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Route 66

Begins in Chicago, Illinois and ends in Los Angeles, California

  • 23 Days / 22 Nights
  • All year round

From cosmopolitan cities to wide open spaces and from historical attractions to modern-day shopping malls, the character-filled state of Illinois offers tourist trails suited to fulfil every visitor’s individual interests. Illinois brings to mind Abraham Lincoln, the towering skyscrapers of Chicago, and the great outdoors. History buffs and museumgoers will enjoy the various historical sites, world-class museums and other attractions scattered throughout the state.

Illinois is also teeming with miles of beaches, rolling hills, woods, open lands, lakes and rugged bluffs, making it the perfect destination for outdoor recreation. With activities like scenic wine trails, golf courses, ziplining and horseback riding adventures to choose from, there’s truly something for all types of travellers in the region.

Top Tips

"The best way to see Chicago is on the two hour Architectural River Cruise. Narration is by volunteers from the Chicago Architecture Foundation. Or take a Segway tour with Absolutely Chicago Segway Tours. They make it safe as well as fun (for ages 14 years and over)."

"Experience breakfast in one of the best Chicago diners, in our opinion. Eleven City Diner is full of character, as well as characters! It's far more fun than a chain restaurant!"

"If you're visiting Chicago during the summer, check out the dates of the two day Chicago Air and Water Show. Get down to the beach and enjoy the outdoor spectacular."

My Kinda Town, Chicago Is

Sitting on Lake Michigan, segmented by the Chicago River, Chicago attracts visitors from near and far to experience its magic. The city’s museums are world renowned, The Art Institute, Field Museum and Museum of Science and Industry to name but a few. Year round outdoor fun can be enjoyed at Navy Pier, Millennium Park, Grant Park and Lincoln State Zoo which also hold some spectacular summertime events. No visit to Chicago is complete without heading to the top of Sears Tower for a birds eye view of the city, or walking the Magnificent Mile, so named for its fabulous mile long stretch of shops and boutiques. Evenings are just as enchanting. Take in a show in the Loop Theatre District, dine in one of the fine American or ethnic restaurants, listen to the Blues in Kingston Mines or enjoy a sporting event at Soldiers Field.

Beyond the City

Renowned as the starting location of the infamous Route 66, symbolising optimism, freedom and the great America dream, this drive is taken by thousands every year retracing the storied route.

In addition, outdoor enthusiasts journey the Great River Road National Scenic Byway, tracing the path of the mighty Mississippi River, glimpsing civil war homes, wineries and historical maritime sites. Follow the Shawnee Hills Wine Trail, hike the Giant City State Park, bike the Tunnel Hill State Trail, canoe Cache River State National Area or practice your swing on the Southern Illinois Golf Trail, or combine them all, the options are almost endless.

Suggested Itineraries

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