Four Seasons Chicago Rating: 4.5 Pearls
The upscale 346-room Four Seasons Chocago boasts one of the best kids program in town, with amenities such as coloring books, a Bedtime Stories Butler, children's toiletries, babysitting services, a visit from the Ice Cream Man, a welcome gift, and even a doctor on call. There's also a gorgeous indoor pool, and the hotel offers cribs and rollaway beds at no extra charge. Parents will probably enjoy the restaurant from Michelin-starred chef Kevin Hickey, the expansive spa, and the elegant (though somewhat generic) rooms with phenomenal views.
The Waldorf Astoria Chicago Rating: 5.0 Pearls
The Waldorf Astoria may be better suited for couples than families, but it's still a great choice for well-heeled travelers with kids in tow. Rooms are big -- starting at over 600 square feet -- and huge two-room suites are also available, such as the Gold Coast Suite with two queen beds and a sleeper sofa in the living room. Connecting rooms, cribs, and babysitting services are available upon request.
Omni Chicago Hotel Rating: 4.0 Pearls
The Omni Chicago features spacious two-room suites with wet bars (mini-fridges upon request), perfect for families with kids. For larger groups, most of the rooms also have a sleeper sofa in the separate living area, and rollaway beds and cribs are available free of charge. There is also an indoor pool to splash about with the kids after a long day walking around Chicago, and a traditional American restaurant with a children's menu. Kids are welcomed with a backpack upon checking in, and parents are provided with first-aid kits and outlet covers. Young travelers can also borrow books and games during their stay.
Hilton Garden Inn Chicago Downtown/Magnificent Mile Rating: 3.0 Pearls
The comfortable, large rooms of the Hilton Garden Inn all come with a microwave, a mini-fridge, and Disney Channel access, which make it a compelling choice for families. The free cookies and the indoor pool definitely add to the fun of traveling with the whole clan. For families with older children, there are larger suites with two separate rooms, one with a king bed and the other with two queen beds. The on-site restaurant serves comfort food, great for even the pickiest kids.
Hotel Palomar Chicago Rating: 4.0 Pearls
For family-style trips, the Hotel Palomar delivers. They've got welcome gifts for kids, in-room child-safety kits (outlet covers, toilet latches, nightlights), and high chairs and booster seats in the hotel's restaurant. And it doesn't end there -- kids can bundle up in child-size animal print bathrobes, drink "mocktails" during the hosted evening wine tasting, and parents can enjoy babysitting services. Plus, the hotel has an indoor pool, connecting rooms, and a 24-hour concierge service that can recommend kid-oriented activities. Rooms with pull-out sofas and larger suites that can sleep up to five guests make this a perfect pick for families.