Los Angeles to Chicago is one of most scenically varied routes on the American passenger rail network, tracing the old Santa Fe Railway across the full breadth of the American continent. The journey begins at a a 1939 Mission Moderne landmark, Los Angeles Union Station, and climbs immediately into drama, threading Cajon Pass in the evening before settling onto the Mojave Desert overnight. Day two is the scenic heart of the trip: passengers wake in Arizona beneath the San Francisco Peaks at Flagstaff, pass the Route 66 nostalgia of Winslow and the vivid badlands of the Painted Desert, then roll into New Mexico for a lunch around Albuquerque. The afternoon brings a steady climb up to the route's high point, the 7,588-foot Raton Pass, before descending into Colorado as the sun goes down. The third day opens on the Kansas plains near Dodge City, with the wide sky and grain elevators of the old cattle frontier stretching to every horizon. After Kansas City, the train crosses the Mississippi at Fort Madison on a swing-span bridge, one of the great quiet spectacles of American rail travel, before threading through the cornfields and river valleys of Illinois toward Chicago. The journey ends in the Windy City at Union Station's soaring 1925 Beaux-Arts Great Hall.
Los Angeles to Chicago
Experience 2,265 miles from Los Angeles to Chicago, crossing the deserts, the red rock country, and the high passes of New Mexico and Colorado.
Discover the journey
Los Angeles to Chicago
Departs from Los Angeles, CA (LAX) and arrives in Chicago, IL (CHI)
Enjoy approximately 43 hours onboard
Itinerary
- Los Angeles, CADay 1 | Board in Los Angeles
Guests board at the iconic 1939 Los Angeles Union Station, a Mission/Streamline Moderne masterpiece. Settle into your private railcar and enjoy a welcome reception as the train heads east through the Inland Empire.
Dinner
- Cajon PassDay 1 | Climbing into the Mojave
An evening climb through dramatic Cajon Pass, where the train threads between the San Gabriel and San Bernardino Mountains and rises onto the Mojave Desert under the stars.
Sleep Onboard
- Flagstaff, AZDay 2 | Beneath the San Francisco Peaks
Wake at the 1926 Tudor-Revival depot in Flagstaff, at 6,910 feet beneath the snow-capped San Francisco Peaks, the gateway to the Grand Canyon and the largest ponderosa-pine forest in North America.
Breakfast
- Winslow, AZDay 2 | Route 66 Country
Mid-morning brings Winslow, the small Route 66 town immortalized in the Eagles' 'Take It Easy' and home to Mary Colter's masterpiece, La Posada Hotel. Beyond the town, the train skirts the colorful badlands of the Painted Desert.
- Albuquerque, NMDay 2 | Heart of New Mexico
An early-afternoon service stop in New Mexico's largest city, with views of the Sandia Mountains and time on the platform to browse Indigenous artisans selling silver and turquoise jewelry.
Lunch
- Lamy, NMDay 2 | Climbing the Sangre de Cristos
The train climbs from Lamy over Glorieta Pass through pinon-juniper country, with the high peaks of the Sangre de Cristo Mountains rising to the north.
- Raton, NMDay 2 | Crossing into Colorado at Raton Pass
A spectacular late-afternoon climb to 7,588-foot Raton Pass, the highest point on America's passenger rail network, with sweeping views of northern New Mexico and the descent into Colorado's coal country at Trinidad.
Dinner
- La Junta, CODay 2 | Onto the Great Plains
An evening service stop in La Junta on the Arkansas River, near Bent's Old Fort and the historic Santa Fe Trail. The train then runs overnight east across the high plains of Colorado and Kansas.
Sleep Onboard
- Dodge City, KSDay 3 | The Old West at Dawn
Wake on the Kansas plains near Dodge City, the legendary cowtown of Wyatt Earp and Bat Masterson, the 'Queen of the Cowtowns' on the old Santa Fe Trail.
Breakfast
- Kansas City, MODay 3 | Arrive in Kansas City
Pull into the magnificent 1914 Beaux-Arts Kansas City Union Station, anchor of the Crown Center district.
- Osawatomie, KSDay 3 | Kansas Prairieland
The train glides east through the rolling Osage Plains, past fields of winter wheat and tallgrass remnants, the same landscape John Brown rode through in the 1850s. Small-town Kansas unfolds in a quiet procession of grain elevators and river crossings.
- Fort Madison, IADay 3 | Crossing the Mississippi
The most dramatic moment east of the Rockies: a slow crossing of the great Mississippi River on a swing-span railroad bridge, with broad views of the muddy river bending south toward St. Louis. Fort Madison's 1910 depot stands steps from the bank.
Lunch
- Burlington, IADay 3 | River Town on the Bluffs
A brief stop at Burlington, perched on limestone bluffs high above the Mississippi. The town's serpentine Snake Alley, once dubbed the crookedest street in the world, climbs the hill above the historic, Civil War-era brick depot.
- Galesburg, ILDay 3 | Carl Sandburg Country
Afternoon arrival in Galesburg, a storied railroad town and one of the busiest hubs in the United States. Watch as trains diverge from the Midwest to the West, Texas, and Pacific Northwest.
- Princeton, ILDay 3 | Into the Illinois River Valley
The train descends gently through Bureau County's corn and soybean fields toward the Illinois River valley. In autumn the bottomland timber blazes gold and copper; in spring the river spreads across its wide floodplain, reflecting sky and swaying cottonwoods.
Dinner
- Mendota, ILDay 3 | The Grand Prairie at Dusk
Threading through the heart of the old Grand Prairie, among the most productive farmland on Earth, the train passes Mendota as the last light gilds the flat horizon in every direction, an ocean of amber grain.
Sleep Onboard
- Naperville, ILDay 4 | The Suburban Approach
Early morning brings the western suburbs of Chicago, where one of the busiest freight corridors in North America fills the right-of-way with a constant procession of intermodal stacks and unit grain trains alongside you.
Breakfast
- Chicago, ILDay 4 | Journey's End at Union Station
The train glides into Chicago Union Station's Great Hall, a soaring 1925 Beaux-Arts landmark with 110-foot coffered ceilings, completing one of the most scenically varied rail journeys in the world, from Pacific surf to Lake Michigan shore.
Inclusions
- Executive Chef
- Steward
- All meals made to order
- Premium beverage service
- In-Station Porter Service
- Hotel and station transfers
Departures
2026 Departures
| Date | Price (USD) | Cars Included | Book |
|---|---|---|---|
| There are no scheduled trips yet, but you can still book a custom departure date. Expeditions start at $30,000 and increase based on staffing needs and your choice of private railcar. | Inquire | ||
2027 Departures
| Date | Price (USD) | Cars Included | Book |
|---|---|---|---|
| There are no scheduled trips yet, but you can still book a custom departure date. Expeditions start at $30,000 and increase based on staffing needs and your choice of private railcar. | Inquire | ||
Frequently asked questions
What are Halloway Expeditions?
Halloway Expeditions are overnight luxury train journeys that travel through incredible scenery throughout North America in plush accommodations and excellent onboard service.
Will other travelers be on the railcars?
When you book an Expedition, you and your party get exclusive use of the private railcars listed. No other travelers will be onboard.
Is gratuity included?
Gratuity for your onboard service staff is optional but always appreciated. It is not included in the price shown.
Can I book just a bedroom for an Expedition?
At this time, Expeditions can only be booked by one group for each departure date. We encourage you to include your closest family and friends in your booking.