Amtrak Vacations
California Zephyr Rail Experience
Seven-day California Zephyr crossing, Chicago to San Francisco
7 daysfrom $909
29% rail
United States
Train tours through Chicago, IL
120 rail vacations stop in Chicago, IL, from 2 operators, 5 to 26 days, from $259 per person. Some pass through for an afternoon and some stay for days; each trip page shows the exact overnights.
Amtrak Vacations
New York City and Washington, D.C. Roundtrip from Chicago
Independent rail loop from Chicago to New York City and Washington, D.C.
7 daysfrom $919
43% rail
Amtrak Vacations
Jazz Blues and Rock 'n' Roll
Nine-day Amtrak journey from Chicago to Memphis to New Orleans
9 daysfrom $969
22% rail
Amtrak Vacations
Riverwalk to the French Quarter Roundtrip from Chicago
Round-trip rail journey from Chicago to San Antonio and New Orleans
9 daysfrom $969
56% rail
Amtrak Vacations
Pacific Rail Experience Roundtrip from San Francisco
Roundtrip rail loop from San Francisco through Chicago and LA
8 daysfrom $979
63% rail
Amtrak Vacations
Empire Builder Rail Experience from Seattle
Seven-day Empire Builder rail trip, Seattle to Chicago
7 daysfrom $989
29% rail
Amtrak Vacations
Empire Builder Rail Experience
Seven-day Empire Builder rail trip, Chicago to Seattle
7 daysfrom $999
29% rail
Amtrak Vacations
Heart of Texas Roundtrip from Chicago
Independent roundtrip rail vacation from Chicago through Texas via Texas Eagle
9 daysfrom $1,019
44% rail
Amtrak Vacations
Rocky Mountains and Fall Foliage
Rail journey from Chicago to Denver for Rocky Mountain fall foliage
6 daysfrom $1,149
33% rail
Amtrak Vacations
Northern Rail Experience with Yosemite National Park
Independent Chicago rail trip to Seattle, San Francisco and Yosemite National Park
9 daysfrom $1,159
56% rail
Amtrak Vacations
Essential American - Majestic Landscapes
Cross-country rail journey linking New York City, Chicago and San Francisco
9 daysfrom $1,269
56% rail
Amtrak Vacations
Hollywood to Broadway
Independent rail trip from Los Angeles to New York City
12 daysfrom $1,279
25% rail
Amtrak Vacations
Northern Rail Experience Roundtrip from San Francisco
Independent 10-day Amtrak roundtrip from San Francisco via Chicago and Seattle
10 daysfrom $1,279
50% rail
Amtrak Vacations
Northern Rail Experience Roundtrip from Seattle
Independent 10-day Amtrak roundtrip from Seattle via San Francisco and Chicago
10 daysfrom $1,299
50% rail
Amtrak Vacations
Jazz Blues and Rock 'n' Roll Roundtrip from Boston
Eleven-day roundtrip Amtrak journey from Boston through Chicago, Memphis, and New Orleans
11 daysfrom $1,319
36% rail
Amtrak Vacations
California Zephyr and Rocky Mountains Discovery Eastbound
Nine-day California Zephyr trip eastbound, San Francisco to Chicago
9 daysfrom $1,329
22% rail
Amtrak Vacations
California Zephyr and Rocky Mountains Discovery Westbound
Nine-day California Zephyr trip westbound, Chicago to San Francisco
9 daysfrom $1,349
22% rail
Amtrak Vacations
Jazz Blues and Rock 'n' Roll Roundtrip from Philadelphia
Eleven-day roundtrip Amtrak journey from Philadelphia through Chicago, Memphis, Orleans
11 daysfrom $1,349
36% rail
Amtrak Vacations
Essential Grand Canyon Discovery
Rail journey from Chicago to the Grand Canyon and Sedona
7 daysfrom $1,359
43% rail
Amtrak Vacations
Jazz Blues and Rock 'n' Roll Roundtrip from New York
Eleven-day roundtrip Amtrak journey from New York through Chicago, Memphis, Orleans
11 daysfrom $1,359
36% rail
Amtrak Vacations
Essential American Eastbound
Coast-to-coast rail journey linking San Francisco, Chicago and New York City
10 daysfrom $1,369
50% rail
Amtrak Vacations
Pacific Rail Experience
Three-train roundtrip rail loop from Chicago to California and back
9 daysfrom $1,419
56% rail
Amtrak Vacations
West Coast to East Coast Rail Experience
Ten-day coast-to-coast rail journey from San Francisco to Washington, D.C.
