The Wintrust

Lights Festival Countdown:

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Partake in all Michigan Avenue has to offer with a number holiday packages and events at the hotels including the return of the Chicago Dibs hotel packages by Hiltons of Chicago. Hotel packages around The Magnificent Mile district include special rates, free/discounted parking and holiday treats!



Hiltons of Chicago

The Drake Hotel, Hilton Chicago and Palmer House, a Hilton Hotel’s forty-foot locomotive float will steam along The Magnificent Mile jingling and mingling with Mrs. Claus as Michigan Avenue illuminates the start of your holiday season during the Wintrust Magnificent Mile Lights Festival procession.

The celebration & train doesn’t stop there.

These Hilton Hotels in Chicago have countless celebrations to add some sparkle throughout your holiday season. Kids (and parents) will delight with holiday afternoon teas, a full host of holiday events, and kid friendly packages like Photos with Santa in addition to holiday letter drop off with reply from Santa at The Drake Hotel.

Future chefs will love the Saturday morning deck-orate the donuts series, annual tree lighting ceremony held on November 18th at 4pm, at the Hilton Chicago.  Nice Listers will receive text messages from Santa and they’ll want to keep an eye out for Santa’s lost buttons on their way to polar plunge at the indoor pool, for a chance to score a nice list pass from Santa and special treat from the elves.

Kiddos will delight at the enchanting tree lighting ceremony on November 18th at 11am with Joffrey Ballet and trying some brownies which were invented at Palmer House, a Hilton Hotel. Learn more about holiday events, seasonal celebrations and exclusive holiday experience at all 3 Hilton Hotels surrounding the Magnificent Mile this holiday season. Visit HiltonsofChicagoDibs.com

  • The Drake Hotel

    Photos with Santa Holiday Package

    The night before Mr. Claus makes his impressive entrance at The Wintrust Magnificent Mile Lights Parade, on November 18, 2022, he arrives at The Drake Hotel for a very special occasion…

    An exclusive photo opportunity will be available with Santa for those that reserve the Photos with Santa Holiday Package including overnight stay on November 18. The package also includes a voucher for three digital images provided by email for download and to print own portraits to share with your loved ones throughout the holiday season. Stroll down for Photos with Santa and let your kids, friends and/or pets check-in with Old Saint Nick and smile big for that special picture that will become a cherished keepsake for your holiday décor.

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  • Palmer House A Hilton Hotel

    Photos with Santa Holiday Package

    A very special guest will arrive later that day… Santa Claus makes his entrance at Palmer House, a Hilton Hotel the night before he participates in The Winturst Magnificent Mile Lights Festival. Take family, friend or pet photos with Santa, making an annual holiday tradition a little less of a chore by combining with a festive getaway for this weekend’s festival. The Photos with Santa Holiday Package includes an overnight stay for up to two adults/two children, photo session with Mr. Claus on Friday Night November 18 and three digital images, delivered by email to share with your loved ones.

    A Magical Experience Holiday Package

    At Palmer House, a Hilton Hotel is where the Magical Christmas happens this year… The Magic Parlour Holiday Package includes overnight accommodation and an intimate evening of classic magic with Dennis Watkins on select dates throughout the season. The award-winning, third-generation magician delivers an evening of sophisticated tomfoolery unlike anything else. Guests gather at the Lobby Bar to enjoy a cocktail prior to the show. You’ll be escorted to a secret venue for 75 minutes of magic… The package is bookable online, $82 per guest per ticket.

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  • Hilton Chicago

    Home Alone 2 Holiday Package | The Kevin

    In the 1992 classic, Home Alone 2: Lost in New York, the memorable and heartwarming scene where Kevin and his family are reunited on Christmas morning was not shot in New York but in the Hilton Chicago’s Conrad Suite. In 2019, Hilton Chicago launched a limited time Home Alone 2 Package allowing guests to live the lavish Kevin McCallister life with exclusive themed experience in the original Conrad Suite featured in the movie. This year, the historic hotel is bringing that back with two new experiences – The Kevin and The ‘Silver Tuna’ of Holiday Offers. 

