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USA Tours from Chicago

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Route 66 starts in Chicago - are you ready to try it? Climb Gateway Arch for St. Louis views, enjoy Branson's live music downtown, visit Grand Canyon's South Rim, tour Hollywood and walk among the stars. There's Lake Michigan, Branson entertainment, canyon sunsets, and basically the classic American road trip everyone dreams about doing at least once.

10 best USA tour packages from Chicago

  • Highlights of Route 66 Tour
     Highlights of Route 66 - 22 destinations
    View Map
    In-depth Cultural

    Highlights of Route 66

    5.0 (120 traveler reviews)

    "The scenery was stunning especially the Grand Canyon."

    Duration
    16 days
    Destinations
    Chicago, Pontiac, Springfield, St. Louis, Tulsa,Oklahoma City,Elk City,Amarillo,Tucumcari,Albuquerque,Gallup,Winslow,Williams,Grand Canyon National Park,Seligman,Las Vegas,Los Angeles,Santa Monica,Beverly Hills+14 more
    Age Range
    All Ages Welcome
    Country Region
    Route 66Sun Belt
    Operated in
    English
    Operator
    Cosmos
    7% Off
    From $3,569
    US$3,319per person
    Price based on Private Double Room
    View tour
  • Chicago to L.A Tour
     Chicago to L.A - 18 destinations
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    Explorer

    Chicago to L.A

    Duration
    11 days
    Destinations
    Chicago, Sioux Falls, Badlands National Park,Mount Rushmore National Memorial,Rapid City,Bighorn National Forest,Cody,Yellowstone National Park,Grand Teton National Park,Salt Lake City,Bryce Canyon National Park,Grand Canyon National Park,Flagstaff,Seligman,Las Vegas,Mojave Desert,Beverly Hills,Los Angeles+15 more
    Age Range
    Ages 21+
    Country Region
    Western USA
    Operated in
    English
    Operator
    Omega Tours
    7% Off
    From
    US$4,040per person
    Price based on Private Double Room
    View tour
  • Route 66 From Chicago to LA - 12 days Tour
     Route 66 From Chicago to LA - 12 days - 12 destinations
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    Explorer

    Route 66 From Chicago to LA - 12 days

    Duration
    12 days
    Destinations
    Chicago, Pontiac, Springfield, St. Louis, Tulsa,Oklahoma City,Amarillo,Albuquerque,Gallup,Petrified Forest National Park,Flagstaff,Los Angeles+7 more
    Age Range
    Ages 16+
    Operated in
    English
    Operator
    On The Go Tours
    7% Off
    From
    US$7,200per person
    Price based on Private Double Room
    View tour
  • 12-Day Route 66 from Chicago to the Pacific Tour
     12-Day Route 66 from Chicago to the Pacific - 11 destinations
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    Explorer

    12-Day Route 66 from Chicago to the Pacific

    Duration
    12 days
    Destinations
    Chicago, Pontiac, Springfield, Tulsa, Oklahoma City,Amarillo,Albuquerque,Flagstaff,Kingman,Barstow,Santa Monica+6 more
    Age Range
    Ages 12+
    Country Region
    Sun Belt
    Operated in
    English
    Operator
    Southwest Adventure Tours
    7% Off
    From
    US$6,499per person
    Price based on Private Double Room
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  • Chicago to LA Tour
     Chicago to LA - 19 destinations
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    Explorer

    Chicago to LA

    4.0 (1 traveler review)

    "It was a breathtaking tour. I loved that we stopped at so many national parks."

    Duration
    11 days
    Destinations
    Chicago, Sioux Falls, Badlands National Park,Mount Rushmore National Memorial,Rapid City,Cody,Yellowstone National Park,Grand Teton National Park,Salt Lake City,Bryce Canyon National Park,Lake Powell, UT,Grand Canyon National Park,Flagstaff,Seligman,Las Vegas,Mojave Desert,Beverly Hills,Los Angeles,San Francisco+16 more
    Age Range
    Ages 21+
    Country Region
    Western USA
    Operated in
    English
    Operator
    Travel Talk
    40% Off
    From $5,584
    US$3,350per person
    Price based on Private Double Room
    View tour
  • Chicago to Golden Gate Tour
     Chicago to Golden Gate - 22 destinations
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    Explorer

    Chicago to Golden Gate

    Duration
    14 days
    Destinations
    Chicago, Sioux Falls, Keystone, Rapid City, Cody,Yellowstone National Park,Grand Teton National Park,Salt Lake City,Bryce Canyon National Park,Lake Powell, UT,Grand Canyon National Park,Flagstaff,Seligman,Las Vegas,Mojave Desert,Beverly Hills,Los Angeles,Santa Barbara,Santa Maria,Carmel,Monterey,San Francisco+17 more
    Age Range
    Ages 21+
    Country Region
    Western USA
    Operated in
    English
    Operator
    Travel Talk
    40% Off
    From $6,037
    US$3,622per person
    Price based on Private Double Room
    View tour
  • Highlights of Route 66 with Mother Road Festival & Albuquerque Balloon Fiesta Tour
     Highlights of Route 66 with Mother Road Festival & Albuquerque Balloon Fiesta - 17 destinations
    View Map
    In-depth Cultural

