Road Trip Co
Bespoke Tour Quote
A trip we've put together just for you.
A bespoke tour by Road Trip Co
Road Trip Co · Self-Drive Fly-Drive
For Rich Camm
Route 66 · Chicago to Santa Monica
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The Trip at a Glance
Nineteen days end to end — the Mother Road at a pace that gives you time to look up.
19Days
17Hotel Nights
10Overnight Stops
8States
Day 01 · Mon 4 Oct
Newcastle → London → Chicago
Early BA flight down to Heathrow, then across to the start of Route 66.
Newcastle
London Heathrow
Chicago O'Hare
Omni Chicago
06:05
Chicago by lunch (local)
BA1341 out of Newcastle at 06:05, in to Heathrow mid-morning. Across to Terminal 5 for BA295 at 11:10 to Chicago O’Hare, arriving mid-afternoon local time. Transfer into the city and check in for two nights at the Omni Chicago — on North Michigan Avenue, right on the Magnificent Mile and a few blocks from the start of Route 66.
Day 02 · Tue 5 Oct
Chicago · a free day
Lake Michigan, the Loop, and the Mother Road warm-up.
Chicago
A full day in Chicago before the car arrives. The Omni is five minutes 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 tomorrow.
Day 03 · Wed 6 Oct
Chicago → Springfield, Illinois
Pick up the keys at eleven, onto the Mother Road.
Chicago
Hertz pickup · 11:00
Route 66 begins
Springfield, IL
11:00
~200 mi
Collect the Hertz car at 11:00 and head south on Route 66. Wind through the Illinois farmland to Springfield, the state capital and Lincoln’s hometown. Tonight is at the State House Inn (Trademark Collection by Wyndham) in the historic quarter — walking distance to the Lincoln Museum and Oak Ridge Cemetery.
Day 04 · Thu 7 Oct
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 · Fri 8 Oct
St Louis · a free day
The Arch, Forest Park, the brewery, the ribs.
St Louis
A free day in St Louis — a bonus night that most Route 66 trips skip. Forest Park has the free zoo, the art museum and 1,300 acres of green; the Anheuser-Busch brewery sits five minutes from downtown; and Pappy’s Smokehouse on Olive Street is the ribs stop locals send you to.
Day 06 · Sat 9 Oct
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 07 · Sun 10 Oct
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 08 · Mon 11 Oct
Oklahoma City · a free day
A second bonus day — Bricktown, the Memorial, Stockyards City.
Oklahoma City
A second bonus day. The Oklahoma City National Memorial sits five minutes from the hotel and is well worth the morning. Stockyards City west of downtown holds the largest live-cattle auction in the world — the auctions run Monday and Tuesday, and Cattlemen’s Steakhouse opposite has been serving since 1910.
Day 09 · Tue 12 Oct
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 10 · Wed 13 Oct
Amarillo → Santa Fe
Climb onto the high desert — and a spa night on the Historic Plaza.
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. The Eldorado is a pueblo-revival landmark two blocks from the Historic Plaza, with the Nidah spa and the Agave Lounge on the rooftop for the view.
Day 11 · Thu 14 Oct
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 12 · Fri 15 Oct
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 13 · Sat 16 Oct
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. The MGM Grand sits at the south end of the Strip, with the Grand Garden Arena, Hakkasan and the lion-habitat lobby all in-house.
Day 14 · Sun 17 Oct
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 15 · Mon 18 Oct
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. Three nights at the Hyatt Centric Delfina, five minutes from the sand — the trip winds down here.
Day 16 · Tue 19 Oct
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 17 · Wed 20 Oct
Santa Monica · a second free day
Malibu up the coast, or the Getty on the hill.
Santa Monica
A second day on the coast. Malibu is 25 minutes up the Pacific Coast Highway from the hotel; the Getty Center sits on the hill above the 405 with free entry and the best contemporary-art view in LA. If you want one last American food moment, the In-N-Out on Lincoln Boulevard is five minutes away.
Day 18 · Thu 21 Oct
Santa Monica → LA → London
Hertz back by two, then the afternoon flight home.
Santa Monica
Hertz back · LAX · 14:00
LAX
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 two, then BA280 at 17:05 — overnight to Heathrow, in by late morning the next day.
Day 19 · Fri 22 Oct
Heathrow → Newcastle
A short hop home.
Heathrow
Newcastle
In to Heathrow mid-morning, afternoon connection to Newcastle. BA1334 at 14:15, home by half past three. Nineteen days behind you — Chicago to the Pacific and most of the Southwest in between.
The moments this trip is built around
Ten overnight stops across America.
15days
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 at a slower pace — ten stops instead of fourteen, four of them two or three nights.
4
Bonus free days
Chicago, St Louis, Oklahoma City, and two days in Santa Monica at the end — the trip gives you room to breathe.
+
Side-trip option · the Grand Canyon
80 miles north of Flagstaff. Ask and we'll add a Grand Canyon South Rim night to Day 12 or 13.
Plus Cadillac Ranch, Standin' on the Corner at Winslow, the Mojave, the Hoover Dam, and the Hyatt Centric three-night stretch on the beach to end the trip properly.
Good to know
How this trip is set up.
Return British Airways flights throughout — Newcastle → Heathrow → Chicago on the outbound, overnight BA280 LAX → Heathrow then BA1334 to Newcastle on the return. Economy with standard BA baggage.
15 days of Hertz all-inclusive car hire — unlimited mileage, insurance, taxes and additional driver included. Chicago pickup → LAX drop.
17 hotel nights across 10 stops — Hilton group through the middle for consistency, with The Omni Chicago, Union Station Curio (two nights), Eldorado Santa Fe, MGM Grand and the Hyatt Centric (three nights) as the standout stays.
Resort fees are paid locally — budget roughly US$343 total across the trip (Chicago, Vegas and Santa Monica are the ones that charge).
October timing: shoulder season across the whole route — dry and warm in the Southwest, cool nights at Flagstaff and Santa Fe at 7,000 ft, perfect weather in Santa Monica.
Free to add a Grand Canyon night at Flagstaff, or extra nights anywhere along the route — just say the word.
What's included
- Return British Airways flights Newcastle ↔ Heathrow ↔ Chicago/LAX, Economy class
- 15-day Hertz car hire — Chicago pickup, LAX drop · all-inclusive insurance, taxes & additional driver
- 17 hotel nights across 10 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
- ATOL protection included (£2.50 per person)
Paid at the hotels or on the ground
- Hotel resort fees — four line items totalling US$342.81 (approx £259.90 at £1 = $1.32): $66.57 · $35.00 · $113.38 · $127.86
- Airport transfers in Chicago (available on request)
- Fuel, meals, activities, Grand Canyon side trip
- Travel insurance, personal spending
Trip total, for two
£7,693
£500
Deposit to hold (due 8 Oct 2026)
Balance due 28 June 2027
Return BA flights Newcastle ↔ Heathrow ↔ USA, 15-day Hertz car hire and 17 hotel nights all included · plus ~£260 in local resort fees
Pay to Road Trip Co: £7,693.00 · pay locally at hotels: approx £259.90 ($342.81 USD). Exchange rates and local fees may vary before your trip.
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 (due 8 October), balance not due until 28 June 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