Great Cities of the Great Lakes

  • Chicago + 1 more
  • Self Drive Ideas
  • 16
from  £1375pp
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From the Blues capital Chicago, enjoy driving through the Great Lakes region, stopping in famous US cities and enjoying a briefly into Canada to visit Toronto and Niagara Falls.

A Free Personalised Road Book is included as standard with our Self Drive itineraries. 


Please note: – This is a suggested itinerary only and is intended to give an overview of what is possible. All of our holiday itineraries are fully customisable and can be tailor-made to suit your own individual requirements.  If you would like to start in a different destination, use specific hotel accommodation, include an extra night here, a side-trip there and/or include tickets to an event please let your Discover North America travel specialist know. They’ll also book you the best value flights to ensure a seamless holiday experience.


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Day 1 Chicago

Arrive Chicago. This evening, enjoy Chicago’s many restaurants, stroll along the shore of Lake Michigan or jive to the beat at a jazz or blues club.

Day 2 Chicago

Today explore some of Chicago’s noted sites. In the morning you may want to the neighboring town of Oak Park and see the birthplace of Ernest Hemingway, or tour one of the homes designed by Frank Lloyd Wright. In downtown Chicago visit Museum Campus or shop along the Magnificent Mile. In the evening stop by Navy Pier and for a cruise along the lake.

Day 3 Chicago-Milwaukee-Green Bay (204mi/329km)

Travel north into Wisconsin and visit Milwaukee. Once known almost exclusively as a brewing powerhouse, the city now boasts the beautiful Milwaukee Riverwalk and Milwaukee Art Museum, with its architecturally impressive addition designed by Santiago Calatrava. The modernist building is shaped like a floating cross, with wings opening and closing from a central base. Even people who’ve never been on a motorcycle will enjoy the Harley-Davidson Museum. Exhibits tell the stories of the extraordinary people, products, history and culture of Harley-Davidson and of-course the fantastic motorcycle collection will captivate all. Continue north to Green Bay for the next two nights.

Day 4 Green Bay-Door County-Green Bay (148mi/238km)

Twice awarded the title of All-America City, Green Bay is known as “Titletown” because of the number of professional football Super Bowl titles its team, the Green Bay Packers has won. It’s also a great starting point to visit Door County, the “Cape Cod of the Midwest”. With five state parks, ten lighthouses and over 300 miles of shoreline, this 75-mile long peninsula was named one of the top ten vacation destinations in North America. Spend the day hunting for treasures in one-of-a-kind shops, galleries, museums & lighthouses. Pick a pail of ripe Door County cherries in the summer or a basket of crunchy apples in fall. Return to your hotel in Green Bay for the overnight.

Day 5 Green Bay-Marquette (177mi/285km)

Continue north to Marquette, the largest city on the Upper Peninsula of Michigan and the home of Northern Michigan University. It is a major port on Lake Superior, the largest of the Great Lakes. Take time for relaxing on the beach or enjoying some recreational hikes. The warm weather months offer many festivals including Art On The Rocks art festival and the Hiawatha music festival.

Day 6 Marquette-Mackinac-Traverse City (298mi/480km)

Travel south to Mackinac Island. Board the ferry in St Ignace for the 20 minute hi-speed ferry to the island where Victorian sensibility predominates. Bicycles and horse-drawn carriages are the modes of transportation on this island in the straits of Mackinac where the upper peninsula of Michigan meets the lower peninsula. Take a self guided hiking tour or rent a bicycle to tour sites such as arch rock, skull cave, sugarloaf, British landing, devil's kitchen and the beach of a bazillion beautiful skipping stones, or just take a carriage tour and eat the fudge the island is famous for. Return to the mainland and travel to Traverse City for the next two nights.

Day 7 Traverse City

Set out for Sleeping Bear Dunes National Lakeshore this morning - a must see. It offers magnificent views over sweeping vistas of Lake Michigan from atop high dunes, miles of perfect freshwater beaches, forested wilderness islands, hiking trails and a series of preserved historic farmsteads. In the afternoon visit some of the local wineries. Located on the 45th parallel, Traverse City is home to vintners who grow grapes and bottle wines on the scenic Old Mission and Leelanau Peninsulas.