    Highlights of Route 66 with Mother Road Festival & Albuquerque Balloon Fiesta

    4.5 (1 traveler review)
    Duration
    16 days
    Destinations
    Chicago, Pontiac, Springfield, St. Louis, Branson,Oklahoma City,Amarillo,Tucumcari,Albuquerque,Gallup,Winslow,Williams,Grand Canyon National Park,Seligman,Las Vegas,Barstow,Los Angeles+12 more
    Age Range
    All Ages Welcome
    Country Region
    Route 66
    Operated in
    English
    Operator
    Cosmos
    40% Off
    From
    US$4,309per person
    Price based on Private Double Room
    View tour
  • Music City to Windy City Tour
     Music City to Windy City - 9 destinations
    View Map
    In-depth Cultural

    Music City to Windy City

    Duration
    15 days
    Destinations
    Chicago, Detroit, Cleveland, Louisville, Central City,Memphis,Muscle Shoals,Tupelo,Nashville+4 more
    Age Range
    Ages 21+
    Country Region
    Eastern USA
    Operated in
    English
    Operator
    Travelling Time
    40% Off
    From
    US$5,328per person
    Price based on Private Double Room
    View tour
  • Mackinac Island  (Chicago, IL to Southfield, MI) (2026) Tour
     Mackinac Island (Chicago, IL to Southfield, MI) (2026) - 6 destinations
    View Map
    In-depth Cultural

    Mackinac Island (Chicago, IL to Southfield, MI) (2026)

    4.8 (57 traveler reviews)
    Duration
    9 days
    Destinations
    Chicago, Grand Rapids, Mackinac Island, Frankenmuth,Dearborn,Southfield+2 more
    Age Range
    All Ages Welcome
    Regions
    Eastern USAMidwest USAGreat Lakes+2 more
    Operated in
    English
    Operator
    Collette
    4% Off
    From $4,199
    US$4,049per person
    Price based on Private Double Room
    View tour
  • Rhythms of the Road (7 destinations) Tour
     Rhythms of the Road (7 destinations) - 7 destinations
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    Explorer

    Rhythms of the Road (7 destinations)

    3.6 (4 traveler reviews)

    "An extra night in each main city would've been great for extra activities."

    Duration
    10 days
    Destinations
    Chicago, St. Louis, Nashville, Memphis, Hammond, Lafayette,New Orleans+1 more
    Age Range
    All Ages Welcome
    Country Region
    Southern USASun Belt+1 more
    Operated in
    English
    Operator
    Cosmos
    10% Off
    From $2,559
    US$2,309per person
    Price based on Private Double Room
    View tour
  • Scenic Great Lakes with Mackinac Island Tour
     Scenic Great Lakes with Mackinac Island - 9 destinations
    View Map
    Explorer

    Scenic Great Lakes with Mackinac Island

    Duration
    9 days
    Destinations
    Chicago, Grand Rapids, Charlevoix, Mackinac Island,Frankenmuth,Detroit,Dearborn+3 more
    Age Range
    All Ages Welcome
    Regions
    Eastern USAMidwest USAGreat Lakes+2 more
    Operated in
    English
    Operator
    Trafalgar
    10% Off
    From
    US$3,995per person
    Price based on Private Double Room
    View tour
  • From Chicago\'s Skyline to Niagara\'s Mist - 8 days Tour
     From Chicago\'s Skyline to Niagara\'s Mist - 8 days - 6 destinations
    View Map
    Explorer

    From Chicago's Skyline to Niagara's Mist - 8 days

    Duration
    8 days
    Destinations
    Chicago, Cleveland, Niagara Falls (USA), Detroit,Saugatuck+1 more
    Age Range
    All Ages Welcome
    Regions
    Eastern USAMidwest USAGreat Lakes+2 more
    Operated in
    English
    Operator
    On The Go Tours
    10% Off
    From
    US$2,420per person
    Price based on Private Double Room
    View tour
  • Chicago - The Home of Skyscrapers Tour
     Chicago - The Home of Skyscrapers - 1 destination
    View Map

    Chicago - The Home of Skyscrapers

    Duration
    7 days
    Destinations
    Chicago
    Age Range
    All Ages Welcome
    Regions
    Eastern USAMidwest USACentral USAGreat Lakes+3 more
    Operated in
    English
    Operator
    Worldee
    10% Off
    From
    US$626per person
    Price based on Shared Room
    View tour
  • Mackinac Island & the Great Lakes 9 Days Tour
     Mackinac Island & the Great Lakes 9 Days - 9 destinations
    View Map
    Discover the freshest adventures available
    New on TourRadar
    Explorer

    Mackinac Island & the Great Lakes 9 Days

    5.0 (114 traveler reviews)
    Duration
    9 days
    Destinations
    Chicago, Holland, Grand Rapids, Traverse City, Charlevoix,Petoskey,Mackinac Island,Frankenmuth,Dearborn+4 more
    Age Range
    All Ages Welcome
    Regions
    Eastern USAMidwest USAGreat Lakes+2 more
    Operated in
    English
    Operator
    Globus
    10% Off
    From
    US$4,599per person
    Price based on Private Double Room
    View tour
  • Mackinac Island featuring the Tulip Time Festival (Chicago, IL to Detroit, MI) (2027) Tour
     Mackinac Island featuring the Tulip Time Festival (Chicago, IL to Detroit, MI) (2027) - 7 destinations
    View Map
    In-depth Cultural

    Mackinac Island featuring the Tulip Time Festival (Chicago, IL to Detroit, MI) (2027)

    4.8 (57 traveler reviews)
    Duration
    9 days
    Destinations
    Chicago, Holland, Grand Rapids, Mackinac Island, Detroit,Dearborn+1 more
    Age Range
    All Ages Welcome
    Regions
    Eastern USAMidwest USAGreat Lakes+2 more
    Operated in
    English
    Operator
    Collette
    10% Off
    From
    US$4,599per person
    Price based on Private Double Room
    View tour

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