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A trip we've put together just for you.
A bespoke tour by Road Trip Co
Road Trip Co · Self-Drive Fly-Drive
For Shaun Hood
Route 66 · Chicago to Santa Monica
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The Trip at a Glance
Fifteen days from Lake Michigan to the Pacific — the Mother Road, start to finish.
15Days
14Hotel Nights
11Stops
8States
Day 01 · Sat 1 May
London → Chicago
Morning United flight into O'Hare, straight into the Loop.
London Heathrow
Chicago O'Hare
The Westin Michigan Avenue
08:00
Chicago by lunch (local)
United UA958 out of Heathrow at 08:00, into Chicago O’Hare mid-afternoon local time. Transfer into the city and check in for two nights at The Westin Michigan Avenue — a stone’s throw from the Magnificent Mile and a short walk to the start of Route 66 on E Adams Street.
Day 02 · Sun 2 May
Chicago · a free day
Millennium Park, the Loop, and the Mother Road warm-up.
Chicago
A full day in Chicago. The Westin is a few blocks from Millennium Park and the Art Institute, with the lakefront a short walk beyond. The ‘Begin Route 66’ sign on E Adams Street at Michigan is a required photo before you set off the next morning.
Day 03 · Mon 3 May
Chicago → Springfield, Illinois
Pick up the keys, and onto the Mother Road.
Chicago
Hertz pickup
Route 66 begins
Springfield, IL
09:00
~200 mi
Collect the Hertz car at 09:00 and head south on Route 66. Wind through the Illinois farmland to Springfield, the state capital and Lincoln’s hometown. Tonight is at the President Abraham Lincoln Springfield — a DoubleTree Hilton right in the historic quarter, five minutes from the Lincoln Museum and Oak Ridge Cemetery.
Day 04 · Tue 4 May
Springfield → St Louis
Cross the Mississippi and the Gateway Arch.
Springfield, IL
Gateway Arch
St Louis, MO
A short drive west to the Mississippi, over the river and into St Louis. The Gateway Arch is a required stop — the tram to the top gives you the view both ways along the river. Tonight is at the Union Station Hotel: AAA Four Diamond, inside the restored 1894 railway station with its mosaic ceilings and gold-leaf detailing.
Day 05 · Wed 5 May
St Louis → Springfield, Missouri
Across the Ozarks to the birthplace of Route 66.
St Louis
Ozarks
Springfield, MO
West through the Ozark Mountains to Springfield, Missouri — the self-styled ‘Birthplace of Route 66’, the town where the road was named in 1926. A short stop at the Route 66 Car Museum is worth it before setting off the next morning.
Day 06 · Thu 6 May
Springfield → Oklahoma City
Through Kansas (briefly) and into the plains.
Springfield, MO
Kansas · briefly
Oklahoma City
Route 66 cuts the north-east corner of Kansas (eleven miles, exactly) before entering Oklahoma. The Sheraton Oklahoma City Downtown sits in Bricktown — the city’s riverfront entertainment district, with a water taxi, the Chesapeake arena and the Oklahoma City Memorial a short walk away.
Day 07 · Fri 7 May
Oklahoma City → Amarillo
Across the Texas Panhandle to Cadillac Ranch.
Oklahoma City
Cadillac Ranch
Amarillo, TX
West into Texas and the Panhandle — Cadillac Ranch is a required photo stop outside Amarillo (bring a can of spray paint, it’s the done thing). The Embassy Suites downtown puts you a short walk from the historic Route 66 stretch along 6th Street and the Big Texan Steak Ranch if you’re hungry.
Day 08 · Sat 8 May
Amarillo → Santa Fe
Climb onto the high desert — and the oldest state capital in the US.
Amarillo
Tucumcari
Santa Fe, NM
West into New Mexico, over the state line at Glenrio and on through Tucumcari — the classic Route 66 town, with every motel sign still standing. The road climbs to Santa Fe at 7,200 ft. Tonight is at the Inn and Spa at Loretto — the pueblo-style landmark on the end of the Old Santa Fe Trail, a few minutes’ walk from the Palace of the Governors and the Georgia O’Keeffe Museum.
Day 09 · Sun 9 May
Santa Fe → Gallup
Via Albuquerque, into Navajo country.
Santa Fe
Albuquerque
Gallup, NM
South to Albuquerque, then west along Route 66 to Gallup — the gateway to the Navajo Nation, with 500 million years of red rock geology outside town. A quiet night at the Hilton Garden Inn before the Grand Canyon state.
Day 10 · Mon 10 May
Gallup → Flagstaff
The Painted Desert, Petrified Forest, and up to the Ponderosa pines.
Gallup
Petrified Forest
Winslow (Standin' on the Corner)
Flagstaff, AZ
The Painted Desert and the Petrified Forest sit either side of the road east of Holbrook — the only national park Route 66 actually crosses. ‘Standin’ on the Corner’ at Winslow and the La Posada Harvey House are the classic stops. Flagstaff is at 7,000 ft in the Ponderosa pines — the Little America is set in 500 acres of forest just off the interstate.
Day 11 · Tue 11 May
Flagstaff → Las Vegas
Off Route 66 at Kingman, then across the Mojave to the Strip.
