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11 Night Self-Drive Illinois Route 66 Adventure

Explore the beginning of the iconic Route 66

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11 Night Self-Drive Illinois Route 66 Adventure



11 nights



Departing from

London Heathrow - Other options may be available

11-Night Self-Drive Illinois Route 66 Adventure from £1,735pp

Explore the beginning of the iconic Route 66 from Chicago to Pontiac and Springfield, before driving through Southern Illinois and back up to Chicago. Price includes return direct flights with bag allowance, 9-day car hire, accommodation in 3-/4-star hotels throughout, ATOL protection, and a FREE £173 donation to the charity of your choice.

Every time you book a holiday with Charitable Travel you can donate 5% of the price to the charity of your choice for FREE!


Day 1 – London to Chicago 
Transfer to 4-Star Millenium Knickerbocker Hotel Chicago where you’ll stay for the next 2 nights. Millennium Knickerbocker Hotel Chicago is the epitome of classic Chicago style, located near the Magnificent Mile in downtown Chicago – a famous stretch that’s home to over 400 retailers and high-end shops. Established in 1927, this historic hotel in Chicago has had many identities, including a Penthouse casino and speakeasy once run by the Capone family. You’ll find markers of this iconic history all around the hotel as the old world meets the new.
Hotel: 4* Millenium Knickerbocker Hotel Chicago
Meals included: None

Day 2 – Chicago 
Explore the windy city today at your own pace. For big and small screen lovers, why not add on a Movie and TV set of Downtown Chicago walking tour from +£43pp, visit sites from Ferris Bueller’s Day Off, The Untouchables, The Dark Knight, The Bear, and more! Visit the infamous theatre venue from Public Enemies, where Billie worked at a nightclub reception, Get a glimpse of Harold Washington Library, featured in Ocean’s Eleven. See sites from Ferris Bueller’s Day Off, including the Chicago Board of Trade, the Calder’s Flamingo Statue, the Art Institute of Chicago, and the spot where the parade was filmed. Relive iconic scenes featured in Blues Brothers. Visit Bruce Wayne’s penthouse, the site of Harvey Dent’s fundraiser, and Harvey Dent’s office building, all seen in The Dark Knight.

Or for the sports fanatics, catch a Cubs game at the famous Wrigley Field. Foodies can’t miss the opportunity to have an authentic deep-dish pizza in its birthplace, Pizzeria Uno on East Ohio Street.

For some evening entertainment, head to Second City, one of the most influential comedy theatres in the world. The Second City opened its doors on a snowy Chicago night in December of 1959 and has since grown to become the world’s premier comedy club, theatre and school of improvisation. The Second City has launched the careers of John Belushi, Mike Myers, Tina Fey, Bill Murray, Stephen Colbert, Steve Carell and many others.
Hotel: 4* Millenium Knickerbocker Hotel Chicago
Meals included: Breakfast

Day 3 – Chicago to Pontiac
This morning, pick up your car hire to begin your onward journey on Route 66. Your car hire is a Chevrolet Spark or similar. Choose to upgrade to an EV, like a Tesla Model Y or similar for an extra £169. Head out to the town of Pontiac for an overnight stay. Centrally located in Illinois, Pontiac offers its visitors a unique collection of interesting places and great things to see. Home of the Route 66 Association of Illinois Hall of Fame and Museum, the Pontiac Oakland Automobile Museum and Resource Center, the Livingston County War Museum, and the Museum of the Gilding Arts, Pontiac has something to suit every taste.

Your hotel for the night, 3* Hampton Inn Pontiac is placed on the i-55, with a Walmart and a handful of restaurants nearby. Historic US Route 66 passes through Pontiac, and you’ll find the highway’s Hall of Fame & Museum just three miles away in the town’s centre, along with local shops. Enjoy daily free hot breakfast and free WiFi.
Hotel: 3* Hampton Inn Pontiac
Meals included: Breakfast

Day 4 – Pontiac to Springfield
Spend time exploring Pontiac today before heading down to Springfield. History comes alive in Springfield, home to more Lincoln sites than anywhere else in the nation. Explore everything from Abe’s house and law offices to his must-see presidential museum. Don’t miss the Route 66 classic diners and kitschy roadside attractions.

