On the shores of Lake Michigan, the ‘Windy City’ has something for everybody. A great destination at any time of the year, Chicago has a beautiful lakefront, breath-taking architecture, world-class shopping, wonderful museums, great theatres, gourmet restaurants and fantastic nightlife. Discover the delights of the Magnificent Mile, get a bird's eye view of the city from the 360 Chicago Observation Deck at the John Hancock Center or from the Skydeck Chicago at the Willis Tower. If heights aren’t your thing take a stroll in Grant Park for a more relaxing option, visit the Shedd Aquarium, Navy Pier or take a boat tour along Chicago River.

Stay two nights in Chicago

Chicago marked the beginning of Route 66, the ‘Main Street of America’, when it opened in 1926, stretching 2448 miles to Santa Monica, in California. Before you embark on your road trip, fill up with breakfast at Lou Mitchell’s legendary Route 66 café on Jackson Boulevard in Chicago. And don’t forget to grab a selfie at the Begin Route 66 sign on E. Adams.

Collect your rental car and head out of the city. Meander past many delightful all- American haunts, including the Polk-A-Dot Drive In and Dixie Travel Plaza. Small towns such as Berwyn, Joliet, where you will find the Old Joliet prison featured in the ‘Blues Brothers’ movie, and Wilmington, home of the iconic Gemini Giant, the 30ft tall statue is of many giant Muffler Man advertising props found throughout America from the 1960s. In Pontiac, stop at the Route 66 Association of Illinois Hall of Fame and Museum with the largest Route 66 shield mural which both make a great photo op, and then continue onto the Pontiac-Oakland Automobile Museum. Further on, stop in Atlanta to see the Paul Bunyon statue, another of the famous Muffler Man props along the Route 66. 

Springfield boasts the annual Illinois Route 66 Mother Road Festival every September. Year-round you can visit the Route 66 Motorheads Bar, Grill & Museum and the Cozy Dog Drive Inn. Experience the new Legends Neon Sign Park at the Illinois State Fairground in Springfield, a homage to the incredible signs found along the Mother Road. 

Springfield is also the state capital of Illinois. While you are here, save some time to visit the Abraham Lincoln Presidential Library and Museum, the Lincoln Home National Historic Site, the State Capitol and Frank Lloyd Wright’s Dana Thomas House.

Stay two nights in Springfield

Today as you leave Springfield stop at the Original Historic Route 66 Brick Road in Auburn before heading for the Mississippi River. On your way you won’t want to miss the Litchfield Museum and Route 66 Welcome Center where you'll be swept down memory lane as you view local historical artifacts and Mother Road nostalgia. 

Continue onto Collinsville for another photo opportunity at the world’s largest 170-foot Catsup bottle water tower and discover its designation as the horseradish capital of the world! 

Make a stop at the Old Chain of Rocks Bridge - this original Route 66 span over the Mississippi River has been reopened as the world's longest pedestrian and biking bridge. The bridge offers a great view of the river. Travel a short distance east on Chain of Rocks Road to reach the Eagle Points Trail and Madison County Transit Confluence Trail.

Then head north along the Mississippi River, to Alton, Illinois, and the Meeting of the Great Rivers National Scenic Byway, also known as the Great River Road in Illinois. The Great River Road runs 2000 miles along the Mississippi, and the roadway from Hartford to Grafton is designated a national scenic byway. It brings together historic towns and three major rivers around Alton. This Midwestern treasure features beautiful stretches of roadway cradled by the rolling waters of the Mighty Mississippi River and majestic limestone river bluffs. Thrill seekers should head for the Aerie’s Resort in Grafton where you can try the Grafton Zipline, the Grafton SkyTour, Aerie's Alpine Coaster, and enjoy ‘The Best View in the Midwest’ from a spectacular bluff overlooking the confluence of the Mississippi and Illinois Rivers above downtown Grafton. Then celebrate with a glass or two of Illinois wine, from one of the wineries in the area.

Stay two nights in Alton

Your next stop on the Great River Road is Quincy with its historic downtown, colourful street murals, intriguing architecture. Also enjoy nature at its best with beautiful river overlooks and outdoor recreation. Rent a bike and take a self-guided tour of the town to see Villa Kathrine and The Quincy Museum, or take to the water in a kayak. In nearby Nauvoo you can take a leisurely horse-drawn carriage tour of Old Nauvoo or relax at the Orvis-endorsed Harpole's Heartland Lodge in Nebo. 

Stay one night in Quincy 

Take the Great River Road along the Mississippi River, north to Galena. Named one of the Top 10 Most Romantic Small Towns in North America, Galena is nestled in northwest Illinois is an ideal location to discover the region’s beautiful scenery, with rolling hills, lush valleys, and the Mississippi River. Enjoy hiking, fishing, kayaking and golfing, or take a tour of one of the area’s many vineyards and wineries. The downtown area boasts historic building, charming boutiques, art galleries and restaurants. 

   

Stay two nights in Galena.