Fieldhouse Jones, Chicago

Vintage dartboards, tennis racquets and wooden gymnasium bleachers in the lobby set the tone for a sporty, laid-back stay in this hotel-hostel hybrid just west of Chicago’s posh shopping street, Magnificent Mile. Socialize in the communal kitchen and basement game room each morning and enjoy a complimentary continental breakfast. Bunk beds are surprisingly comfortable and private rooms include flat-screen TVs, original art and walk-in showers. Hang out in the lobby-level coffee shop, Top Spin, by day or the basement speakeasy cocktail bar, Janitor’s Closet, by night. Grab a remote and you’ll feel like a kid again as you race miniature electric slot cars on replica 1960s tracks in the basement. Private rooms from US$70. Amber Gibson

ARRIVE, Palm Springs

This 32-room boutique hotel embodies the relaxed vibe of Palm Springs while also giving a nod to the city’s mid-century modern design sensibilities. There’s no formal front desk—check-in happens at the bar—and all hotel services are available via text message. An architectural gem, the building makes use of rusted steel and wood and boasts a butterfly roof. For an extra-special stay, half the rooms feature private patios with outdoor fireplaces.

You’ll find guests sunning themselves around a pool with private cabanas, a bocce court and table tennis nearby. Reservoir restaurant features Southern California dishes with Asian and Latin influences—try the Sesame Seed Crusted Tuna Burger with wasabi mayo. A bar, coffee shop and ice cream shop round out the delicious offerings. Rates from US$249. —Sara Samson

The Surfjack Hotel & Swim Club, Waikiki, Oahu

A short stroll from Waikiki Beach, The Surfjack brings a serious measure of style to the area. This 112-room boutique hotel offers a modern take on vintage Hawaii decor with details like thatched ceilings, wooden panelling and custom-made furniture such as guest room headboards—complete with restored Aloha fabrics. Local artwork has been heavily incorporated into the hotel’s design, from photos of the North Shore and the South Shore by local photographer Mark Kushimi in the lobby to the hand-painted “Wish You Were Here” script painted on the bottom of the pool by local artist Matthew Tapia.

There’s also buzz around the on-site Mahina & Sun’s restaurant from award-winning local chef Ed Kenney. Sustainable seafood and local fruit and produce have starring roles on the menu. Highlights include the Mahina’s Bowl—try it with spicy ‘ahi palaha (white tuna) poke—and the grilled he’e (octopus) and watercress salad. There’s also a killer cocktail menu that incorporates local ingredients such as fruit juices and Ko Hana Agricole Rum from Kauai. Monthly hotel activities include fitness classes such as yoga, musical performances and nightly live music and poolside film screenings. For some stylish apparel or accessories and an iced coffee, visit the on-site Olive & Oliver boutique. Rates from US$197. —Sara Samson