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Chicago, Illinois has a rich history as one of the oldest big cities in the US with skyscrapers punching the skyline like towers to the heavens. One such tower is the iconic art-deco masterpiece that is now The Robey, a swanky hotel that will take you back to the streets of Chicago when smoky jazz flowed out of dimly-lit lounges, like bourbon-induced inhibition.

At the cross-section of Bucktown’s charming artist community with unique shops and restaurants, and grand Wicker Park Victorian homes, lies The Robey.
The Robey Chicago/Facebook
Since 1929, this historic building has overlooked this intersection of old-Chicago neighborhoods. Originally the North West Tower office building, this art-deco skyscraper was transformed into The Robey Hotel. Now you can feel like you are a part of rich Chicago history at this iconic hotel.
Stunning views of Chicago lights and big city sights under the stars, 13 stories in the air. There is no better view for miles around than the Up Room terrace.
The Robey Chicago/Facebook
Venture inside the Up Room for an old-world Chicago-style feel. This stunning 13th-floor lounge will take you back to the 1920s when big cars, big guns, and big personalities ruled the streets.
The Robey Chicago/Facebook
Round out your evening with fine dining at the Robey Cafe. Gourmet dinners, huge amazing burgers, and cocktails of every flavor, color, and swanky variety.
The Robey Chicago/Facebook

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You can even pick up a picnic basket and take it to the Cabana Club roof pool! (We'll save that gem for last.)
The Robey Chicago/Facebook
Enjoy light-filled rooms with amazing views of the city and the soft rumble of the Blue Line “L” train below.
The Robey Chicago/Facebook
All windows are sound-proofed, so you get the feeling of being immersed in the big city without it sounding like you are right in the middle of the action. Enjoy a peaceful stay at this historic hotel on the six-corner intersection of Wicker Park and Bucktown.
Of course, this isn't only an ideal romantic getaway hotel for couples; it is family-friendly with these cool modern industrial bunk bed loft rooms!
The Robey Chicago/Facebook
The pièce de résistance, of course, is the Cabana Club rooftop pool.
The Robey Chicago/Facebook
During the day, enjoy some family time overlooking the city in this unique pool experience. As the stars come out the lights dim and you can order some drinks and relax in the lap of luxury.

Will you take a trip back to old-world Chicago at The Robey? Whether you go for a getaway with that special someone or you treat the kids to a unique rooftop pool experience, this hotel is a fun way to get a feel for 1920s Chicago.

If you are beginning to fall in love with Chicago, perhaps this will tip you over the edge. Take a look at why we think Chicago is one of the coolest cities in the world.

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The Robey, 2018 W North Ave, Chicago, IL 60647, USA