Chicago
USA Music Cities Fly Drive to New Orleans with Route 66 from Chicago

Stay in hand‑picked 3 to 4 star premium hotels across Chicago, Springfield Illinois, St Louis, Nashville, Memphis and New Orleans, following iconic highways and legendary cities. Discover the heart of American music with included Memphis attraction tickets to the Music Hall of Fame, Sun Studio, Rock and Soul Museum and more. From jazz and blues to country and rock ’n’ roll, this drive‑through adventure combines classic Americana, famous landmarks and unforgettable music heritage.
What’s included
- Return flights from the UK with checked baggage allowance
- 12 days' Intermediate SUV hire with GPS , tax , insurance and one-way drop off fee included
- Two nights' four-star room-only accommodation in central Chicago (in hotel featured or similar)
- One night's four-star room-only accommodation in Springfield Illinois (in hotel featured or similar)
- One night's three-star bed-and-breakfast accommodation in central St Louis (in hotel featured or similar)
- Two nights' four-star room-only accommodation in central Nashville (in hotel featured or similar)
- Two nights' four-star room-only accommodation in central Memphis (in hotel featured or similar)
- Memphis music museum attraction tickets including Sun Studios, Music Hall of Fame, Rock and Soul Museum and more
- Three nights' four-star room-only accommodation in New Orleans French Quarter (in hotel featured or similar)
- Pick-up Hire Car at Chicago Airport and drop-off at New Orleans airport for a seamless one-way journey
- Please note that the included one-way drop off fee is payable locally (so this will be deducted from your final invoice cost) to enable you to pay the fee locally
- Please note that hotel taxes and fees may be payable directly to the hotel upon check in - please call for details.
Hotels
Millennium Knickerbocker Chicago
4 star
Located just steps from Chicago's vibrant Rush Street, this luxurious hotel offers stylish accommodations with premium amenities, state-of-the-art event facilities, and exceptional dining experiences. A prime destination for shopping, dining, and business in downtown Chicago, the hotel is conveniently located near iconic attractions such as Water Tower Place, Michigan Avenue, the John Hancock Tower, and Navy Pier. World-class museums, including the Museum of Contemporary Art and the Art Institute of Chicago, are also within easy walking distance. The hotel boasts an impressive 5, 480 square meters of flexible function space, ideal for a variety of meetings and events. Its famed Crystal Ballroom, complete with a built-in illuminated dance floor and stunning crystal chandeliers, has hosted countless elegant wedding receptions. Please note, an additional fee of $20 per person applies for guests over 13 years old. Overnight stays are $76 (including tax) with unlimited in/out privileges. Shorter stay options are also available, ranging from $28 to $45 (including tax) for stays between 2 and 8 hours. Self-parking is available for $55 per night without in/out privileges.
President Abraham Lincoln Springfield
4 star
The following services and amenities are available, but with reduced service: Airport Shuttle, Concierge, Executive Lounge, Fitness Center, Breakfast, Pool.The following services and amenities are currently not available: On-site Restaurant(s), Room Service, Valet Parking.Enjoy homelike comforts and a fantastic location when you stay at the President Abraham Lincoln Springfield, a DoubleTree by Hilton Hotel. Savor a warm chocolate chip cookie upon arrival and enjoy impeccable service from our friendly staff. Set in historic downtown Springfield, we offer easy access to the Prairie Capital Convention Center, several corporations and popular Springfield attractions including the Abraham Lincoln Presidential Museum and Library, The Dana Thomas House and Illinois State Capitol. A complimentary shuttle service is available to and from nearby AMTRAK and the Abraham Lincoln Capital Airport. Each beautiful guest room and suite at this hotel in Springfield, IL, offers a variety of modern amenities. Enjoy a restful sleep in the sumptuous bed and check emails with complimentary high-speed internet access. Host an important meeting, seminar or wedding at this Springfield, IL hotel with over 13,000 sq.ft. of flexible conference space and the latest in A/V technology. Catch up with work in the 24-hour business center, offering a variety of useful services. Exercise in the 24-hour fitness center or swim lengths of the heated indoor swimming pool. Enjoy a family meal or a cozy dinner for two in the inviting Lindsay's Restaurant, serving delicious local specialties for breakfast, lunch and dinner. In the evening, sip hand-crafted drinks and premium draft beers in The Globe Tavern bar as you catch up on the news with the bar's seven flat screen TVs.
Hampton Inn St. Louis-Downtown (At the Gateway Arch)
4 star
The Hampton Inn St. Louis Downtown at the Arch is located in the heart of St. Louis, Missouri, just steps from Busch Stadium (home of the MLB Cardinals), the Scottrade Center (home of the NHL Blues), the Dome at America's Center, the historic Laclede's Landing, the Gateway Arch, and the National Blues Museum. This 17-story hotel offers 190 guest rooms with amenities such as free Wi-Fi, a TV with premium channels including HBO, in-room coffee, a hairdryer, an iron and ironing board, and Neutrogena toiletries. Guests can enjoy a complimentary hot breakfast buffet daily, or grab an On the Run Breakfast Bag for those in a hurry. The hotel also features a heated indoor pool, a fitness center, and a video arcade. For meetings and events, there are 5, 000 square feet of space with audio/visual equipment. The on-site Tigin Irish Pub offers drinks, meals, and catering services.
