Route66 - Fly&Drive from 1.450 €

price per person From

€1,450

Based on 2 adults

Created: Friday 8 May 2026 - Departure: Tuesday 20 October 2026

Destinations: Chicago IL, United States of America , Springfield IL, United States of America , Rolla MO, United States of America , Tulsa OK, United States of America , Amarillo TX, United States of America , Santa Fe NM, United States of America , Gallup NM, United States of America , Flagstaff AZ, United States of America , Kingman AZ, United States of America , Barstow CA, United States of America , Santa Monica CA, United States of America

Themes

Romantic Family Beach Nature Adventure Winter Weddings COUPLES

Your day to day

View in Google Maps

20 Oct

Transport from Milan to Chicago IL

Departure

08:30

Malpensa (MXP)

12h 20m

13:50

Chicago Ohare Intl (ORD)

1 PC

American Airlines - AA 6718

08:30 - Milano, Malpensa (MXP)

09:35 - London, Heathrow London (LHR)

Transport: AA6718

Operated by: British Airways

Cabin Class: Economy

1h 35m - Connection in London, Heathrow London (LHR)

American Airlines - AA 7004

11:10 - London, Heathrow London (LHR)

13:50 - Chicago, Chicago Ohare Intl (ORD)

Transport: AA7004

Operated by: British Airways

Cabin Class: Economy

20 Oct

Car rental

A CHEVROLET SPARK or similar

Includes:

Deposit: Pickup full return full
Automatic transmission
Unlimited mileage

A/C

4 doors

4 persons

Extras (Pay at pick-up office)

20 Oct

1. Chicago IL

Stay

About the destination: Chicago, once a small trading post on Lake Michigan, has grown into one of the most famous cities in the country. Visit "The Windy City" and tuck into a deep dish pizza for a truly unique holiday experience. Follow "The Loop," the city's main business district, and marvel at its array of skyscrapers, consulates, and universities. There's plenty of shopping and fine dining to be had in this area. If you've worn yourself out in the city centre, take it easy at the Riverwalk, a pedestrian path along the Chicago River, or visit the many museums and parks the city has to offer. You'll hardly believe you're actually in the city centre when you walk through the Garfield Park Conservatory, and the Art Institute of Chicago will allow you to appreciate creative works from around the globe. The most important places to visit in Chicago are: the Willis Tower, an iconic symbol of the city, the Millennium Park, a fantastic urban park, among the most famous landmarks of Chicago and a site for many major city events, the Shedd Aquarium, one of the world's largest aquariums. Known as the front lawn of Chicago, the Grant Park is a beautifully landscaped park and offers many spots for an urban escape, the Navy Pier, located right on Lake Michigan, has a festive atmosphere with entertainment, shops and restaurants. No tour of Chicago is complete without a mention of the nightlife, so end your day at a jazz lounge and let the sweet sound of music carry you away.

More info

20 Oct

Hotel

1 Night

View accommodation

Select

View accommodation

Select

View accommodation

Select

View accommodation

Select

View accommodation

Select

View accommodation

Select

View accommodation

Select

View accommodation

Select

View accommodation

Select

View accommodation

Select

Carlton Inn Midway

Chicago IL - Show on map > 3.0 miles from Center

6.9

Nice

2626

24-hour reception

Luggage room

Pets allowed

Double room. one bed

WITH BREAKFAST

Free cancellation

See details

21 Oct

Car journey 197 Miles - 3h 12m

Chicago IL

Springfield IL

Open map

21 Oct

2. Springfield IL

Stay

About the destination: Springfield is the capital of the state of Illinois and also the administrative centre of Sangamon County. The city was founded in 1819; it became an administrative centre in 1823, and received its charter in 1840. It became the capital of Illinois in 1837. The legislative assembly was convened here, for the first time, in 1839. According to the 2010 census, 111,454 inhabitants live in the city. Originally, around 1810 the city was named Calhoun, after South Carolina Sen. John C. Calhoun, but after the population had been disillusioned with Calhoun, the city was renamed Springfield. Abraham Lincoln is one of the most important and prominent inhabitants of the city; moved to the area in 1831, but did not live in the city itself until 1837. U.S. President Ulysses S. Grant also maintained ties to Springfield.

More info

21 Oct

Hotel

1 Night

View accommodation

Select

View accommodation

Select

View accommodation

Select

View accommodation

Select

View accommodation

Select

View accommodation

Select

View accommodation

Select

View accommodation

Select

View accommodation

Select

View accommodation

Select

Super 8 by Wyndham Springfield East

Springfield IL - Show on map > 2.4 miles from Center

5.9

1736

Breakfast

24-hour reception

Wheelchair-accessible

Double room. one bed

WITH BREAKFAST

See details

22 Oct

Car journey 201 Miles - 3h 6m

Springfield IL

Rolla MO

Open map

22 Oct

3. Rolla MO

Stay

22 Oct

Hotel

1 Night

View accommodation

Select

Econo Lodge Rolla I-44 Exit 184 Near Missouri University of Science and Technology