Day 8 Traverse City-Detroit (256mi/412km)

Known as Motor City because of its’ notoriety as the world's traditional automotive center, and as Motown for its importance as a source of popular music legacies, the city offers a host of activities to the traveler that lends itself to both cultures. Spend the next two nights in Detroit.

Day 9 Detroit

Spend the day visiting Detroit’s highlights such as the Henry Ford Museum and Greenfield Village, and the Motown Museum, better known as “Hitsville USA”. Here one can stand in Studio “A” where the likes of Stevie Wonder, the Temptations, the Four Tops, Gladys Knight and the Pips, Diana Ross and the Supremes, and the Jackson Five, among others, recorded their hits.

Day 10 Detroit-Toronto (245mi/394km)

Cross the border into Canada today. Toronto is the world's most ethnically diverse city. Upon arrival this afternoon explore some of the vibrant retail areas for shopping or ethnic cuisine. Five Chinatowns, Little Italy along St. Clair West, the Greek community along "The Danforth," Little Portugal at Dundas and Bathurst Streets, and Gerrard India Bazaar at Gerrard and Greenwood. Stay in downtown Toronto for two nights.

Day 11 Toronto

Toronto’s waterfront provides a scenic backdrop for many popular attractions including Harbourfront, the site of art galleries, theatres, craft boutiques restaurants, and marinas. Visit the CN Tower, recently nominated one of the Seven Wonders of the Modern World. the CN Tower features glass floor bservation decks, a revolving restaurant, and a Simulator Theatre.

Day 12 Toronto -Niagara Falls, Ontario (79mi/127km)

Spend the morning at leisure in Toronto before departing for Niagara Falls, staying on the Canadian side of the Falls. Niagara Falls is composed of two major sections separated by Goat Island: Horseshoe Falls, the majority of which lies on the Canadian side of the border, and American Falls on the American side. The best way to explore the Falls is by Hornblower boat tour. The boat starts off at a calm part of the Niagara River, near the Rainbow Bridge, and takes its passengers past the American and Bridal Veil Falls, then into the dense mist of spray inside the curve of the Horseshoe Falls. Stay the night in Niagara Falls.
Also enjoy some of the area activities, such as Cave of the Winds, a journey behind the Falls, or visit the 1.5 acres of lush floral gardens that depict the Great Lakes region above the Falls, including grassy areas in the shapes of the Great Lakes as well as a walkway that follows the course of the Niagara River.

Day 13 Niagara Falls – Geneva on the Lake (177 mi/ 189 km)

Follow the Great Lakes Seaway Trail to Geneva on the Lake a beautiful area filled with numerous recreational activities. Spend the afternoon relaxing and enjoying the amenities of the hotel.

Day 14 Geneva on the Lake -Cleveland (103 mi/ 166 km)

Travel to Cleveland and spend the morning at the Rock n’ Roll Hall of Fame. Housing rare artifacts, stage wear belonging to the biggest names in music, and numerous video and audio displays, one can trace the evolution of Rock n’ Roll. Exhibits feature rock treasures such as Jimi Hendrix’s guitar, John Lennon’s report cards, and one of Michael Jackson’s gloves. Dine along East 4th st.

Day 15 Cleveland -Nappanee, (257 mi/ 414 km)

Today, travel to Nappanee to discover its a long heritage of Amish and Mennonite. Time stopped here over a century ago and preserves, in the Amish, a way of life adhering to nearly forgotten patterns of living. Visit Amish Acres to see the legacy of the three generations of the family who lived at this authentic farm and homestead. In the evening, enjoy a theme dinner and regional theater in the Round Barn Theater.

Day 16 Nappanee-Chicago (109 mi/ 175 km)

Depart for Chicago this morning. Time allowing, do some last minute shopping along Chicago’s famous Magnificent Mile before transferring to the airport.