Summer Evening on Chicago River

Midwest History & Culture Circle Tour


Chicago, Cincinnati, Detroit

The Midwest is filled with iconic cities. This trip will make stops in Chicago, Cincinnati, and Detroit before ending in Chicago. En route, you will also pass through other iconic cities such as Indianapolis, Columbus, and Cleveland. Be wowed by the sceneries of the region, as well as the right history and cultural events that took place on these land over the course of the American History.

Start location: Chicago, IL
End Location: Chicago, IL

  • Product ID
  • Vacation Style Family Friendly, Illinois, Indiana, Michigan, Midwest to Southeast, Ohio, United States, Year Round
    • Activity Level Easy
    • Duration 7 Days 6 Nights
    All about the Midwest History & Culture Circle Tour.

    Midwest History & Culture Circle Tour

    This itinerary will empower you with the knowledge from the past.

    Starting your journey in Chicago, where many have viewed it as the cultural heart of USA. Experience harmonious blend of opposites — bustling big city steeped in Midwestern charm, towering skyscrapers framed by miles of tranquil beaches, it’s a city in a garden.

    Then, watch as the Midwestern urban vibe collides with the charm of the southerns in the city of Cincinnati. Here, you will also learn and experience how the path to equality started with the National Underground Railroad, and how these stories forged the ongoing journey at the National Underground Railroad Freedom Centre.

    Continuing the circle tour, we will visit the German Village just south of downtown Columbus. Built by German settlers hundreds of years ago, this area is defined by its brick homes and shops and carries with it a unique charm as it meets with modern tweaks. After an overnight stop in Pittsburgh where you will head to the Duquesne Incline to view where three river meets, you will again head out to the Stan Hywet Hall & Gardens, one of the largest houses in the United States that used to belong to the co-founder of Good Year Tires F.A. Seiberling before arriving in Motor City USA, Detroit, Michigan to view all its famous architecture and visit the Henry Ford Museum of American Innovation.

    Back in Chicago, your tour will include stops in some of the most recognizable architectures such as Buckingham Fountain in Chicago’s Grant ParkThe Art Institute of Chicago, Millennium Park, and Navy Pier, where you will take part in the Chicago Classic Lake Tour to take in the stunning sights of Chicago’s skyline from Lake Michigan.


    The Cloud Gate sculpture, aka “The Bean” in Millennium Park in Chicago.

    Trip Distances:

    for references only
    • Chicago – Cincinnati ( 476km / 296mi )
    • Cincinnati – Pittsburgh ( 483km / 288mi )
    • Pittsburgh – Detroit ( 462km / 287mi )
    • Detroit – Chicago ( 455km / 283mi )

    – Trip Highlights –

    experience the charm of the Midwest

    Architecture, Histories, Natural Sceneries

    • in Illinois: City of Chicago
      • Chicago Water Tower
      • Grant Park & Buckingham Fountain
      • Millennium Park & The Art Institute of Chicago
      • Michigan Avenue (Magnificent Mile)
      • Navy Pier & Classic Lake Tour
    • in Indiana:
      • Purdue University
    • in Ohio: City of Cincinnati
      • National Underground Railroad Freedom Center
      • Smale Riverfront park & John A. Roebling Suspension Bridge
      • Hyde Park Square
      • German Village
      • Stan Hywet Hall & Gardens
    • in Michigan: City of Detroit
      • Detroit city tour: Cadillac Tower, Fox Theatre, Detroit Opera House, Detroit Institute of Arts, Fisher Building
      • Henry Ford Museum

    – Trip Dates –

    *Please contact us for available travel dates.

    Note: This itinerary maybe converted to a self-drive package and modified to suit your travel interests, time frame, and budget. Please contact our travel specialists for your customized package.

    Benefits of a Self-Drive Tour?

    Private & Customizable

    You can see what you want, when you want, how you want. A trip that’s perfectly timed and well organized.

    Unique Experience

    Experiences that help you take in the region in a different way, and advice to help you get the most out of your trip.

    Freedom to Explore

    Time to enjoy and take in each place. Add days in places you want to explore. Do only the activities you want to do.

    Can't find what you're looking for?

    Our specialists can take away the stress and create a custom trip tailored to your exact interests and budget.

    or Call  1-604-207-9188

    1. Day 1 Welcome Midwest

      Welcome to Chicago, your gateway to the Midwest. Upon arrival at the Chicago O’Hare International Airport, your tour guild will greet you at the airport, and be transferred to the hotel for check-in.

      Depends on the time of your arrival, feel free to roam the city at your leisure.

        Accommodation suggestion
      Doubletree by Hilton Chicago North Shore (3 ) or more selective

    2. Day 2 Hello CinCity

      Today we will drive across the State of Indiana ending in Cincinnati, Ohio.

