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Chicago Vacation Packages, Tours & Travel Experiences


  • Chicago is renowned for it's bold architecture and museums

Chicago is located in northeastern Illinois on the southwestern shores of freshwater Lake Michigan. The fourth-largest city in the United States, Chicago is one of the country’s most architecturally striking and culturally dynamic urban centres. The city is home to incredible museums and world-famous art galleries, delightful eateries, green parks, a stunning waterfront, and some of the world’s tallest buildings. Activities and attractions include the Magnificent Mile shopping district, Millennium Park, a Chicago River architecture boat tour, the impressive Art Institute of Chicago, and the John Hancock Tower 360-degree observation deck on the dizzying 94th floor.

Music fans flock to the city’s renowned jazz and blues scene. Sports fans come for the major sports venues, including Wrigley Field Major League Baseball stadium. The diverse music scene delivers an electrifying variety of genres, including blues, soul, and jazz, and the lively city boasts a thriving theatre, concert tour, and world-renowned performing arts scene.

Chicago is also surprisingly green, offering strolls along the Chicago Riverwalk, through the beautiful lakefront parks along Michigan Avenue, or around Museum Campus, a 57-acre park encompassing five of the city's most notable attractions, including the Adler Planetarium, Shedd Aquarium, and the Field Museum of Natural History. An expert tour guide can help navigate the city’s whirlwind of attractions and is often a local who has plenty of tales about Chicago life together with an in-depth knowledge of its character.

Dining options in the bustling city’s thousands of restaurants include everything from Chicago-style hot dogs to deep-dish pizza to Maxwell Street Polish sausages to fine dining at one of 22 Michelin-starred restaurants.

Chicago, United States

  • Historic Route 66

    FIRST-CLASS |SELF DRIVE: Still a bucket list item for many, Route 66 has an allure that suggests freedom, America’s wide-open spaces, supported by a rollcall of cities immortalized in the song (Get your Kicks) On Route 66. Chicago kicks it off in style before you, ideally, walk the last few blocks towards Santa Monica Pier where it ends. The Grand Canyon provides a moment of drama, but Route 66 purists will delight in all the old Route 66 motels, gas stations and vintage buildings that are featured along the entire trip. A road trip like no other
    Duration:
    16 Days
    Prices From:
    US$ 2,470
    Trip Type:
    Classics (Bestsellers), Self-Drives
    United States See Trip Details
  • New York to Hollywood

    MODERATE | ESCORTED COACH TOUR: Cross the United States and compare the excitement and glamour of Manhattan in the East with that of Hollywood in the West. The places you see in between could be on most bucket lists with Niagara Falls, Yellowstone, the Grand and Bryce Canyon delivering the dramatic landscapes, while after a visit to Mount Rushmore you follow the trail of the Bison into Montana. History is well served with visits to Philadelphia, Washington, and Gettysburg. Then there’s Chicago, parts of Route 66 and the glitter of Las Vegas.
    Duration:
    17 Days
    Prices From:
    US$ 3,350
    Trip Type:
    Escorted Coach Touring
    United States See Trip Details
  • Rhythms of the River Chicago to New Orleans

    MODERATE | SELF DRIVE: A trip along a fascinating route down south to New Orleans, full of fabulous landscapes, wonderful local culinary experiences, and plenty of history. But it’s the final layer that makes this trip very special: music. From Chicago you are heading out on Route 66, a drive immortalized by the famous (Get Your Kicks on) Route 66. St. Louis boasts the National Blues Museum while Nashville and New Orleans are, naturally, prominently featured. But it’s places like Clarksdale, Cleveland, and Natchez along the Mississippi Blues Trail, that might strike a special chord.
    Duration:
    9 Days
    Prices From:
    US$ 1,460
    Trip Type:
    Self-Drives
    United States See Trip Details
  • The Great Lakes

    MODERATE| SELF DRIVE: A terrific trip introducing you to four of the Great Lakes. From Chicago, north along the shores of Lake Michigan to the point where it meets Lake Huron. Down to Detroit along Lake Erie into Canada and Lake Ontario until you close the loop driving the southern shores of Lake Erie back to Chicago. Milwaukee, famous for brewing and Mackinac Island, steeped in history are stops enroute, as are Niagara Falls and Toronto. The Rock’n’Roll Hall of Fame in Cleveland is worth a visit before returning to the ‘Windy City’.
    Duration:
    15 Days
    Prices From:
    US$ 2,549
    Trip Type:
    Self-Drives
    United States See Trip Details
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