Chicago Road Trip Itineraries – Fun Things to Do

12 Best Road Trips In & Around Chicago

Looking for ideas on what to do during your visit to Chicago and its surrounding communities? Chicago Moms have put together travel itineraries to spark your creativity. Indulge in world-class shopping, notable architecture, beautiful gardens and historic sites.

Aurora & Fox River Valley Area

Farnsworth House, Chicago Premium Outlets

About 60 miles west of Chicago in pastoral Plano, visit the Farnsworth House, the minimalist masterpiece designed by Ludwig Mies van der Rohe in 1951. The famous glass house epitomizes modernist architecture— the less is more philosophy—unprecedented in its day and a marvel still. This stellar structure of steel and floor-to-ceiling glass seemingly “floats” above the rambling Fox River and offers unsurpassed views through transparent “walls”.

Before returning to downtown Chicago, don’t miss Chicagoland’s best-kept secret: Chicago Premium Outlets, housing over 120 designer and brand-name retailers, while offering everyday savings of 25-65% from such impressive designers as Ralph Lauren, Polo, Kate Spade and Ferragamo.

Chicago’s North Shore

Northwestern University, Bahá’i House of Worship, Grosse Point Lighthouse, Chicago Botanic Garden, Cuneo Museum & Gardens

Nothing compares to the unsurpassed beauty and distinctive charm of Chicago’s North Shore and Lake County. Affluent old towns with gracious houses and mansions hug the shores of Lake Michigan. The drive up Sheridan Road is rich in architectural history with astounding homes and natural sites of wonder.

Driving up the North Shore from Evanston to Lake Forest, stops can be made at Evanston, a cosmopolitan college town (Northwestern University) on Lake Michigan, the Bahá’i House of Worship, Grosse Point Lighthouse, a National Landmark and one of the finest lighthouse structures on the Great Lakes, the Chicago Botanic Garden, featuring 385 acres and 23 gardens including an exquisite Japanese garden, a waterfall garden, an English Walled Garden, and 11 bridges spanning sparkling lakes. The Cuneo Museum & Gardens, a historic Venetian style mansion featuring art, tapestries, European furnishings and formal gardens. .

Trains, Trolleys & Treasures

Illinois Railway Museum, Fox Trolley Museum, Blackhawk Forest Preserve

Hop aboard at America’s largest railway museum, Illinois Railway Museum, and visit vintage trains, trolleys and interurbans. Barn after barn of historic locomotives, signs, lights, and other railroad fixtures await your eyes. Enjoy a peaceful ride at the historic Fox Trolley Museum along the beautiful Fox River on a trolley line that dates back to the turn of the century. The electric transport era helped the Chicago region grow to become one of North America’s great metropolitan areas.

Enjoy a great lunch buffet at On-Q/Hennessy’s Steak and Seafood Restaurant. Outdoor dining overlooking a beautiful pond will delight and engage your senses. During your visit be sure to stroll along the Fox River at the Blackhawk Forest Preserve and enjoy what nature has to offer. Your visit to Chicagoland’s Northern Fox River Valley will educate those of all ages. Trains, Trolleys & Treasures

Lock and Dams

Illinois and Michigan Canal, Old Public Landing, Gaylord Building

Arrive in historic Lockport where the Illinois and Michigan Canal (I&M;) became a center of shipping and passenger activity. The I&M; runs from Chicago to LaSalle-Peru. With the opening in 1848, one could go from the east coast to the Gulf of Mexico via this historical waterway. Designated in 1984 as the Nation’s First National Heritage Corridor, this area has been preserved for all to learn of its historical significance to the Midwest.

The first lock is still intact today and the area known as the Old Public Landing consists of a hands-on exhibit, interpretive park featuring a statue of Lincoln (opening February 2009) and tow-path trails. A plated lunch is available at the Gaylord Building in the Public Landing Restaurant. Return through Lemont, the canal town which was settled in 1863 for a look and feel of the past combined with a progressive eye to the future. Stop in downtown Lemont to browse in several specialty shops which include antiques and crafts.

