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Holiday Hotel Packages

This festive season, book your home away from home with special rates from hotels on The Magnificent Mile. Elevate your stay with unique winter packages perfect for a long weekend getaway or a full week of winter fun! 

Featured for The Festive Season

Read on for featured holiday highlights. Head back to The Festive Season on The Magnificent Mile landing page for more great ideas, and be sure to visit our Shopping, Dining and Events Calendar to see what else is happening around The Magnificent Mile district through the new year! 

  • The Peninsula Chicago

    Holly Jolly Family Holiday Package
    • In-room holiday tree or Menorah
    • Holiday welcome amenity
    • Access to a library of holiday themed movies, books, and games
    • Daily Peninsula breakfast for four (two adults and two children)
    • Daily valet parking 

    This package is offered for stay dates between November 26, through December 30, 2021.

    Merry and Bright Couple’s Holiday Package
    • In-room holiday tree or Menorah
    • Bottle of red or white wine or Champagne upon arrival
    • Holiday shopping US$ 100 gift certificate from Neiman Marcus to use at the Michigan Avenue store
    • Daily Peninsula breakfast for two adults
    • Daily valet parking 

    This package is offered for stay dates between November 26, through December 30, 2021.

    Book Your Stay

  • Chicago Marriott Downtown Magnificent Mile

    Enjoy 50% Off your Second Room for the Holidays

    Bring the family together for holiday shopping, festive Chicago lights, and enjoy 50% off your 2nd room.

    Moments are better when we share them together. Bring the family to the Chicago Marriott Downtown Magnificent Mile to experience holiday shopping, festive lights, and to make endless memories in the Windy City this holiday season.

    With this offer, enjoy 50% off your second room, complimentary daily self-parking, milk and freshly baked cookies for the family, plus two cocktails at Reviver bar for the adults.

    Discount applied upon arrival if the second room is occupied by children aged 16 and under at the time of stay. Hotel may provide connecting guestrooms pending room type requests at the time of reservation.

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  • Embassy Suites by Hilton Chicago Downtown Magnificent Mile

    Deck the Halls Suite

    Embassy Suites by Hilton Chicago Downtown Magnificent Mile "Decks the Halls," while you bring the Holiday Cheer! The Christmas Suite Package comes with your suite decorated with a holiday tree, lights, a special holiday welcome amenity, a faux fireplace and more. Book for arrival between November 20, 2021 and December 30, 2021

    BOOK YOUR STAY
  • Trump Hotel Chicago

    Holiday Indulgence Package

    Make this Holiday indulgent. Enjoy the morning at the spa or spend time at the pool with the kids. Later gather the family as our executive chef has prepared a ribeye dinner to be enjoyed in the privacy of your home-away-from-home for up to 5 people.

    Includes a whole salt-crusted ribeye, chef's selection of sides, and chef's choice of dessert.

    Offer terms and Conditions: This offer is for new reservations only and can not be combined with any other promotional offers. Cancellation policy is 72 hours prior to 4 PM local time day of arrival. Cancellations made within the cancellation period will be assessed a charge of one night plus applicable taxes. Dinner is only offered on December 25th 2021 Christmas day. No substitutions allowed. Reservation must be guaranteed with a valid credit card at the time of booking. Offer is subject to availability and blackout dates apply.

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    Baby It's Cold Outside Package

    Cozy up in one of our specious guest rooms with some Hot Toddies and enjoy winter morning with a warm breakfast in bed or at Terrace 16.

    Baby its Cold Outside package features:

    • Overnight accommodations for two
    • Two Hot Toddies (or other warm beverage of choice) in Rebar
    • $60 Breakfast credit for 2 guests, for use in In-room dining or Terrace 16

    Offer valid for bookings with stay dates December 1, 2021 through December 25, 2021. Subject to availability and blackout dates apply. New reservations only. Must be booked 48 Hours in advance. Rate is per room/per night, based on double occupancy, exclusive of taxes, gratuities, fees, and other charges. Any unused food and beverage credit may not be combined and/or rolled over, nor be applied to future charges. No refund or credit for unused portions.

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    Home for The Holidays

    This holiday season, guests can travel to Chicago without missing a day of the yuletide spirit. Upon arrival, your Grand Deluxe Suite will be decorated with a Christmas tree, personalized stockings hung by the fireplace and milk and cookies at turndown.  

    Available for stays December 3 through December 25, 2021, the Home for the Holidays package features:

    • Grand Deluxe Suite accommodations for two nights
    • In-suite faux Christmas tree
    • Holiday welcome amenity
    • Stockings hung by the fireplace
    • Milk and cookies turndown amenity 

    Offer terms and Conditions: This offer is for new reservations only and can not be combined with any other promotional offers. Cancellation policy is 72 hours prior to 4 PM local time day of arrival. Cancellations made within the cancellation period will be assessed a charge of one night plus applicable taxes Reservation must be guaranteed with a valid credit card at the time of booking. Offer is subject to availability and blackout dates apply.

