Route 66 East

  • Chicago
  • St Louis
  • Springfield
  • Tulsa
  • Oklahoma City
  • Dallas
  • 15 nights from
  • £2,595 per person
  • Trip Code: SD-1283

Holiday Overview

Route 66 East 

The perfect itinerary for anyone wanting to drive the iconic Route 66 without spending hours behind the wheel. In this trip experience a section of the Route 66 from Chicago to Dallas. Along the route journey through four US States including Illinois, Missouri, Oklahoma, and Texas.

Discover the history of Route 66 by driving through Missouri-Ozark region, the birthplace of Route 66. Explore what makes each town along Route 66 unique by visiting local museums, natural scenery and local restaurants.

16 Days / 15 Nights

Route 66 East includes:

  • International Flights
  • Car Hire
  • 15 Nights Accommodation

Day 1 - Fly UK to Chicago

Arrive at Chicago Airport, collect your car hire and make your way to your hotel.

The glittering metropolis of Chicago awaits you with cutting-edge architecture and the tallest buildings in the world. A first walk gets you in the right mood for your stay in this fascinating City. It is famous for its high recreational value and the cultural offerings. We suggest taking a tour of Chicago or visit Millennium Park (not included) which is a world leader of art and architecture in a public, outdoor, urban setting. Invoking a sense of calm, refuge, and reflection, each visitor can indulge in a unique artistic experience. Chicago is the Midwest's hub, and it is well-known for its magnificent skyline that stretches across the waters of the massive freshwater Lake Michigan.


Hotel Suggestion – Whitehall Chicago


Day 2 - Chicago

Today explore the metropolis city of Chicago! Visit their world-class museums, kilometres of sandy beaches, sprawling parks, public art, and maybe the most beautiful city in the world. Chicago's premier commercial district, the Magnificent Mile, is where to go to get all your Chicago shopping done!

An alternative way of experiencing Chicago is one of the Mob and Crime tours (not included). It's not for the faint of heart, though, exploring the sites of Chicago's most famous and notorious crimes took place. It's the perfect activity for those rainy or windy days when you can't explore Chicago on foot. See famous Chicago crime scenes from the 19th century through to modern times. You'll learn about Al Capone, the Untouchables, the Chicago Mob, Terrible Tommy O'Connor, the Chicago Black Sox, Leopold and Loeb, Cap George Streeter, and more. You'll also hear about some of the most daring heists in history!

Go for a ride on the iconic Centennial Wheel with fantastic views over Chicago and Lake Michigan. Explore virtual reality or test your strength on the climbing wall. Navy Pier is also the primary departure point for many lake cruises and bus tours, so it's the perfect place to go if you have a little more time than expected! (Tours not included in the package)


Hotel Suggestion – Whitehall Chicago

Unmissable Experiences

Chicago Experiences


Day 3 - Chicago to St Louis

Today head south on Route 66 and enjoy the old "truck stop" of McLean, follow the Pontiac Trail all the way to St. Louis. The top stops along the way from Chicago to Saint Louis (with short detours) are Abraham Lincoln Presidential Library and Museum, Lincoln Home National Historic Site, and Frank Lloyd Wright Home & Studio. Other popular stops include Harrah's Joliet, Lincoln Monument Association, and Route 66 Association of Illinois. The stretch of Route 66 from Chicago, Illinois, to St. Louis, Missouri, is home to aluminium-and-chrome diners, historic, family-owned cafes, bizarre attractions, and other reminders of the route's charming past. Leave Downtown Chicago early. You can bypass the city's avenues and incoming rush hour traffic by taking I-55 westwards. Leave at Exit 274 to visit your first Route 66 landmark: Historic Dell Rhea's Chicken Basket in Willowbroo. Continue along and leave at Exit 268 onto IL-53 towards Joliet; this state highway is the original 1926 - 1939 alignment of Route 66, and from 1940 to 1977 it was ALT 66. Stop at the 1920s The White Fence Farm restaurant in Romeoville, and then as you approach Joliet along N. Broadway there are some classics: The Joliet Kicks on 66 Shield-sign and Dick's Towing heading into Joliet is the Site of World's First Dairy Queen and Route 66 meets Lincoln Highway marker. Head south along Route 66 into Pontiac and see the murals and attractions at the Route 66 Association of Illinois Museum. 

Start your second leg of the day, in Lincoln visit the Mill Museum on Route 66. Then get onto I-55 at Exit 123. You will bypass Springfield and stay on the freeway all the way to Mt. Olive. Take Exit 44 to visit the Historic Soulsby's Shell Service Station. Stay on the old Route 66 into Staunton to visit Henry's Rabbit Ranch, next stop to Kitsch spot on US 66, the Pink Elephant Antique Mall in Livingston Take I-55 at Exit 33 all the way to Exit 15A. Follow IL-259 into Collinsville to visit the Historic Largest Catsup Bottle in the World. Head towards the last stop for the day along I-255 and I-270. Then take Exit 3 onto Chain Of Rocks Rd. to visit the historic bridge: It has been a long drive from Chicago (6h 05min behind the wheel and 309 miles) so enjoy the Historical Chain of Rocks Bridge (Madison). A full day along Route 66.


