We love a storied past! 1927 building has housed everyone from JFK to The Rolling Stones (and a penthouse floor casino run by Al Capone’s brother).

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

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

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

Located in the historic Astor Street District and near vibrant nightlife of Rush Street.

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

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!)

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

The former hat factory on the banks of the Chicago River features newly renovated and richly decorated rooms.

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

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

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

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

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

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

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

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

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.

Relax, early riser. Buffet Breakfast included.

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

Fab location, just off the Mag Mile, adjacent to the famed John Hancock building.

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.

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

The outdoor pool takes vacay vibes to new heights.

A Chicago classic, grand host to US Presidents, international celebs, foreign dignitaries and more since 1893.

Walking distance to the Magnificent Mile? Check. Lakefront trail? Check. Public transportation? Check.

Cozy and classy got together and made these rooms.

Apartment-style living at its finest with updated amenities and space galore.