USD $2,609 Per Person
Chicago and Great Lakes Explorer
Immerse yourself in a journey that threads Chicago’s architectural genius with lake-country charm. From the shimmering skyline and art filled corridors of Millennium Park to the steel and glass stories told on an architecture cruise, this itinerary reveals a city of bold contrasts. Glide from the Willis Tower’s dizzying heights to Milwaukee’s historic Third Ward, where harbor breezes mingle with galleries, cozy cafés, and storied factories turned creative spaces. The Harley Davidson legacy anchors a day of engine roar and mythology, then Lake Geneva unveils serene lakeside mansions and wind kissed shoreline. Inland coves, state parks, and scenic boat cruises weave a gentle rhythm of discovery, where culture, cuisine, and natural beauty collide in a portrait of the Midwest’s heart. You’ll travel with a chauffeur guided team, savor local bites, and linger in vibrant neighborhoods at your own pace, making room for spontaneous detours, photo stops, and sunset reflections. By week’s end you’ll leave with a richer sense of Chicago’s iconic pulse and Wisconsin’s tranquil charms, anchored by comfortable, shared moments with family, friends, or fellow explorers.
O Hare International Airport, Chicago, US
Arrival
Private Tours
Tour Type
O Hare International Airport, Chicago, US
Departure
03
Cities
Featured Inclusions
Chicago Millennium Park Tour
Iconic park landmark visit
Daily Breakfast
Morning Fuel
Private Tours
Personalized sightseeing experience.
Listed Hotel
3 Hotels-
The Gwen
Room Type: Standard
Chicago: 2 Nights
-
The Pfister Hotel
Room Type: Standard
Milwaukee: 2 Nights
-
The Ridge Hotel
Room Type: Standard
Lake Geneva: 2 Nights
Tour Highlights
Your journey at a glance
© Stadia Maps © OpenMapTiles © OpenStreetMap contributors
A quick visual summary of this itinerary.
What's included
Featured Inclusions
Chicago Millennium Park Tour — Iconic park landmark visit
Daily Breakfast — Morning Fuel
Private Tours — Personalized sightseeing experience.
Guide
Chauffeur Driven Service — Travel comfortably with a professional chauffeur driver throughout your journey
Private Tours
Taxes
Government & Local Taxes — All applicable government taxes included
Transport
Air-Conditioned Transportation — Travel in comfort with fully air-conditioned vehicles
Airport Transfers — Enjoy smooth airport pick-up and drop-off services
Included activities
- Attraction Entrance Fees — Included entry to attractions listed in the itinerary
- 24/7 Local Support — Benefit from dedicated on-ground assistance throughout your journey
What's excluded
Exclusion activities
- Visa Assistance — Receive professional support with visa documentation and guidance
- International Air Travel — International flight connectivity for a seamless global journey
Itinerary
Arrival at O Hare International Airport in Chicago where you will be welcomed by your chauffeur driver guide and transferred to your hotel for check in. After some rest, begin your city exploration at the iconic Millennium Park and view the famous Cloud Gate also known as The Bean. Continue to the world renowned Art Institute of Chicago showcasing global art collections. Enjoy evening leisure time exploring downtown Chicago. Return to hotel for overnight stay.
After breakfast proceed with your chauffeur driver guide for a visit to the famous Willis Tower Skydeck for panoramic city views. Continue to the highlight experience of Chicago River with a guided architecture cruise showcasing the city’s skyline. Explore the architectural heritage and modern design of Chicago. Evening at leisure for shopping, dining, or theatre experiences. Return to hotel for overnight stay.
After breakfast check out and proceed with your chauffeur driver guide towards Milwaukee. Arrive and visit the famous Harley Davidson Museum showcasing motorcycle heritage and history. Continue to the vibrant Historic Third Ward known for shopping, galleries, and dining. Enjoy evening leisure exploring the lakeside city. Check in to hotel for overnight stay.
After breakfast proceed with your chauffeur driver guide for a local experience at Milwaukee Public Market offering gourmet tastings and local specialties. Continue to Lakefront Brewery for an optional beer tasting and guided brewery tour. Explore the cultural and culinary side of Milwaukee throughout the day. Enjoy free time in the evening. Return to hotel for overnight stay.
After breakfast proceed with your chauffeur driver guide for a day trip to Lake Geneva. Enjoy a scenic boat cruise on the beautiful Geneva Lake surrounded by luxury homes and natural beauty. Continue with a short nature walk at Big Foot Beach State Park offering peaceful lake views. Experience relaxation in one of Wisconsin’s most scenic destinations. Return to Milwaukee for overnight stay.
After breakfast check out and proceed with your chauffeur driver guide back to Chicago. Arrive in the city and enjoy optional sightseeing such as the famous Navy Pier or a relaxing stroll along Lake Michigan. Spend the afternoon at leisure exploring shopping areas or cafés. Enjoy your final evening in Chicago at your own pace. Return to hotel for overnight stay.
After breakfast check out and proceed with your chauffeur driver guide for transfer to O Hare International Airport. Assistance will be provided for smooth departure formalities. Your Great Lakes journey concludes with memorable city, lake, and cultural experiences.
FAQ
Cancellation policies vary depending on the experience, season, and supplier terms.
Cancellations made after confirmation may be subject to partial or full cancellation charges.
No-shows or early departures are non-refundable.
Refunds (if applicable) are processed according to supplier policies and timelines.
All bookings are subject to availability at the time of confirmation.
A booking is considered confirmed only after receipt of the required payment.
Prices are based on current market rates and may change due to supplier adjustments, taxes, or currency fluctuations.
Itinerary order, accommodations, or inclusions may be adjusted due to operational requirements without affecting the overall experience.
Cancellation policies vary depending on the experience, season, and supplier terms.
Cancellations made after confirmation may be subject to partial or full cancellation charges.
No-shows or early departures are non-refundable.
Refunds (if applicable) are processed according to supplier policies and timelines.
