Ultimate Illinois Route 66 Road Trip Itinerary

Get your kicks on Route 66. Immortalized by the Nat King Cole song, Route 66 is the ultimate American road trip experience. The historic highway has come to symbolize freedom and the search for a better future. Here’s a handy Illinois Route 66 road trip itinerary with tips for what to see along the way.

Illinois Route 66 Road Trip Itinerary

In Illinois, you can still drive on segments of the original red brick Route 66. Due to the length of the original road, it’s a good idea to choose a section of the route for your road trip.

We recommend the Illinois section for its great mix of quirky roadside attractions, cultural sights and historical interest. You’d also be hard pressed to find a friendlier bunch of people than the inhabitants of Illinois.

Route 66 History

On 3 December 1818, Illinois became the 21st State in the Union. Route 66 opened on 11 November 1926, although the iconic road signs were only erected a year later. This iconic road connected 8 American States, Illinois, Missouri, Kansas, Oklahoma, Texas, New Mexico, Arizona and California.

Also known as the Mother Road, the Will Rogers Highway and the Main Street of America, Route 66 linked many farming communities. Diners, motels and gasoline stations sprung up along the route.

In the 30s, when crops were affected by dust storms, known as the Dust Bowl, people temporarily migrated West via Route 66. In 1939, John Steinbeck penned his classic novel, The Grapes of Wrath, referring to the classic highway: “66 is the mother road, the road of flight.“

When historic Route 66 first opened, only 800 miles were paved. The Illinois and Kansas sections of the highway were completely paved by 1929, and the whole route was paved by 1938.

Over the years, sections of US 66 were replaced by the Interstate Highway System. In 1985, the original Route 66 was officially decommissioned from the United States Highway System.

Luckily, parts of the iconic highway have been designated a National Scenic Byway and new signage has sprung up to guide visitors to Historic Route 66. Thanks to the Route 66 Corridor Preservation Program, financial assistance is provided to maintain the heritage of the road.

Route 66 Facts

• How long is Route 66? The original Route 66 was 2,448 miles long (3,940 km).
• How long to drive Route 66? You could cover the whole distance in a week but at least 2 weeks to a month is preferable.
• What is the best time of year to do a Route 66 road trip? In mid Winter there is a risk of snow in parts. Spring and Autumn are good times to drive Route 66. Summer is also pleasant and you should consider booking accommodation in advance.
• Are there historic Route 66 attractions that you can still see today? Yes many, read on for our full guide to the Illinois segment of the route.
• Where does Route 66 start? In Chicago, Illinois.

Route 66 Chicago Attractions

Chicago, Illinois is well known as the start of Route 66, but it was also the end of Route 66 for those travelling eastwards. Both signs are great photo opportunities.

• Route 66 Begin sign – 99 E Adam St. (intersection with Michigan Ave.).
• Route 66 End sign – E. Jackson Blvd. (intersection with S. Michigan Ave.).
• Lou Mitchell’s – 565 W Jackson Blvd. This famous diner opened in 1923 and became popular with travellers on Route 66 when the highway opened in 1926. Ever since, it’s been serving tasty comfort food. Lou Mitchell’s is listed in the National Register of Historic Places for its original neon sign dating from 1949.

Other Must See Chicago Attractions

• Cloudgate – nicknamed The Bean, this statue by Sir Anish Kapoor is located in Millennium Park in the Loop community area.
• Absolutely Segway Tour 300 Monroe St., Chicago. A fun way to take in sights such as Buckingham Fountain, the Lakefront and Museum Campus.
• Shoreline Architecture Cruise – you’ll see over 40 Chicago landmarks on this architecture tour and learn a lot from the expert guides. The cruise departs from Michigan Avenue Dock.
• CityPASS – you can save 53% on Chicago’s best attractions with CityPASS including a fast pass to Skydeck Chicago, VIP entry to The Field Museum, express entry to 360 CHICAGO Observation Deck.
• Shopping on The Magnificent Mile – for luxury fashion and historic sights like the Wrigley Building skyscraper.
• The Ledge at Skydeck Chicago – admire the city from the glass viewing box on the 103rd floor. Admire the 360 degree views and look 1,353 feet down.
• Andy’s Jazz Club – since the ’70s, Andy’s on E. Hubbard St. has been one of the most popular jazz clubs in Chicago. 3 bands play every day of the week and there’s also a modern American dining menu with Cajun influences.
• Chicago Water Taxi – one of the most fun ways to get around Chicago is to take a water taxi from one of 7 riverside locations. The Ogilvie/Union West Loop passes by some interesting architecture such as the Willis Tower and the Lyric Opera House.

