Chicago has plenty of options for families on the go. The Hampton Inn & Suites keeps the kids in a good mood with a pool, Nintendo, and proximity to the Hard Rock Cafe and the Rainforest Cafe. Children 17 and under stay free in their parent's room. Kiddies also stay free at the Chicago City Centre Hotel & Sports Club, which has a large outdoor pool, access to an indoor pool at an adjoining health club, and is near Navy Pier and the beach. The Best Western River North Hotel won't win any prizes for its no-frills decor, but it's one of the best values in River North and lies within walking distance of many family restaurants. The indoor pool and outdoor deck -- with great city views -- are another big draw.
When you want a little extra room to spread out, both Homewood Suites and Embassy Suites make traveling en masse a little easier with separate bedrooms and kitchenettes (so you can save money on food). The Hilton Chicago has lots of public space for wandering, and many of the rooms come with two bathrooms.
Of course, luxury hotels can afford to be friendly to all of their guests. At the Four Seasons Hotel, kids are indulged with little robes, balloon animals, Nintendo, and milk and cookies; the hotel also has a wonderful pool. The concierge at the Ritz-Carlton Chicago keeps a stash of toys and games for younger guests to borrow, and kids' menu items are available 24 hours; the hotel even provides a special gift pack just for teenage guests. The upscale Westin Chicago River North also caters to families with baby accessories and programs for older kids, respectively.