Gaylord Opryland Resort And Convention Center
4 star
The Gaylord Opryland Resort & Convention Center in Nashville's Opryland area is conveniently located within a 15-minute drive of the Grand Ole Opry and Nissan Stadium. This upscale resort is just a half-mile from the beautiful Opryland Hotel Gardens and a short mile from Opry Mills. Unwind at the full-service spa with massages, body treatments, and facials, or enjoy the resort's recreational amenities, including two outdoor swimming pools, a water park (surcharge), and a sauna. Additional conveniences include concierge services, an arcade/game room, gift shops, and a complimentary shuttle to nearby shops. Each of the 2, 888 guestrooms features a refrigerator and Smart television, along with premium bedding and down comforters for a restful sleep. Satellite programming and wired/wireless internet access (surcharge) are also provided. Private bathrooms include showers, designer toiletries, and hair dryers. The resort offers a wide selection of dining options with 18 restaurants, room service (limited hours), and two coffee shops/cafés. Five bars/lounges provide refreshing drinks throughout the day. Full breakfasts are available daily (fee applies). A business center, limousine/town car service, and express check-out are among the featured amenities for business and leisure travelers alike.
Hotel Napoleon, Ascend Hotel Collection Member
4 star
The non-smoking Hotel Napoleon, Ascend Hotel Collection hotel in Memphis, TN near Beale Street is located in the heart of downtown Memphis, right on the trolley line and within walking distance to restaurants, shops and entertainment. Our hotel has been constructed inside a historic 1902 building built by Napoleon Hill. Amenities include Free WiFi, a business center and fitness center. Each guest room is decorated with historic character and features modern conveniences like 50-inch HDTVs, recharge devices, and refrigerators. Earn rewards with every stay with our Choice Privileges Rewards program.
Maison Dupuy
4 star
Enjoy a stay at the historic Maison Dupuy Hotel, centrally located in New Orleans, a short walk from Bourbon Street and Canal Street. The hotel offers an outdoor pool, a 24-hour fitness center, and complimentary Wi-Fi. Make use of the concierge services, gift shops, and room service (limited hours). Business amenities include a business center and express check-out. The hotel also boasts conference space and meeting rooms, totaling 2, 616 square feet. Each of the 200 guestrooms features a flat-screen television, a pillowtop bed with down comforters and premium bedding, and a private bathroom with complimentary toiletries and a hair dryer. Nearby attractions include Louis Armstrong Park, the Historic New Orleans Collection, and the New Orleans Jazz Museum. Louis Armstrong New Orleans International Airport (MSY) is approximately 16 miles away.
Itinerary
Fly to Chicago, collect your hire car and drive to your hotel for an overnight stay, Millennium Knickerbocker Chicago. Located just steps from Chicago's vibrant Rush Street, this luxurious hotel offers stylish accommodations with premium amenities, state-of-the-art event facilities, and exceptional dining experiences. A prime destination for shopping, dining, and business in downtown Chicago, the hotel is conveniently located near iconic attractions such as Water Tower Place, Michigan Avenue, the John Hancock Tower, and Navy Pier. World-class museums, including the Museum of Contemporary Art and the Art Institute of Chicago, are also within easy walking distance. The hotel boasts an impressive 5, 480 square meters of flexible function space, ideal for a variety of meetings and events. Its famed Crystal Ballroom, complete with a built-in illuminated dance floor and stunning crystal chandeliers, has hosted countless elegant wedding receptions. Please note, an additional fee of $20 per person applies for guests over 13 years old. Overnight stays are $76 (including tax) with unlimited in/out privileges. Shorter stay options are also available, ranging from $28 to $45 (including tax) for stays between 2 and 8 hours. Self-parking is available for $55 per night without in/out privileges.
October 2026
Calendar shows the price for the selected city. The table below is the full list.
| Origin | Trip start | Trip end | Price | |
|---|---|---|---|---|
| Heathrow | 31 Oct 2026Saturday | 12 Nov 2026Thursday | £2,749 | |
| Heathrow | 7 Nov 2026Saturday | 19 Nov 2026Thursday | £2,769 | |
| Heathrow | 14 Nov 2026Saturday | 26 Nov 2026Thursday | £2,529 | |
| Heathrow | 21 Nov 2026Saturday | 3 Dec 2026Thursday | £2,419 | |
| Heathrow | 28 Nov 2026Saturday | 10 Dec 2026Thursday | £2,769 | |
| Heathrow | 5 Dec 2026Saturday | 17 Dec 2026Thursday | £2,769 | |
| Heathrow | 12 Dec 2026Saturday | 24 Dec 2026Thursday | £2,519 | |
| Heathrow | 19 Dec 2026Saturday | 31 Dec 2026Thursday | £3,059 | |
| Heathrow | 26 Dec 2026Saturday | 7 Jan 2027Thursday | £2,869 | |
| Heathrow | 2 Jan 2027Saturday | 14 Jan 2027Thursday | £2,999 |