Where to Eat in Chicago

• Gino’s East – famous for its deep dish pizza and graffiti decor since 1966. Several locations including the original one at 162 E. Superior St. where guests can write their names or a message on the walls.
• Imperial Lamian – serving authentic, modern Chinese cuisine and fantastic tea-infused cocktails in stylish surroundings on West Hubbard St. in the River North neighbourhood. Watch the chefs making the hand-pulled Lamian noodles from the open-plan kitchen.

• Hugo’s Frog Bar & Fish House –  fresh seafood delivered daily at 1024 North Rush Street.

Where to Stay in Chicago

The Warwick Allerton Chicago has a fantastic location at 701 N Michigan Avenue. It’s a historic building that dates from the 1920s yet has been completely renovated, with spacious rooms and Specialty Suites. From the marble bathrooms to the luxurious bathrobes and great views of Chicago, it’s a great place to stay.

Chicago to Heritage Corridor – around 50 miles

The I&M Canal National Heritage Corridor stretches all the way from Chicago to Starved Rock State Park in Oglesby. It’s a scenic area with 61 miles of canalside trails, together with historical attractions and Route 66 landmarks.

• Joliet Area Historical Museum – at the museum’s Route 66 Experience, you can see a replica 50s Corvette, parked in a drive-in. Stepping forward in time, find out more about John Houbolt, the NASA engineer and former Joliet resident who played a key role in the American moon landing program in the 60s.
• Old Joliet Prison – From 1958 to 2002, Old Joliet Prison was in operation. It featured in The Blues Brothers as well as TV show Prison Break. A fundraising effort is underway to renovate the building and open it up to the public.

• MyGrain Brewing  – This cleverly named craft beer brewery is located in the former Union Station on 50 East Jefferson Street, Joliet. It was opened by friends Gregory and Vince, who both had a passion for beer. You can see the craft beer being brewed through a glass window, whilst you enjoy a refreshing beverage, burger, tacos or beer beignets.
• Gemini Giant and The Launching Pad – One of the most iconic Route 66 sights is the Gemini Giant, a 30 foot tall statue on 810 E. Baltimore Street, Wilmington. It’s one of the best examples of a Muffler Man, fibreglass statues that were used for advertising. Next to the Gemini Giant you’ll find The Launching Pad, a Route 66 gift shop and restaurant that has been lovingly restored by Holly Barker and Tully Garrett.

Heritage Corridor to Pontiac – around 60 miles

Pontiac, Illinois boasts fascinating Route 66 exhibits, 4 interesting museums, a historic courthouse, 3 swinging pedestrian bridges and 24 large murals.

• Route 66 Hall of Fame and Museum – At 110 W. Howard Street, Pontiac, admire the huge mural of the Mother Road on the outside of the building. Inside, there’s a large collection of Route 66 memorabilia and personal stories of the people associated with the road. One of the most unique was Bob Waldmire, a travelling artist who lived in a VW van on display at the museum.
• Pontiac Oakland Auto Museum – an impressive display of Pontiac and other classic cars at 205 N. Mill Street, Pontiac.
• Museum of the Gilding Arts – unique exhibits of gold and silver leaf, information on the methods of application and a recreation of the M. Swift and Sons gold beating room, at 217 N Mill Street, Pontiac.

• Route 66 murals on Main Street – 23 murals including 18 painted in 2009 by the Walldogs, a group of sign painters.
• Dongbai International Air Brush Art School – acclaimed artist Tang Dongbai teaches the art of air brushing and exhibits his own intricate paintings at 425 W Madison Street.
• Bernardi’s – one of the best restaurants in Pontiac, serving Italian specialties and American classics like fried chicken in a relaxed atmosphere on North Mill Street.
• The Cup and The Scone – inspired by British coffee houses, this recent addition to the Pontiac dining scene has a great selection of single origin roasts, stone cold brews, cakes and muffins.

