Boutique Hotels in Chicago

Oyster knows what travelers look for when it comes to charm, elegance and comfort. When we review properties around the world, we evaluate how every feature stacks up against the competition, from the rooms to the pools to the restaurants. So if you're planning a getaway and don't know where to start, you've come to the right place. Take a look at our top picks for boutique hotels and get inspired!

Hotel Palomar Chicago


Hotel Palomar Chicago Rating: 4.0 Pearls

Categories: Boutique, Luxury

A great indoor pool with beautiful views of the surrounding skyscrapers, a free nightly wine hour, and big, stylish rooms with high-end amenities are only a few of the perks at the Hotel Palomar. It's quite unique for less money than other luxury hotels in vibrant River North area. Its lobby, divided into two areas, one chic and completely white, the other cozy and classic with a homey fireplace, is the perfect place to chill before a great dinner at the hotel's sleek restaurant.

Villa D' Citta


Villa D' Citta Rating: 4.0 Pearls

Categories: Boutique, Luxury, Romantic

The quaint, six-room Villa D' Citta is a romantic bed-and-breakfast located in residential Lincoln Park. The hotel actually feels like a luxury Italian mansion, with an outdoor whirlpool and sun deck overlooked by the bright, luxurious rooms; a charming arched courtyard with a barbecue; and a large communal kitchen and living room. While there are no real services in the hotel, the dozens of small details certainly make the guests feel pampered. You won't find a cozier hotel in town.

Dana Hotel and Spa


Dana Hotel and Spa Rating: 4.0 Pearls

Categories: Boutique, Luxury, Romantic

This adults-only boutique is an urban retreat with zen decor, a spa, a stylish Asian restaurant, and the popular Vertigo Sky Lounge, located three blocks from the Magnificent Mile. The hotel's serene vibe continues into the luxurious rooms, which feature hardwood floors, large, spa-inspired showers, plush beds, and floor-to-ceiling windows or balconies.

Hotel Monaco Chicago


Hotel Monaco Chicago Rating: 4.0 Pearls

Set amid skyscrapers, the stylish Hotel Monaco has large, bright, quirky rooms, many with comfy window seats and views of the river -- perfect for unwinding after a busy day in the city. For further pampering, the hotel features a 24-hour fitness center and in-room spa services. It also has some solid freebies, including evening wine tastings and morning coffee and tea, plus a great location in the Loop, within easy walking distance to some of Chicago's top attractions.

View all Chicago Hotels

More Chicago Recommendations

Browse Hotels by Area

Browse Hotel Slideshows

Like Us on Facebook! You'll Be Glad You Did

Loading Live Rates