For relatives coming from far away
After a long flight, guarantee your guests get some shut-eye on the padded-headboard beds at Hotel Sax Chicago. For some extra pampering, they can take advantage of the in-room spa services from Windy City Massage. Hotel Sax Chicago, Chicago, (312) 245-0333
For guests with tykes in tow
Tell friends and family bringing kids to give The Four Seasons a heads up about their little ones, and staff members will bring up free child-sized bathrobes, kid-friendly toiletries and milk and cookies at bedtime. The Four Seasons, Chicago, (312) 280-8800
For your parents' friends
Give them a taste of old-world Chicago at The Drake Hotel, which was built in 1920. Guests can relax in marble bathtubs and dine in any of the four onsite restaurants. The Drake Hotel, Chicago, (312) 787-2200
For your friends
The Affinia Chicago is a modern boutique hotel right on the Magnificent Mile, so your friends can walk to the Water Tower and Navy Pier. When they're not shopping or sight-seeing, they can sip cocktails on the hotel's rooftop lounge. Affinia Chicago, Chicago, (312) 787-6000