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).

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

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

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

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

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

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.

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

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

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.

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

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

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

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

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).

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

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

Bring your furry friends along for the ride. This place is pet friendly.

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

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

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

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

Spot-on location for all things medical campus – near UIC Chicago and Rush. PS: Little Italy dining nearby too(!).

Hit nearby Lou Mitchell’s for breakfast. It’s a Chicago institution and the starting point of Route 66.

Style in this 20s-era gem is trendy in a laid-back kinda way. And it’s perfectly placed in a venture-worthy boutique-and-gallery-dotted ‘hood.

Ideal Mag Mile address just steps from endless shopping & world-class eateries.

Suite-style rooms offer up max 'home away from home' vibes.

Killer River North location by the Mag Mile and Riverwalk.

All rooms are at least 15 stories above the city. Street noise? Nuh-uh.

The newly opened rooftop bar & restaurant is a must when you’re in the mood to wine and dine with a side of stellar views.

Spacious 545 sq ft suite