Chicago
Chicago
You’ll find magic in such sparkling Chicago attractions as Navy Pier – the Midwest’s top tourist destination – and its boardwalk, 150-foot Ferris wheel, boat and segway tours, and countless dining or shopping options. Millennium Park offers dazzling music, art, landscape design and architecture – including the mammoth stainless-steel Cloud Gate sculpture – plus ice skating in the winter, splashing around in the interactive Crown Fountain during summer, and alfresco dining from spring to fall. Travel to the city of Chicago by train with Amtrak Vacations and see what you've been missing.
For more information or to make a reservation,
call our rail vacation experts at 1-800-AMTRAK-2
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Chicago, Illinois - Getaway : Package Prices Start at $239
Experience the Scope of the Windy City’s Landmarks Venture out onto the Skydeck’s glass floor extension at Willis Tower for a 1,353-feet-high introduction to Chicago. For more thrills, take a Chicago River architectural cruise of the city. Or walk the Magnificent Mile. | More
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Grand Canyon Discovery Tour : Tour prices start at $1,599
- Chicago>
- Santa Fe>
- Grand Canyon / Williams>
- Flagstaff>
- Sedona
The Grand Canyon has long been described as something to experience at least once in a lifetime. Enjoy a short stay in Chicago before boarding the Southwest Chief® and heading to ... | More
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The Northern Border & Pacific Northwest : Pricing from $2,299
- Chicago>
- Minneapolis>
- Glacier Park>
- Seattle
In the north are some of the last truly wide-open space left, and the Amtrak® Empire Builder® takes you there. Board the train in Chicago and take the Northern route to the West ... | More
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Jazz, Blues and Rock 'N Roll By Rail : Package Prices Start at $1,239
- Chicago>
- Memphis>
- New Orleans
Celebrate American rhythm on a nine-day rail journey through three cities pulsing with legendary music. Launch your vacation in Muddy Waters’ Chicago. | More
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Jazz, Blues and Rock 'N Roll By Rail Escorted : Prices start at $3,450
- Chicago>
- Memphis>
- New Orleans
Celebrate American rhythm on a eight-day rail journey through three cities pulsing with legendary music. Launch your vacation in Muddy Waters’ Chicago. | More
Save up to $350 Per Person
Early Booking Discount
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Simply Jersey Boys in Chicago : Package Prices Start at $398
It's just too good to be true!" (Clive Barnes, New York Post) Broadway's biggest success story takes you behind the music of Frankie Valli & The Four Seasons-and, as The New York Times says, "the crowd goes wild!" Follow the rags-to-rock-to-riches tale of four blue-collar kids ... | More
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Chicago Show: Blue Man Group
Blue Man Group is one of New York's longest-running shows and one of its hardest to describe! | More
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Chicago Show: Million Dollar Quartet
MILLION DOLLAR QUARTET recently received 3 nominations for Jeff Awards, including Best Production of a Musical (Large) and Best Ensemble. | More
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Chicago Show: War Horse
War Horse, the winner of five 2011 Tony Awards including Best Play, travels from the English countryside to the fields of France and Germany at the outbreak of World War I. | More
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Field Museum
Travel around the world, go back in time, and discover things you never knew at The Field Museum! Whether you're a first-time guest or a frequent visitor, we're your home for endless adventures. | More
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Gray Line - Historic Chicago South Shore Tour
Here is a tour full of interest, history, and beauty! | More
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Gray Line - Inside Chicago - The Grand Tour
A comprehensive tour of all Chicago has to offer. | More
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Gray Line - Inside Chicago - The Grand Tour & Hancock Tower
Enjoy the Inside Chicago - Grand Tour and a visit to the Hancock Tower! See the sites from one of Chicago’s tallest landmarks. | More
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Gray Line - Panoramic & Scenic North Side Tour
This is the tour for those looking to experience the vitality and excitement of Chicago! | More
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Hancock Observatory
Get an in-depth view of Chicago 94 stories high above the Magnificent Mile! | More