Hotel Suggestion - Hampton Inn St. Louis Southwest


Day 4 - St Louis

Today, we suggest visiting The New Cathedral Basilica of St. Louis with one of the largest mosaic collections in the Western hemisphere. The Cathedral is in the heart of the city of St. Louis, just east of Forest Park, and is one of the must see in St. Louis. Self-guided tours do not require reservations. Guided tours are available Monday - Saturday by appointment only. (free) Top attractions in St Louis include The Arch, Forest Park, Museum of Transportation, Cahokia Mounds (UNESCO World Heritage Site) and Purina Farms. From taking in the stunning view from the Gateway Arch to visiting the one-of-kind City Museum you're sure to have a great time.

The Gateway Arch is a 630-foot-tall monument in St. Louis. Clad in Stainless steel and built in the form of a weighted catenary arch, it is the world's tallest arch and Missouri's tallest accessible building. If time permits visit the Missouri Botanical Garden located at 4344 Shaw Boulevard. At the Saint Louis Science Centre, you can explore 700-plus exhibits, the OMNIMAX Theatre, James S. McDonnell Planetarium, special traveling exhibitions and more.Open daily. (General admission is free) St. Louis is a place where history and imagination collide, and the result is a destination like no other.


Hotel Suggestion – Hampton Inn St. Louis Southwest


Day 5 - St Louis to Springfield

Today the journey takes you through the beautiful Missouri-Ozark region birthplace of the famous Route 66. Visit some must-see highway stops such as the Dixie Truck Stop, Litchfield or the Our Lady of the Highway statue and Paris Stop Cafe. On the way to the Mississippi check out the Meramec Caverns and the famous Chain of Rocks Bridge. The true nature of Springfield, Missouri is rooted in the genuine desire to celebrate life's simple pleasures. From the natural beauty of the Ozarks to the vibrancy of a metropolitan city, Springfield is filled with memorable attractions. Springfield top attractions include Pythian Castle, Wilson's Creek National Battlefield, The Air and Military Museum of the Ozarks, Nathanael Greene/Close Memorial Park, Fantastic Caverns and the Route 66 Car Museum.

Driving through the outskirts of St. Louis stop by Ted Drewes, a family runs frozen custard shop. A Route 66 Treat. Make sure to stop at Route 66 State Park. It is on the abandoned site of the town of Times Beach, a summer resort spot in the 1920s for the city dwellers of St. Louis. The Visitor Centre is the former Bridgehead Inn, a 1935 roadhouse that sat on the original Route 66.


Hotel Suggestion - Best Western Coach House


Day 6 - Springfield

Today in Springfield, enjoy the many free museums, parks, historic sites public gardens, a butterfly house where native species can be observed and nature centre. You can let your feet take you on a sculpture walk, a hike on the Ozark Greenways Trails or an exploration of historic Commercial Street where you can do the C-Street Stroll. You'll be stunned by The Library Centre and the Library Station, the Missouri Institute of Natural Science, and the Springfield Art Museum.


Hotel Suggestion – Best Western Coach House


Day 7 - Springfield to Tulsa

Today along the way, visit the mining town of Web City and Missouri's last major city, Joplin. Drive through the short 13 miles of Route 66 in Kansas (Galena, Riverton and Baxter Springs) before reaching your first Oklahoma Route 66 town, Miami. Miami, Oklahoma, pronounced 'My-am-uh' takes its name from the Miami Indians and became the first chartered town in Indian Territory Here we will visit the Coleman Theatre and drive a piece of the actual 'ribbon road' when departing for Ed Galloways Totem Pole Park in Chelsea Territory. The nation's longest drivable stretch of Route 66 crosses Oklahoma, making its way past charming towns, roadside diners, and quirky attractions. Next stop is the Will Rogers Museum in Claremore and the Blue Whale in Catoosa before reaching Tulsa.

Hotel Suggestion - Days Inn by Wyndham Tulsa Central


Day 8 - Tulsa

Today explore Tulsa, which is located on the Arkansas River and home to cosmopolitan delights coupled with Southern Hospitality, a dynamic city known for a variety of bustling urban districts, exceptional dining, and unsurpassed love of the arts and one of the largest collections of art deco architecture in the nation. Route 66 related iconic photo stops include (Buck Atoms Space Cowboy, the Golden Driller, Praying Hands, East Meets West symbolic halfway point, and Neon Park at Centennial Plaza).


Hotel Suggestion – Days Inn by Wyndham Tulsa Central


Day 9 - Tulsa

Today explore Tulsa’s must-see attractions which include the Bob Dylan Centre, Woody Guthrie Centre, the Church Studio, Greenwood Rising, Philbrook Museum and Gardens, and the Gathering Place. This city is packed with live music, fantastic restaurants, and craft breweries to enjoy the better-than-the coast food and drink scene... You also will have time for a side daytrip to Cherokee National History Museum complex in Tahlequah. Some fun facts about Tulsa: Black Wall Street, Tulsa's Giant Gold Statue, 'The Golden Driller', The 'Yield' Sign was invented in Tulsa, Garth Brooks is a Tulsa Boy, A Cult Movie was filmed in Tulsa 'The Outsiders' 1983 classic film by Francis Ford.


