Experience the splendor of each of the five Great Lakes (Lake Michigan, Lake Superior, Lake Huron, Lake Erie, and Lake Ontario) with this ten-stop ~1,300-mile road trip. The Great Lakes, massive freshwater lakes that almost appear to resemble the ocean based on their sheer size, are certain to amaze. This road trip starts in Chicago, Illinois, takes you north up Wisconsin and into the Upper Peninsula of Michigan, continues around the peninsula, and then down Michigan, along the northern coastline of Ohio, northeasterly to Niagara Falls, and ends in Toronto.

Great Lakes Road Trip Map and Itinerary
Follow along with or book this Great Lakes Road Trip Itinerary on the Winetraveler App.

Travel Tips and Practicalities

Fly into the Chicago O’Hare International Airport (ORD) to start this road trip and fly home via the Toronto Pearson International Airport (YYZ) (assuming you’re ending the trip in Toronto). Finding flights should be easy as both are large airports. If you’re flying home via a USA airport, the Buffalo Niagara International Airport (BUF) and Niagara Falls International Airport (IAG) are two options. You can view current flight deals here and additional hotel options here for any of the destinations we mention below.


NOTE: As of the time of writing this (March 2021), discretionary/optional travel into Canada remains prohibited, and thus, you will not be able to make it to the final two stops for purposes of this itinerary until said restrictions are lifted.


Renting a car to navigate this journey will be the most efficient (unless you’re a local or driving long distance), but be prepared for a probable one-way fee. If the fee for dropping off in another country is excessive, consider returning the car in New York and then find other modes of transportation to Toronto and Niagara Falls.

Stop 1: Chicago, Illinois – Lake Michigan

Chicago, set on the banks of Lake Michigan, is an excellent starting point for this road trip. Since this trip is centered on savoring in the Great Lakes, make time to at least walk along the Navy Pier that stretches out over Lake Michigan. Maybe even take a cruise out onto Lake Michigan, and try at least a few of Winetraveler’s selection of must-visit wine bars in Chicago.

If you give yourself more time in this energetic city, soak in the city’s legendary architecture by taking a cruise down the Chicago River and/or strolling down Chicago Riverwalk. Tickets for the cruise can be purchased here. Stroll around Millenium Park, and make it to the iconic modern art sculpture, the Cloud Gate (better known as “The Bean”). Don’t go to Chicago without trying at least one deep-dish pizza from favorites such as Lou Malnati’s, Giordano’s, and/or Pizzeria Uno.

Soar high up above the city by riding the elevators to the observation floors on the 103rd floor of the Willis Tower f/k/a Sears Tower (Skydeck Chicago) and the 94th floor of 360 Chicago (still colloquially referred to as the John Hancock Center).

From Skydeck Chicago, glass cube ledges extend over 4 feet from the edge of the building. It may be a little intimidating to step onto the glass floor from over 100 floors high, but the bird’s-eye view is unique and quite an experience.

The 360 Chicago offers spectacular views of Lake Michigan along with skyline city views. From 360 Chicago, engage in the tilting experience whereby you step onto a glass-enclosed balcony with a moveable platform that tilts downward over the edge of the building for a brief moment. Alternatively or additionally, grab a pricey cocktail at the Signature Lounge on the 96th floor. While the drinks are on the pricer side, the admission is free and the views are unforgettable (planning to reopen for service on April 9, 2021).

The Embassy Suites by Hilton Chicago Downtown Magnificent Mile is a great hotel for families located in the heart of many of Chicago’s finest attractions. It’s only about ~0.7 miles west of the Navy Pier. The Allegro Royal Sonesta, with an old-style boutique feel, is also a lovely stay within walking distance to many sites.

If you’re hungry for a bratwurst and/or are looking for a lively atmosphere to watch a sports game, stop in at Brat Stop in Kenosha on your way to Milwaukee. Brat Stop has been around since 1961 and is enjoyed by locals and tourists alike.

While in Kenosha, satisfy your craving to try Wisconsin cheeses with a stop at Tim and Tom’s Cheese Shop. The store displays many refrigerators full of a variety of Wisconsin cheeses, along with sausage, cheesy popcorns, condiments, and more. If you have ever wanted a foam cheese hat or other fun items, you may be in luck here.

Drive ~90 minutes to Milwaukee. 

