• a group of people in a city

Tours in Chicago

Although not celebrated in the same way as New York, Chicago is a vibrant, attractive, and modern place to visit with many diverse attractions. Enjoy a performance at the riverside outdoor theatre or Navy Pier, wander along the river and observe the floating gardens, listen to live music in the famous Blues bars and cool off in the water at one of the lakeside beaches. A breeze to navigate via elevated ‘L’ trains and local, on-off tour buses, Chicago has charm in abundance and will entertain all your senses.

Our Great American Road Trip tour combines the buzz and excitement of several cities with the freedom of the iconic, open road, offering sublime vistas of celebrated national parks along the way. Before you go, let Chicago woo you with a cooling river trip winding through the spectacular skyscraper landscape, the taste of its world-famous deep pan pizzas, inspiring art galleries and the opportunity for relaxation in the modern 606 Park.

Alternatively, if you envy passing bikers, the roar of their engines, the aromas of open farmland and the cool mountain breeze running through your hair, our exhilarating EagleRider Route 66 Guided Motorcycle Tour will inspire you. Starting in the cheerful city of Chicago, you’ll take the more conventional ‘Mother Road’ via the mid-west, as you make your way to California.

16 days Route 66

Route 66 Holidays

Guide Price  £2,399  pp  

Our Historic Route 66 Self Drive is a journey you’ll never forget, beginning in Chicago and ending at the Santa Monica Pier in Los Angeles. On the way you’ll experience classic Americana, hike in majestic national parks and visit some...

Multi centre holidays

Route 66 Holidays
15 days Eaglerider road trip along Route 66

EagleRider Route 66 Guided Motorcycle Tour

Guide Price  £5,299  pp  

The EagleRider Route 66 Guided Motorcycle Tour is a journey to the American interior on the world’s most famous road - beginning in Chicago and finishing in Los Angeles. On the way you’ll cross mountains and forests, cruise through high...

Iconic journeys

EagleRider Route 66 Guided Motorcycle Tour
17 days Statue of Liberty and City Skyline

New York to Hollywood Escorted Tour

Guide Price  £3,199  pp  

Our New York to Hollywood tour promises a full spectrum look at the best the United States has to offer. Travel from the East Coast all the way through to the West Coast in just over two weeks. Your trip...

Escorted tours

New York to Hollywood Escorted Tour
22 days a large body of water with a city in the background

The Great American Roadtrip Self Drive


The Great American Roadtrip Self Drive is an epic 5,000km journey from New York City to San Francisco, taking in the country’s national parks, fabulous cities and legendary roads. On the way you’ll discover America’s rich history and culture, crossing...

Self drive holidays

The Great American Roadtrip Self Drive
8 days Traverse City Sunrise

Great Lakes Explorer Tour


Explore the USA's magical Great Lakes region on this spectacular eight day small group tour. With a mix of lively cities, scenic landscapes and unique small town communities the Great Lakes draw visitors from across the world, discover the unique...

USA road trips

Great Lakes Explorer Tour
13 days Chicago Skyline

The Heartland's Beat

Guide Price  £2,499  pp  

There are not many countries in this world where you are able to spend 12 nights driving through five states learning about the history of the country while enjoying the vast difference in music between the states. The Heartland’s Beat...

Self drive holidays

The Heartland's Beat
24 days an empty park bench next to a tree

Route 66 Motorhome Itinerary


When you think of taking a road trip around America, there is only one route which jumps to mind, driving along Route 66. A route which takes you through eight different states, over 2000 miles of road and through 90...

Fly drive holidays

Route 66 Motorhome Itinerary

Expert Tips


Senior Destination Manager

“I’d choose EagleRider any day.  Open up on Route 66 and experience the American road the way it's meant to be."


Destination Manager

“I’d recommend the romantic Chicago river walk at night. There’s an outdoor theatre, live Blues bars, places to eat and a real buzz.”


Destination Executive

“If you want to get a great overview of Chicago, take a river boat tour, or ride the elevated L train. You get a comprehensive sense of the city that way.”

Frequently Asked Questions

Willis Tower’s Skydeck Chicago offers a breath-taking view. It has a 1300 feet high, glass ledge extending four feet out from the building.

For three days in early June the free to enter Chicago Blues Festival takes place. Here you can catch well known artists and rising stars of the jazz world.

Chicago’s Wrigley Field is home to baseball, hockey, football and other sports – sometimes all at the same time. It’s also a concert venue. Look online to see what’s on while you’re here.

Visit Chicago’s America for its forward-looking attitude, beautiful modern architecture, clean open spaces and laid back Blues.  When you’re finished in the city for the day, lie back on the lakeside beaches, or play in the refreshing water. Chicago is a great first step to your eclectic holiday.

Why you'll love Chicago...

• Listening to live blues music in Chicago’s blues bars
• Strolling the atmospheric Chicago River Walk by night
• Cooling off with lakeside fun and relaxation
• Being overwhelmed by the stunning views over city and lake from Willis Tower’s Skydeck
• Taking in the contrasting vistas of city skylines
• Gliding along Chicago River, snaking through the modern architecture towering above you
• Riding the L train high above the streets of Chicago
• Watching and wondering at the rules of baseball in Wrigley’s Field
• Tasting your way around the city, starting with your favourite toppings on classic Chicago deep pan pizzas
• Playing with the magic of the Cloud Gate sculpture
• Trying something quirky with a doughnut tour of the city
• Cycling along the lakefront and taking in the lake’s vast waters

Did you know?

• Chicago is known as The Windy City because of the cooling winds coming off Lake Michigan.
• The Cloud Gate sculpture was built by a British artist, Sir Anish Kapoor. It’s built to give the appearance of liquid mercury.
• Chicago’s downtown area is known as The Loop.