- Best Splurge: The Waldorf Astoria Chicago, steps from Barneys New York and Prada on the Gold Coast, fits right in with its swanky neighborhood. King rooms come with fireplaces, Italian luxury linens, and extra-large soaking tubs; guests can lounge at the spa, or take advantage of the hotel's fleet of Lexus automobiles to head beyond downtown.
- Best Bang for Your Buck: The Hampton Inn & Suites not only offers consistently lower rates than other hotels in centrally located River North, it's also more stylish than the name implies, with Deco-style touches in the lobby and common rooms. What really sets it apart, though, are the amenities that come with those reasonable rates: an indoor pool with hot tub, rooftop deck, and a free hot breakfast buffet.
- Best Historic Hotels: The Drake Hotel is Chicago's original luxury hotel, and walking into its grand, formal lobby is like stepping back into the 19th century, especially if you settle down for afternoon tea in the elegant Palm Court. The comfortable rooms don't have quite as much character, but those facing north offer only-in-Chicago views of Lake Michigan and Lake Shore Drive. To experience Chicago architectural history first-hand, book a room at the Hotel Burnham, a complete rehab of the revered Reliance Building, one of the world's first glass-walled skyscrapers.
- Best for Business Travelers: Virtually every hotel in Chicago qualifies, but the Swissôtel Chicago combines extensive business services with stunning views from all rooms. Traveler-friendly amenities include generously sized desks and ergonomic chairs in each room, and the light-filled penthouse fitness center allows you to admire the city while working out.
- Best Service: The attention to detail, regal pampering, and well-connected concierges at both the Ritz-Carlton and the Four Seasons make them the hotels of choice for travelers who want to feel like royalty.
- Most Romantic: For a splurge, the Peninsula pampers couples with luxurious rooms and top-notch amenities, including massages in the onsite spa and an outdoor terrace for lounging; the dimly lit, sexy lobby bar makes a good spot for a nightcap, especially if you snag a spot by the fireplace. For a cozier getaway, try the Talbott Hotel, which is centrally located but tucked away from the crowds. Book the hotel's Romance Package, and you'll get a set of monogrammed bathrobes, as well as a late-afternoon checkout.
- Best Views: Almost every hotel in town has rooms with great views—and others that look straight into neighboring offices. The Swissôtel and the Park Hyatt Chicago are both set apart from surrounding buildings, giving their rooms unobstructed views across the city (the higher the room, the more you'll see). For a distinctly urban vista, The Wit Hotel looks out over the Loop's busy El tracks; its rooftop lounge is the perfect place to admire the city lights by night.
- Best for Families: With every room a suite, the Embassy Suites and Homewood Suites are ideal for families looking for a little more space than the typical hotel room provides (units at Homewood Suites also include a full kitchen, so parents can save money by preparing their own meals). Both have indoor pools, so the kids can splash around no matter what the weather, and offer a free hot breakfast buffet.
- Best Hotel Pool: With its floor-to-ceiling windows overlooking Michigan Avenue, the pool at the Peninsula Chicago is a bright, stylish oasis flooded with natural light. But for historic charm, it's hard to beat the Spanish-styled junior Olympic-size pool at the InterContinental Chicago. Considered an engineering marvel when it was constructed in 1929, it was a favorite training spot for Olympic gold-medal swimmer (and later Tarzan star) Johnny Weissmuller.
- Best Off-the-Beaten-Path Hotels: The City Suites Hotel, the Majestic Hotel, and the Best Western Hawthorne Terrace, located in residential North Side neighborhoods, have a more personal feel than many downtown hotels. They're also convenient to public transportation.
Note: This information was accurate when it was published, but can change without notice. Please be sure to confirm all rates and details directly with the companies in question before planning your trip.