Chicago Holiday Hotel Packages For A Festive Stay

Holiday Season

At Aloft Chicago Mag Mile guests can experience holiday magic by booking the Christkindlmarket Package which includes breakfast for two and one 2023 Christkindlmarket souvenir mug at check in (people come from all over to collect these mugs!). While strolling to the Christkindlmarket, the hotel’s prime location makes it easy to squeeze in some holiday shopping along the festively decorated Mag Mile. This package is valid through December 26, 2023.

The Blackstone’s Stay Like A Kennedy Package (Through January 1, 2024) invites guests to experience an enchanting escape filled with festive extravagance. The Suite of Presidents will transform into an immersive homage to the lavish 1960s Kennedy White House décor. Complete with historical accents that transport guests to the captivating Kennedy Christmas, the Stay Like A Kennedy package invites travelers to sip hot cocoa spiked with JFK’s favorite scotch and craft personalized Christmas ornaments while classic holiday tunes serenade you from a vintage record player. Embrace an over-the-top escape filled with festive enchantment and create cherished memories at The Blackstone, where history and luxury meet in the heart of Chicago’s iconic Cultural Mile. Rates start at $550 per night. 

  • From January-March 2024, the Presidential Suite will transform into The Winter of Jazz package, welcoming guests to experience the whimsical historic atmosphere of The Blackstone through an immersive musical stay. The package includes an in-room hot cocoa bar, a collection of iconic albums, and beautiful vintage decor, celebrating a timeless era of smooth tunes.

The Four Seasons Chicago’s festival holiday packages include a festive-themed welcome amenity, an in-room visit from the festive ice cream cart, nightly valet parking for one vehicle, and a USD $50 donation to the Chicago Cares Festive Drive. Package valid for selective bookings between November 20, 2023 – January 2, 2024.

At Hilton Chicago, discover the true meaning of Christmas in Chicago. Inspired by the all-new original holiday movie premiering November 5, the Santa Summit suite is made with Hallmark devotees in mind. Be surrounded by Santas of all shapes and sizes and get cozy in your Santa-themed bed — cookie kit included.

Hotel Zachary’s Winterland Package includes 2 complimentary drink vouchers for cocktails in Alma, 2 throwback Federal League stocking hats, 2 Christkindlmarket holiday mugs, and admission to Winterland inside Wrigley Field with skate rental for two. (Skating is open daily, except select holidays, from November 21, 2023 to January 7, 2024, weather permitting.) 

At InterContinental Chicago Magnificent Mile, St. Nick’s best friend is back and he’s visiting Chicago to ensure the kiddos have been nice! This winter, stay steps away from all the holiday festivities and shopping on the Mag Mile while your family interacts with The Elf on the Shelf. The Elf on the Shelf Family Package includes overnight accommodations, an elf on the shelf doll (parents responsible for moving the doll) and breakfast at Center Court. The doll is also available for purchase if you’d like to bring your new mischievous friend home!

The Langham, Chicago announced its 2023 holiday season accommodation, dining, and activities offers. Reservations are available for booking now:

  • ‘Santa’s Toy Stories’ Holiday Tea at the Pavilion – Celebrate the magic of the season and childhood memories by delighting in the timeless tradition of afternoon tea with loved ones. Indulge your taste buds with delectable pastries and tea sandwiches while creating a personalized Letter to Santa during this quintessential ‘Santa’s Toy Stories’ themed tea experience. Offered daily from November 24, 2023 – January 7, 2024; reservations can be made via Tock
  • ‘Oh Christmas Tree’ Package – Celebrate the spirit of Christmas in your home away from home. This special package includes luxurious one-bedroom suite accommodations with a lavish in-suite Christmas tree; deconstructed champagne cocktails inspired by the season; bespoke cheese and charcuterie–ideal for an intimate tree-side respite. Reservations can be made here; Booking & offer period until December 31, 2023. 
  • Visit with Santa – Share your Christmas wishes with Santa at the Flavours of Langham shop, located on the second-floor lobby. Offered December 2, 9, 10, 16, 17, 23, 24 from 1:00 – 4:00 p.m., and December 25 from 11:30 a.m. – 3:30 p.m. No tickets or reservations are needed. 
  • Tree Lighting Celebration at The Langham, Chicago – Gather with loved ones as you sample offerings from the hot chocolate bar and enjoy a festive performance from holiday carolers during The Langham, Chicago’s annual tree-lighting celebration. Saturday, November 25th from 4:00 – 7:00 p.m. Located in the second-floor lobby; No tickets or reservations are needed.  

GingerBed + Breakfast at the Loew’s Chicago  welcomes families with a sweet seasonal stay – spacious guest rooms complete with a holiday tent, seasonal movie, Holiday Bedtime Story Cart, and hot cocoa. Head down to ETA for a delicious breakfast (daily $50 breakfast credit) and your little ones can enjoy decorating Gingerbread cookies while they wait. Valet parking for one vehicle per night. The offer ends on January 10, 2024. 