    Book Your Stay
  • Four Seasons Hotel Chicago

    Festive Getaway

    Join the festive fun for a memorable holiday retreat that includes a Hotel credit of USD 100 per stay. On select Saturdays, guests may also enjoy complimentary cookie decorating. This offer is available when booking a minimum of two nights, by using "STAYCREDIT2021" online, or call 312-280-8800 and mention "STAYCREDIT2021". This offer is valid until December 28, 2021. Black-out dates may apply. 

    BOOK YOUR STAY
  • Swissotel Chicago

    The Swissôtel Chicago Santa Suite is back for the eighth consecutive year and Santa Claus is ready to show off his swanky Chicago pad! Each year the Swissôtel Chicago Presidential Suite is transformed into Santa’s home-away-from-the-Pole for the holiday season welcoming Chicagoans and visitors alike. The suite offers sweeping views of the city, where Santa can closely monitor the weather patterns before his busy Christmas Eve and provides a cozy retreat for finalizing his naughty and nice list. This year for the holiday season, Santa is taking a more intimate approach with his planned festivities by offering deluxe accommodations and private experiences, outlined below.

    Overnight accommodations for the 2021 holiday season include:

    Holiday Penthouse Hideaway
    • Available to book in the Santa Suite and Duplex Suite.
    Santa Suite
    • Stay where Santa calls home when he visits the Windy City! This spacious, 2,000-square-foot Presidential Suite is decked out for the holidays featuring countless glistening Christmas trees complimented by sweeping views of the magical winter cityscape. The suite sleeps up to six guests who will be welcomed with a cheerful pop of champagne and holiday treats. Then, wake up to daily breakfast and cozy up with the kids, in the comfort of your own space, with toys and games, holiday crafts, letter writing to Santa, cookie decorating and a build your own Swiss Hot Cocoa bar. In addition, overnight parking, a $50 donation to SOS Children’s Villages Illinois and a keepsake holiday ornament are also included in the package, starting at $1,500/night. Available to book Mondays through Thursdays from November 20 through December 26.
    Duplex Suite
    • This two-story loft suite is 1,200 square feet and features spectacular views of the Chicago River and skyline adorned with festive holiday décor. Sleeping up to eight people at $1,200/night, guests will enjoy a welcome champagne toast, holiday treats, daily breakfast, holiday crafts, letter writing, cookie decorating, build your own Swiss Hot Cocoa bar, overnight parking, a $50 donation to SOS Children’s Villages Illinois and a keepsake holiday ornament. Available to book Mondays through Thursdays from November 20 through December 26.
    Elf Decorated Room Package
    • Book an Elf Decorated Room to enjoy a quaint and cozy space with a festive welcome amenity upon arrival. Available to book starting November 20 through December 26 at $339/night, families can also upgrade the experience for $100 to include kid toys, books and games to enjoy in the comfort of your own room.
    Trees of Hope Room Offer
    • Available to book now through January 31 at $139/night, guests are invited to give back this holiday season by supporting SOS Children’s Villages Illinois. $10 of the daily room rate is donated to the organization, bringing holiday cheer to children in need.
    Book Your Stay
  • Omni Hotel Chicago

    Oh What Fun It Is To Stay

    This holiday season, celebrate what fun it is to stay with Omni Chicago Hotel! Enjoy even more winter fun with 15% off our best available rates and a $25 hotel credit.

    Book Your Stay
  • Sheraton Grand Chicago Riverwalk

    Elf Life Suite

    It's the most wonderful time of the year at Sheraton Grand Chicago Riverwalk! Spend this holiday season at your home away from home in downtown Chicago. Experience striking views of the lake, river and Chicago cityscape from an Elf Life Suite that includes festive decorations, beverage coupons to Link Café for hot chocolate, candy canes and an elf to bring back home as well as a 2PM late check-out. Have a cup of cheer and magical stay this December!

    Book Your Stay
  • Waldorf Astoria

    Waldorf Winter Escape Package

    Cozy up to an in-room fireplace to experience an unforgettable winter family getaway to Waldorf Astoria Chicago. Families are invited to add the Waldorf Winter Escape Package to their reservation and upgrade their stay with a complimentary valet, a cozy room upgrade, an in-room movie featuring seasonal and family favorites, movie theater-style popcorn, and other theater amenities to keep warm and watch with. Dependent on room type, younger guests will be surprised to find a play tent and teddy bear waiting in their rooms upon arrival. Even four-legged family members can experience Waldorf Astoria luxury with a range of services and amenities for their paws only.   

    Book Your Stay


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