View accommodation

Select

View accommodation

Select

View accommodation

Select

View accommodation

Select

View accommodation

Select

View accommodation

Select

View accommodation

Select

View accommodation

Select

View accommodation

Select

Econo Lodge Rolla I-44 Exit 184 Near Missouri University of Science and Technology

Rolla MO - Show on map > 1.2 miles from Center

6.7

Nice

693

Parking

Breakfast

24-hour reception

Double room. one bed

WITH BREAKFAST

Free cancellation

See details

23 Oct

Car journey 290 Miles - 4h 20m

Rolla MO

Tulsa OK

Open map

23 Oct

4. Tulsa OK

Stay

About the destination: Tulsa is the second largest city in the US state of Oklahoma, and the 46th largest in the United States, with a population of 391,906 inhabitants. What is now known as Tulsa was once part of Indian territory, established as part of the relocation of the Five Civilised Tribes - Choctaw, Cherokee, Creek (Muskogee), Chickasaw and Seminole. These tribes were moved into the region following the enactment of the "Indian Removal Act" of 1830, when they were forced by the federal government to give up their lands east of the Mississippi River in exchange for land in Indian Territory.

More info

23 Oct

Hotel

1 Night

View accommodation

Select

View accommodation

Select

View accommodation

Select

View accommodation

Select

View accommodation

Select

View accommodation

Select

View accommodation

Select

View accommodation

Select

View accommodation

Select

View accommodation

Select

DoubleTree by Hilton Tulsa Downtown

Tulsa OK - Show on map > 0.5 miles from Center

7.6

Good

522

Parking

Late Check-out

24-hour reception

2 Double Beds

ROOM ONLY

See details

24 Oct

Car journey 366 Miles - 5h 25m

Tulsa OK

Amarillo TX

Open map

24 Oct

5. Amarillo TX

Stay

About the destination: Amarillo, which means "yellow" in Spanish, is the heart of the Texas Panhandle, situated on the brink of the Great Plains. Amarillo offers a genuine Western heritage, a unique geographical area with vast open spaces and stunning sunrises and sunsets. With its relatively mild climate, the city is rated as having some of the cleanest air in the country. Indians, conquistadors, buffalo hunters, settlers, cowboys, adventurers, lawmen, gunfighters, and the railway all contributed in many ways to the development and growth of the area. That heritage is still felt here, where "cowboy" is still a respected profession. Here you can enjoy the very best of the Old and New West! Today Amarillo is one of the dominant cities in the Panhandle Plains and is home to a variety of industries along with a number of places to interest tourists, especially those on the Route 66. Amarillo is also the gateway to Palo Duro Canyon, America's second largest canyon. Palo Duro Canyon is unique with rock formations and a valley with wonderful views and pictures.

More info

24 Oct

Hotel

1 Night

View accommodation

Select

View accommodation

Select

View accommodation

Select

View accommodation

Select

View accommodation

Select

View accommodation

Select

View accommodation

Select

View accommodation

Select

View accommodation

Select

View accommodation

Select

Days Inn by Wyndham Amarillo East

Amarillo TX - Show on map > 2.1 miles from Center

6.3

Nice

3157

Parking

Breakfast

24-hour reception

Double room. one bed

WITH BREAKFAST

See details

25 Oct

Car journey 279 Miles - 4h 16m

Amarillo TX

Santa Fe NM

Open map

25 Oct

6. Santa Fe NM

Stay

About the destination: Santa Fe, New Mexico is a magical, exuberant, colourful journey at any time of the year. Its legendary history and culture will captivate and inspire you. Its art galleries and diverse visual arts span ancient traditional techniques to the most contemporary and edgy. Santa Fe is home to more than a dozen fascinating museums that document the region's history, art and cultures. Here you'll find the country's only museum dedicated to a female artist, Georgia O'Keeffe. Many visitors travel here to experience fascinating historic sites, including stunning remnants of ancient Native American communities near Santa Fe and pueblo communities that are still vibrant today.

More info

25 Oct

Hotel

1 Night

View accommodation

Select

View accommodation

Select

View accommodation

Select

View accommodation

Select

View accommodation

Select

View accommodation

Select

View accommodation

Select

View accommodation

Select

View accommodation

Select

View accommodation

Select

Motel 6 Santa Fe, NM - Downtown

Santa Fe NM - Show on map > 0.7 miles from Center

7.5

Good

1995

Internet

24-hour reception

Wheelchair-accessible

Double room. one bed

ROOM ONLY

Free cancellation

See details

26 Oct

Car journey 198 Miles - 3h 5m

Santa Fe NM

Gallup NM

Open map

26 Oct

7. Gallup NM

Stay

About the destination: Gallup is a town in the state of New Mexico. Gallup is an important gateway to the Navajo Nation and other nearby attractions. The numerous trading posts, galleries and shops in Gallup offer a unique blend of Native American Culture with a rich abundance of authentic Indian and Southwest Hispanic arts and crafts. The landscape is beyond words, with red mesas to the north and east, and the mountains and painted deserts of Arizona to the west. An incredible selection of ancient Indian ruins, stunning scenic attractions, and fascinating historic sites are within a 90-minute journey from your holiday base in Gallup. No trip to the southwest is complete without experiencing this area of New Mexico.

