Chicago hotels with rooftop pools.

Chicago, the Windy City, stands as a testament to American ambition and architectural prowess. Nestled on the shores of Lake Michigan, this Midwestern metropolis has long been an epicenter of commerce, culture, and innovation. Its skyline, punctuated by iconic skyscrapers, tells a story of a city that rose from the ashes of the Great Fire of 1871 to become a global hub. The Board of Trade and the Mercantile Exchange underscore its significance in the world of finance, while its jazz clubs and theaters echo the city’s rich cultural tapestry. It’s a fine place to spend some time, and we’ve picked out some of our favorite spots.

EXTRAORDINARY PICK

The Viceroy Chicago has one of the finest rooftop pools in the City, surrounded by an exquisite drink selection and an impeccable ambience. Excellent.

Obviously, it’s Chicago – so you’ve got nice wind protection while you’re here. This hotel is a 4* hotel.

  • Hotel class: 4*
  • Location: Near North Side
  • Pool size: A little small to swim… big enough to put a smile on your face
  • Hotel website

QUIRKY PICK

The Hoxton Chicago is one of the ever growing Hoxton group hotels, with a beautiful rooftop pool. You’ll find a bar and restaurant (Peruvian, if you were wondering) and some incredible views across the city. Another sublime 4* hotel.

  • Hotel class: 4*
  • Location: Fulton Market
  • Pool size: Dippable. Smileable.
  • Hotel website

THE FUN PICK

Visiting the Robey Hotel in Chicago? Good news. There is a beautiful little rooftop pool (it’s not huge), with a few chilled out places to sit. Yes, it’s near the bar too. Yep, you guessed it, this one is a 4* hotel.

  • Hotel class: 4*
  • Location: Wicker Park
  • Pool size: A little small to swim… big enough to put a smile on your face
  • Hotel website

JIM and Hels’ view

Although winter in Chicago can be brutally cold, summer is amazing. The Hoxton is a great pick if you’re looking for somewhere to enjoy, and while you’re at it… make sure you have a little dip in the lake! There are a few other good hotels to visit, the Waldorf Astoria in Chicago is a real peach.


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