    The package includes a whole Cheese pizza from Herb ‘N kitchen, made especially by our Executive Chef who is Pizza-aioli certified. A pool reservation for Cannon Ball Practice, Suite accommodations, Paint Can for Sticky Bandit candy fill-ups at HNK and an ADA approved toothbrush.

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    Home Alone 2 Holiday Package | The Silver Tuna

    The Silver Tuna of Holiday Offers is as lavish as the name suggests. With this package, guests will be hosted in the famed Conrad Suite, a lavish 5,000-sq.ft. Suite spanning two floors making it perfect for the entire family. Just like in the movie, the suite will be fully decorated with holiday décor – with one guest room transformed into Duncan’s Toy Chest. An array of ‘silver tuna’ amenities will be available including a fully stocked ‘Wet Bandit Bar’, a special ‘turtledove’ ornament, Rocking Around The Christmas Tree holiday party complete with in-room themed cocktails and passed hors d’oeuvres, daily personal training session for ‘Battle Plan’ agility, a personal photographer, and much more. Guests will also take a VIP luxury limousine ride to and from the McCallisters’ iconic brick and white column house while enjoying a personal pizza and champagne. And in true holiday spirit, a donation to the local children’s hospital will be made in the guests’ name along with a delivery of cheese pizza for the nurses, doctors and first responders at the hospital.

    To reserve The Silver Tuna Package, or for more information, guests can reach out to the hotel at (312) 922-4400, requesting Silvia Aleszczyk. A three night stay minimum is required. For stays now through December 30, 2022

Holiday Packages

  • The Talbott Hotel

    The Talbott Hotel welcomes The Magnificent Mile Association guests to stay and receive 15% off guestrooms.

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    Join The Talbott Hotel for a delicious breakfast and a special visit from Santa. Bring the whole family for pancakes, applewood smoked bacon, scrambled eggs, toast, and fresh orange juice or milk!
    December 3, 10, and 17 from 9:00 a.m. – 2:00 p.m.

    $22 for adults and $17 for kids (ages 3-12)

  • Four Seasons Hotel Chicago

    Stay Longer

    Spend more time experiencing the very best of Chicago – it's on us. Book this offer to receive a complimentary third night at Four Seasons Hotel Chicago on Chicago's Magnificent Mile.

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  • The InterContinental Chicago Magnificent Mile

    Celebrate the holiday season with a festive visit to The InterContinental Chicago Magnificent Mile. A stunning display of glittering holiday décor right on The Mag Mile and an exciting weekly event series is sure to make the season bright. Make your spirits bright by joining a champagne cocktail class, soak up live jazz in the hotel's art deco lobby while sipping on a hot bourbon cider, and more.

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  • Swissotel Chicago

    Santa Suite

    Stop by Santa’s Presidential Pad at the Swissotel Chicago with up to 20 guests to visit the man of the season and overindulge in unlimited Swiss hot cocoa, champagne and holiday treats. Kids can enjoy holiday crafts, cookie decorating and face painting, complete with a visit from Santa.

    Holiday treats to include Iced Molasses Cookies, Reindeer Chow, White Chocolate Brownie Tarts, Mixed Berry SnoBalls, Peanut Butter Cherry Bars with Golden Peanuts, Vanilla, Apple and Dulce de Leche Verrine.

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  • Claridge House Chicago

    Sweater Weather

    It's sweater weather! All you need is a cozy sweater and a good book. Book our Sweater Weather package and receive up to 40% off of your stay at Claridge House Chicago.

    Book by November 30, 2022, and stay by March 31, 2023. Minimum two-night stay required. First night deposit required at time of booking. Refundable if canceled more than 72 hours prior to check-in date. Based on availability. Blackout dates apply.

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  • Hyatt Centric Chicago Magnificent Mile

    Book Now & Save

    Book your room with the Hyatt Centric Chicago Magnificent Mile during the month of November to received 15% off. Offer valid for stay dates through April.

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  • Eurostars Magnificent Mile Chicago

    Enjoy 10% off your stay with Eurostars Magnificent Mile Chicago when booking using code MAGMILE.

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