Flagstaff
Williams
Seligman (classic Route 66)
Kingman
Hoover Dam
Las Vegas
The longest surviving stretch of original Route 66 runs through Seligman and Peach Springs to Kingman — the one you’ve seen in every photograph of the road. From Kingman the interstate takes you north across the Hoover Dam and into Nevada. ARIA sits in CityCenter, right in the middle of the Strip, with the fountains and the Bellagio directly opposite.
Day 12 · Wed 12 May
Las Vegas · a free day
The Strip, old-town Fremont, or a day trip into Red Rock Canyon.
Las Vegas
A free day in Vegas. The Strip is best at night; the old Fremont Street downtown is best during the day. If you want to get out of the city, the Red Rock Canyon scenic loop is twenty minutes west — a thirteen-mile one-way drive through the sandstone, back at the hotel for dinner.
Day 13 · Thu 13 May
Las Vegas → Santa Monica
Through the Mojave to the end of Route 66 at the Pacific.
Las Vegas
Mojave Desert
Santa Monica Pier · end of Route 66
Santa Monica
South-west across the Mojave to Barstow, then into the LA basin and out to the coast. Santa Monica Pier is the Pacific end of Route 66 — the sign is right at the entrance, as traditional as the one you photographed in Chicago. The Hyatt Centric Delfina is five minutes from the sand.
Day 14 · Fri 14 May
Santa Monica · a free day
The beach, the Pier, and the Palisades.
Santa Monica
A free day in Santa Monica. The beach runs south to Venice (bikes everywhere), Third Street Promenade is the local shopping street, and the Hyatt is a short Uber from Beverly Hills or the Hollywood sign if you want a day in central LA.
Day 15 · Sat 15 May
Los Angeles → London
Hertz back at LAX, a last day in Santa Monica, then the overnight flight home.
Santa Monica
Hertz back · LAX · 13:00
London Heathrow
A last morning in Santa Monica — the Pier, breakfast on the pacific, one more look at the sand. Drop the car at Hertz LAX by one, then the long way home: overnight to Heathrow, in by the morning. Fifteen days behind you, Chicago to the Pacific — a proper trip.
The moments this trip is built around
Eleven stops across America.
13days
Hertz Car Hire — all-inclusive
Unlimited mileage, LDW, LIS, taxes, airport fees and additional driver. Chicago pickup, LAX drop.
2,500mi
The Mother Road
Chicago to Santa Monica Pier — 2,500 miles of Route 66 at your own pace, with eleven overnight stops.
1,857m
Grand Canyon (optional)
80 miles north of Flagstaff. Ask and we'll add a Grand Canyon South Rim night to Day 10 or 11.
0m
Santa Monica Pier
The Pacific end of Route 66 and the finish line of the whole trip.
Plus Cadillac Ranch, Standin' on the Corner at Winslow, the Mojave, the Hoover Dam, and two nights at the end to breathe on the beach.
Good to know
How this trip is set up.
Return flights throughout — United UA958 London Heathrow → Chicago on the outbound, overnight return LAX → Heathrow on the back, Economy class with standard baggage.
13 days of Hertz all-inclusive car hire — unlimited mileage, insurance, taxes and additional driver included. Chicago pickup → LAX drop.
14 hotel nights across 11 stops — Hilton group through the middle for consistency, with The Westin Michigan Avenue (Chicago), Union Station Curio (St Louis), Inn and Spa at Loretto (Santa Fe), ARIA (Vegas) and the Hyatt Centric (Santa Monica) as the standout nights.
Resort fees are paid locally — roughly US$199 total across the trip (mostly Las Vegas and Santa Monica).
May timing: shoulder season in the Southwest (dry and warm), the Grand Canyon still cool enough to walk the rim without fuss.
Free to add a Grand Canyon night at Flagstaff, or extra nights anywhere along the route — just say the word.
What's included
- Return flights London Heathrow ↔ USA — United out, overnight BA/United return (Economy)
- 13-day Hertz car hire — Chicago pickup, LAX drop · all-inclusive insurance, taxes & additional driver
- 14 hotel nights across 11 stops — all one-room / 2 adults
- Mix of bed & breakfast and room-only (per hotel · all listed in the day-by-day)
- Route plan with suggested stops at Cadillac Ranch, Winslow, Seligman, the Hoover Dam and the Santa Monica Pier sign
Not included — paid locally or booked directly
- Hotel resort fees — budget ~US$199 total across the trip (mostly Las Vegas and Santa Monica)
- Hotel transfers (available on request)
- Fuel, meals, activities, Grand Canyon side trip
- Travel insurance, personal spending
Trip total, for two
£8,702
£500
Deposit to hold
Balance due 23 January 2027
Return flights (Heathrow ↔ Chicago out · Los Angeles ↔ Heathrow back), car hire and 14 hotel nights included
The route
Chicago to the Pacific.
Tap the days to follow the trip — the Mother Road, Chicago to Santa Monica Pier.
Ready when you are
Shall we lock it in?
Reply to your quote email or drop me a line — £500 holds it today, balance not due until 23 January 2027. Everything is on request until the deposit lands, so the earlier the better.
Get in touchA tailor-made trip by Road Trip Co · ATOL protected as a flight-inclusive package