Chicago Tours in September 2026
Planning for a trip to Chicago during September? We offer 20+ tour packages to Chicago departing in September 2026 that have 100+ customer reviews. Operated by our hand-picked, qualified travel experts, you will experience the best of Chicago on your September holiday.
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10 Best September 2026 Tours in Chicago
Join one of these handpicked Chicago September 2026 tour packages, tailored to the season.
Step into a world of timeless charm with the 9-day Mackinac Island tour, featuring the colorful Tulip Time Festival. This relaxed city sightseeing trip begins in Chicago and concludes in Southfield, guiding you through the heart of Illinois and Michigan in classic Midwestern style. Perfect for travelers who appreciate heritage and comfort, the itinerary blends elegant stays with engaging cultural experiences.
Revel in two nights of luxury at the famed Grand Hotel on Mackinac Island, where a horse and buggy tour transports you to a bygone era. Explore Chicago’s vibrant cityscape with a local guide and discover Frankenmuth’s Bavarian character. In Dearborn, delve into American innovation at the Henry Ford Museum and explore the historic homes of visionaries like Thomas Edison and Henry Ford at Greenfield Village.
With accommodations, transport, and meals included, this group tour ensures a seamless experience. A standout highlight is the exclusive Grand Hotel stay on Mackinac Island, paired with the spectacle of the Tulip Time Festival—offering a unique blend of luxury, tradition, and seasonal beauty.
9 days
From the iconic skyline of New York to the vibrant buzz of Las Vegas, embark on the 'Essential East Coast and Western Classics' tour for 19 unforgettable days. This city sightseeing journey is specially tailored for seniors, offering a gentle pace through historic and cultural highlights in Quebec City, Chicago, Los Angeles, and more. Enjoy the convenience of guided group travel, with hotel stays, transport, and meals all taken care of. The unique selling point of this tour is its carefully balanced itinerary, allowing travelers to experience the best of both coasts without the rush—perfect for those seeking comfort and variety.
19 days
Discover the highlights of America's great cities on the 'Chicago, Niagara and New York end Washington' trip. Spanning 10 days, this easy city sightseeing tour is crafted for seniors who enjoy exploring at a relaxed pace. Starting in Chicago and ending in Washington D.C., the itinerary includes the majestic Niagara Falls and vibrant New York City. With hotels, meals, and transportation fully organized, travelers can enjoy the journey without stress. A key feature of this tour is its thoughtfully selected route, offering a taste of urban diversity while ensuring a comfortable and accessible experience for mature travelers.
10 days
Experience the grand sweep of North America’s diverse cities with the 'Canadian Capitals with Chicago and the entire West Coast' tour package, tailored for senior travelers seeking comfort and discovery. Over 20 leisurely days, this guided sightseeing trip begins in Montreal and winds through the vibrant capitals of Canada, the dynamic streets of Chicago and Detroit, and the iconic attractions of the West Coast before concluding in San Francisco. Carefully crafted for those who appreciate a relaxed pace, this journey offers accessible walks and plenty of rest, making it especially appealing for seniors. The itinerary covers noteworthy destinations such as Ottawa, Los Angeles, and multiple cities across both the USA and Canada, with all hotel accommodations, transport, and meals seamlessly included. What sets this tour apart is its harmonious blend of urban exploration and scenic journeys, providing a comprehensive North American experience with all the ease and comfort senior guests deserve.
20 days
From Midwest marvels to California cool, the Chicago to Golden Gate tour is a 14-day odyssey for young adults and families seeking the full American experience. Begin in Chicago and journey west through pastoral Wyoming, the geothermal wonders of Yellowstone, and the majestic Teton Mountains. Savor local mountain culture in Utah and witness the grandeur of the Grand Canyon.
A stop on Route 66 leads to Las Vegas’ vibrant nightlife, before the trip winds down with Santa Barbara’s beaches and San Francisco’s iconic cityscapes. What sets this tour apart is its comprehensive route—showcasing the best of America’s landscapes, culture, and legendary road trip spirit.
14 days
Set out on "The Great American Crossing," a 20-day odyssey from New York to San Francisco crafted for young adults craving both iconic cities and sweeping natural landscapes. This guided city sightseeing trip weaves together the spirit of American liberty in Philadelphia and Washington D.C., the urban energy of Chicago, and the natural grandeur of New England, Niagara Falls, and the Great Lakes.
As you travel west, the scenery transforms—colorful Bryce Canyon, the vast Mojave Desert, and the glitz of Las Vegas all await before you reach the Pacific’s golden coast. Four days in San Francisco allow time to soak in the city’s laid-back charm. With an easy activity level, this group tour is perfect for young travelers and families seeking adventure without strenuous demands.
The standout feature? A meticulously curated route that covers the breadth of the USA, balancing city buzz with outdoor wonders, and offering a true coast-to-coast American experience in one unforgettable trip package.
