Illinois By Road & Santa Monica Explorer

Follow part of the legendary Route 66 from Chicago through Illinois, discovering classic roadside Americana along the way. Then fly to Los Angeles to complete your journey in Santa Monica, where the famous “End of the Trail” sign marks a memorable and unique Route 66 adventure.

Accommodation Highlights

The Drake Hotel, Chicago

  • Prime location on the Magnificent Mile, close to top attractions
  • Historic hotel with classic elegance and timeless décor
  • Easy access to Lake Michigan and Oak Street Beach

Wyndham Springfield City Centre, Illinois

  • Central downtown location near key landmarks
  • Close to State Capitol Complex and Abraham Lincoln sites
  • Comfortable rooms with modern amenities and city views

Hampton Inn Collinsville, Illinois

  • Convenient Route 66 stopover location
  • Close to the iconic World’s Largest Catsup Bottle
  • Complimentary breakfast and comfortable, family-friendly rooms

Gateway Hotel Santa Monica, Los Angeles

  • Well located for Santa Monica beach and attractions
  • Complimentary Wi-Fi and on-site fitness centre
  • Relaxing garden sun decks for downtime after exploring

 

Prices

Year Dates Prices From
2026-2027 Bookable All Year Round £1789 per person
Based on 1st March 2027 - Call us for your ideal departures

Wide range of dates available
Call 020 3542 8888 for more details

What’s Included:

  • UK return flights
  • 3 nights at The Drake Hotel, Chicago
  • 2 nights at Wyndham Springfield City Centre, Illinois
  • 2 nights at Hampton Inn Collinsville, Illinois
  • Car hire from Chicago to St. Louis
  • Internal flight from St. Louis to Los Angeles
  • 3 nights at Gateway Hotel Santa Monica, Los Angeles
  • Full ABTA protection

Based on 2 Adults Sharing, flights from London, 1st March 2027, subject to change & availability

 

About Illinois By Road & Santa Monica Explorer

Description

Experience an iconic 300-mile journey along historic Route 66, the legendary “Mother Road.” Begin in downtown Chicago at the famous “Begin” sign. Then drive through Illinois before flying to Los Angeles to finish in Santa Monica at the “End of the Trail.”

Chicago, Illinois

Start in Chicago, one of America’s most exciting cities. Stay on the Magnificent Mile, close to Lake Michigan and top attractions. Explore Millennium Park, Navy Pier and Skydeck Chicago with ease.

For sightseeing, hop-on hop-off bus tours offer a simple way to see the city. As you leave, consider a stop at Old Joliet Prison, a famous filming location.

Springfield, Illinois

Next, continue to Springfield, the Illinois state capital. Stay in a central downtown location, close to key landmarks and attractions.

The city offers history, culture and easy access to Route 66 highlights. Comfortable hotels and convenient amenities make this a great overnight stop.

Collinsville & Route 66 Highlights

Along the route, discover classic Route 66 attractions. Take photos at the World’s Largest Catsup Bottle, a true roadside icon.

You can also visit Cahokia Mounds, a UNESCO World Heritage Site. This landmark showcases ancient Native American civilisation.

Santa Monica, Los Angeles

After your Illinois road trip, fly to Los Angeles for a coastal finale. Stay in Santa Monica, close to the beach and shopping areas.

Spend time on the beach or explore Third Street Promenade. Finally, visit Santa Monica Pier and capture a photo at the “End of the Trail” sign.

This Route 66 holiday combines city highlights, classic Americana and a California beach ending. It offers the perfect mix of culture, history and adventure.

Call TravelPlanners on 020 3542 8888 for more details or to book.

Book your California holiday today!

from £1789 per person

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