Want to get right to the romancing and not waste any time on the road? Then the opulent Trump Hotel downtown is just the place. Even if you plan to forgo the blissful spa services, spring for a Spa Guest Room with calming features such as heated eye and neck pillows and indulgences like a mini-fridge stocked with organic wine and champagne. With the exquisite dining options of Sixteen and the alfresco Terrace at Trump offering views of Lake Michigan, the Chicago River and the Wrigley Clock Tower, going off the property is entirely unnecessary. Rates start at $336.