If you’re planning a family staycation or a couple’s trip to Chicago during the winter, I can help! We tend to do lots of staycations whether using our Chase Sapphire points (highly recommend if you travel a lot!) or on collaborations with various hotels.

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

• Fairmont Chicago Millennium Park – Each winter, the Fairmont Chicago, Millennium Park transforms into a wintry wonderland called Festive at Fairmont. 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!
• InterContinental Chicago Magnificent Mile – An iconic hotel right on Magnificent Mile! It’s beautifully decorated with a great location and a stunning indoor pool.
• Loews Chicago – Loews Chicago always has the cutest winter packages! This year’s theme is Artic Dreams and includes a pop-up tent for the kids, books to check out from their Holiday Bedtime Story Cart, a $50 breakfast credit, and 50% off valet parking.
• 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. We recently did their Hot Chocolate Bar in the lounge and it’s really cute. Check out their “Playcation” offer here! The indoor pool is the perfect size and depth for kids!
• 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.
• Sofitel Chicago – We just had our first family staycation here! The outdoor decorations were beautiful! We were up on the 17th or 18th floor and the views were great! We stayed in a Junior Suite which had a main bedroom and a living area with a pull out couch for the kids. It was really nice! I have to say that the beds were actually very very comfortable! The start of the Magnificent Mile Lights Parade is just two blocks from the hotel so we were able to easily walk over! See my vlog here!
• St. Regis Chicago – We used Marriott points to stay here and it’s one of our favorite hotel pools. It’s pricey, but if you can use points, I highly recommend! We were upgrading to a junior suite because Marriott members and it was so nice.
• 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.

Hotels and Packages for the Adults

• Arlo Chicago – Arlo Chicago is a hotel on Michigan Avenue steps from Millennium Park that is ideal for a solo or girl’s trip, especially during the holiday season! The rooms have a modern design and smart amenities with a new take on an old landmark building from 1916. See my stay and itinerary here!
• Chicago Athletic Association – This is the final year for Happy’s, the Chicago Athletic Association’s annual over-the-top holiday pop-up bar. This Millennium Park hotel is historic but you can also order room service from the ground floor Shake Shack or the rooftop restaurant, Cindy’s.
• Four Seasons Hotel Chicago – The Four Seasons always decorates beautifully and you know the service will be impeccable! We used our Chase Sapphire points as well and got an upgrade to a suite and free breakfast. Their holiday tea time is also incredible.
• 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 “Mistletoe on Michigan Avenue” package, which includes Prosecco, holiday sweet treats, and a late checkout. The city views are so pretty! Love this for a date night, too.
• 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!
• 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 Peninsula Chicago – Another points trip and it’s so so so nice. Up there in my top 5 favorites. Rooms are spacious, pool is amazing and close to all the holiday activities.
• 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! It’s also a Hilton if you can use points!

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:

• 2025 Chicago Holiday Gift Experiences
• Bright Lights in the Big City: Chicago Holiday Attractions
• My Guide to Chicagoland’s Best Indoor Pools

Christine