10 daysfrom $1,489
40% rail
Amtrak Vacations
Grand National Parks of the Southwest
8-day round-trip rail journey from Chicago to Utah's Mighty 5 parks
8 daysfrom $1,499
25% rail
Amtrak Vacations
National Parks of the Southwest - Bryce and Zion to the Grand Canyon
Nine-day Chicago roundtrip past Bryce, Zion, and the Grand Canyon
9 daysfrom $1,539
44% rail
Amtrak Vacations
Grand Canyon Express
One-way Chicago to Los Angeles rail trip via the Grand Canyon
10 daysfrom $1,569
40% rail
Amtrak Vacations
Grand Canyon to Yosemite Roundtrip from Chicago
Roundtrip rail trip from Chicago to the Grand Canyon and Yosemite
11 daysfrom $1,629
45% rail
Railbookers
Northern Rail Experience
Independent cross-country rail trip: Chicago to Seattle to San Francisco and back
9 daysfrom $1,629
56% rail
Railbookers
Great Southwest Featuring the Grand Canyon
7-day Amtrak and Grand Canyon Railway trip, Chicago to Los Angeles
7 daysfrom $1,649
57% rail
Amtrak Vacations
Highlights of America - Coast to Coast
Independent cross-country rail trip, Washington DC to Los Angeles
11 daysfrom $1,659
45% rail
Amtrak Vacations
Northern Rail Experience
Independent 9-day Amtrak loop from Chicago through Seattle and San Francisco
9 daysfrom $1,659
56% rail
Amtrak Vacations
East Coast to West Coast Rail Experience
Ten-day cross-country rail trip, Washington DC to San Francisco
10 daysfrom $1,669
40% rail
Amtrak Vacations
Grand Canyon Discovery
10-day rail trip from Chicago to Sedona via the Grand Canyon
10 daysfrom $1,679
30% rail
Railbookers
Grand Canyon Discovery
Independent Southwest rail vacation from Chicago to the Grand Canyon
10 daysfrom $1,679
30% rail
Amtrak Vacations
Essential Grand Canyon to Yosemite Roundtrip Chicago
Grand Canyon and Yosemite rail roundtrip from Chicago on four named trains
9 daysfrom $1,699
56% rail
Amtrak Vacations
Southern Rail Experience
Round trip Amtrak rail loop from Chicago to Seattle, LA, New Orleans
12 daysfrom $1,699
75% rail
Amtrak Vacations
Western Rail Experience Roundtrip from Los Angeles
Los Angeles roundtrip Amtrak loop through San Francisco, Seattle, and Chicago
11 daysfrom $1,699
36% rail
Amtrak Vacations
Western Rail Experience Roundtrip from San Francisco
San Francisco roundtrip Amtrak loop through Seattle, Chicago, and Los Angeles
11 daysfrom $1,699
36% rail
Amtrak Vacations
Western Rail Experience
Chicago roundtrip Amtrak circuit through Los Angeles, San Francisco, and Seattle
11 daysfrom $1,709
36% rail
Amtrak Vacations
Northern Rail Experience with Rocky Mountain National Park
Independent Chicago to Denver rail trip via Rocky Mountain National Park
11 daysfrom $1,749
45% rail
Railbookers
The All American
Round-trip Amtrak journey from Chicago via New York, New Orleans, San Francisco
15 daysfrom $1,799
40% rail
Amtrak Vacations
The All American
Fifteen-day round trip Amtrak rail circuit from Chicago, Coach class
15 daysfrom $1,809
67% rail
Amtrak Vacations
Route 66 by Rail
14-day Amtrak rail journey along Route 66, Chicago to LA
14 daysfrom $1,839
36% rail
Railbookers
Route 66 by Rail
Route 66 by rail from Chicago to Los Angeles on Amtrak
14 daysfrom $1,839
36% rail
Amtrak Vacations
Grand Canyon Discovery Roundtrip from Washington, D.C.
13-day roundtrip rail journey from Washington, D.C. to the Grand Canyon
13 daysfrom $1,899
38% rail
Amtrak Vacations
Scenic America by Rail with the Grand Canyon
13-day Amtrak trip, New York to Los Angeles via the Grand Canyon
13 daysfrom $1,939
31% rail
Amtrak Vacations
Grand Canyon Explorer Roundtrip from Chicago
11-day roundtrip rail journey from Chicago to the Grand Canyon
11 daysfrom $1,989
45% rail
Amtrak Vacations
Rocky Mountains to Yosemite Roundtrip Chicago
Chicago roundtrip rail loop to Denver, Salt Lake City, and Yosemite
11 daysfrom $2,049
45% rail
Amtrak Vacations
West Coast to East Coast Rail Experience from Los Angeles
Cross-country Amtrak rail journey, Los Angeles to Washington, D.C., on three trains
11 daysfrom $2,059
45% rail
Railbookers
Great American - Majestic Landscapes
Independent 12-day, coast-to-coast Amtrak trip, New York to San Francisco
12 daysfrom $2,059
25% rail
Railbookers
Grand Rail Experience
14-day cross-country Amtrak rail circle from Chicago
14 daysfrom $2,079
86% rail
Amtrak Vacations
Journey Through Presidential History - Boston to Texas by Rail
Sixteen-day Amtrak rail journey through U.S. presidential history, Boston to Austin
16 daysfrom $2,099
38% rail
Amtrak Vacations
Route 66 by Rail and Road
15-day Route 66 trip combining Amtrak rail with a Southwest self-drive segment
15 daysfrom $2,109
27% rail
Amtrak Vacations
Scenic America by Rail Eastbound
12-day rail trip, Los Angeles to New York via Grand Canyon
12 daysfrom $2,139
42% rail
Amtrak Vacations
USA and Canada Eastern Rail Journey
Independent rail journey from New York City through Canada to Chicago
11 daysfrom $2,209
36% rail
Amtrak Vacations
Glacier National Park and Seattle from Chicago
One-way Amtrak rail trip from Chicago to Glacier National Park and Seattle
7 daysfrom $2,229
29% rail
Amtrak Vacations
The Empire Builder and Alaska Rail and Sail with the Norwegian Jade®
12-day Amtrak and Alaska cruise from Chicago to Anchorage
12 daysfrom $2,259
25% rail
Amtrak Vacations
Grand National Parks of the Southwest - Bryce and Zion to the Grand Canyon
10-day rail loop from Chicago to Utah's parks and the Grand Canyon
10 daysfrom $2,299
50% rail
Amtrak Vacations
Rails Across America The Beautiful
16-day rail journey from Chicago to San Francisco on the California Zephyr
16 daysfrom $2,369
31% rail
Amtrak Vacations
Highlights of America Eastbound
Independent cross-country rail trip, Los Angeles to Washington DC
12 daysfrom $2,409
42% rail