Pontiac to Springfield – around 105 miles

You’ll discover some great examples of Route 66 roadside memorabilia on this section of your journey, including:

• Paul Bunyon Hotdog Statue – at 112 SW Arch Street, Atlanta. Often misspelt as Paul Bunyan, this 19 feet tall statue is another of the Muffler Men. These fibreglass sculptures are hollow on the inside and were built between 1963-1972. This one was made in 1966 and is located opposite the Palms Grill Café, which plays music from the 30s and 40s, the heyday of Route 66.
• World’s Largest Covered Wagon – acknowledged by the Guinness Book of World Records as the largest covered wagon in the world. The Railsplitter Covered Wagon is is 7.6 m tall, 12.2 m long and 3.65 m wide and is situated on the front lawn of the Best Western Lincoln Inn on 1750 5th Street, Lincoln.

Springfield

Famous as the home of Abraham Lincoln, Springfield Illinois has some Route 66 historic sights that you shouldn’t miss.

Route 66 Springfield Il Attractions

• Route 66 Cozy Dog Drive In – this Springfield Route 66 landmark was opened in 1949 by Ed Waldmire, the father of the artist Bob Waldmire. They specialize in cozy dogs, a hot dog on a stick with fried batter made to their own secret recipe. Ed’s grandson runs the business today and you can pick up Route 66 souvenirs including artwork created by Bob.
• Route 66 Motorheads Bar, Grill, & Museum – packed with vintage signs and neons, this is a fun place to stop for a beverage at 600 Toronto Road, Springfield.

Historical Attractions in Springfield

• Lincoln Home National Historic Site – faithfully restored to its appearance in 1860, the Lincoln family home on South 8th St. gives you a glimpse of Abraham Lincoln’s family life. There are 12 other historic houses in the area around the museum to admire.
• Old State Capitol – this Greek revival style building was reconstructed in the 1960s. Lincoln delivered his famous House Divided speech in the original Representatives Hall in 1858.
• Abraham Lincoln Presidential Museum – this interactive museum brings the past to life thanks to holographics, special effects and live actors who will answer your questions on Abraham Lincoln and his legacy.
• Lincoln Tomb – one of the most visited historical cemeteries in the United States, it is the final resting place of Abraham Lincoln and his family (the eldest son was buried in Arlington National Cemetery).
• Illinois State Capitol – crowned by a 405 foot glass dome, this striking example of Renaissance Revival and Italianate styles was completed in 1888.
• Dana Thomas House – this masterpiece of Prairie Style architecture was created in 1902 by Frank Lloyd Wright for Susan Lawrence Dana.  It contains a beautiful collection of original furniture and glass over 12,000 square feet of living space which includes 3 main levels and 16 varying levels in all.

Where to Eat in Springfield

The state of Illinois has gathered together some of the finest artisans, breweries and restaurants under the banner Illinois Made. Two of the finest examples can be found in Springfield and Peoria:

• Engrained – enjoy delicious microbrewed beers and farm to table cooking at 1120 West Lincolnshire Blvd in Springfield.
• Custom Cup – locally roasted coffee at 319 E Monroe St.,  Springfield. They specialize in small batch and roast to order coffee.

Where to Stay in Springfield

The Wyndham Springfield City Centre on E. Adams Street has a handy central location as well as a swimming pool and a restaurant with panoramic views over the city. The rooms are extremely spacious and have all mod cons.

Springfield to Great Rivers & Routes – around 85 miles

On the final leg of your Route 66 Illinois road trip, in the Great Rivers & Routes region you’ll encounter vintage roadside diners, picturesque countryside and an impressive UNESCO World Heritage Site.

• Historic Route 66 Brick Road – Don’t miss the opportunity to drive on the original red brick Route 66 at Curran Road and Snell Road in Auburn. The scenic 1.4 mile drive next to corn fields was laid by hand in 1931. It’s generally not very crowded but look carefully before posing for photo opportunities on the road itself.
• Pink Elephant and Route 66 experience – the name comes from the giant pink elephant adorning the facade of this popular Route 66 attraction at 908 Veterans Memorial Dr., Livingston. There’s a huge antiques centre and 1950s style diner inside, and a candy store will open soon. 
• Weezy’s on Route 66 – since opening in the 1930s, this diner at 108 S. Old US Route 66 in Hamel has been wowing the crowds with its Horsehoe Sandwiches and other Midwestern specialties.
• World’s Largest Catsup Bottle – this catsup or ketchup bottle was built in 1949 for Brooks Catsup It stands 170 foot tall and can be found at 305 Railroad Ave., Collinsville.

