Call Us Today!call:
Hours
Menu

Chicago Getaway Roundtrip from Boston

5 Days from

$669

Boston Chicago Boston

Reservations:
1 (800) 268-7252
Request a Quote
from your Amtrak Station:
Click Here

Chicago Getaway Roundtrip from Boston

5 Days from

$669

Boston, MA Chicago, IL Boston, MA

Reservations:
1 (800) 268-7252
Request a Quote
from your Amtrak Station:
Click Here

Trip Overview

Enjoy everything Chicago has to offer on this 5-day roundtrip getaway. After arriving from Boston, begin exploring the Windy City’s many attractions. Stop by Chicago’s Navy Pier, go shopping along the Magnificent Mile, and listen to some amazing music at one of Chicago’s many blues clubs. Visit such top attractions as the Skydeck, Shedd Aquarium, and the 360° Chicago for fun and exciting experiences! With so much to do and see, there is no telling how much fun you will have in this fabulous city!

Highlights

  • 2 nights' hotel accommodations
  • Chicago CityPASS®*
  • Multi Day Hop-on, hop-off sightseeing tour of Chicago
  • Roundtrip Amtrak® in Coach accommodations from Boston, MA on the Lake Shore Limited®


Personalize Your Trip:

  • Sightseeing cruise
  • Dinner at a popular restaurant

*Chicago CityPASS® includes admission to the following attractions: Shedd Aquarium, SkyDeck Chicago, The Field Museum, and Museum of Science and Adler Planetarium OR Art Institute of Chicago and 360 Chicago.

Disclaimer:

Package prices are per person, double occupancy, tax included. Prices do not include rail from your hometown. Please call for pricing. Package prices are subject to change without notice, and all reservations are based upon availability at the time of booking. Amtrak travel is for Coach accommodations unless otherwise noted. Upgrades to Roomette or Bedroom accommodations on board Amtrak are available. Call for pricing. Other restrictions may apply. Activities referenced in the itinerary during free time are for suggested purposes only and are not included. Seasonal activity (if applicable): During the off-season, some tours may not be available. In this case, a similar tour will be substituted. Passports (if applicable): Passports are required when crossing the Canadian border. Amtrak and Amtrak Vacations are registered service marks of the National Railroad Passenger Corporation.

DAY 1 OVERNIGHT ONBOARD AMTRAK
This afternoon board Amtrak's Lake Shore Limited route for your trip to Chicago. Settle in for your leisurely ride to the Midwest! (Overnight onboard Amtrak)

DAY 2 CHICAGO
Welcome to Chicago! Experience the best of what “The Windy City” has to offer on a hop-on, hop-off sightseeing tour. Visit the Magnificent Mile for some shopping, journey up to the Skydeck at the Willis Tower, or visit the iconic Bean in Millennium Park. You can also start using your Chicago CityPASS® which gives you access to visit some of the most popular attractions like the Shedd Aquarium or the Adler Planetarium. (Overnight in Chicago)

DAY 3 CHICAGO
Explore more of Chicago today and start using your multi-day hop-on, hop-off tour. Visit Chicago's Navy Pier, go see Sue the world's largest and most complete T-Rex at the Field Museum, or stop at the many shops and restaurants at the River North neighborhood. There is plenty to do and see in Chicago! (Overnight in Chicago)

DAY 4 OVERNIGHT ONBOARD AMTRAK
Today you will have a free day to visit whatever spots you may have missed during your stay. Then tonight board Amtrak in Chicago's Union Station for your return trip to Boston. Sit back and relax, and reflect upon the wonderful experience you had in “The Windy City”! (Overnight onboard Amtrak)

DAY 5 YOUR GETAWAY ENDS IN BOSTON

Legend for meals: B - Breakfast, BR - Brunch, L - Lunch, D - Dinner

Holiday Inn Chicago Mart Plaza

Located in the center of downtown Chicago’s exciting River North area and minutes from the Loop and Michigan Ave the contemporary Holiday Inn Chicago Mart Plaza offers exceptional views of the Chicago River and the Chicago skyline. Our recent $20 million redesign is apparent in every aspect of the Holiday Inn Mart Plaza, from our stunning atrium lobby to our 521 comfortable and contemporary guest rooms and suites.

JW Marriott Chicago

The JW Marriott Chicago is a luxurious and majestic Chicago Loop hotel. This luxury hotel in downtown Chicago is located near State Street, Millennium Park, Magnificent Mile and historic Chicago museums.

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. A modern Chicago grand hotel, the Palmer House is a lively destination within walking distance of the best attractions the city of Chicago has to offer like Millennium Park, the Art Institute of Chicago, and the theater district. The guest rooms and suites match the hotel's French Baroque styling with metropolitan flair.

The Westin Michigan Avenue

The Westin Michigan Avenue Chicago Hotel, which is located on Chicago's famed Magnificent Mile, is steps from Lake Michigan, Michigan Avenue restaurants and premier Michigan Avenue shopping.

Select Your Departure Date

For more information or to make a reservation, call our rail vacation experts at:
1 (800) 268-7252

Disclaimer:

Package prices are per person, double occupancy, tax included. Prices do not include rail from your hometown. Please call for pricing. Package prices are subject to change without notice, and all reservations are based upon availability at the time of booking. Amtrak travel is for Coach accommodations unless otherwise noted. Upgrades to Roomette or Bedroom accommodations on board Amtrak are available. Call for pricing. Other restrictions may apply. Activities referenced in the itinerary during free time are for suggested purposes only and are not included. Seasonal activity (if applicable): During the off-season, some tours may not be available. In this case, a similar tour will be substituted. Passports (if applicable): Passports are required when crossing the Canadian border. Amtrak and Amtrak Vacations are registered service marks of the National Railroad Passenger Corporation.

Other Vacations you might like

Yosemite Half Dome
Grand National Parks with Grand Canyon, Yosemite, and Glacier National Park

Roundtrip Vacations

Chicago Williams Grand Canyon National Park Seattle Glacier National Park

14 Days - from $3,399

Prepare to take in all the grand natural beauty of three of America’s most beloved national...

View Details
Leavenworth-Maypole
Leavenworth Getaway

Rail Getaways

Leavenworth

3 Days - from $279

Enjoy the festive and historic city of Leavenworth on this 3-day visit. Explore this unique...

View Details
Grand Canyon Sunset
Grand Canyon Getaway

National Parks

Williams Grand Canyon National Park Williams

4 Days - from $469

Explore all the beauty the Grand Canyon has to offer on this fabulous 4-day getaway. Your scenic...

View Details
Charleston
Charleston Getaway

Rail Getaways

Charleston

3 Days - from $169

Enjoy three days of sightseeing in a classic Southern city on this Charleston Getaway! Explore...

View Details
NIA4
Niagara Falls Explorer from New York City

Rail Getaways

New York City Niagara Falls New York City

6 Days - from $889

Enjoy a night in New York City before heading north into Canada on Amtrak for your journey to...

View Details

Where do you want to go?

Here are all of the destinations we travel to.

Loading...