Housed in a Tuscan-style villa that dates to 1897, this ritzy B&B with a winding staircases is located in trendy Lincoln Park, a 5-minute walk to DePaul University and 8 minutes to the nearest El train station. The posh, Italian-themed rooms and suites feature hardwood floors, tufted headboards, private baths (some unattached), free WiFi and flat-screen TVs. Some rooms add 4-poster beds, sitting areas, private terraces and fireplaces. Perks include a brick patio with a hot tub, complimentary made-to-order breakfast, a stocked gourmet kitchen with snacks, and bike rentals.