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Hop On Hop Off Trolley & Upper Decker Tours
Our EXPLORE CHICAGO TOUR is the best value and most fun tour Chicago offers! | More
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Private Tour Chicago - Full Day
The "City Tour" starts with a Chauffeur picking you up at the address of your convenience. | More
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Private Tour Chicago - Half Day
The "City Tour" starts with a Chauffeur picking you up at the address of your convenience. | More
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Skydeck Chicago Admission
You’ll see the best view and best overview of Chicago. At 1,353 feet (412 meters), the Skydeck is the highest observatory in Chicago. | More
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The Chicago Theatre Marquee Tour
The Chicago Theatre is a National Landmark hosting hundreds of concerts, comedians, theatrical productions and special events every year. | More
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Allegro Hotel Chicago
Welcome to our Downtown Chicago Hotel near Michigan Avenue. Residentially inspired with a touch of contemporary sophistication, our Chicago hotel welcomes guests with tailored amenities, exemplary service and an experience which embraces the individuality of each guest. | More
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Essex Inn Chicago
After an exciting day in this vibrant city, the rooms and suites at the Essex Inn provide the comfort and relaxation you'll need to unwind and rev up for another day! | More
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Palmer House Hilton
Welcome to The Palmer House®: a Hilton Hotel - an iconic, world-class downtown Chicago hotel and gateway to Chicago's rejuvenated Loop scene. | More
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Conrad Hotel Chicago
Welcome to our Downtown Chicago Hotel near Michigan Avenue. Residentially inspired with a touch of contemporary sophistication, our Chicago hotel welcomes guests with tailored amenities, exemplary service and an experience which embraces the individuality of each guest. | More
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Hilton Chicago
Hilton Chicago is a landmark downtown pet friendly property located on the "Cultural Michigan Avenue Mile" overlooking Grant Park and Lake Michigan, Millennium Park and Museum Campus. | More
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Holiday Inn Chicago Mart Plaza Hotel
Located in the center of downtown Chicago’s exciting River North area and minutes from the Loop – the New Chicago – the contemporary Holiday Inn Chicago Mart Plaza offers exceptional views of the Chicago River and the Chicago skyline. | More
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Dinner at Hard Rock Cafe Chicago
Entertainment in Chi-Town varies from fast and loud to sophisticated and subtle. | More
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Dinner at Italian Village Restaurants
The Italian Village Restaurants are 3 restaurants located at their Monroe St. location. | More
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Dinner at Phil Stefani's 437 Rush
Phil's Stefani's 437 Rush is the latest Phil Stefani Signature Restaurant. | More
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Dinner at Riva Crabhouse Restaurant
Enjoy the breathtaking views of the Chicago skyline and Lake Michigan at Riva on Navy Pier. | More
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Dinner at Tuscany Restaurant
TTuscany is a comfortable trattoria featuring mouthwatering northern Italian specialties | More
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Shoreline Chicago Sightseeing Architecture Cruise
Join Shoreline on an exciting journey as we tour the Chicago River and its architectural landmarks. | More
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Shoreline's Chicago Skyline Tour
See all of Chicago's fabulous lakefront sights with a convenient half-hour boat ride from any of our three convenient, lakefront docks. Choose from either of our two Navy Pier docks or the Shedd Aquarium/Museum Campus dock in Grant Park. | More
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Spirit of Chicago Dinner Cruise
You’ll know you’re in for a special evening the moment you step aboard elegant decks and are escorted to your candlelit table. | More
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Spirit of Chicago Lunch Cruise
Big smile - a keepsake photo of you and your party will be taken upon boarding, so go ahead and “mug” for the camera. | More
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Private Chicago Transfers - One Way & Round Trip
All travelers know that every airport; train station and cruise terminal are unique and sometimes difficult to maneuver around. | More