tuna It takes the Kevin McCallister experience a step further and includes three nights in the famous Conrad Suite, which will be decorated to the extreme with a recreation of Duncan’s Toy Chest, a fully stocked ‘Wet Bandit Bar’, an in-room holiday party complete with Signature cocktails and appetizers, a daily “Battle Plan” personal agility training session, personal photographer, plus a luxury VIP limousine to and from the McCallisters’ brick house, and more, make this the most-than-best vacation package in town.

Insider tip: Hilton Chicago Call Dibs on the sled parking package It features an overnight stay, self parking, and bottomless coffee or cocoa during your stay.


Ideally located on Michigan Avenue, Drake It stars in many of Chicago’s seasonal festivities. The classic hotel is even decorated for the holidays during the holiday season, starting with a large tree adorned with handmade ornaments that welcomes guests into the lobby.

You might already recognize the hotel as the movie’s elegant backdrop Blues BrothersAnd the dangerous workAnd the My dear friend’s wedding. Designed in the 1920’s Italian Renaissance style, everyone from Winston Churchill to Amelia Earhart to Princess Diana called the Drake home for a night or two.

Enjoy holiday tea in the historic Palm Room. Afternoon tea has been served in the Palm Room for more than a century, and it remains the premier place in town for holiday tea. Palm Court Holiday Tea Service It is hosted seven days a week through January 8, 2023. Holiday carolists and harpists will provide background music on select dates over Christmas. Advance reservations are highly recommended for this popular annual tradition.

Drake Hotel

Take a selfie with Santa. St. Nick himself comes to The Drake to meet the guests and let them know if they’re on the nice list or the naughty ones. The Pictures with Santa holiday package Includes a one-night stay on November 18 or December 2, plus a coupon for three digital selfies with Santa.

Celebrate the New Year at the most historic party in town. Since the hotel’s opening ceremony on New Year’s Eve in 1920, Drake’s Annual Celebration It remains one of the hottest tickets in town. Count down to 2023 with a balloon drop, champagne toast, top local DJs, and plenty of Art Deco chic. Book a general admission overnight accommodations package for up to two adults, tickets to the party, plus free hats, hype and party favors.

Insider advice: The Drake is located in one of Chicago’s most popular shopping districts, The Magnificent Mile. Drake Reserve Drive-In package For Hassle-Free Vacation Shopping: You’ll get luxury accommodations plus drive-in and drive-in privileges at the 900 N. Michigan parking garage.

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