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).

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.

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.

Dicen que el desayuno es la comida más importante del día. Y aquí, dicen... que es gratis también.

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

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

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

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

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

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

The outdoor pool takes vacay vibes to new heights.

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

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.

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).

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

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

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

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

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

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

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.

Sip signature cocktails at MSC, a stylish bar where guests and locals gather for great conversation and an inviting atmosphere.

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

Un verdadero festín en el desayuno calentito: diario y gratis. Además, entre semana tienes una opción para llevar, por si tienes que marcharte a la carrera.

Diseño alegre e industrial con intensos detalles artísticos y de color.

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

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

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

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