Suite hotel with an indoor pool and complimentary hot breakfast is 28 miles from Chicago and five minutes from the expansive Woodfield Mall

Kanan Yacht stocked with cash bar sails along Lake Michigan for stunning skyline views skyline while a live DJ spins tunes into the night

Downtown hotel outfitted with Internet-ready smart TVs and wireless audio, located in trendy area close to Mag Mile

Downtown hotel outfitted with Internet-ready smart TVs and wireless audio, located in trendy area close to Mag Mile

Ocean liner cruises Caribbean waters with ocean-view cabins and amenities such as spa, pool, Las Vegas–style casino, and free meals

One-way trip in a shared shuttle to Chicago's O'Hare or Midway airport

Chicago Transit Authority 3-day pass grants unlimited rides on buses and trains within the city and 40 surrounding suburbs

Located near the Magnificent Mile, this towering hotel has impressive photograph collection, plus rooms with floor-to-ceiling windows

All-suite hotel's amenities include a heated indoor pool, an in-room fireplace, WiFi, and hot breakfast

Staff members help streamline travel with VIP valet parking, aiming to check in patrons and shuttle them to Midway Airport in three minutes