Kimpton Hotel Palomar Chicago
For a swim with a view, book a stay at the Kimpton Hotel Palomar Chicago. The heated, indoor 17th-floor pool will keep you cozy on the rainiest of days, while floor-to-ceiling windows offer stellar views of the city’s River North district. There’s also a rooftop sundeck for summertime lounging, where you can order creative cocktails from the on-site restaurant, Sable Kitchen & Bar. Rooms are adorned with heavy crimson curtains and black-and-white pictures of old Chicago.