Named for a hedonistic little ancient Greek town known for its indulgent ways. Right on.

Sophisticated and chic, with just enough quirk to keep things cool.

There’s a reason it’s been voted one of the best hotels in the city – everything is top-notch, from the views, artwork & modern décor to the nostalgic cocktails.

Smart, stylish digs in the masssssive, architecturally impressive former Cook County Hospital building. (It’s a stunner!)

Loop location means you're steps from the bustling Financial District and (far bustlier) Theater District.

Right at the Chicago Stock Exchange in the Financial District. Good thing hard work here gets you serious pampering.

A historic gem in the heart of Chicago’s downtown Theatre District, this boutique haven boasts lavish theatrics all its own with its elegant hobnobbing and glamour.

Stellar Mag Mile location puts the city's best eateries and endless shopping on your doorstep.

Goooood-looookin' new digs in the reno’d historic Cook County Hospital (ER fans? Anyone??). Onsite museum documents the landmark’s story.

Excellent authentic Italian resto onsite with fab deep dish pizza (natch).

Stellar River North location makes urban exploring a breeze.

Polished flair throughout, with soaring ceilings and designery touches. Adjacent to the new Wintrust Arena, if that’s where you’re headed.

Magnificent Mile’s within a half-mile (read: minimal toting of your shopping spoils required).

Playful-meets-industrial-chic design with bold, colorful and artistic accents.

Modern interiors within a cool old building, ideally situated in the heart of the city, steps from the Magnificent Mile.

Modern design and bohemian-chic flair flow throughout this vibrant atmosphere.

Head to the rooftop lounge for killer drinks and views (especially if it’s a Navy Pier fireworks night!).

This boutique hotel also houses its very own art museum filled with 21st-century pieces from emerging artists.

Sleek, modern and eclectic design welcomes the beautiful people. Now you can be one of them!

You’ll find chic galleries, buzz-worthy restaurants and vibrant nightlife in this hub for arts and entertainment.

Bar Pendry's a loungey spot for a late-night glass of wine. Pro tip: seasonal rooftop bar's a must-do in the warmer months.

Chicago biggies like the Symphony Center & Willis Tower (skydeck is a must!) are within walking distance.

The outdoor pool takes vacay vibes to new heights.

It's shimmery and glittering. Makes sense for the Gold Coast locale.

On a quiet residential street, providing a relaxing respite in the bustling city.

Can’t-be-beat address on the Magnificent Mile (!).

Drops ya in the heart of a vibrant, trendier-than-thou ‘hood teaming with vintage shopping, cool eateries & hoppin’ nightlife.

This hip London-based brand transformed 3 meatpacking warehouses into a stylish new hotel inspired by the local architecture and galleries.

Stay fit in the fitness center, or head outside for bocce ball or a game of hoops on the rooftop basketball court.

Free WiFi, so you can brag about your cool trip in real time.