• Cahokia Mounds State Historic Site – discover the remains of the largest Pre-Columbian settlement North of Mexico. Cahokia Mounds is a UNESCO World Heritage Site as well as a State Historic Site, spread over 2,200 acres. There are over 70 historic mounds, built between AD 900 and 1200 by Native Americans, as well as a reconstructed Woodhenge and informative visitors’ center.
• Fast Eddie’s Bon Air – a good place to cool off thanks to its air misters, cool beers and colorful decor at 1530 E. 4th St., Alton..
• Robert Wadlow Statue – officially the world’s tallest man, Robert Wadlow was known as the Gentle Giant and was 8 ft. 11.1 inches tall. at the time of his death aged just 22 years old.
• Miles Davis Statue – the legendary jazz musician was born in Alton and his statue can be found at 117 W. 3rd St.
• McPike Mansion – Alton is famous for its ghosts and the McPike Mansion is reputed to be one of the most haunted buildings in the USA. Sharyn and George Luedke are restoring it to its former glory and there are regular tours.
• Lewis & Clark Confluence Tower – this landmark tower gives you a panoramic view of the point where the Missouri and Mississippi rivers converge. It’s also the spot where iconic explorers Meriwether Lewis and William Clark established Camp River Dubois in 1803 to prepare for their three year expedition.

• Pere Marquette Lodge – nestled within scenic Pere Marquette State Park, this stylish lodge and restaurant are well worth a visit. Guests can relax in the Great Room, dine in the restaurant or stay in a lodge room or log cabin.
• Grafton Winery The Vineyards – with a lovely setting overlooking a lake, this winery and 4 acre vineyard specializes in Chardonnel, Vidal and Vinoles grapes.
• The Loading Dock – a great spot to enjoy lunch on the Mississippi River. There’s a monthly Flea Market from April to October, regular live music sessions and even an ice rink in the Winter.
• Historic Elsah – This beautiful place is known as the village where time stood still and is listed on the National Register of Historic Places.
• Piasa Bird – the piasa is a mythical monster that was painted on the Mississipi bluffs near Alton and first discovered by Father Jacques Marquette in 1673. The dragon-like bird was painted by Native Americans and you can see a replica at Piasa Park, outside Alton.
• Gentelin’s On Broadway – with a stunning view of Alton’s Clark Bridge, this restaurant has a delicious selection of pasta, seafood and steak as well as an extensive wine and Martini list.

Where to Stay in Great Rivers & Routes

Whether you prefer to stay in a hotel or a bed and breakfast, there are some good options in the Great Rivers & Routes area.

• Best Western Premier Alton – large bedrooms, complimentary high speed WiFi, swimming pool and whirlpool.
• Beall Mansion – this award-winning Bed and Breakfast Inn at 407 E. 12th St., Alton is situated within an elegant mansion. Decorated with the finest antiques, there’s a complimentary chocolate buffet.
• Tara Point Inn & Cottages – Noted in Midwest Living magazine as a riverside retreat for the romantic, the Tara Point Inn & Cottages in Grafton, Illinois is known for its incredible accommodations and breathtaking views (of the Mississippi River and Illinois rivers).

Getting to Route 66

By Plane

• Chicago O’Hare International Airport (ORD)
• Chicago Midway International Airport (MDW)
• Domestic flights to Bloomington-Normal, Moline, Peoria, Rockford, Springfield and more
• Lambert International Airport, St. Louis

By Train

• Amtrak serves 26 cities in Illinois, including Alton, Chicago, Joliet and Springfield.

By Car

• You must wear a seatbelt when travelling by car in Illinois, or a helmet if making your trip by motorbike.

Have you ever been to Illinois? We hope to have inspired you to take a road trip on Route 66.

Interested in the USA? Check out these other US travel features: Best Natural Hot Springs in the US | Best Restaurants in Naples FL | Best Things to Do in Springfield Illinois | The Most Expensive Cities to Live in the US | The Most Historic Houses in the US |

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This Route 66 road trip was arranged in association with Enjoy Illinois.

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