Route 66 - Chicago & Midwest Americana
USA
7 days / 6 nights
Fly Drive Holiday
Guide Price €749 per person (based on 2 adults sharing)
Fly Drive Holiday
Duration: 7 days/6 nights
Experience Route 66’s classic Americana and discover its 100-year history, with its high density of iconic landmarks, roadside diners and fascinating museums, this one-week itinerary promises the perfect introduction to the ‘Mother Road’ and the Midwest.
- Enjoy exciting sightseeing in Chicago and St Louis
- Road trip part of the iconic Route 66
- Stop at exciting roadside attractions
from €749
per person (based on 2 adults sharing)
Interested in this holiday? Call and speak to one of our travel experts.
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Itinerary
Day 1 Chicago
Arrive in Chicago, a vibrant Midwestern city offering fantastic landmarks, a stunning skyline and unique cuisine.
Day 2 Chicago
Admire the architecture of this wonderful city, with soaring skyscrapers and the famous Cloud Gate sculpture. Perhaps head up to the viewing decks of the Willis Tower or John Hancock Center for panoramic views across the cityscape. After a day exploring the city, try some well-known Chicago dishes, such as deep-dish pizza or a Chicago-style hot dog.
Day 3 Chicago
Today why not visit some of the world-class museums this city offers? See the phenomenal collection of artworks on display at The Art Institute of Chicago or learn about astronomy at the Adler Planetarium.
Day 4 Chicago to Springfield
Pick up your car and commence your journey to Springfield, with this stretch of the historic Route 66 offering many roadside attractions worth stopping at along the way. Visit the Old Joliet Prison, made famous for its appearances in the 1980s film The Blue Brothers as well as the TV show Prison Break. After, fuel up with some classic American food at the iconic Dell Rhea’s Chicken Basket, before carrying on to sights including the Pontiac Route 66 mural, vintage style Ambler’s Texaco Gas Station in Dwight and the World’s Largest Covered Wagon in Lincoln.
Day 5 Springfield to St Louis
Set off in search of even more kitsch americana, as you continue your Route 66 journey to St Louis. Visit some of the intriguing museums along the route, such as the Shea’s Gas Station Museum, filled with unique memorabilia. En route, stop to take great photos of roadside attractions such as the giant Lauterbach Muffler Man and the World's Largest Catsup Bottle. Cross the Old Chain of Rocks Bridge over the Mississippi River as you arrive at your final stop, St Louis.
Day 6 St Louis
Known as the ‘Gateway to the West’, see the impressive Gateway Arch which marks St Louis’ pioneering origins. Explore the attractions of the expansive Forest Park or the beautiful Missouri Botanical Garden, as you get to know this important city.
Day 7 St Louis
Drop off your car at the airport ready for your onward travels.
Price & Inclusions
- 6 nights 3★+ to 4★ hotels
- 4 days Alamo Inclusive Compact car hire including zero insurance excess, unlimited mileage, 24 hour Roadside Assistance and 1 additional driver. A one way drop-off fee is payable locally
We negotiate new offers daily from discounted flights, tours and vehicle hire to free upgrades, added value and unique inclusions. Please call for our latest offers.
The tour itinerary, inclusions and departures are based on travel from 01/12/2025 to 15/12/2026. For holiday guide price terms and conditions, click here.Flights
As we can offer you such a flexible choice of flights, we don't include international airfares with our tour prices. The price you pay will be determined by the time of year you travel, your departure airport, airline and availability.
Your Trailfinders Travel Consultant will be able to find the best flights to suit you and your choice of tour. Contact us for our latest flight offers or take a look at our flights pages for a general idea of prices.
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