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.

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.

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

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

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

The outdoor pool takes vacay vibes to new heights.

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

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

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).

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

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

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

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

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

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

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

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

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

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.

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

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

En suite deets include a whirlpool bath, walk-in shower, fireplace and plenty of serene styling.

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.

Cheery, modern lobby’s all stacked stone and comfy convo areas. Commandeer one of the fireside spots and map out your plan.

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

A super recent reno has left rooms lookin’ pret-ty darn fresh. Style’s sleekly Art Deco, with pops of whimsy.

Free shuttle service to O'Hare International Airport as well as shops, restaurants and attractions within a five-mile radius.

Two-room suites give you plenty of space to stretch out.

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