      Along the way, stop by the world-renowned Purdue University, known for its public research that advances discoveries in science, technology, engineering and math. Upon arrival in Cincinnati, head to the National Underground Railroad Freedom Center for an afternoon of history lessons on a crucial period of American History that has a profound influence in even today’s society.

      End the evening with a nice stroll at the Smale Riverfront Park where you will have a plenty of angle to view the John A. Roebling Suspension Bridge, which was once longest suspension bridge before John A. Roebling designed the Brooklyn Bridge.

        Accommodation suggestion
      Hilton Cincinnati Netherland Plaza (3 ) or more selective

    3. Day 3 Good Evening Pittsburgh

      Day 3, before leaving Cincinnati and heading toward Pittsburgh this morning, stop by the Hyde Park Square for a unique photo-op! This Unique and well preserved neighbourhood was founded and built over a hundred years ago by a by a group of prosperous citizens who wanted to design a community that would preserve natural and architectural beauty and provides a peaceful place for Cincinnatians to call home.

      Making a pit stop at the German Village and grab some lunch. This distinctive neighbourhood was built by German settlers hundreds of years ago, the area is defined by its brick homes and shops, as well as brick-lined streets.

      Arriving in Pittsburgh by early evening, head to Mount Washington and head toward the top of Duquesne Incline Observation deck for an unforgettable sunset view over looking the Pittsburgh skyline.

        Accommodation suggestion
      Doubletree by Hilton Pittsburgh Downtown (3 ) or more selective

    4. Day 4 Motor City USA

      Today’s journey will take you from Pittsburgh up the Interstate into Detroit, Michigan, also known as Motor City USA.

      But before leaving the state of Ohio, make a stop at Akron, Ohio and visit the Stan Hywet Hall & Gardens, the first and largest National Historic Landmark in the US. Learn how the Stan Hywet came to be one became a non-profit historic house museum, opening for tours so that the public could benefit from the cultural, educational, and inspirational riches of one of the most significant achievements in architecture and horticulture to come out of America’s Industrial Age.

      When you arrive in Detroit, enjoy a quick city tour visiting some of the most icon buildings in the likes of The Cadillac Tower, Fox Theatre, Detroit Opera House, Detroit Institute of Arts, and Fisher Building.

        Accommodation suggestion
      Doubletree by Hilton Detroit-Dearborn (3 ) or more selective

    5. Day 5 Windy City

      Day 5 will take you back to your arrival city, Chicago Illinois.

      Before heading out onto the Interstate, make your way to the Henry Ford Museum of American Innovation and into a world where past innovations fuel the imagination of generations to come. Learn and experience the strides of America’s greatest minds while fully immersing yourself in their stories.

      Arriving in Chicago before dinner time, we will make a stop at 806 N. Michigan Ave. for a photo opportunity with a Historical Landmark, the Chicago Water Tower. Constructed back in 1867 and 1869, this municipal water system originally housed a 135 foot iron standpipe used to regulate the city’s water pressure, and is significant today because it is one of the few buildings that survived the The Great Chicago Fire of 1871.

        Accommodation suggestion
      Embassy Suites Chicago Downtown (3 ) or more selective

    6. Day 6 The Magnificent Mile

      In the morning, bring a pair of comfortable walking shoe as we will be visiting Grant Park. This 319 acres green oasis by the lake is a gathering place for the cities biggest events, and acts as a culture hub as it hosts Chicago’s most famous landmarks.

      Some of the most notable features includes <b>Millennium Park</b>, <b>Maggie Daley Park</b>, <b>Buckingham Fountain,/b>, the <b>Art Institute of Chicago</b>, and the <b>Museum Campus</b>.

      In the afternoon, visit the iconic <b>Magnificent Mile</b> of Chicago on North Michigan Avenue. It’s an example of a successful and sustainable mixed-use community, with the most vibrant and successful commercial, residential, cultural and tourist destinations in the world.

    7. Day 7 Chicago 360 & River Tour

      With a full day of touring the city on foot the day before, it’s time to change your perspective on the city, literally!

      The first stop of the day will be at <b>360 Chicago</b> for Chicago’s best view, from 1,000 ft up in the sky! On the 360 Chicago Observation deck, you get a 360 degree, unobstructed view of Chicago. Optional is the TILT + Experience, the thrill ride of a lifetime as you lean against the glass looking down toward the Magnificent Mile underneath.

      The next stop will be at the Navy Pier for the classic Chicago River Tour as we navigate through the three branches of the Chicago River, discovering from hidden gems to the City’s most recognizable landmarks.

      After the tour and one last photo op, you will be transported to Chicago’s O’Hare International Airport for your flight home.

    Chicago Millennium Park
    Chicago River
    Detroit Comerica Park