Chicago Milwaukee and Lakes 6 Day Tour

An Honest Look at the Chicago, Milwaukee, and Lakes 6 Day Tour

This 6-day excursion offers a broad taste of the Great Lakes region, focusing on Chicago, Milwaukee, and some of Michigan’s most scenic spots. While we haven’t personally been on this tour, its detailed itinerary, clear highlights, and user reviews suggest it’s an engaging option for travelers eager to combine city life with natural beauty.

What makes this tour stand out? First, the variety—you’ll experience bustling urban scenes, historic landmarks, and awe-inspiring lakeside scenery. Second, the value—at around $1,300 per person, it covers transportation, some admissions, and a variety of experiences. On the flip side, a potential challenge might be the tight schedule—expect long days with lots of moving parts, which could be exhausting if you prefer slower-paced travel. This trip is best suited for travelers who love a mix of sightseeing, nature, and culture, and don’t mind a busy itinerary.

Key Points

• Diverse experiences from city tours to lakeshore exploration.
• Value for money considering included transportation, guided commentary, and some admissions.
• Active days packed with sightseeing—expect early mornings and full afternoons.
• Ideal for travelers who enjoy a structured schedule and varied scenery.
• Group size capped at around 55, maintaining a friendly, manageable atmosphere.
• Comfortable accommodations with hotel rooms for 2-4 guests, depending on availability.

A Deep Dive Into the 6-Day Itinerary

Day 1: Arrival and Chicago Night Tour

Starting at Chicago O’Hare International Airport, your first perk is complimentary airport pickup. This smooth start sets the tone, avoiding the hassle of figuring out transportation right away. Depending on your arrival time, you can opt to join an optional night tour of Chicago—a smart choice if you arrive early and want to glimpse the city’s famous skyline lit up at night. The tour lasts about 1.5 hours, and although tickets are extra, it’s a chance to see iconic sights like Millennium Park and the Chicago River.

Pro tip: If you’re tired from travel, skip this optional tour and save your energy for the days ahead.

Day 2: Milwaukee and Green Bay

Your adventure kicks off with a visit to Milwaukee, Wisconsin’s largest city. The Harley-Davidson Museum offers a fascinating look at over 100 years of motorcycle craftsmanship—great for bike enthusiasts or anyone curious about American manufacturing. The museum houses more than 450 motorcycles and artifacts, though note that admission isn’t included.

Next, the Milwaukee Public Market provides a lively indoor scene, perfect for a quick lunch or snack. You’ll find about 24 vendors offering everything from handmade jewelry to delectable local foods. It’s a lively, authentic spot that gives a real sense of Milwaukee’s local flavor.

Afterward, a brief stop in Green Bay—famous for its football culture—lets you enjoy the city’s vibrant dining scene and perhaps catch a sporting event if schedules align. It’s a quick 30-minute visit, but enough to get a feel for this community.

Travel tip: This day’s focus on cities offers a good balance of history, culture, and local life without overwhelming travel time.

Day 3: Michigan’s Lakes and Waterfalls

A highlight of this tour is the Pictured Rocks National Lakeshore—a stunning stretch along Lake Superior known for its colorful sandstone cliffs, waterfalls, and untouched beaches. The in-depth tour includes Miners Castle, Miners Beach, and Tahquamenon Falls, each offering spectacular views and photo opportunities.

Expect approximately 2 hours and 40 minutes at these sites, so bring your camera and comfortable shoes. The scenery here is the kind that makes you pause and appreciate nature’s artistry.

On the way, you’ll pass the Point Iroquois Lighthouse, a picturesque spot overlooking where Lake Superior connects to Lake Huron. It’s a quick stop but perfect for snapping some memorable photos.

The day rounds off with a visit to Soo Locks, an engineering marvel that allows large ships to bypass rapids and travel between Lake Superior and the lower Great Lakes. Watching ships move through the locks is both fascinating and a reminder of the region’s industrial importance.

Note: All these sites are free to visit, but do keep in mind that some attractions or specific tours might have additional costs if you want a more detailed experience.

Day 4: Mackinac Island and Traverse City

Today’s adventure shifts to Michigan’s iconic Mackinaw City, where you’ll take a ferry to Mackinac Island. Known for its ban on motor vehicles, the island’s charm comes from horse-drawn carriages, bike rides, and walking tours. You’ll get about four hours to explore, including the famous Carriage Tours—a must-do to see the island’s historic sites and scenic vistas.

Later, the tour heads to Traverse City, a lovely town on Lake Michigan’s shores. Known for its beaches, vineyards, and outdoor activities, it’s a great spot to relax and enjoy the regional scenery. With only a short stop, you might want to plan your own additional exploration if time allows.

Travel insight: The ferry ride and car-free streets give you a rare glimpse into a slower-paced, more traditional way of life.

Day 5: Holland, Windmill Island, and Gilmore Car Museum

This day takes you south to Holland, Michigan, famed for its Dutch heritage. Windmill Island Gardens features the authentic De Zwaan windmill shipped from the Netherlands, plus gardens and historic buildings. It’s a delightful stroll through Dutch culture, especially if you’re a fan of architecture or garden design.

