Whether you’re coming into town for some holiday shopping or to take in the splendor of the twinkling holiday lights, Chicago is a magical place to visit during the holiday season.

Check out some of the top holiday happenings in Chicago this holiday season, plus let the celebrations continue with holiday events and packages at Chicagoland Hilton hotels.

Navy Pier’s Winter WonderFest: take in all the magic of an indoor winter wonderland at Fifth Third Bank Winter WonderFest located in the Pier’s Festival Hall from 12/6/2019 – 1/12/2020. Get a 20% discount on admission for up to 4 tickets plus more great savings with Hilton!   

Millennium Park Ice Rink: skate downtown at the iconic ice rink in Millennium Park. Hilton guests get free ice skates – includes up to 2 pairs of skates per room reservation.

Holiday packages & events:

  • Hilton Chicago: Every year the Hilton Chicago bakes up a Gingerbread City, featuring the Chicago skyline. Make sure to check it out and get your photo in front of the newly added Soldier Field. Plus, decorate (and eat) holiday cookies near the Great Hall Christmas Tree on select dates.
  • Embassy Suites by Hilton Chicago Downtown Magnificent Mile: Really get into the holiday spirit in a suite that’s decked out in holiday cheer. The Christmas Suite Package comes with a tree, lights, hot chocolate and Christmas cookies on your first night stay, and then cookies and milk on your second night stay.
  • theWit Chicago – a DoubleTree by Hilton Hotel: snap a photo of the hotel’s holiday gingerbread express train, baked up by the pastry team and inspired by The Polar Express, Bumble the Abominable Snowmonster, and Elf. The holiday train will be on display through December 30th. Plus while you’re there, take advantage of the ROOF Happy Hour, offering 20% off the entire menu on weekdays from 4:30-7:30. If you’re downtown visiting a local theatre or the Christkindlmarket, show your ticket or mug from your visit to receive one complimentary drink with the purchase of one drink – valid any day of the week except Fridays and Saturdays after 9pm. See site for details. 
  • DoubleTree by Hilton Lisle Naperville: take in the holiday lights at the Morton Arboretum’s Illumination where you’ll enjoy interactive lighting effects on a one-mile paved path along with seasonal music. Book the “Illumination” package to get breakfast for two and transportation to and from the Arboretum included with your stay. Plus, take advantage of other holiday happenings at the hotel. Have breakfast with Santa on December 14 from 8:30AM – 11AM. Enjoy crafts, a magic show, and photos with Santa, plus special holiday room rates starting at $79. And don’t forget to make your reservation for Christmas Day brunch, call 630-245-7650 to reserve.

Shopping packages:

  • The Rose Hotel Chicago/O’Hare, Tapestry Collection by Hilton: looking to visit the Fashion Outlets of Chicago for some pre-holiday shopping? Book the “Snack, Shop, and Slumber with The Rose” package to get complimentary breakfast for two, a Fashion Outlets Saving Pass (worth up to $800 in savings), shuttle service to and from The Fashion Outlets of Chicago, parking at the hotel for one vehicle, late checkout of 2PM, and complimentary passes for coat check and bag hold at The Fashion Outlets of Chicago.
  • Hampton Inn & Suites Chicago Schaumburg: book the “Shop & Stay” package for free hot breakfast, complimentary Wi-Fi and $50 Simon gift card to use at the Woodfield Mall.
  • Hampton Inn & Suites Chicago/Mt. Prospect: visiting Randhurst Village Shopping Center? Check out the “Shop and Drop” package to get a $25 gift card and discounts for area shops in the Randhurst Village Shopping Center, free, hot breakfast, and complimentary parking.
  • Hampton Inn & Suites Chicago/Waukegan: spend your day shopping at Gurnee Mills! Book the hotel’s “Shopping Package” and receive a $25 Simon gift card, savings passport, and swag bag (a $40 value) during your stay.
  • American Girl® Chicago Store at Water Tower Place: stay at some of our nearby hotels to ensure you, your family, and your American Girl Dolls are treated to an unforgettable stay. Book the Homewood Suites by Hilton Chicago-Downtown to get milk and cookies for your kids and their dolls, American Girl Doll fold out beds to take home, a complimentary hot breakfast buffet, and a chance to win an American Girl Doll each quarter – book the package for one Doll or two. Both the Homewood Suites by Hilton Chicago Downtown/Magnificent Mile and Hampton Inn Chicago Downtown/Magnificent Mile have packages that include an American Girl Doll fold out bed to take home plus an American Girl bracelet, popcorn, and an American Girl DVD rental for the night. The Drake, a Hilton Hotel offers a bed for your American Girl, fresh baked cookies and milk with turndown service, and a voucher for a Shirley Temple or Pink Lemonade from the famed restaurant at The Drake.

New Years Eve Packages and Events:

  • The Drake, A Hilton Hotel: Ring in the new year in style in The Drake’s Palm Court for the hotel’s New Year’s Eve Ball with a performance from Rosie and the Rivets, Hors d’Oeuvres, small plates, and a premium bar. Or get your tickets for the Chicago Scene New Year’s Eve Party, offering music from local DJs, over 40 fully staffed bars, a balloon drop at midnight, and more!
  • theWit Chicago – a DoubleTree by Hilton Hotel: plan NYE out at theWit’s famed rooftop with the ROOF’s third annual Monte Carlo Party. Enjoy a platinum open bar, delicious food, live entertainment, roulette, black jack, and more.
  • DoubleTree by Hilton Lisle Naperville: Celebrate New Years Eve with party & dinner packages; call 630-245-7600 for information and reservations.

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