Hotel Suggestions – Days Inn by Wyndham Tulsa Central


Day 10 - Tulsa to Oklahoma City

As you depart Tulsa on Route 66 toward Oklahoma City, visit the Heart of Route 66 Auto Museum and the World's Largest Gas Pump in Sapulpa before hitting the interesting towns of Stroud (Rock Cafe), and Chandler (Route 66 Interpretive Centre). Stop in Luther at the Chicken Shack and in Arcadia at the Round Barn and POPS Soda Ranch before arriving in Oklahoma City. Oklahoma boasts more than 400 miles of Route 66 - more than any other state and Oklahoma City serves as the centre point. You will find a mix of historic and modern experiences along the route, as Oklahoma is home to some of the Mother Road's most iconic landmarks, attractions, and destination dining.


Hotel Suggestion - Baymont by Wyndham Oklahoma City/Quail Springs


Day 11 - Oklahoma City

Today in Oklahoma City visit their must experience attractions in Oklahoma City include First Americans Museum, The National Cowboy and Western Heritage Museum, Oklahoma City National Memorial, River Sport Adventures, Stockyards City (Cattlemen's Cafe and OKC Opry), and Bricktown, Midtown, Uptown and the Paseo Arts District for diverse food and plenty of night time entertainment. You must travel down Oklahoma City's bustling 23rd Street for nostalgic neon signs, iconic concert venues and dining destinations paying homage to Route 66.


Hotel Suggestion – Baymont by Wyndham Oklahoma City/Quail Springs



Day 12 - Oklahoma City to Sulpur

As you have now reached the halfway point of Route 66, today you will head south from Route 66 toward Dallas there is so much to experience on the way! Make your way from Oklahoma City to Sulphur which is a town tucked in the rolling prairie of cross-timber country, Sulphur is the gateway to Chickasaw National Recreation Area It is known to Native Americans as 'the land of the rippling waters' due to the mineral waters, streams, lakes crisscrossing the area.


Hotel Suggestion - Best Western Plus Chickasha Inn


Day 13 - Sulphur

Today discover gorgeous hiking trails, creeks, lakes, hills, and swimming holes in Sulphur. Visit Chickasaw Cultural Centre and each at Smokin' Joes Rib Ranch in Davis. Next day enjoy the beautiful outdoor Chickasaw Recreational Area, Travertine Falls Nature Trail, and the Artesian Spa. Overnight at the Artesian Hotel & Spa.


Hotel Suggestion – Best Western Plus Chickasha Inn


Day 14 - Sulpur to Dallas (Grapevine)

Today as you head south from Davis stop to see Turner Falls and don't miss tasting an Arbuckle Original Fried Pie. Eat it now or take it for later - but don't miss it. Historic Downtown Grapevine you will find great boutique shops, galleries and artisans, wineries, Food Tours, Grapevine Vintage Railroad a 1920's-era Coach & Depot (with daily round trip departures to Fort Worth) and Nash Farm a late 19th century farm. Grapevine has emerged into a fun, western, shopping, historic small city in the Dallas metroplex. LEGOLAND Discovery Centre and SEA LIFE Aquarium is the cornerstone of the Grapevine Mills Mall (Meow Wolf will be opening at Grapevine Mills in 2023) This is an interactive and immersive art experience. Experience an award-winning Wild West Murder Mystery Dinner Theatre production at the Texas Star Dinner Theatre in downtown historical Grapevine, Texas (not included).


Hotel Suggestion – Wingate by Wyndham DFW / North Irving


Day 15 - Dallas (Grapevine)

Today explore Grapevine, enjoy a picnic, fishing, boating, kayaking, or swimming at the Grapevine Lake. Enjoy a glass of wine along the Grapevine Urban Wine Trail, with multiple wineries tasting rooms located within the Historic Main Street District. Experience a local culinary tour with Grapevine Food Tour or Grapevine Wine Tours and dine in one of over 200 local restaurants offering Texas favourites such as BBQ, Tex-Mex and steaks as well as many other culinary cuisines. Saddle up at the bar at one of the local saloons or purchase yourself some western wear at one of the local shops before heading to dinner. See why Texas is known for their steaks at Cattlemen's or H3 Steakhouse. Grapevine's famous Parade of Lights is one of the largest lighted Christmas parades in North Texas, while the Twinkle Light Boat Parade is certainly of the quirkiest.


Hotel Suggestion – Wingate by Wyndham DFW / North Irving


Day 16 - Fly Dallas to UK

Today check out your Grapevine hotel and make your way to Dallas Airport. Drop off your car hire and check in for your return flight to the UK.

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