Sheraton Grand Chicago Riverwalk’s one-of-a-kind Elf Life Suite features festive decorations, a hot cocoa bar, candy canes, an elf to take back home, breakfast for two adults and two children and a 2 p.m. late check-out. This package is available to book between now and January 1, 2024 for stays between November 23, 2023 and January 7, 2024. 

  • But that’s not all! Sheraton Grand Chicago Riverwalk is also offering The More, The Merrier package because moments are better when we share them together. Book The More, The Merrier room package and bring the extended family along to receive 50% off a second room (connecting if available). This offer cannot be combined with any other promotions. Book between now and February 29, 2024, for stays through February 29, 2024. 

For the tenth year, Swissôtel Chicago will transform its 2,000-square-foot Presidential Suite into Santa’s Chicago holiday home. Family and friends can book Santa visits, pop into the hotel’s holiday speakeasy, or wake up surrounded by 17 Christmas trees in the Santa Suite.

  • Too busy to spend an overnight but want to make it a party? Stop by Santa’s Presidential Pad 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. (Multiple dates between  Dec 2 and Dec 22, 2023, and a portion of the proceeds will be donated to SOS Children’s Villages Illinois.)

Celebrate the holiday season along The Magnificent Mile with The Peninsula Chicago’s Holly Jolly Family Package built for the whole family. With an in-room holiday tree or menorah, holiday welcome amenity, access to our holiday library of movies and games, and more, our Holly Jolly Family Holiday package will make your season bright. 

  • Or opt for the Merry and Bright Package for a pair of adults. (Valid for stays from November 24 through December 31, 2023.)
  • Afternoon Tea during the festive season at The Peninsula Chicago is an annual tradition for many guests. The 20-foot Christmas tree and lavish holiday décor enhance this special experience, which features a traditional English tea menu including a variety of finger sandwiches, scones with house-made preserves and Devonshire clotted cream, and petite seasonal pastries. Vegan and gluten-free options are available. Entertainment includes performances from a string duo daily, plus visits from Santa on weekends from 3:30 pm – 5:30 pm*. (Daily from November 24, 2023 through January 7, 2024. Seatings are at 2:30 pm and 4:30 pm. Pricings start at $140 per adult (including a glass of Champagne) and $65 per child (ages 5-12) Monday-Thursday and $150 adult/$85 child on Friday-Sunday.)
  • Additionally, did you know that The Peninsula Sky Rink is the only hotel skating rink in Chicago? Returning for its 11th season on November 18, this 2,100 sq foot synthetic ice rink is tucked into a winter wonderland featuring festive music and snowflake lighting. Surrounded by Chicago’s skyscrapers and twinkling lights, guests can enjoy a selection of hot beverages and snacks available at the Chalet. The Sky Rink is available for groups to rent or for private events, such as marriage proposals. Skates are available to rent for $20 for adults and $10 for children 12 and under, with 100% of the skate rental proceeds donated to two Chicago children’s charities: Ann & Robert H. Lurie Children’s Hospital of Chicago, and Hephzibah Children’s Association.
  • For more information on Chicago holidays, visit Choose Chicago.

Celebrate the Holidays in Chicago: Great Happenings

Running now through January 7, 2024, Lightscape at the Chicago Botanic Garden (located in Glencoe, Chicago’s North Shore) returns for its fifth season with an illuminated outdoor trail dazzling with brand new installations from around the world and beloved returning favorites such as the Winter Cathedral and a reimagined version of the Fire Garden.New works from international artists include Lilies, from UK artist Jigantics (illuminated 5-foot lilies float elegantly on water, providing a mesmerizing view from the bridge above and igniting a sense of warmth and excitement), Night Lights, from French artist TILT (delicate lamp-shaped lights that extend nearly 19 feet high amplify a cozy atmosphere with a display of soft ambient colors) and Sea of Light, from UK artist Ithaca (thousands of individually controlled balls of LED light make Evening Island sparkle and dance their way to a bespoke soundtrack in multiple patterns and colors). Tickets sell out quickly so it is recommended to book your time and date in advance; advance tickets for adults (non-members) begin at $34 and children (ages 3-12) at $19. 

