If you’re planning a family staycation or a couple’s trip to Chicago during the winter, 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. Lots of hotels offer packages, so we included some of that info below!

Family Friendly Hotels

• Swissotel Chicago—This hotel is one of our favorites! We have stayed many times. The location is great with a short walk to Millennium Park, Michigan Avenue and the river. It has special “elf”-decorated rooms and a 2,000-square-foot “Santa Suite” that you can either book or stop by on certain dates to take pics, do some crafts, and enjoy hot cocoa. 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 always has the cutest winter packages! This year’s theme is Nordic Night Lights and includes a decorated room, a tent for the kids, books to check out from their Holiday Bedtime Story Cart, an in-room movie, a $50 breakfast credit, and 50% off valet parking.
• 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 – Each winter, the Fairmont Chicago, Millennium Park transforms into the Fairmont Lodge. It’s beautifully decorated, and I recently visited their newest restaurant, Toro, which I highly recommend!
• Hotel Zachary – Hotel Zachary is in Lake View, right across the street from Wrigley Field, meaning the Gallagher Way Winter Wonderland is at your doorstep. There’s lots of holiday decorated bars in the area, Santa Baby is the most family friendly during the day. We LOVE their Teddy Bear Tea and Breakfast with Santa, but tickets go fast. I also love the Outdoor Globes on the Terrace at Alma!
• Park Hyatt Chicago – The Park Hyatt Chicago has been recently remodeled, and the rooms are stunning. It’s perfect for a special occasion staycation – see my video here. The views, service, and rooms are exceptional. Enjoy a 20% discount here. The indoor pool is the perfect size and depth for kids!

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 (see my experience here!). They have packages like “Bed & Breakfast” or “Spa Stay.” From now until January 31, 2025, LH transforms its 22nd-floor rooftop into a festive holiday extravaganza! The views are incredible, and the decorations are adorable.
• 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 – Viceroy Chicago is a cozy and stylish getaway located in the Gold Coast neighborhood. This hotel features warm, inviting spaces for relaxation and offers stunning views from the rooftop bar. One of my favorite holiday restaurants, Butch McGuire’s, is nearby, along with the famous Magnificent Mile.
• The Langham Chicago – The Langham’s lobby and restaurant, Travelle, are stunning year-round, but they are particularly beautiful during the holidays! They also offer a lovely holiday afternoon tea in their Pavilion off the main lobby, and this year’s theme is the Grinch!
• 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!

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:

• My Guide to Chicagoland’s Best Indoor Pools
• Winter Break Activities
• Bright Lights in the Big City: Chicago Holiday Attractions
• Shop Gift Guides

Christine