(312) 932-0800Gift Cards
Tour Calendar

Multi-Day Sample Itineraries

Multi-Day Itineraries Your Group Will Love

As your in-market receptive tour operator, you can rely on us to create a trip that will sell, and to execute every aspect to meet your highest standards. Start by looking through these sample itineraries, then get in touch to start planning your customized trip.
We offer group tour leaders:
  • No required deposit
  • No cancellation fee
  • Planning for groups of all sizes and mobility
  • One comp per 25 paid attendees for your driver and escort
  • All-inclusive pricing
Call (312) 932-0800

Chicago Group Travel Itineraries

Windy City Wonderland

Chicago
3 or 5 days

Immerse yourself in the festive spirit of Chicago with our 'Windy City Wonderland' tour. Spanning either 3 or 5 days, this holiday-themed adventure showcases the city’s dazzling winter lights, bustling markets, and joyous celebrations. Explore iconic locations decked in holiday finery, such as the Magnificent Mile and Millennium Park, and experience unique Chicago traditions and gourmet seasonal delights. Whether you’re marveling at the Christkindlmarket or enjoying a special holiday concert, this tour offers a magical blend of activities that capture the heart and excitement of the season.

Beyond the Skyline

Chicago
3 or 5 days

Embark on an unforgettable journey through Chicago's vibrant history and culture. From iconic architecture and historical landmarks to hidden gems and diverse neighborhoods, this tailored 3 or 5-day tour offers a deep dive into the true spirit of the Windy City. Experience a comprehensive exploration guided by local experts, designed to enrich your understanding and appreciation of Chicago's unique heritage. Ideal for those seeking an adventure beyond the typical tourist paths.

Chicago & Milwaukee Group Travel Itineraries

Holiday Highlights

Chicago & Milwaukee
3 days

Embrace the festive spirit with a special holiday-themed tour through Chicago and Milwaukee. This 3-day getaway is designed to showcase the holiday magic of both cities. You'll stay in a comfortable hotel in Chicago for the entire duration of the tour. In Chicago, revel in the glittering lights of the Magnificent Mile and the enchanting Christkindlmarket. On one of the days, we'll take a delightful day trip just 90 minutes north to Milwaukee, where the holiday cheer continues with a charming European-style market and vibrant neighborhood decorations. Enjoy bright lights, local crafts, and warm, festive treats that bring out the joy of the holidays.

Best of the Midwest

Chicago & Milwaukee
3 days

Discover the heart and soul of the Midwest as you journey through two of its greatest cities: Chicago and Milwaukee. This 3-day getaway perfectly blends cultural richness, historical depth, and culinary delights. Start your adventure in Chicago by exploring the renowned Art Institute, marveling at the architectural wonders of the Loop, and strolling through the vibrant neighborhoods of West Loop and Chinatown. Then, travel just 90 minutes north to Milwaukee, where you'll tour the historic Pabst Mansion, visit the Harley Davidson Museum, and enjoy the scenic views of Lake Michigan's waterfront. Our expert guides ensure you experience the most memorable and authentic aspects of each city.

Midwest Hidden Gems

Chicago & Milwaukee
5 days

Uncover the best of the Midwest with our 5-day tour between Chicago, Illinois, and Milwaukee, Wisconsin. Start your adventure in Chicago, where you'll explore hidden gems like lesser-known museums and cultural centers, and discover the diverse ethnicities that built Chicago through its 77 unique neighborhoods. Visit vibrant communities such as Pilsen, Chinatown, and Greektown, each offering a rich tapestry of history, art, and cuisine. Then, journey just 90 minutes north to Milwaukee, where you'll experience the local craft beer scene with visits to historic breweries, explore the Milwaukee Art Museum's unique collections, and enjoy the scenic Lake Michigan waterfront. This tour blends the urban excitement of Chicago with the rich heritage and charm of Milwaukee, showcasing the true hidden gems of the Midwest for an unforgettable experience.

Lakeside Adventure

Chicago, Lake Geneva, Milwaukee
5 days

Experience the best of the Midwest with our 5-day adventure through Chicago, Lake Geneva, and Milwaukee. Begin your journey in Chicago, uncovering hidden gems like the vibrant street art of the Pilsen neighborhood, the historic charm of Andersonville, and the culinary delights of West Loop. Then, escape to the charming town of Lake Geneva for a day of scenic beauty and relaxation by the lake. Conclude your trip in Milwaukee, where you'll visit historic breweries, explore the Milwaukee Art Museum, and enjoy the vibrant waterfront. This tour offers a perfect blend of urban excitement and serene landscapes, ensuring an unforgettable Midwest experience.

Chicago & Beyond Group Travel Itineraries

Lake Michigan Highlights

Lake Michigan
5 or 7 day

Experience the diverse beauty of the Lake Michigan region with our Great Lakes Loop tour, available in both 5-day and 7-day options. Begin your journey in Chicago, exploring hidden gems, vibrant neighborhoods, and rich cultural landmarks. Travel north to Milwaukee to visit historic breweries, the Milwaukee Art Museum, and enjoy the scenic Lake Michigan waterfront. Continue your adventure with potential stops in charming towns such as Muskegon, known for its beautiful beaches, and Traverse City, famous for its vibrant art scene and wineries. Explore the picturesque landscapes of Door County with its quaint villages, or head to the Upper Peninsula to visit Manistique and Escanaba, both offering stunning natural beauty. Discover the rich history and unique charm of Green Bay before concluding your adventure back in Chicago. This captivating loop around Lake Michigan blends urban excitement, natural beauty, and cultural richness, ensuring you experience the best of what the region has to offer.

Great Lakes Expedition

Lakes Michigan, Superior, and Huron
7+ days

Embark on an unforgettable journey with our Great Lakes Expedition, offering flexible itineraries of 7 days or more, circling Lakes Michigan, Superior, and Huron. Begin your adventure in Chicago, where you'll explore hidden gems, vibrant neighborhoods, and rich cultural landmarks. Travel north to Milwaukee to visit historic breweries and the Milwaukee Art Museum. Continue your journey to the picturesque towns of Door County, known for their charming landscapes and quaint villages.

Head further north to the stunning Upper Peninsula, stopping in Manistique and Escanaba, where you'll experience the natural beauty of Pictured Rocks National Lakeshore and the rugged shores of Lake Superior. Explore the vibrant city of Marquette, the breathtaking views of Munising, and the serene Apostle Islands. Visit the enchanting Mackinac Island and the scenic shores of Lake Huron, before heading to the charming towns of Bayfield and Duluth. Complete the circle by exploring the bustling city of Green Bay, famous for its rich history and cultural attractions, before returning to Chicago.

This tour offers a perfect blend of urban excitement, natural wonders, and cultural experiences, showcasing the best of the Great Lakes region. Whether you choose a 7-day adventure or extend your stay, this expedition promises an unparalleled exploration of the Midwest's most iconic landscapes and cities.

Check “event planning” off your list.

We do not ask for a deposit or signed contract, simply fill out the form below with as many details as possible.

We will contact you to confirm your booking. At this time, we ask you provide your tentative head count so we can confirm reservations with your selected locations.

Five days prior to your tour date we will need a final headcount, list of any allergies or dietary restrictions, and payment via credit card or check.

"*" indicates required fields

MM slash DD slash YYYY
Desired Start Time
:
Hidden
This field is for validation purposes and should be left unchanged.