13 Chicago Holiday Hotels to Book Now

October 23, 2023

If you’re planning a family getaway or a couple’s trip to Chicago during the holidays, I can help! I’ve rounded up my favorite holiday hotels and packages for you! It can be daunting to know which hotel is right for you, so we divided our list into family and couple packages. No matter where you get your R&R this winter, Chicago will wow you with its decor, service, and sights!

Family Friendly Hotels

  • Swissotel Chicago – This hotel is one of our favorites! For its tenth consecutive season, Santa Claus will check into Swissotel Chicago’s 2,000-square-foot Presidential Suite, debuting a sparkling Holiday Jewel theme. The suite’s decor exudes a magical charm with 17 Christmas trees, each meticulously adorned to represent the 12 birthstones, casting a kaleidoscope of colors throughout the space. They’ve just released a Winter Sale package where you can enjoy up to 20% off your stay when you book by March 29, 2024, for stays through April 30, 2024.
  • Loews Chicago – Loews Chicago has the cutest package, GingerBed + Breakfast. This special staycation includes a spacious room, a tent for the kids, books to check out from their Holiday Bedtime Story Cart, hot cocoa, an in-room movie, a daily $50 breakfast credit and a gingerbread cookie decoration kit, and valet parking for one car per night.
  • Radisson Blu Aqua Hotel – We love these rooms and the location! They have a balcony with Millennium Park or Lake Michigan views! The Radisson is within walking distance of Millennium Park, Navy Pier, and the Mag Mile. They have an indoor pool, a fitness center, an outdoor running track, and a steam and sauna room.
  • Fairmont Chicago Millennium Park – Fairmont Chicago, Millennium Park is delighted to announce the return of Fairmont Lodge for its third consecutive year, running from November 16, 2023, through February 2024. Fairmont Lodge has swiftly evolved into an eagerly anticipated winter tradition, providing the ideal backdrop for celebrating the season in the heart of Chicago. Nestled between Millennium Park and the Magnificent Mile, the Lodge offers a warm and unexpected holiday haven for families, visitors, and neighbors.
  • Waldorf Astoria Chicago – The Waldorf Astoria is the BEST in winter with its amazing lobby decor, in-room fireplaces, and decorated trees! I have stayed here with the kids AND alone for a momcation. It’s one of my favs. Plus, the bar and pool area are really nice!
  • Hotel Zachary – Hotel Zachary is in Lake View, right across the street from Wrigley Field, which means the Gallagher Way Christkindlmarket and Winter Wonderland are literally at your doorstep. The hotel is offering a Winterland Package that includes cocktails in Alma, Christkindlmarket holiday mugs, and admission to Winterland inside Wrigley Field with a skate rental for two! PLUS, we LOVE their Teddy Bear Tea and Breakfast with Santa but tickets go fast. They’ll be released on October 26, so mark your calendar! Their terrace globes open on November 17.

Hotels and Packages for the Adults

  • The Hoxton Chicago – The Hoxton Chicago in the West Loop is swanky and modern! I would love a romantic staycation or a girl’s holiday experience here. This area has tons to do, and it’s not far from Michigan Avenue and downtown. The hotel lobby bar is beautiful, and you can have dinner at Cabra on the rooftop OR drinks at the speakeasy-ish Lazy Bird.
  • LondonHouse Chicago – LH is another favorite of mine. I love their decked-out lobby, rooftop igloos, and afternoon tea. They have a few packages like Bed & Breakfast or spa stays. From November 18th to January 28th, LH will transform its 22nd-floor rooftop into a holiday extravaganza! The views are amazing, and the decor is super cute.
  • The LaSalle Chicago – I checked out this new-ish luxury boutique hotel from Marriott, which was beautiful! The downtown location is perfect, and the rooms are huge and GORGEOUS! Plus, they have 24-hour room service. Book the Christkindlmarket Package to get a deluxe room, two 2023 Christkindlmarket souvenir mugs, and two drink coupons for Gluhwein at the famous market.
  • The Gwen Chicago – This luxury hotel has all the amenities! Rooftop fire pits and curling, amazing restaurants, afternoon tea, and a great happy hour. Check out their “Love in the Windy City” package, which includes Prosecco, a $50 daily dining credit, and a late checkout. The city views are so pretty! Love this for a date night, too.
  • Viceroy Chicago – The Viceroy is going all out for the Holidays this year! Check out their Winter Hut (Available November 26, 2023 – January 28, 2024): Book your chalet experience for a two-hour reservation and choose either a Campfire theme with s/mores kits, or the Romance package with chocolate fondue and champagne. And just FYI, the hut is cozy with pillows and blankets but is not heated. Plus, every Saturday and Sunday, the hotel transforms into a holiday village where you can pick out your Christmas tree and enjoy special treats. Santa and The Grinch will even be there on certain days! Check out their full holiday calendar here.
  • The Emily Hotel – one of West Loop’s newest boutique hotels, has a coffee shop, restaurant, and cocktail lounge. I got to try out their curling experience, and it was so fun and reasonably priced! The downstairs lobby has huge fire pits and heaters!
  • The Langham Chicago – The Langham’s lobby and restaurant, Travelle, are gorgeous during the holidays! Choose from various holiday offers, like the ‘Oh Christmas Tree’ Package, which includes a lux one-bedroom suite with its own Christmas tree, champagne cocktails, and a charcuterie board. The ‘Light Up the Holidays’ Package coincides with the Magnificent Mile Lights Festival and Parade on November 18. Book this deal to get a one-bedroom suite, access to the Langham Club with panoramic city views, and four tickets to reserved seating at The Lights Festival! They also have a beautiful holiday afternoon tea in their Pavilion off the main lobby; this year’s theme is Santa’s Toy Stories!

I hope this helps you plan your holiday staycation in downtown Chicago! There are so many holiday hotels to choose from! Be sure to check out all my Chicago holiday blogs below:


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