Mile after Magnificent Mile! A Flavour of Route 66!

Chicago • Springfield • Peoria • Rockford

This 7 night/8 day self drive itinerary gives a flavour of Route 66 with a Chicago City as your starting point throughout Illinois.Stroll through quaint small towns or revel in Chicago’s big city delights.
Discover Springfield, the State Capital and be sure to visit Bill Shea’s Route 66 Gas Station Museum. Enjoy the quaint towns of Elsah and Grafton, with their wineries and unique inns and cottages. Marvel at the height of the world’s tallest man – Robert Wadlow. Explore the land that Abraham Lincoln called home or retrace the route of Lewis and Clark. Get your kicks along America’s mother road and most historic highway, Route 66!
From €1175pp

What's Included

  • Return flights to Chicago from Dublin
  • Compact Car Rental Pick up and drop off Chicago for 5 days fully inclusive insurance
  • 2 NIGHTS Chicago
  • 1 NIGHT Springfield
  • 1 NIGHT Alton
  • 1 NIGHT Peoria
  • 1 NIGHT Galena
  • 1 NIGHT Rockford
  • Quote ref 1030727

Staff Tips

Chicago-Bike past giant red and pink painted steel horses or stroll by an apple rocket in stainless steel and bronze at the Skokie Northshore Sculpture Park, which combines original contemporary sculpture and two miles (3.2 kilometers) of walkways—all for free.

Claire Somers

Travel Expert

Chicago-Head to the underwater viewing area to catch a glimpse of swimming sea lions or take a guided tour of the hundreds of species on view at the Lincoln Park Zoo. Admission to the zoo is free seven days a week.

Jennifer Mulligan

Travel Expert

Your Adventure...

Arrive Chicago
At Leisure in Chicago
Chicago to Springfield
Springfield to Alton/Grafton
Alton/Grafton to Peoria
Peoria to Galena
Galena to Rockford
Rockford to Chicago
  • Day 1 Arrive Chicago
    Arrival Chicago and pick up your rental car on arrival. Drive to your selected Chicago hotel for your overnight stay.
  • Day 2 At Leisure in Chicago
    The history of Chicago comes alive when you take the Chicago Architecture Foundation’s Architectural River Cruise. Learn why Chicago is known for its innovative architecture. Be sure to take in the Field Museum, Art Institute of Chicago, John Hancock Observatory and Shedd Aquarium to round out your trip. Here you can explore the Magnificent Mile – a veritable mecca for shoppers. Discover stunning architecture. Walk miles of sandy beaches along ocean-like waters. Savour Michelin-starred cuisine. Browse works of art that begin in museums and spill into city squares and lakeside parks such as Millennium Park. Overnight: Chicago
  • Day 3 Chicago to Springfield
    Driving distance today is 200 Miles/322 KM
    Cruise down Route 66 and explore the fun, small towns along the Mother Road on your way down to Illinois’ capital, Springfield. You can re-live President Abraham Lincoln’s legacy as you explore his home and law office, the Old State Capitol, his tomb and the Abraham Lincoln Presidential Library and Museum. For your Route 66 experience, be sure to visit Bill Shea’s Route 66 Gas Station Museum, stop for a Cozy Dog and see a movie at the Route 66 Twin Drive-In Movie Theatre. Other highlights for your stay include Frank Lloyd Wright’s Dana-Thomas House and nearby Lincoln’s New Salem – a reconstruction of the village where Lincoln spent his early adulthood. Overnight: Springfield
  • Day 4 Springfield to Alton/Grafton
    Driving distance today is 88 Miles/ 142 KM
    Continue down Route 66 to the Alton area and see the confluence of three rivers – the Mississippi, Illinois and Missouri – along a 33-mile stretch of road rich in history and beautiful limestone cliffs. Discover the quaint towns of Elsah and Grafton, with their wineries and unique inns and cottages. Find painted on the cliffs the replication of the Piasa bird that explorers Marquette and Joliet discovered in 1673. Marvel at the height of the world’s tallest man – Robert Wadlow. Don’t miss the Lewis and Clark State Historic Site that tells the story of Lewis and Clark in Illinois at Camp River Dubois – the “point of departure” for the Corps of Discovery. Stand in awe of the Mississippi River at the National Great Rivers Museum at the Melvin Price Locks and Dam (#26) that is the centre of commerce and transportation along the Mississippi. Overnight: Alton
  • Day 5 Alton/Grafton to Peoria
    Driving distance today is 165 Miles / 266 KM
    Start your visit at the Riverfront Visitors Centre, housed in one of the oldest buildings in Peoria. Explore Peoria’s Riverfront, the site of popular festivals and home to the newly opened Peoria Riverfront Museum, featuring a 3D theatre and planetarium. Wander the newly opened Caterpillar Visitors Centre that features a 24-foot tall replica of a 797 mining truck and exhibits highlighting the company’s history and heritage. You’ll want to take a cruise on the Spirit of Peoria and enjoy the scenic views on the Illinois River. Overnight: Peoria
  • Day 6 Peoria to Galena
    Driving distance today is 154 Miles / 248 KM
    Travel back up the Great River Road to Galena. Along the way, stop in Fulton to see the Windmill “de Immigrant” and the Albany Indian Mounds State Historic Site. The Mississippi River played an integral part in Galena’s history and growth. It was a bustling town in the early 1800s and grew quickly with the discovery of lead in the surrounding hills. Over 85 percent of the town is on the National Register of Historic Places and has been noted as one of the Top 10 Most Romantic Small Towns in North America. The area’s rich history can be traced back to the Black Hawk Wars between the Native Americans and settlers. Don’t miss the Apple River Fort in Elizabeth. Ulysses S. Grant, the 18th President of the United States, settled here after the Civil War and his home is a State Historic Site. Overnight: Galena
  • Day 7 Galena to Rockford
    Driving distance today is 152 Miles / 245 KM
    A short drive through rolling hills and small towns takes you to Rockford. Rockford offers a perfect stop before departing for home. Don’t miss the Burpee Museum, home to “Jane,” a rarely-found teenage T-Rex. Stroll through Anderson Japanese Gardens names “The Best in North America”. The magnificently restored Coronado Theatre offers a variety of performances. History comes to life at the late nineteenth century village at Midway Village Museum. For outdoor adventure, go kayaking along the Rock River or biking through Rock Cut State Park. If golf is your interest, Rockford has a variety of affordable, high-quality courses. Overnight: Rockford
  • Day 8 Rockford to Chicago
    Driving distance today is 86 Miles/ 138 KM
    Chicago O’Hare International Airport Is an easy hour drive from Rockford so you can either take your leisure in Rockford before departing for the Airport for your return flight to Dublin leaving enough time to drop off your rental car.

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