Chicagoland’s Arboretum Corridor in DuPage

The Morton Arboretum in Lisle and Downtown Naperville

Visit The Morton Arboretum in Lisle, one of the world’s foremost public gardens, noted for its exceptional plant collection, Visitors Center, Ginkgo Restaurant and ever-changing landscape. Enjoy the beauty of nature as an Arboretum guide conducts a one-hour narrated tour aboard the bus, highlighting the Arboretum’s legacy and the Morton Salt family dynasty.

Seasonally, you’ll see blossoming trees, wildflowers and fall foliage. Spend the afternoon in downtown Naperville with its mixture of Midwest hospitality and metropolitan sophistication.

Naturally appealing, this community includes unique and family-owned shops. Enjoy three miles of winding brick paths along the DuPage River in the adjacent Riverwalk, featuring covered bridges, gazebos and playgrounds.

The Wright Destination

Frank Lloyd Wright Home & Studio, Frank Lloyd Wright’s Unity Temple, Ernest Hemingway Birthplace Home, Pleasant Home

Start your visit at the Visitors Center, located within walking distance of major architectural and historical attractions, numerous restaurants and specialty shops. Then take a tour of the Frank Lloyd Wright Home & Studio, which served as the world- renowned architect’s residence and studio from 1889 to 1909. A guided walking tour of the Frank Lloyd Wright Historic District allows you to discover “an outdoor museum of architectural history.” Also be sure to stroll to Frank Lloyd Wright’s Unity Temple, Wright’s first public commission and only surviving public building from his Prairie period.

Also visit the Ernest Hemingway Birthplace Home and Museum to find displays featuring rare photos, early writings and memorabilia from this Nobel Prize-winning author’s life. And be sure to stop at the 30-room Pleasant Home, designed by architect George W. Maher in 1897, where visitors will find the Edgar Rice Burroughs Tarzan Museum. Explore Oak Park, less than ten miles from downtown Chicago.

Tea Room Lunch in a Quaint Village

Historic Frankfort, Trolley Barn, Breidert’s Green

Enjoy a leisurely visit to Historic Frankfort. This modern community has retained the history and charm of early America. Founded in 1855, Frankfort’s rich heritage continues to be evident throughout the Village. From its historic downtown district to the Prairie-style architecture of many buildings, heritage has been carefully preserved. Upon arrival, you will be greeted for a 10 minute narration. Browse through several specialty and antique shops, as well as the historical society museum.

The Trolley Barn and Breidert’s Green are just two interesting locations in Frankfort. The 1840s brought German settlers from the Pennsylvania area to Frankfort. Frankfort township was named by Frederick Cappel after his native city, Frankfurt-Am-Main in Germany. Built in 1885, the Trolley Barn once housed trolleys on the old Joliet and Northern Indiana Trolley Line. Numerous other rail lines passed through Frankfort, which was known at that time as a “stop on your way West.” Today, Frankfort is thriving and has become known as the “Jewel of the South Suburbs”. Tearoom Lunch

Antiquing & Flea Marketing in St. Charles

Antique Markets I & II, Kane County Flea Market

St. Charles is an antique lover’s destination. This pretty city on the Fox River is a perfect destination to find a wide selection of antiques and collectibles. Explore the Antique Markets in historic downtown St. Charles. Over 60 dealers display their wares at Antique Markets I & III. Put on your tennis shoes and explore the expansive Kane County Flea Market featuring over 1,000 dealers.

Find that special collectible, antique or eclectic piece that fills the fairgrounds buildings inside and out. Sample the delicious food fest at the Flea Market from roasted nuts, mouth watering corn to a down home country breakfast on Sunday. Held the first Sunday of every month and the preceding Saturday.

Shopping & Dining in historic St. Charles & Geneva, Illinois

Geneva’s Historic Third Street, Fabyan Windmill, Old St. Charles, Fox Island Square, Century Corners

Naturally charming St. Charles and historic Geneva offer unique boutique & antique shopping and dining experiences. Geneva’s Historic Third Street has shops of distinction, including the Little Traveler, a shopper’s delight since 1922. Next stop—a tour of Geneva’s Fabyan Windmill. Restored to its original mid 1800’s grandeur, the windmill, in a picturesque Fox River setting, is the nation’s best example of an authentic Dutch windmill.