Stop 2: Milwaukee, Wisconsin – Lake Michigan

Milwaukee is a beautiful city situated along Lake Michigan. Stroll along the lake and around the expansive parks with open fields. Immerse yourself in museums, such as Discovery World (plans to re-open on March 27, 2021), the Harley-Davidson Museum, and the Charles Allis Art Museum (still appears to be closed as of the time of this writing, but hopefully will re-open by the time of your trip). The Milwaukee County War Memorial serves as a memorial to honor Wisconsin’s men and women who served in the U.S. armed forces. Posters along the walls contain pictures of fallen soldiers with notes paper-clipped from loved ones.

Drive ~1 hour 45 minutes to Green Bay.

Stop 3: Green Bay, Wisconsin

Green Bay has many options for the whole family, from Lambeau Field, Green Bay Packer Hall of Fame, the National Railroad Museum, botanical gardens, a wildlife sanctuary, an amusement park, a zoo, and much more. Try some wines at the nearby Ledgestone Vineyards & Winery (in-person visits by reservation only until at least Spring 2021).


Winetraveler Tip: Door County is only ~45 minutes from Green Bay. Explore Door County with Winetraveler’s: How to Spend a Few Days in Door County Wisconsin.


For those traveling with kids, the Tundra Lodge Resort Waterpark & Conference Center has an indoor waterpark and arcade. There’s an on-site restaurant and the lobby features large wooden timbers and a 45-foot stone fireplace. The Lambeau Field is visible from the hotel and is only a 6-minute drive from downtown Green Bay.

Lake Michigan will be visible during a decent portion of the drive. You will pass into Michigan, and through the Escanaba River State Forest and the Hiawatha National Forest. The state of Michigan touches four of the Great Lakes: Lake Michigan, Lake Superior, Lake Huron, and Lake Erie.

Drive ~3.5 hours to Munising.

Stop 4: Munising, Upper Peninsula of Michigan – Lake Superior

To experience Pictured Rocks National Lakeshore on the shores of Lake Superior, getting onto the water is a must. The rocky cliffs stretch for 15 miles along the shoreline. Take a cruise along the incredible rocky shore to admire the brilliantly colored cliffs, sea caves, and pristine beaches. The most popular cruise is ~2.5-hours that takes you ~32 miles roundtrip. Book your cruise here. The size of Lake Superior, the largest of the Great Lakes, with a surface area of 31,700 square miles, amazes many travelers. To put its size in perspective, it’s approximately the size of Austria or South Carolina.

Pictured Rocks National Lakeshore on the shores of Lake Superior.
Pictured Rocks National Lakeshore on the shores of Lake Superior. Image courtesy Lenore Parr.

The options for outdoor enthusiasts (seasonally dependent in some instances) include hiking, fishing, and hunting (with licenses), kayaking, swimming, cross-country skiing, snowmobiling, snowshoeing, and ice climbing. The National Park Service’s website lists numerous hiking trails of varying lengths.

The Holiday Inn Express Munising – Lakeview, located up on a hill on the shorelines of Lake Superior, offers balconies featuring stunning Lake Superior views. Before retiring to bed, relax on the balcony with a glass of wine and listen to the waves crash against the shore while the light of the moon shines down into the lake. The Duck Pond is a cute little restaurant, just over 2 miles from the hotel, with delicious food and many local beer options.

The Mackinac Bridge connects the Upper and Lower Peninsulas of Michigan. It is ~5 miles long and is one of the world’s largest suspension bridges. Lake Michigan is to the west of the bridge, and Lake Huron is to the east.

Drive ~2 hours down the Upper Peninsula, and continue southward down the iconic and spectacular Mackinac Bridge and to Mackinaw City. From Mackinaw City, take a ~16-minute ferry to Mackinac Island.

Stop 5: Mackinac Island, Michigan – Lake Huron

Be swept away by the charm and history felt at every step on the small Mackinac Island. The fact that no cars are permitted enhances the charm. Modes of transportation include horse-drawn carriage rides, bicycles, and walking. Walk around the island, admire the old-style homes, old churches, tour the Fort Mackinac, shop, dine, and don’t forget to try the fudge. While in Mackinaw City, taste local wines at Mackinac Island Winery.

Stay overnight in Mackinaw City and/or Mackinac Island. If you stay in Mackinaw City, the Best Western Plus Dockside Waterfront Inn is located along the shore of Lake Huron, lakefront balconies are available, and the hotel is within walking distance to the ferry to Mackinac Island. For those staying overnight on Mackinac Island, the historic and elegant Grand Hotel is an icon.

