1. The St. Regis Chicago
Chicago (and, let’s be honest, the world) has been waiting for this undulating tower by Jeanne Gang—the tallest building in the world by a female architect—to open for years, and the wait was worth it: Glorious city, lake, and river views, a stellar hotel gym, two restaurants with an indoor pool and outdoor terrace, and a butler for every room (even in the entry-level category), all set in an easily accessible corner of downtown conspire to truly raise the bar on what a city boutique hotel can be. Bring your workout clothes. The roughly 12,000-square-foot Athletic Club is free to guests and has every brand and type of machine you love. There are also three group fitness rooms and a set schedule of classes, from yoga to mat Pilates. Sweat it out, then jump in the pool.
2. The Gwen, a Luxury Collection Hotel, Michigan Avenue Chicago
The Gwen is named for Gwen Lux, a Chicago–born pioneering female sculptor of the 20th century and a fitting icon for the Chicago installment of Marriott’s Luxury Collection, which aims to make each hotel reflect the character of its place. The hotel, located on the city’s famed Magnificent Mile and in the landmark McGraw-Hill building—with its 1928 facade wholly preserved—does just that. Art Deco interiors with taupe- and gold-hued rooms emanate old-fashioned glamour and chic modernity all at once. The rooftop bar and restaurant, Upstairs at the Gwen, is buzzy as can be when the weather is nice, and your best shot for mingling with a crowd beyond the hotel’s typical guests on business travel.
3. Four Seasons Hotel Chicago
Tranquil and refined, the Four Seasons towers over Lake Michigan. The residential-style rooms make you feel like the most luxe of locals, as do the concierges, who are so skilled and accommodating that they may even be able to score those coveted Bears tickets. On floors 30 to 46, rooms have stellar skyline views and suites have doors that separate living from sleeping quarters, but even the smallest rooms have a residential feel with armchairs, matching ottomans, and circular dining tables. Dinner at Adorn is a must, and come summer, the hotel has a private 52-ft yacht experience for guests to experience the beauty of Lake Michigan and the buzz of the Chicago River by boat.
4. The Peninsula Chicago
This high-rise hotel might be home to the city’s best-kept secret: a sprawling, 80-foot pool some 19 floors up, with floor-to-ceiling windows and a view you can’t peel your eyes from. You could easily spend all day there in unperturbed bliss—block off a whole day to alternate between dips in the pool. Fortunately, there’s plenty of relaxing to be done in the guest rooms, many of which are more spacious than a Chicago apartment. You know a hotel is at the top of its game when the towels are so plush they feel as though they were woven on-site and there are neatly labeled amenity drawers so you don’t have to pry each one open to find what you’re looking for. Peninsula hotels are known for their intuitive technology (in-room tablets let you control the lights, request housekeeping, and check your flight status). If you’re in need of a good night’s sleep, spend a night at a Peninsula hotel.
5. Viceroy Chicago
Set in the Gold Coast Historical District, the contemporary-chic Viceroy has a retro Chicago façade and mid-century furnishings within. Textures and patterns grab the eye, including an abstract headboard wall, a carpet that looks like a sand-hued topographic map, and—yes—quotes from Marcel Proust, reproduced on the lobby’s 30-foot wall. You’ll love the Southwestern–style throw pillows and the teal curtains, which inspire tranquility at night, while the Nespresso machine serves a valued purpose in the morning. Don’t skip their onsite restaurant, Somerset, which serves seasonal American fare and classic cocktails like the Gold Rush and State (aptly named for the hotel’s location) with bourbon, Amaro Montenegro, and honey.