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Dine / Stay / Play

Westin Michigan Avenue Hotel
Westin Michigan Avenue Hotel

Set on Chicago's famed Magnificent Mile, Westin Michigan Avenue offers guests a ...

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Billy Goat Tavern - The Original
Billy Goat Tavern - The Original

There are few things as identifiable to Illinois and Chicago as the Billy Goat T...

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Buddy Guy's Legends
Buddy Guy's Legends

Chicago's premier blues club now at it's new location, owned by Buddy Guy; local...

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Reconnect with Nature in Illinois' Picturesque Backyard

Reconnect with the state’s natural beauty in Shawnee Forest Country. Pack your hiking gear, grab a camera and prepare to be amazed at the picturesque landscapes right in Illinois’ backyard. Explore by foot, canoe, horse – or even cable, as you traverse wetlands, lakes, trails and canopies. At the end of the day, recharge with delicious food, fine wine and cozy cabins.

Eat, Stay and Play on your Route 66 Adventure

  • Days 1 & 2: Chicago

Route 66 Sign, Chicago

A world-class time in a world-famous city

Your legendary journey begins in the heart of downtown Chicago. Snap the perfect selfie at the very spot Route 66 begins. You'll find the iconic Route 66 Begins sign on E. Jackson Blvd.

From there, you're spoiled for choice! Drink in Chicago's world-famous architecture in style on an architecture boat tour, before stopping off for all the fun of Navy Pier. Get in some serious shopping on The Magnificent Mile, home to America's greatest retail offerings. There's plenty of culture to be had, too. Discover the history of the windy city at the Chicago History Museum, and learn more about the wider world at the Museums of Broadcast Communications and Science & Industry. See the iconic sights of Chicago from ground-level at Millennium Park and from on-high at the Skydeck and 360 Chicago. As night falls, dive into Chicago's legendary music scene at Buddy Guy's Legends and House of Blues.

Deep dish Pizza

Dine & Stay in Style

You want dining options? You better believe we got 'em. Fill up for the next stage of your road trip visiting some of Chicago's finest eateries, serving up some delicacies you won't find anywhere else (or won't find anywhere else done right).

Once you've got a belly-full of fare, rest your weary head at one of these spots along the way - or choose your own spot at Choose Chicago.

  • Day 3: Heritage Corridor

Dell Rhea's Chicken Basket

Willowbrook, Joliet & Wilmington

Now you're on the road and your Route 66 adventure is truly under way. And even though your primary transport might be motorized, make sure you wear comfortable shoes. You're gonna do a lot of walking today!

Once you hit Joliet, swing by the Old Joliet Prison Tour for an authentic Jake Blues experience. Then it's on to Wilmington for your first pit stop at either Dell Rhea's Chicken Basket or the Launching Pad Diner (or how about both?). You'll also want to get yourself a photo with the Gemini Giant - you can't miss it!

Route 66 Hall of Fame and Museum Pontiac

Pontiac

No Route 66 journey is complete without a visit to one (or all) of the Mother Road’s classic museums. A must-see is the Illinois Route 66 Hall of Fame and Museum in Pontiac, packed full with the finest memorabilia associated with the history of Route 66. Among the artifacts, you’ll find the bus and van of Route 66 icon, Bob Waldmire—a true legend of the Mother Road. Step around back for a photo op with the World’s Largest Route 66 shield.

Want a little more auto-history? Head through the Pontiac-Oakland Automobile Museum. And while you're stopped in those parts, check out the Historic Swinging Bridges (great photo op)

Atlanta

  • Days 3 & 4: Springfield

The Land of Lincoln

  • Day 5: Great Rivers and Routes

Bringing it all to a close...

Snaps from Fellow Route 66 Adventurers

Imagine Yourself on the Mother Road

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