For The Route 66 Enthusiast

Day 02

Masterworks & Skyline Dining

Spend the morning exploring The Art Institute of Chicago or discovering world renowned museums, including the Barack Obama Presidential Center. In the afternoon, enjoy a scenic architectural boat cruise along the river for skyline views from the water. End the day with an exceptional multi course Michelin starred dining experience at Alinea.

Day 03

Mid-Century Icons of Oak Park

Travel west of downtown Chicago to Oak Park to explore Frank Lloyd Wright’s Home & Studio & the striking Unity Temple. Home to 25 buildings designed or redesigned by Wright, Oak Park includes his home & studio, where he worked from 1889 to 1909. In the evening, unwind with rooftop cocktails overlooking the Chicago skyline.

Day 04

Route 66 Centennial Journey

Begin your Route 66 adventure from the new official starting point at Navy Pier in Chicago. Along the way, explore the historic Old Joliet Prison, visit the Gemini Giant in Wilmington & the Route 66 Hall of Fame & Museum in Pontiac before arriving in Springfield. Stay at President Abraham Lincoln Springfield, a DoubleTree by Hilton Hotel.

Day 05

Springfield Heritage & Historic Architecture

Spend the day exploring Springfield's political & architectural heritage, from beautifully preserved historic districts to landmarks linked to Illinois history. As your Route 66 journey continues, discover the stories that define one of the Mother Road's most significant stops, including Cozy Dog Drive In. Unwind at Obed & Isaac's.

Day 01

Arrival in Lakefront Chicago

Arrive in Chicago & be greeted by your local host before heading to The Ritz-Carlton, Chicago on the Gold Coast. Settle into your luxurious suite overlooking the skyline & Lake Michigan, then enjoy a relaxed afternoon taking in the city views. The evening is at leisure amid the elegant waterfront atmosphere.

Day 06

Route 66 to the Mississippi River

Follow the final stretch of Illinois' Route 66 journey toward the towering bluffs of the Mississippi River. Pause at scenic overlooks & historic river communities before reaching Alton, where the landscapes, history & character of the Mother Road give way to the grandeur of America's great waterway. Stay at Beall Mansion in Alton.

Day 07

Until the Next Adventure

As you depart Illinois, iconic Route 66 landmarks, vibrant cityscapes, historic towns & classic Americana offer a memorable farewell, leaving you with lasting memories of a journey shaped by architecture, heritage & the enduring spirit of the Mother Road.

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Best Time to Travel

Visit Illinois in May to June for Chicago's waterfront architecture, river cruises & mild weather, while Sep to Oct brings autumn colours, scenic Route 66 drives & ideal conditions for exploring historic towns, cultural landmarks & roadside attractions.

For the Route 66 Enthusiasts

Exploring The Art Institute of Chicago
Visit Barack Obama Presidential Center
The Skyline Cruise Architecture Views
Frank Lloyd Wright Landmark Masterworks
Oak Park Legacy Wright Collection
Route 66 Centennial Route Drive
Classic Stops Along Route 66
Deep River Valley Exploration

About the Destination

From Chicago's iconic lakeside skyline to the historic towns of Route 66, Illinois invites you to explore world renowned museums, vibrant live music & the landmarks that shaped the Mother Road. Along the way, big city energy gives way to the timeless charm of classic Americana.