20 days
Ready to uncover the best of Canada and the USA in comfort? The 'Canadian Capitals with Chicago and West Coast' tour offers a 16-day city sightseeing adventure, starting in Montreal and winding up in the dazzling lights of Las Vegas. Designed specifically with seniors in mind, this group tour balances gentle exploration with enriching experiences, taking you through Toronto’s lively streets, the architectural marvels of Chicago, and the natural beauty of Flagstaff. With accommodations, meals, and all transport arranged, you can immerse yourself in each destination without worry. The unique highlight of this tour is its effortless combination of Canada’s cultural hubs and America’s vibrant cities, making it ideal for seasoned travelers eager for diversity and ease.
16 days
Journey through the heart of America’s eastern region with the 16-day 'Eastern Round ends Chicago' tour. Perfect for seniors who seek a blend of history and culture at an easy pace, this trip weaves together Toronto, Chicago, Detroit, and more. The itinerary is packed with visits to cultural, historic, and religious landmarks, all with group guidance, comfortable accommodation, and all meals included. The unique draw of this package is its comprehensive sweep of the eastern USA, allowing travelers to immerse themselves in a variety of cityscapes and traditions with complete peace of mind.
16 days
Explore the best of North America from Toronto to Las Vegas on the "Toronto, Niagara, and Chicago with Western Classics ending Las Vegas" tour. Spanning 12 days, this city sightseeing group trip features stops at Niagara Falls, Flagstaff, Los Angeles, and more, making it especially suitable for seniors seeking a varied yet easy-paced adventure. With all accommodations, transport, and meals taken care of, you can focus on the journey’s highlights. Its distinctive feature is the combination of Canada’s renowned attractions and the American Southwest’s wonders in one seamless itinerary.
12 days
Journey from French-speaking Montreal to the towering skyline of Chicago on the 11-day 'Unmissable Canada, Niagara and Chicago' sightseeing trip. Tailored for seniors, the itinerary features Montreal, Toronto, Quebec City, Niagara Falls, and more, offering a rich selection of North American highlights. Group guidance, comfortable hotels, and all meals and transport are included for an effortless experience. This tour’s unique benefit is its blend of Canadian culture and American city life, promising a vivid and accessible adventure.
11 days
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Top Chicago Tour Activities for September 2026
From city sightseeing tours to cultural, religious and historic sites and others, here are some popular tour activities in Chicago with departures in September 2026.
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From Midwest marvels to California cool, the Chicago to Golden Gate tour is a 14-day odyssey for young adults and families seeking the full American experience. Begin in Chicago and journey west through pastoral Wyoming, the geothermal wonders of Yellowstone, and the majestic Teton Mountains. Savor local mountain culture in Utah and witness the grandeur of the Grand Canyon.
A stop on Route 66 leads to Las Vegas’ vibrant nightlife, before the trip winds down with Santa Barbara’s beaches and San Francisco’s iconic cityscapes. What sets this tour apart is its comprehensive route—showcasing the best of America’s landscapes, culture, and legendary road trip spirit.
14 days
Set out on "The Great American Crossing," a 20-day odyssey from New York to San Francisco crafted for young adults craving both iconic cities and sweeping natural landscapes. This guided city sightseeing trip weaves together the spirit of American liberty in Philadelphia and Washington D.C., the urban energy of Chicago, and the natural grandeur of New England, Niagara Falls, and the Great Lakes.
As you travel west, the scenery transforms—colorful Bryce Canyon, the vast Mojave Desert, and the glitz of Las Vegas all await before you reach the Pacific’s golden coast. Four days in San Francisco allow time to soak in the city’s laid-back charm. With an easy activity level, this group tour is perfect for young travelers and families seeking adventure without strenuous demands.
The standout feature? A meticulously curated route that covers the breadth of the USA, balancing city buzz with outdoor wonders, and offering a true coast-to-coast American experience in one unforgettable trip package.
20 days
Ready for a cross-country adventure packed with cultural icons and natural wonders? The New York to Hollywood tour is a 17-day trip perfect for young adults and families eager to experience the diverse landscape of the United States. Travel from the energy of New York City through the Midwest’s storied cities and national landmarks, all the way to the glamour of Los Angeles.
From city highlights in Chicago to the awe-inspiring canyons of the Southwest, every day introduces a new chapter—history, adventure, and local flavors in cities like Salt Lake and Sioux. Guided activities ensure you see both the must-visit attractions and the hidden sides of America. The trip’s defining feature is its coast-to-coast sweep, offering travelers the chance to capture the spirit of the USA on one unforgettable tour package.
17 days
Set out on a landmark adventure from the Windy City to the West Coast on the Chicago to LA trip, an 11-day journey crafted for young adults and families. Start with a lively day in Chicago, exploring its arts, dining, and nightlife, then hit the open road to discover the rugged beauty of Badlands National Park and the Black Hills.
Continue through Wyoming’s mountain landscapes, trek the trails of Yellowstone, and marvel at the Grand Canyon’s grandeur. The trip concludes in the glitz of Las Vegas and the laid-back vibes of California. The USP here is the coast-to-coast exploration, offering a dynamic mix of city life, national parks, and classic American road trip appeal.
11 days
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