Drive ~2.5 hours to Bay City. If time management isn’t pressing, drive along US 23 Heritage Route along the Lake Huron shoreline (which would extend the trip by about 100 minutes).

Stop 6: Bay City, Michigan – Lake Huron

Stroll in and out of boutique shops, pretty churches, many parks, over the river via the scenic Saginaw Pier, and walk along Saginaw River via the Riverwalk Trail in the charming Bay City. Ship enthusiasts or anyone who enjoys ships should visit the Saginaw Valley Naval Ship and/or reserve a sailing experience onto Lake Huron aboard the schooners Appledore IV or Appledore V.

The Doubletree by Hilton Hotel Bay City – Riverfront, on the Saginaw River, is conveniently located in the historic downtown area and across the river from the Veterans Memorial Park. The romantic Historic Webster House Bed and Breakfast offers classic elegance.

Drive ~1 hour 40 minutes to Detroit.

Stop 7: Detroit, Michigan

Make time to explore Detroit, as it is about the halfway point between Bay City and Sandusky. The famous Detroit Zoo, a zoo that extensively uses exhibits without bars, is a great stop. The zoo is home to giraffes (that you can feed!), grizzly bears, polar bears, seals, gorillas, anteaters, rhinos, penguins, wolves, kangaroos, and so much more. The Arctic Ring of Life has a 70-ft. tunnel that passes under a pool for polar bears. Lucky travelers will see a polar bear swim overhead. Seeing a seal swimming is much more likely.

Drive ~2 hours to Sandusky.

Stop 8: Sandusky, Ohio – Lake Erie

Sandusky, situated on the shores of Lake Erie, is best known for the Cedar Point Amusement Park. Cedar Point’s Hotel Breakers is a luxury hotel located along a soft sandy beach at the shores of Lake Erie and right next to the Cedar Point Amusement Park (plans to re-open in May 2021) and Cedar Point Shores water park. Walk along the beach, the boardwalk, go to the amusement park, sunbathe at the beach, and go swimming. Watch the sunset below the rollercoasters.

Drive ~4.5 hours to Niagara Falls, Ontario, Canada. If time permits, stop overnight in Cleveland and/or many other places along the Erie shore en route to Niagara Falls.

Stop 9: Niagara Falls

Niagara Falls, the collection of three breathtaking waterfalls that straddle the international border between the Canadian province of Ontario and the US state of New York is spectacular. It’s the world’s fifth-largest waterfall by flow rate. There are many lovely hotels boasting falls-view rooms. The Niagara Falls Marriott Fallsview Hotel and Spa is a great option. The views of the falls from the rooms are incredible. At night, changing colors of lights project the falling water. Snuggle up with your special someone in your room with a glass of wine and listen to the roaring sound of the waterfalls while watching the night show.


Winetraveler Tip: For those who don’t mind the cold, consider planning your visit during the winter. Many things will be closed for the season, including the Maid of the Mist, but you might get a great deal on a falls-view room.


Easily turn your Niagara stay into a wine tasting vacation with Winetraveler’s Niagara Escarpment (New York) & Buffalo Itinerary: Top Wineries, Restaurants & Hotels.

Drive ~90 minutes to Toronto.

Stop 10: Toronto, Ontario – Lake Ontario

Toronto, a lively city, with much to explore is right along the shores of Lake Ontario. Ride the elevator up to the 114th floor of the CN Tower for floor-to-ceiling views of Lake Ontario, as well as the city. The 113th floor has a small segment of windows on the floor brave tourists can stand, sit, and walk across.

Ripley’s Aquarium is right next door and a great family place. The Casa Loma, a gorgeous gothic-style castle, is not to be missed. Scope out great food and drinking spots while in the city, and of course, Winetravelers should try Ice Wine.  

The Delta Hotels by Marriott Toronto is essentially right across the street from the CN Tower. The Rogers Centre, CN Tower, the railroad museum, Lake Ontario, and Ripley’s Aquarium are all visible from the hotel. The CN Tower is lit up at night with lights that change colors.


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    ABOUT THE AUTHOR

    Lenore Parr is a commercial bankruptcy attorney and stay-at-home-mom with a passion for adventurous and family-based travel with her husband and children (4yo and 1 yo). She has traveled with the kid(s) to 34 states and 23 countries.

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