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).

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.

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

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

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.

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

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

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

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

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

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

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.

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

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).

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.

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

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

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

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

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

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

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

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

Easy-breezy accommodations west of the windy city, with a bevy of nearby eats and quick access to I-355.

Got the munchies? The onsite snack shop's got you covered.

Harken all ye perpetually-late-for-flights. This place is a mere 3 miles from O’Hare, with a courtesy shuttle to escort you to/from your terminal.

Most airport hotels don't have full-time curators to care for their onsite art gallery and exhibition halls.

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.

Free breakfast served daily – plus a fully equipped kitchen in every suite. You will not go hungry.

Catch a free shuttle ride to/from O’Hare airport or to the CTA train station which’ll zip you into the city in no time. (Museums await!)