In the afternoon, visit the Gilmore Car Museum—the largest collection of vintage and classic cars in Michigan. Car lovers will appreciate the vast array of vehicles spanning many decades, displayed in a charming, expansive setting.

Return to Chicago later in the day, bringing a full circle to the week’s mix of landscapes, history, and culture.

Day 6: Chicago’s Architectural Marvels and Art

Your final day is packed with Chicago sights. It begins with a walk through Millennium Park, home to Cloud Gate (the “Bean”), a modern sculpture that’s become a city icon. It’s an ideal spot for photos and people-watching.

Next, you’ll embark on a Chicago architecture tour, lasting about 100 minutes. The city’s skyline is famous worldwide, and this guided walk gives insight into the buildings that define Chicago’s identity.

Then, visit The Art Institute of Chicago, one of the world’s top art museums. With works from Van Gogh to Monet, it’s a treasure trove for art lovers. Allocate about two hours here for a good overview.

If you’re up for more, 360 Chicago observation deck offers panoramic views from atop the John Hancock Tower. This optional add-on is a fantastic way to see the city from above, especially at sunset or dusk.

Note: Please be aware that some attractions, like the Art Institute or 360 Chicago, are optional and may involve extra fees.

What Travelers Say and Why This Tour Might Be Perfect for You

While reviews are limited, the feedback highlights knowledgeable guides, stunning scenery, and good value. Many appreciate the mix of city and nature, and the chance to see several major lakes, picturesque islands, and historic sites without planning each detail themselves.

The tour is generally praised for its well-organized itinerary and comfortable transportation, which is vital when moving between diverse locations. The group size, capped at around 55, strikes a balance between intimacy and efficiency.

However, some reviews mention that the schedule can be intensive, with long days and limited free time. That’s a good thing if you want to see as much as possible, but if you prefer a slower pace or more leisure, this might feel rushed.

The hotel accommodations are standard, with rooms designed for 2-4 guests, depending on availability. While they are not luxury, they are comfortable and well-located.

One noteworthy feature is the flexibility—if you want separate rooms or are traveling with a larger group, you’ll need to create separate bookings, which requires some advance planning.

Why This Tour Offers Good Value

At $1,307 per person, the tour covers transportation, some admissions, and guided commentary. While it doesn’t include meals or personal expenses, the inclusion of several must-see spots and scenic highlights makes it a solid deal.

The optional activities, like the Chicago architecture tour or 360 Chicago, give you the option to customize your experience without complicating the main schedule. The tour’s price point makes it accessible for a wide range of travelers interested in a comprehensive, organized trip.

Who Should Consider This Tour?

This experience is ideal for travelers who want a structured, all-in-one adventure in the Great Lakes region. It suits those who enjoy city sightseeing, scenic landscapes, and historic sites but don’t want to plan each detail themselves. It’s perfect if you’re comfortable with tight schedules and enjoy learning from guided commentary.

If you’re traveling with family, friends, or a group of up to four per room, the accommodations are flexible enough to meet your needs. It’s also a good choice for those seeking value for money—a well-rounded tour that hits major highlights without breaking the bank.

FAQs about the Chicago, Milwaukee, and Lakes 6 Day Tour

Is airport pickup included?
Yes, complimentary pickup is offered from Chicago O’Hare International Airport between 9:00 a.m. and 9:00 p.m. on the first day.

Can I join an evening Chicago night tour?
Yes, if you arrive before 5 p.m., you can opt for an optional night tour for an extra surcharge to see the city lights.

Are hotel rooms twin or double beds?
All rooms are based on two Full/Double beds or one King/Queen bed, depending on availability. The maximum occupancy per room is four.

What attractions are free to visit?
Sites like Green Bay, Point Iroquois Lighthouse, Soo Locks, and Traverse City are free to explore, although some specific activities might cost extra.

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

Are children under 6 allowed?
Yes, children under 6 need a booster seat and are welcome, provided they meet safety requirements.

Can I book separate rooms?
Yes, but you need to create separate bookings if your group exceeds four guests or if you want individual rooms.

What should I bring?
Comfortable walking shoes, weather-appropriate clothes, sun protection, drinks, and cash for personal expenses.

What happens if some attractions are closed?
The tour operator will provide alternative options; attractions’ hours may vary due to weather or other factors.

Is gratuity included?
No, gratuities for guides and drivers are appreciated but not included.

Final Thoughts

The Chicago Milwaukee and Lakes 6 Day Tour offers a well-rounded slice of the Great Lakes area, blending urban exploration with stunning natural wonders. It’s a smart option for travelers who want to see a lot without the hassle of planning every detail themselves. Expect knowledgeable guides, scenic views, and a good value, especially if you’re eager to experience the lakes, historic sites, and vibrant cities in one trip.

This trip is best suited for those who enjoy organized travel, a variety of landscapes, and a mix of cultural and outdoor activities. If you’re prepared for full days and like having a guide to point out the best sights, this tour could be your next memorable adventure in the Midwest.

Note: Always double-check current details and confirm bookings in advance. Weather and attractions can change plans, but flexibility and a good attitude will make your trip all the more enjoyable.