The Christkindlmarket celebrates its 27th season at Daley Plaza, its fifth year at Gallagher Way in Wrigleyville, and its second time at RiverEdge Park in Aurora.  This year, Christkindlmarket is introducing its first ceramic beer stein with a holiday-themed design ($20), as well as location-specific $8 souvenir mugs with unique designs at each market (for example: the Chicago mug shows off downtown landmarks like the City Hall building and Daley Plaza’s Picasso sculpture while the Wrigleyville mug shows off Hotel Zachary, the intersection sign of Clark & Addison, and much more.) These mugs are hotly anticipated collector’s items for locals who have turned Christkindlmarket into a holiday tradition since 1996. Modeled after the 16th-century holiday markets in Germany, the free-admission outdoor bazaar is a hub for traditional German fare, delightful warm beverages and handcrafted gifts for purchase, and charming holiday vibes the entire family can enjoy. And now in its third year, another popular favorite is back – the annual Christkindlmarkt ornament, hand-painted and glass blown in Europe, portraying a market scene with holiday elements on its ice blue background ($41 at all info booths).

  • Admission to the market is free but food, beverages, and handcrafted gifts all must be purchased. All markets open on November 17; Aurora and Chicago locations close on December 24 and Wrigleyville on December 31. 

Christmas Around the World and Holidays of Light at the Museum of Science and Industry (running through January 7, 2024) is a beloved annual tradition that began in 1942 with a single tree. Today the Museum features a four-story floor-to-dome Grand Tree, surrounded by more than 50 trees and displays decorated by volunteers to represent holiday traditions from cultures around the world.

This year the museum will also be celebrating the wonders of snow, with an exhibition in the Lower Court featuring intricate photographs of snowflakes taken by Caltech physicist Ken Libbrecht.

Illumination: Tree Lights at The Morton Arboretum (Though January 6, 2024) invites visitors to celebrate the holidays and marvel at how light transforms a magnificent landscape. Journey along a 1-mile paved walking path (that is fully ADA compliant for guests with limited mobility), amid festive music and lighting effects, explore exciting new features and immersive installations. Afterwards, warm up by a cracking fire and roast marshmallows for s’mores, or stop in one of the concession tents for a snack and beverage. Ginkgo Restaurant in the Visitor Center will serve dinner guests view the display’s finale on Meadow Lake. The Arboretum Store will also be open for holiday shopping; gifts include a special temperature-activated, color-changing ceramic mug that will be available for purchase during all Illumination dates. Tickets start at $28 per person for nonmembers. 

People ice skating at the McCormick Tribune Plaza Ice Rink in Chicago’s Millennium Park; December 2021.

The McCormick Tribune Ice Rink in Millennium Park offers ice skating all winter, through March, weather permitting.  Admission is free, but online reservations are required and skate rentals are available. You’ll be surrounded by the downtown skyline, with magical Christmas lights from the City of Chicago Christmas tree reflected in ‘The Bean’ / Cloud Gate sculpture. OR, head over to Maggie Daley Park, right next to Millennium Park, to the picturesque Skating Ribbon that meanders around snow-dusted pine trees and whimsical play spaces. The path is twice the length of a lap around a traditional skating rink. 

The Immersive Nutcracker: A Winter Miracle (November 24 – December 31, 2023) at Lighthouse Artspace Chicago brings cutting-edge technology to meet the artistry of ballet dancers. This mesmerizing 30-minute immersive experience, set to Tchailkovsky’s music, weaves the classic tale of Marie and her toy nutcracker. Join them, on their magical adventure through the Land of Sweets, brought to life by renowned ballet dancers and innovative projection mapping technology. Pricing begins at $29.99 per person. 

  • While you’re here… Lighthouse ArtSpace Chicago is bringing a new pop-up bar experience, Bar Humbug, to reign in the holiday season. The ArtSpace will be transformed into a winter wonderland with wall-to-wall holiday scenes. A lot like traditional German beer halls, there will be long tables and plush banquettes for groups to gather. Bar Humbug will present live musicians and DJs playing the holiday classics. Guests must be 21 to enter.

ZooLights Presented by ComEd and Invesco QQQ will include new and exciting LED light displays,  photo ops, and interactive programming including a never-before-seen garden-themed light show on the zoo’s South Lawn. Festive photo ops will dot the zoo, as well as costumed characters and Victorian carolers on select nights. Food and beverages including festive cocktails and hot cocoa will be available at Edie Levy’s Landmark Café. Snowy’s Sprits & S’more and various snack stations around the zoo. Check the calendar for special events such as sensory-friendly nights, a family-friendly New Year’s Eve celebration, and adults-only evenings. General admission ZooLights tickets are $7 per person. Tickets on Fridays, Saturdays, Thanksgiving Eve (Nov. 22), and New Year’s Eve (Dec. 31) are $10 per person. As part of the zoo’s ongoing commitment to accessibility, general admission is FREE on Mondays. Ticket sales from ZooLights directly support the zoo’s world-class animal care, global conservation efforts, and innovative learning programs and help keep the zoo free to the public 365 days a year. ZooLights will run through January 7, 2024. 

For more information on Chicago holiday happenings, visit Choose Chicago.