Lunchtime at St. Charles’ Onesti Dinner Club is a truly unique dining experience. This casually elegant restaurant is in the heart of historic downtown St. Charles. Once re-energized by a great meal, discover a superb collection of shops and antique stores in Old St. Charles, Fox Island Square and Century Corners, each quaintly situated on St. Charles’ east and west river sides.

A Royal Day in Chicago

Bob Chinn’s Crab House, Arlington Park Racecourse

Enjoy a delicious lunch at the nationally famous Bob Chinn’s Crab House, Chicagoland’s highest volume restaurant serving jet-fresh seafood from all over the world, the Midwest’s best steaks and Bob Chinn’s world famous Mai Tais – all in a fun casual atmosphere!

A visit to Arlington Park Racecourse, one of America’s premier racecourses, is the only way to enjoy the “Sport of kings” with spirited Thoroughbreds vying for high stake rewards. The view from the Million Room high atop the grandstand, owners talking to jockeys in the paddock area, and on weekends the picnic area with a petting zoo for the families all add to the ambiance of the experience.

A Great Day in Woodfield Chicago Northwest

Woodfield Mall, Lynfred Winery

Start the day in the Woodfield Chicago Northwest area, one of the country’s largest and most complete shopping areas. With nearly 300 stores and restaurants, Woodfield Mall is Illinois’ number one tourist destination. At Woodfield, you’ll find many of the country’s top retailers, along with dozens of the newest concepts and specialty shops, which can’t be found anywhere else in the Midwest.

During your visit to Woodfield, be sure to dine at one of it’s 30 plus restaurants and specialty food stores, such as, The Cheesecake Factory, P.F. Chang’s China Bistro, Rainforest Café, Red Robin, Stir Crazy, or Todai Seafood Buffet. Don’t forget to have a laugh at the new IMPROV Comedy Club.

Finish off a day of power shopping and enjoy a couple of mellow hours at the Lynfred Winery, the oldest and largest winery in Illinois. Producing over 50 varietals and 25,000 cases of wine per year, this winery

Experience the architectural history of the Chicago Area

Farnsworth House, Baha’i House of Worship, Muirhead Farmhouse, Frank Lloyd Wright’s Home and Studio

The Farnsworth House is the epitome of minimalist architecture and the model from which all subsequent glass houses were designed, this significant structure in only one of three residences by Mies van der Rohe in the United States. Aurora is also home to the largest collection of Sears Mail Order Homes.

The Baha’i House of Worship in Wilmette, is one of only seven in the world and the only one in North America, the Baha’i House of Worship is the largest and the oldest surviving Baha’i Temple. Standing on the shores of Lake Michigan, the auditorium, with its walls of lace-like ornamentation and its dome rising 135 feet above the main floor, offers a scene of unsurpassed beauty.

It is surrounded by exquisite gardens and fountains. This imposing and dramatic structure has received numerous design awards, and is on the National Register of Historic Places. Chosen as one of the “Seven Wonders of Illinois”.

Muirhead Farmhouse in Hampshire, is located in a peaceful country setting just northwest of Chicago. The Muirhead Farmhouse is a little known architectural wonder and the only known farmhouse designed and built by Frank Lloyd Wright during his lifetime.

The Muirhead Farmhouse offers you a chance to live and experience Usonian architecture and take in the tranquility and beauty of the Illinois Prairie and its sunsets. Recipient of the 2007 Driehaus Preservation Award, this Frank Lloyd Wright designed home offers suites with private baths, historical artifacts, surrounded by nearly 800 acres.

Frank Lloyd Wright’s Home and Studio, Oak Park – the birthplace of an architectural revolution. Wright used his first home (1889) to explore design concepts that contain the seeds of his architectural philosophy. The adjacent studio (1898) is where Wright and his associates developed a new American architecture – the Prairie style. Guided tours by trained interpreters are provided for your tour.