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In the Loop, you can always find someone running to catch a train, coffee in hand. It’s in the business district of Chicago, named after the loop that the elevated train makes around a rectangle. With an “L” stop at almost every corner, Millennium Park’s famous Cloud Gate and an abundance of luminescent theaters to visit, a stay in the Loop means the best of Chicago is right on your doorstep.
Sharing the same building as the James M Nederlander Theatre, the Cambria Hotel is an ideal retreat after witnessing the bright lights of Chicago’s theater district. Inside the bar and lobby, you’ll find a sleek combination of blueprint-style art and a sci-fi-reminiscent palette of cobalt blues and metallic leather furniture. For business travelers, each contemporary room maximizes comfort and convenience, featuring a 40in flat-screen TV, an executive desk with an ergonomic chair and free high-speed Wi-Fi. In the evenings, treat yourself to a bit of friendly competition on the foosball and pool tables in the game room.
The 1890s Venetian Gothic building of the Chicago Athletic Association hotel exudes old-world charisma. The playful spirit of its former life as an exclusive sports club echoes throughout the 20th-century-style rooms. Pommel horses double as ottomans, and boxing-style robes await in the Carrara marble bathrooms. Explore all the nooks and crannies of the former athletic club, including the original lap pool and enigmatic game room. When it comes to dining, you are spoiled for choice – the Cherry Circle Room’s farm-to-table fare and the sun-drenched atrium of rooftop restaurant Cindy’s are just two of the options.
Take advantage of Kimpton Gray Hotel’s curated concierge service, which offers help with everything from bar recommendations in the Loop to engagement surprises on the beach. Top-notch amenities include the on-site Tie Bar, bikes to rent and Lululemon yoga mats in the fitness center. The bedrooms are the epitome of simple sophistication, lined in textured wallpaper with luxurious linens in a palette of soothing grays and blues.
LondonHouse Chicago resides in a striking Beaux-Arts structure, one of Chicago’s original skyscrapers. Previously housing radio studios and jazz clubs, the 22-story building now comprises a state-of-the-art gym, a tranquil spa with eco-friendly treatments (try the Warm Honey Drizzle) and glamorous rooms with sweeping views of the Chicago River. The jewel in its cloud-brushing crown is the three-floor rooftop bar, a magical spot to sip on a Forbidden Fruit cocktail, which combines gin, blueberry, lemon and sparkling wine.
Since its 1920s construction, Kimpton Hotel Allegro has played host to various vaudeville stars, post-Prohibition parties and velvet-toned vocalists. Elements of its storied history are retained throughout, with original light fixtures and Art Deco wallpaper adding a vintage flair to rooms. If you’re feeling decadent, treat yourself to a stay in one of the cavernous suites with a Jacuzzi tub. Dining at in-house restaurant 312 Chicago is also a fancy affair – try the house-made limoncello and authentic Italian dishes such as black squid ink linguini.
A neon-yellow lightning bolt carves its way down the glass facade of theWit Chicago – fitting architecture for a hotel that pulses with the same energy as the surrounding theater district. The acclaimed rooftop bar thrives throughout the seasons, thanks to its retractable roof, and features ceiling-high shelves stacked with alcohol and amber-hued nightclub-style lighting. Be sure to try one of the punny cocktails – You Can Ask Me Hennything counts Aperol, Hennessy VS and brutal honesty among its ingredients. Downstairs, you can dig into locally sourced dishes such as short rib steak at the State and Lake Chicago Tavern.
The champagne bottle-shaped tower of the St Jane hotel was created as a rebellious response to Prohibition. Inside, the landmark Art Deco building matches its enchanting gold-leafed facade with gilded latticework and creamy marble. In the rooms, vintage-style furniture and surrealist art depicting figures shrouded in smoke add a fanciful edge, and Nespresso machines provide welcome morning brews. The secluded lobby lounge and the leather booths in Free Rein, a brasserie, are perfect spots for catching up with friends or indulging in an evening tipple.
This article is an updated version of a story created by Jacquelyn Lumley.