Route 66 Road Trip Holiday
Our Historic Route 66 Self Drive is a journey you’ll never forget, beginning in Chicago and ending at the Santa...
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City holidays
Embark on an Illinois holiday and wander through this classic Midwestern state. Take to the Great River Road and follow the Mississippi River on its winding journey through the state. Discover Illinois’s gems among the rolling farmland, from the humming city of Chicago to magnificent canyons, waterfalls and other natural wonders.
Illinois is a state of farmland, open prairies and natural wonders, punctuated every now and then by charming cities and towns. A nature lover’s paradise, it offers endless miles of hiking trails. Find yourself in wilderness and walk through the canyons at Starved Rock State Park, stumbling across flowing waterfalls as you go, or head to Shawnee National Forest and find Burden Falls, one of the tallest waterfalls in the state. Marvel at the unusual rock formations at Matthiessen State Park and take in the park’s unique mix of forest, streams and prairies. Take a break from the boundless nature and journey to the beautiful town of Galena. A town overflowing with history, its streets are lined with Greek Revival, French Colonial, Gothic Revival and Queen Anne buildings waiting to be explored.
Illinois’s Beating Heart
Juxtaposed against Illinois’s luscious country is one of America’s most famous cities: Chicago. Walk the city’s streets and marvel at the awe-inspiring architecture and impressive skyline, whilst notes of live blues music floats by from the nearest cocktail bar.
If you feel up for it, why not take on Route 66 and drive across the country to Los Angeles, making stops at some unforgettable destinations along the way, like the Route 66 Museum in Oklahoma, Las Vegas and the Santa Monica Pier.
Great sample itineraries
Take some inspiration from our sample itineraries below and give our Destination Specialists a call so we can put together your perfect Illinois holiday.
Chicago, Galena & Springfield
Why look anywhere else for history and beautiful scenery when Illinois has it all. Rich in presidential history, you really...
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City holidays
Washington Dc Multi Centre Holidays
Washington DC and Chicago combine to give the perfect mix of city sights, history and culture. Arrive in awe-inspiring Washington...
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Cultural holidays
Route 66 Guided Motorcycle Tour
The EagleRider Route 66 Guided Motorcycle Tour is a journey to the American interior on the world’s most famous road...
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USA road trips
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"There’s so much to see on an Illinois holiday and the best way to see it all is to hire a car. Start your holiday in Chicago and drive through the state, stopping in places like Galena, Springfield and Peoria."
"Illinois has a lot more to offer than just Chicago so don’t be tempted to spend your whole time in the city. Head to Starved Rock State Park and go hiking through towering trees, scenic overlooks and beautiful rock formations. Explore the area at water level and hire canoes and paddle boats too."
St. Patrick’s Day
Every year on the 17th of March, Illinoisans come together across the state to celebrate St Patrick’s Day. Wherever you are in the state, you’ll find a parades and celebrations of Irish heritage, with plenty of Irish dancing and music.
Springfield Old State Capitol Art Fair
The Springfield Old State Capitol Art Fair has become a beloved tradition and one of the most popular art fairs in the country. There’s tonnes of original artworks to see in all types of media.
Alton Memorial Day Parade
The oldest consecutive running parade in the country, the Alton Memorial Day Parade has been running for over 150 years. People line the streets of Alton for a parade that celebrates the history of the city and those who have fought for the country.
Local Cuisine
Like most of the United States, Illinoisans have a fondness for delicious grub. There are many delicacies you’ve got to try on a trip to Illinois.
Hot Dogs
Though you’ll find plenty of delicious hot dogs throughout the state, if you’re in Springfield, you can’t miss the Cozy Dog Drive Inn’s famous fresh-battered cornbread hot dog on a stick. This iconic eatery makes the hot dog from a family recipe and is well worth a visit.
Chicago’s Deep Dish Pizza
This is one you simply cannot miss on a trip to Chicago. It’s part pizza, part pie, and fully delicious.
Italian Beef Sandwiches
Another Illinois speciality originating from Chicago, Italian beef sandwiches are a favourite throughout the state. The sandwich was first brought to the city by Italian immigrants, consisting of seasoned thinly sliced beef dipped in gravy and sweet peppers or Giardiniera served in an Italian bread role, and it’s been popular ever since.
Our Illinois destinations
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The Hayes & Jarvis Way
We've been tailor making holidays for 65 years. With over 60 destinations to choose from, talk to us and we'll listen to your travel ideas to create unforgettable holiday experiences.