Tonight you’ll stay in the President Abraham Lincoln Hotel, in downtown Springfield, a short walk from the Bank of Springfield Center and Abraham Lincoln Presidential Museum and Library. Illinois State Museum, Knights Action Park, and Abraham Lincoln Capital Airport are less than 15 minutes drive away. The hotel has a free local shuttle, a pool, and a 24-hour business centre. Enjoy a warm DoubleTree cookie on arrival.
Hotel: 4* President Abraham Lincoln Springfield – a DoubleTree by Hilton Hotel
Meals included: Breakfast

Day 5 – Springfield to East St. Louis
Across the Mississippi River from St Louis, Missouri, East St. Louis offers a combination of natural and historical sites, and a petrol-head scene not to be missed, thanks to the World Wide Technology Raceyway and the Gateway Kartplex.  If you have time, skip across the Mississippi and spend some time in St. Louis as well.

You’ll sleep and feel like royalty when you stay at the Casino Queen Hotel. Inside this smoke-free hotel, each room is guaranteed to feel like the comforts of home. Enjoy spectacular views of the Gateway Arch, downtown St. Louis and first-class amenities while being just steps away from world-class gaming, dining and DraftKings at Casino Queen Sportsbook.
Hotel: 4* Casino Queen Hotel
Meals included: Breakfast

Day 6 – East St Louis – Carbondale
The natural beauty of Carbondale – including rivers, lakes, a variety of golf courses, and Shawnee National Forest – entices many visitors to enjoy numerous outdoor activities, including beautiful national and state parks, bicycle paths, four public golf courses, and 14 public parks. Spend the next 2 days getting the most out of this area of natural beauty.

This hotel is on the east side of the city on Illinois Route 13, just 10 minutes from South Illinois University. Enjoy a free hot breakfast before hitting the greens at Crab Orchard Golf Course, five miles away. The popular Shawnee Hills Wine Trail is a 40-minute drive. Relax on a sundeck and enjoy free WiFi.
Hotel: 3* Hampton Inn Carbondale
Meals included: None

Day 7 – Carbondale
Continue your exploration of Carbondale’s natural beauty today. Rent a bike and cycle through Shawnee National Forest, visit Cedar Lake and get out on the water, or sample some local wines at Monte Alegre Vineyard & Cellars.
Hotel: 3* Hampton Inn Carbondale
Meals included: Breakfast

Day 8 – Carbondale to Effingham/ Casey
Continuing your journey through Illinois, today you’ll drive from Carbondale to Casey, via Effingham, home to America’s Largest Cross. Keeping with the super-sized theme, Casey is home to The Twelve Largest Things, including the world’s largest mailbox, windchime, and rocking chair.

Enjoy a bright start to your trip to the Casey area when you stay at Days Inn & Suites Casey Hotel. Easy to get to from I-70, this hotel is close to restaurants, outdoor activities, and businesses. Pet-friendly, non-smoking, and accessible rooms are available.
Hotel: 3* Days Inn + Suites Casey
Meals included: Breakfast

Day 9 – Casey to Champaign
While the University of Illinois draws travellers to Champaign, people soon discover the surrounding region’s off-the-beaten-path attractions, thriving cultural scene, agritourism opportunities and technology sector – all radiating Midwestern authenticity. Visit at any time of the year, but summer and autumn months are packed with festivals, outdoor entertainment, theatre, sports and, of course, stunning autumn foliage.
This historic hotel with modern amenities is less than a mile from the University of Illinois, adjacent to Lincoln Square Mall with artisan shops and restaurants. Krannert Center, Spurlock Museum, State Farm Center, Meadowbrook Park and Riggs Beer Company are all within four miles. This hotel offers an indoor pool, fitness centre and restaurant.
Hotel: 3* Hotel Royer Urbana Tapestry Collection by Hilton
Meals included: Breakfast

Day 10 Champaign to Chicago to UK
Today you’ll drive the 2.5 hour to Chicago O’Hare to return your car hire and fly back to the UK.
Meals included: None

Price is correct as of 24/10/2023

Varied meal plan
Return direct flights with bag allowance
Car hire throughout
Accommodation in 3 or 4 star hotels throughout
ATOL protection
And a FREE £173 donation to the charity of your choice
Prices are per person (unless stated otherwise). Prices are not live and are subject to change at any time. Where applicable prices include any advertised discounts. Holidays are subject to availability and tour operator/supplier’s booking conditions apply. Offers can be changed or withdrawn without notice. The latest price/availability and operator details will be confirmed at the time of inquiry – ask for more information. The donation amount is calculated at the final sale and as such may not reflect the figure shown here. A minimum 5% donation is required to receive a maximum 5% discount.


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