Illinois Route 66 and The Great River Road

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8 Nights

Visit Some Superb Destinations: Chicago, Springfield, Grafton & Galena

Or call us on 0203 542 8888 our travelplanners are waiting to assist you
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  • 2 Nights Millennium Knickerbocker, Chicago
  • 1 Night Comfort Suites, Springfield
  • 2 Nights Best Western Plus Parkway Hotel, Grafton
  • 2 Nights Galena Hotel & Day Spa, Galena
  • 1 Night Hampton Inn, Rockford
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About Illinois Route 66 and The Great River Road

Discover Chicago’s rich heritage with our Illinois Fly Drive, an adventure for everyone – from couples and families to solo explorers. Experience the city and its iconic attractions with ease. Explore Chicago, Springfield, Alton, Grafton, Galena and Rockford.

Days 1 & 2 – Chicago 
Begin your adventure in Chicago, a city full of architectural marvels, museums, theaters, and iconic spots like Navy Pier and the Chicago 360 Observation Deck. Take the Chicago Architecture Foundation’s River Tour to learn about the city’s innovative buildings, explore the Art Institute of Chicago, or trace the Frank Lloyd Wright trail. For family-friendly fun, visit Shedd Aquarium and the John Hancock Center, or enjoy the shops along the Magnificent Mile. Wind down with alfresco dining, a stroll through Millennium Park to see the famous Cloud Gate (“The Bean”), and an evening in the lively Theater District, complete with live music and the city’s best deep-dish pizza.

Day 3 – Springfield
On day three of your fly drive hit the road toward Springfield along historic Route 66, with stops at fascinating roadside attractions. Along the Mother Road on your way into the capital, discover Abraham Lincoln Presidential Library and Museum and Lincoln Home National Historic site. This scenic byway offers plenty of interesting opportunities for you to explore, the new Legends Neon Sign Park at the Illinois State Fairground in Springfield, the park is an homage to incredible signs. Stop by at The Cosy Dog Diner. You also wouldn’t want to miss Bill Shea’s Gas Station and Museum. Make unique memories as you travel through Springfield, reliving a remarkable era in Illinois’ history.

Day 4 & 5 – Alton/Grafton
Discover the Meeting of the Great Rivers as you continue your journey down Route 66. As you travel through Alton, along the forested river bluffs and beautiful limestone cliffs you can see the Mighty Mississippi, Missouri and Illinois Rivers converge.

Explore scenic wineries, inns, and historic sites like the Piasa Bird, the Lewis and Clark State Historic Site, and the Cahokia Mounds. At the National Great River Museum, take in the panoramic river views or tour the Melvin Price Lock and Dam. Enjoy a meal at local favorites like Fast Eddie’s Bon Air or Mac’s Time Out Lounge.

Day 6 & 7 – Galena 
The cosy town of Galena can satisfy the needs of city goers with its modern-day style and wine tasting vineyards. Travel up the Great River Road and stop off in Fulton to see the ‘de Immigrant’ Windmill. Take advantage of Galena’s title – being one of the top 10 most romantic small towns in North America and have a romantic meal at a quaint restaurant. With 85 percent of Galena featuring on the National Register of Historic Places. Carefully preserved nineteenth-century buildings nestled in the Mississippi River Valley are the perfect attraction for sightseeing; you could also enjoy a day of shopping, golfing or kayaking.

Day 8 – Rockford
Rockford offers the perfect stop before departing for home. With its small towns and rolling hills, this city greets visitors with history, natural beauty and artistic touches, creating the perfect atmosphere. Visit the Burpee Museum or natural history home to a T.Rex named Jane. Stroll through the beautiful Anderson Japanese Gardens. It’s a beautifully designed space featuring koi ponds, waterfalls, and traditional Japanese structures. Rockford offers something for everyone, including high quality golf courses, a Rock River ideal for kayaking or a Rock Cut State Park perfect for biking. The Chicago O’Hare International Airport is an easy one hour drive from Rockford, so you can relax and enjoy your fly drive right down to the very last minute.

The Illinois Fly Drive is suitable for all ages and all types of people who wish to explore Chicago’s heritage, whether you’re planning to venture as a couple, a family, or travel independently there is something for everyone. The Fly Drive provides tourists with an easy way to see the city and its main attractions.  If you are interested in the history of Chicago the Illinois Fly Drive is definitely something for you. Call our travelplanners 020 3542 8888 to book this amazing fly-drive holiday today!

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