Chicago Milwaukee and Lakes 6 Day Tour

Chicago Milwaukee and Lakes 6 Day Tour: An In-Depth Look

Imagine spending six days exploring some of the most stunning and culturally rich spots in the Great Lakes region. This tour, priced at $1,307 per person, offers an immersive journey from the vibrant cityscape of Chicago to the serene waters of Lake Michigan, Lake Superior, and Lake Huron. Led by knowledgeable guides, you’ll visit major cities like Milwaukee and Green Bay, explore iconic sights such as Mackinac Island and Pictured Rocks National Lakeshore, and finish in Chicago with its world-famous architecture.

What we love about this experience is the chance to see both natural beauty and urban charm in one trip — from the breathtaking vistas of Tahquamenon Falls to the historic Harley-Davidson Museum. Plus, the inclusion of ferry rides, scenic drives over the Mackinac Bridge, and visits to unique islands make this tour feel well-rounded and authentic.

One possible consideration is the pace — with so many stops packed into six days, it’s a busy itinerary that might leave some wanting more time at each spot. So, this tour suits travelers who enjoy a full schedule and want a rundown of the Great Lakes region without the hassle of organizing logistics themselves. Perfect for those new to the area or travelers eager for a mix of outdoor scenery and city sights.

Key Points

• Natural beauty and scenic vistas at Pictured Rocks and Tahquamenon Falls
• Cultural highlights like the Harley-Davidson Museum and Windmill Island Gardens
• Convenient logistics with transportation, hotel stays, and some optional attractions included
• Authentic experiences such as Mackinac Island’s car-free charm and carriage tours
• Flexible options for guided city tours or optional add-ons like 360 Chicago Observatory
• Value for money considering the number of locations visited and inclusions

Exploring the Itinerary in Detail

Day 1: Arrival and Chicago Night Tour

The tour kicks off with complimentary airport pickup at Chicago O’Hare between 9 a.m. and 9 p.m., which is a stress-free way to start. For those arriving early, the optional Chicago night tour (for an additional surcharge) provides a fantastic way to see the city’s illuminated landmarks like the Crown Fountain and skyline. Though the admission isn’t included, it’s a worthwhile addition if time allows.

Day 2: Milwaukee and Green Bay

Starting in Milwaukee, we love how the Harley-Davidson Museum offers insight into America’s iconic motorcycle brand. With over 450 motorcycles and artifacts, it’s a highlight for enthusiasts and curious travelers alike. The guide explained that the museum showcases “some of the finest ‘choppers’ in the world,” making it a must-visit for motorcycle lovers.

Next, the Milwaukee Public Market provides a lively indoor experience with 24 specialty food vendors. Here, you can sample local cheeses, fresh seafood, or handmade jewelry — a perfect lunch spot offering a taste of Milwaukee’s vibrant food scene. It’s free to browse, but you might want to budget for snacks or souvenirs.

Later, the group stops briefly in Green Bay, famed for its sports culture and welcoming atmosphere. Although the visit is only about 30 minutes, it offers a quick taste of this lively city.

Day 3: Lake Superior and Pictured Rocks

This day is a highlight for fans of natural scenery. The Pictured Rocks National Lakeshore tour involves visiting Miners Castle, Miners Beach, and Tahquamenon Falls — the latter a massive, impressive cascade. We love how the guide explained these stops are “mandatory”, offering in-depth views of the area’s striking geology and waterfalls.

Expect plenty of photo ops and time to walk around, but keep in mind that admission tickets are not included — so pack your camera and a sense of adventure. The stop at Point Iroquois Lighthouse offers a quick, scenic overlook where you can see where Lake Superior meets Lake Huron.

The Soo Locks are another natural marvel, allowing ships to navigate between Lake Superior and the lower Great Lakes. This is an engineering feat and a busy shipping route, though the visit lasts only about 30 minutes, so don’t expect a long tour here.

Day 4: Mackinac Island and Traverse City

This day balances outdoor adventure with charming small-town vibes. The ferry ride to Mackinac Island is a favorite, especially since motor vehicles are prohibited. Instead, you’ll see horse-drawn carriages, bikes, and walking paths. The Carriage Tours give you a glimpse of the island’s historic and scenic spots, although the tour does not include the carriage ride itself.

Later, heading to Traverse City, we love its reputation for outdoor activities and local wineries. The 30-minute stop provides just enough time to appreciate this lively, lake-front town known for beaches and seasonal fun.

