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Chicago, IL: Point of Interest Map
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Chicago, IL Vacations Packages


Chicago, on Lake Michigan in Illinois, is the third-largest city in the United States and the largest city in the Midwest region. Famed for its bold architecture, it has a skyline punctuated by skyscrapers such as the iconic John Hancock Center, 1,451-ft. Willis Tower (formerly the Sears Tower) and the neo-Gothic Tribune Tower. A must-visit place for tourists is ritzy Michigan Avenue, part of which is the famed `Magnificent Mile`. Chicago is renowned for its museums, including the Art Institute of Chicago, which sits between Grant Park and the beginning of historic Route 66.

Best Chicago, IL Vacation Packages:

Chicago

Chicago, IL

Hotels and Activities

SUGGESTED Chicago, IL VACATION PACKAGES:

  • Chicago and Indianapolis (Self Drive)
    6 nights from $927*
  • Take the Midwest States of Illinois and Indiana into your own hands, travelling between these charming cities with a Rental Car. Start this trip in the sophisticated "Wind City"; Chicago (with its steely skyscrapers, museums and rocking festivals). Then, drive to Indiana and ends this trip, with a pleasant stay in "Indy" Indianapolis (the state capital, with its speeding race cars, plenty of green space, glistening waterways and remarkable memorials). This is a flexible vacation package. Select your number of nights in each city, desired hotel and activities.
    Included:
    • Flight into Chicago and out of Indianapolis
    • Rental Car for 4 days
    • Hotel for 3 nights in Chicago
    • Hotel for 3 nights in Indianapolis
    • Driving Time
      Chicago - Indianapolis: 3 hrs. approx.



  • Chicago and St. Louis (Self Drive)
    6 nights from $1,037*
  • Take Illinois and Missouri into your own hands, travelling between this popular cities with a rental car. Visit Chicago (Famed for its bold architecture and renowned for its museums and many loyal sports fans) and St Louis (a major city in Missouri along the Mississippi River, known for the Gateway Arch, the tallest monument constructed in the United States). This is a flexible vacation package. Select your number of nights in each city, desired hotel and activities.
    Included:
    • Flight into Chicago and out of St Louis Airport
    • Rental Car for 7 days
    • Hotel for 3 nights in Chicago
    • Hotel for 3 nights in St Louis
    • Driving Time
      Chicago - St Louis: 4hr 35mn approx.



  • Chicago and Indiana Dunes State Park (Self Drive)
    6 nights from $2,099*
  • Cosmopolitan city, open green spaces and music await you with this Self-Drive Package in these two cities in Illinois State. Start this trip with a visit to "The Windy City"; Chicago (famed for its bold architecture, with the Sears Tower; with its museums and many loyal sports fans). After that, drive to Indiana Dunes State Park (natural sand dunes occurring at the southern end of Lake Michigan in the American State of Indiana. They are known for their ecological significance). This is a flexible vacation package. Select your number of nights in each city, desired hotel and activities.
    Included:
    • Flight into Chicago and out of South Bend Airport
    • Rental Car for 7 days
    • Hotel for 3 nights in Chicago, IL
    • Hotel for 3 nights in Indiana Dunes State Park, IN
    • Driving Time
      Chicago, IL - Indiana Dunes State Park, IN: 53 mins. approx.
      Indiana Dunes State Park, IN- South Bend: 54 mins. approx.



  • Route 66 - Illinois to Oklahoma the Highlights (Self Drive)
    7 nights from $849*
  • Venture from east to west along the iconic Route 66, the most famous U.S. Highway System. Popular sights for families, adventurers, and lovers of small town Americana, beckon visitors to explore the heart of the country. Start in Illinois, with a stay in "The Windy City" - Chicago (famed for its bold architecture and renowned for its museums and many loyal sports fans), then journey to Missouri known as the "Show Me State" while exploring St. Louis (known for the Gateway Arch, the tallest monument constructed in the U.S.) and Springfield (the "Queen City of the Ozarks" which offers beautiful and scenic outdoor recreational activities). Before ending this whirlwind trip, your next stop is in Oklahoma, with a pleasant stay in its capital city; Oklahoma City (known for its cowboy culture and capital complex, surrounded by working oil wells). This is a flexible vacation package. Select your number of nights in each city, desired hotel and activities.
    Included:
    • Flight into Chicago and out of Oklahoma City
    • Rental Car for 8 days
    • Hotel for 3 nights in Chicago
    • Hotel for 1 night in St. Louis
    • Hotel for 1 night in Springfield
    • Hotel for 2 nights in Oklahoma City
    • Driving Time
      Chicago - St. Louis: 5 hrs 25 mins approx.
      St. Louis - Springfield: 3 hrs 20 mins approx.
      Springfield - Oklahoma City: 4 hrs 15 mins approx.



  • Route 66 - Illinois to Texas the Long Ride (Self Drive)
    More details
  • Explore iconic Route 66 on a long ride from east to west, venturing through Illinois, Missouri, Oklahoma, and Texas - with nearly endless opportunities to experience culture, excitement, and beauty. Combine Chicago (set on beautiful Lake Michigan the city is well regarded for interesting architecture - like the Sears Tower - and its cultural highlights from museums to theaters and more), Springfield, Illinois (home of President Abraham Lincoln as well as his Presidential Library), St. Louis (whose beautiful and famous Gateway Arch welcomes visitors to this city on the Mississippi River), Springfield, Missouri (an Ozark city with lots of Route 66 history), Tulsa (Oklahoma`s vibrant second-largest city, with a sizable arts scene), Oklahoma City (the capital of Oklahoma and home to the National Cowboy and Western Heritage Museum and the Oklahoma City Memorial) and finally Amarillo (nicknamed `The Yellow Rose of Texas`, boasts a great food scene, historic districts, and easy access to Palo Duro Canyon). This is a flexible vacation package. Select your number of nights in each city, desired hotel and activities.
    Included:
    • Flight into Chicago Airport and out of Oklahoma City Airport
    • Rental Car for 16 days
    • Hotel for 3 nights in Chicago
    • Hotel for 2 nights in Springfield, IL
    • Hotel for 2 nights in St. Louis
    • Hotel for 2 nights in Springfield, MO
    • Hotel for 2 nights in Tulsa
    • Hotel for 2 nights in Oklahoma City
    • Hotel for 2 nights in Amarillo
    • Driving Time
      Chicago– Springfield, IL: 3hrs 14min approx.
      Springfield, IL- St. Louis: 1 hr 28 mins approx.
      St. Louis- Springfield, MO: 3hrs 22mins approx.
      Springfield, MO- Tulsa: 3 hrs approx.
      Tulsa - Oklahoma City: 1hrs 34mins approx.
      Oklahoma City - Amarillo: 4hrs approx.



  • Chicago and the Quad Cities (Self Drive)
    More details
  • This self-drive, independent vacation package will introduce you to these beautiful cities through Illinois. Combine Chicago (The wind city will blow you away with its steely skyscrapers, museums and rocking festivals) and Quad Cities (a region of five cities in the U.S. states of Iowa and Illinois: Davenport and Bettendorf in southeastern Iowa, and Rock Island, Moline, and East Moline in northwestern Illinois); with a Rental Car. This is a flexible vacation package. Select your number of nights in each city, desired hotel and activities.
    Included:
    • Flight into Chicago and out of Quad Cities
    • Rental Car for 6 days
    • Hotel for 3 nights in Chicago
    • Hotel for 2 nights in Quad Cities
    • Driving Time
      Chicago - Quad Cities: 2 hrs. 51 mins. approx.



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