Millennium Park is Chicago's fabulous lakefront showplace for the arts. Stroll the 24.5-acre grounds and discover the contemporary Lurie Garden, the reflective Cloud Gate sculpture, the multimedia Crown Fountain and the Jay Pritzker Pavilion, a stunning performance venue designed by renowned architect Frank Gehry. Travel north and spend time at the beautiful Chicago Botanic Garden in suburban Glencoe to experience more than 25 different gardens. Power shop in the afternoon for bargains at Gurnee Mills, home to more than 200 manufacturer and retail outlet stores that include Nike, Gap, Nine West, and Bass Pro Shops Outdoor World (a destination in itself, with a huge aquarium and 40-foot climbing wall). Be sure to make your first stop the Customer Service Center, where you can pick up a valuable coupon book. Then enjoy music under the stars at Ravinia Festival in Highland Park, which hosts summertime outdoor concerts.

Begin your morning in Lisle and its famed Morton Arboretum, home to 1,700 acres and 14 miles of gardens. Travel to Aurora for designer bargains from Giorgio Armani, Coach, Ralph Lauren and more at Chicago Premium Outlets, housing 120 outlet stores. Explore the banks of the Fox River and historic Downtown St. Charles. Here, a dozen turn-of-the-century homes have been turned into quaint shops and restaurants. Don't miss the Kane County Flea Market (one of the largest open air markets in the Midwest), held the first Saturday afternoon and Sunday of each month. Hundreds of sellers display everything from antiques to home decor and jewelry. Also nestled in the Fox River Valley is the tiny town of Geneva. Its downtown area is known for its 100 specialty shops and boutiques housed in Victorian-era storefronts in the historic Third Street District, as well as romantic waterfront restaurants on the Fox River. In the evening, enjoy Illinois wine at the Galena Cellars tasting room and gift shop. Plan to spend the night at the historic Hotel Baker.

Begin the morning in Rockford with a stroll through the tranquil Anderson Japanese Gardens. Considered to be one of the most authentic Asian gardens outside of Japan, Anderson features tumbling waterfalls, formal Japanese gardens, pagodas, koi ponds and a 16th century-style teahouse. Next, come face-to-face with Jane, one of the 10 most important dinosaur discoveries of the past 100 years, at the Burpee Museum of Natural History. Afterwards, check out Rockford's Klehm Arboretum & Botanic Garden. This 150-acre “living museum” boasts rare trees and shrubs that were planted back in 1910. Enjoy lunch at the quaint Lucile's Tea Room. Then, board the turn-of-the-century Trolley Car #36 at Riverview Park and meander through the lovely riverside Sinnissippi Gardens. For dinner, indulge in family-style German fare at Der Rathskeller Restaurant & Bar, a Rockford dining tradition since 1931.