Day 5: Holland and Gilmore Car Museum

Holland’s Windmill Island Gardens offers a genuinely Dutch experience with authentic windmills and tulip gardens, even if you visit outside the bloom season. The chance to see De Zwaan, shipped directly from the Netherlands, makes it feel like a mini-European escape.

The Gilmore Car Museum is a treat for automobile buffs. With the largest collection of vintage cars in Michigan, it presents a fascinating look at automotive history from many eras, making it a good stop for families or car enthusiasts.

In the afternoon, the tour returns to Chicago, offering a chance to unwind after a busy week.

Day 6: Chicago’s Architectural Marvels

The final day offers a chance to soak in Chicago’s famed architecture. The Millennium Park visit, including the iconic Cloud Gate sculpture, is quick but iconic. The Chicago Architecture Aesthetics Tour lasts about 1 hour 40 minutes, taking you past landmarks like the Wrigley Building and the Tribune Tower.

The Art Institute of Chicago is a major highlight for art lovers, with works by Van Gogh, Monet, and Cezanne. The two-hour visit is enough to appreciate the breadth of the collection.

Lastly, for those who want an aerial view, the optional 360 Chicago observation deck provides stunning city vistas, especially if you’re visiting during good weather. Keep in mind, this is an optional add-on, with tickets not included.

The Practicalities: What You Need to Know

This tour strikes a good balance between guided visits and free time, allowing you to enjoy key sights without feeling rushed. The hotel accommodations are based on double or King/Queen beds, with a maximum of four travelers per room. For larger groups or separate rooms, you’ll need to book multiple spots.

Transportation is provided in professional vehicles, which ensures comfort and reliability, and the group size caps at 55 travelers, maintaining a friendly, manageable atmosphere. Since most attractions don’t require pre-purchased tickets (except for some optional sites), you have flexibility on the day.

The tour’s price includes hotel stays, a driver-guide, transportation, and some optional admissions, representing a good value given the number of locations visited. However, food, personal expenses, and tips are extra, so budget accordingly.

This tour is suitable for most travelers, including families with children over six (who need booster seats) and anyone comfortable with a full schedule. It’s particularly appealing if you want a rundown of the Great Lakes region, without the stress of planning each stop yourself.

Who Would Love This Tour?

This trip is ideal for first-time visitors to the Great Lakes who want to see a wide range of sights efficiently. Nature lovers will appreciate the scenic stops at Pictured Rocks and Tahquamenon Falls, while history and culture buffs will enjoy the museums and architectural tours. It’s also perfect for those who prefer guided travel to navigate logistics and enjoy local insights.

Since the tour balances city highlights with outdoor adventures, it suits those with a penchant for variety — you’ll experience urban landscapes, small-town charm, and natural beauty all in one trip.

Frequently Asked Questions

Is airport pickup available?
Yes, complimentary airport pickup is provided at Chicago O’Hare between 9 a.m. and 9 p.m. on the first day of the tour.

Can I join the night tour of Chicago?
Yes, if arriving before 5 p.m., you can opt for the Chicago night tour for a surcharge. It’s optional but offers a scenic introduction to the city.

Are the attractions’ admission fees included?
Most attractions are included if you choose the optional package, but some, like the Art Institute, 360 Chicago, and Mackinac Island ferry, have additional costs if you opt to visit them.

What is the hotel accommodation like?
All rooms are based on two Full/Double beds or one King/Queen, with a maximum capacity of four per room. Special requests for separate rooms should be booked separately.

Is transportation comfortable?
Yes, the tour uses professional vehicles suited for the group size, ensuring a comfortable ride between attractions.

Can children participate?
Children over six can join, but they require booster seats due to state law. Pregnant women under 24 weeks are welcome.

What should I bring?
Comfortable shoes, sun protection, sunscreen, cash, and drinks are recommended for a day’s outing, especially for outdoor stops.

Final Thoughts

This 6-day Great Lakes tour offers a well-rounded experience combining natural beauty, fascinating museums, and vibrant cityscapes. It’s geared toward travelers who enjoy a busy but rewarding schedule, with enough flexibility to add optional experiences. The inclusion of highlights like Mackinac Island, Pictured Rocks, and Chicago’s skyline makes it a compelling choice for anyone looking to get a taste of this unique region.

You’ll love the knowledgeable guides, the stunning vistas, and the mix of outdoor and cultural sights. The value for the price is evident when you consider the diverse destinations covered, the included transportation, and the comfortable accommodations.

If you’re eager for an adventure that captures the essence of the Great Lakes with minimal planning on your part, this tour could be your perfect match. Just be ready for a fast-paced, scenic, and cultural journey through some of America’s most picturesque and historic spots.

Happy travels, and don’t forget your camera!