More info

26 Oct

Hotel

1 Night

View accommodation

Select

View accommodation

Select

View accommodation

Select

View accommodation

Select

View accommodation

Select

View accommodation

Select

View accommodation

Select

View accommodation

Select

View accommodation

Select

View accommodation

Select

Super 8 by Wyndham Gallup

Gallup NM - Show on map > 1.6 miles from Center

5.9

1051

Parking

Breakfast

24-hour reception

Double room. one bed

WITH BREAKFAST

See details

27 Oct

Car journey 185 Miles - 2h 50m

Gallup NM

Flagstaff AZ

Open map

27 Oct

8. Flagstaff AZ

Stay

About the destination: Flagstaff is a city situated in northern Arizona. A destination for all seasons, Flagstaff is brimming with cultural diversity, beauty, history and opportunities for recreation and science. At a cool elevation of 7,000 feet, nestled in the world's largest ponderosa pine forest, Flagstaff is close to seven national parks and monuments and 80 miles from the Grand Canyon. Northern Arizona is also rich in Native American history and culture with nearby Navajo and Hopi reservations.

More info

27 Oct

Hotel

1 Night

View accommodation

Select

View accommodation

Select

View accommodation

Select

View accommodation

Select

View accommodation

Select

View accommodation

Select

View accommodation

Select

View accommodation

Select

View accommodation

Select

View accommodation

Select

Canyon Inn Motel

Flagstaff AZ - Show on map > 0.4 miles from Center

7.7

Good

356

Wheelchair-accessible

Pets allowed

Accessible parking

Twin/Double room

ROOM ONLY

See details

28 Oct

Car journey 148 Miles - 2h 17m

Flagstaff AZ

Kingman AZ

Open map

28 Oct

9. Kingman AZ

Stay

28 Oct

Hotel

1 Night

View accommodation

Select

View accommodation

Select

View accommodation

Select

View accommodation

Select

View accommodation

Select

View accommodation

Select

View accommodation

Select

View accommodation

Select

View accommodation

Select

View accommodation

Select

Motel 6 Kingman, AZ - Route 66 West

Kingman AZ - Show on map > 0.4 miles from Center

7.1

Good

2222

24-hour reception

Wheelchair-accessible

Pets allowed

Double room. Smokers, one bed

ROOM ONLY

Free cancellation

See details

29 Oct

Car journey 206 Miles - 3h 32m

Kingman AZ

Barstow CA

Open map

29 Oct

10. Barstow CA

Stay

29 Oct

Hotel

1 Night

View accommodation

Select

View accommodation

Select

View accommodation

Select

View accommodation

Select

View accommodation

Select

View accommodation

Select

SUPER 8 BY WYNDHAM BARSTOW

Barstow CA - Show on map > 3.0 miles from Center

7.7

Good

1159

Junior Room with Queen Bed Non-Smoking - RM1

WITH BREAKFAST

Free cancellation

See details

30 Oct

Car journey 134 Miles - 2h 33m

Barstow CA

Santa Monica CA

Open map

30 Oct

11. Santa Monica CA

Stay

30 Oct

Hotel

1 Night

View accommodation

Select

View accommodation

Select

View accommodation

Select

View accommodation

Select

View accommodation

Select

View accommodation

Select

View accommodation

Select

View accommodation

Select

View accommodation

Select

View accommodation

Select

Hotel Carmel

Santa Monica CA - Show on map > 1.0 miles from Center

7.1

Good

3202

Valet parking

Windsurfing

24-hour reception

Double room. one bed

ROOM ONLY

Free cancellation

See details

31 Oct

Transport from Santa Monica CA to Milan

Return

10:30

Los Angeles Intl (LAX)

15h 25m

09:55

Malpensa (MXP)

+1 day 1 PC

Iberia Airlines - IB 4488

10:30 - Los Angeles, Los Angeles Intl (LAX)

18:35 - Miami, Miami Intl (MIA)

Transport: IB4488

Operated by: American Airlines

Cabin Class: Economy

50m - Connection in Miami, Miami Intl (MIA)

Iberia Airlines - IB 8281

19:25 - Miami, Miami Intl (MIA)

09:55 - Milano, Malpensa (MXP)

Transport: IB8281

Operated by: American Airlines

Cabin Class: Economy

1 Insurances

Assicurazione (Unipol Sai Medico Bagaglio) - Regione (Continentale (non Europe)) - Giorni (13)

Unipol Sai Medico Bagaglio - Unipol Sai Medico Bagaglio

If you want to expand this information:

Foglio Informativo

price per person From

€1,450

Based on 2 adults

Direct booking

Want it!

Enlarge map

Trip summary

2 Adults

20 Oct 2026 - 1 Nov 2026

Nights 11

2236 Miles

This idea includes

Destinations 11

Transports 2

Accommodations 11

Cars 1

Insurances 1