Emeryville to Chicago

Emeryville to Chicago

A 2,400 mile journey from the West Coast to the Windy City through the Rocky Mountains.

Emeryville to Chicago

Discover the journey

Emeryville to Chicago

Departs from Emeryville, CA (EMY) and arrives in Chicago, IL (CHI)

Enjoy approximately 52 hours onboard

Experience an extended version of one of the most celebrated rail routes in America. Departing from Emeryville on the shores of San Francisco Bay, this private railcar Expedition climbs through the dramatic Sierra Nevada, passing over Donner Pass where Gold Rush pioneers once sought riches, before descending into the high desert of Nevada. Overnight travel in spacious bedrooms carries you across the salt flats of Utah and into Colorado, where the train winds along the Colorado River through the breathtaking Glenwood Canyon. Crossing the Continental Divide is only mid-way on this epic journey. From Denver, continue through the Midwest and into Chicago. With three days of ever-changing scenery, a completely custom dining experience, and plush sleeping accommodations, this journey is as memorable as any destination.

Itinerary

  1. Emeryville, CA
    Day 1 | Board in Emeryville

    Your journey begins at Emeryville station, just across the Bay from San Francisco. Board the train, settle into your private railcar, and watch the East Bay shoreline give way to the Central Valley as the train heads northeast.

  2. Sacramento, CA
    Day 1 | The California Capital

    The train pauses in California's capital city before turning northeast toward the Sierra Nevada foothills. Take in views of the Sacramento River delta and enjoy a leisurely lunch in the dining car as the landscape begins its climb toward the mountains.

    Lunch

  3. Donner Pass
    Day 1 | Sierra Nevada Summit

    The train crests the Sierra Nevada near Donner Pass, threading through snow sheds and tunnels that pierce the granite ridgeline at over 7,000 feet. Catch sweeping views of Lake Tahoe's crystalline blue water visible to the south and pine-blanketed slopes plunging into the Truckee River canyon below.

  4. Reno, NV
    Day 1 | The Biggest Little City

    Descending the eastern slope of the Sierra, the train arrives in Reno, Nevada. The Truckee River runs through the heart of the city, and the surrounding basin opens onto the vast high-desert expanse of the Great Basin, one of the most remote and visually striking stretches of the entire route.

  5. Elko, NV
    Day 1 | Nevada High Desert

    As the sun dips behind the Ruby Mountains to the south, the train rolls into Elko, a ranching and mining town in the heart of the Great Basin. Dinner is served in the dining car while the vast Nevada sky turns shades of crimson and violet outside your window. After dinner, settle into your sleeper as you press east into the night.

    Dinner

  6. Salt Lake City, UT
    Day 1 | Gateway to the Wasatch

    Late in the evening, the train skirts the southern edge of the Great Salt Lake, its shimmering white salt flats visible even under moonlight, before pulling into Salt Lake City. Most guests are already settled into their sleeping accommodations as the train continues east into the Wasatch Range overnight.

    Sleep Onboard

  7. Green River
    Day 2 | Canyon Country at Dawn

    The train crosses into the canyon country of eastern Utah in the early morning hours, threading along the Green River as the first pale light touches the sandstone mesas. Wake to vast red-rock scenery as you enter the Colorado Plateau, a landscape unlike anything on the western leg of the journey.

  8. Grand Junction, CO
    Day 2 | Colorado River Country

    Good morning, Colorado. Grand Junction sits at the confluence of the Colorado and Gunnison rivers, flanked by the Book Cliffs to the north and the Colorado National Monument's red-rock towers to the south. Breakfast is served as you follow the Colorado River east into an increasingly dramatic canyon landscape.

    Breakfast

  9. Glenwood Canyon, CO
    Day 2 | The Colorado River Gorge

    Widely considered the most spectacular segments, Glenwood Canyon is a 12-mile slot carved by the Colorado River through 1,800-foot Precambrian granite walls. The train hugs the canyon floor, crossing the river multiple times on tight curves. Enjoy view of waterfalls, kayakers, and towering cliffs from your private oasis.

  10. Granby, CO
    Day 2 | Rocky Mountain High Country

    The train climbs into the broad valley at the headwaters of the Colorado River, surrounded by the peaks of Rocky Mountain National Park to the east and the Arapaho National Forest to the west. Lunch is served as you wind through mountain meadows at nearly 8,000 feet, the alpine scenery at its most vivid in summer wildflower season.

    Lunch

  11. Moffat Tunnel
    Day 2 | Crossing the Continental Divide

    The train plunges into the 6.2-mile Moffat Tunnel beneath James Peak, crossing the Continental Divide at 9,239 feet, the highest point on route. Waters east of here flow to the Gulf of Mexico; waters west flow to the Pacific. When you emerge from the tunnel, you are on the eastern slope of the Rockies, with Denver less than two hours away.

  12. Denver, CO
    Day 2 | The Mile High City

    Descend the Front Range foothills as the Denver skyline comes into view against the backdrop of the Rocky Mountains.

    Dinner

  13. Hastings, NE
    Day 2 | Into the Great Plains

    After leaving Denver, the train transitions into the vast flatlands of Nebraska. The train crosses the 100th meridian, the historic boundary between the humid East and the arid West, as it rolls through Hastings. Settle into your sleeper as the endless prairie sky fills with stars.

    Sleep Onboard

  14. Lincoln, NE
    Day 3 | Nebraska's Capital at Dawn

    Wake up to the rolling prairies of eastern Nebraska as the train pulls through Lincoln. The golden dome of the Nebraska State Capitol is visible on the horizon in the early morning light. This is classic Midwest farm country: vast fields of corn and soybeans stretching in every direction under an enormous sky.

    Breakfast

  15. Iowa Countryside
    Day 3 | The Rolling Hills of Iowa

    Unlike the flat stereotype of the Midwest, Iowa's western landscape rolls in gentle glaciated hills. The train winds through a patchwork of farms, small towns, and wooded river valleys. Lunch is served as you pass through some of the richest agricultural land on Earth.

    Lunch

  16. Mississippi River Crossing
    Day 3 | Crossing the Mighty Mississippi

    One of the journey's most iconic moments: the train crosses the Mississippi River on a high bridge, offering sweeping views up and down the broad, barge-laden river. This is the great dividing line of the American interior. East of here, the landscape shifts from plains to the wooded hills and river valleys of the upper Midwest.

  17. Princeton, IL
    Day 3 | Central Illinois Heartland

    Rolling through central Illinois, the train passes through Princeton, a charming county seat surrounded by the Illinois River watershed. Dinner is served in the dining car as the afternoon light turns golden over the Illinois farmlands. The skyline of Chicago, still hours away, begins to feel tangible as the countryside subtly shifts from deep rural to suburban fringe.

    Dinner

  18. Chicago, IL
    Day 3 | Journey's End: Chicago Union Station

    The train pulls into Chicago Union Station, a Beaux-Arts masterpiece with its soaring Great Hall, completing one of the most celebrated rail journeys in the world. From the Pacific shore to the shores of Lake Michigan, crossing two mountain ranges, the Great Basin, the Rockies, the Great Plains, and the Mississippi: nearly 2,500 miles of America at its most spectacular.

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.