Chicago Tours in September 2025
Planning for a trip to Chicago during September? We offer 10+ tour packages to Chicago departing in September 2025 that have many customer reviews. Operated by our hand-picked, qualified travel experts, you will experience the best of Chicago on your September holiday.
See all Chicago September 2025 Tours
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10 Best September 2025 Tours in Chicago
Join one of these handpicked Chicago September 2025 tour packages, tailored to the season.
From the vibrant streets of New York City to the glitz of Hollywood, the 'New York to Hollywood' tour offers a sweeping 17-day city sightseeing adventure across the USA. Designed for travelers of all ages—families, seniors, and young adults—this easy-paced trip covers iconic highlights including the historic landmarks of Philadelphia, the monumental sights of Washington D.C., the presidential faces of Mount Rushmore, and the natural wonders of Yellowstone National Park. Cruise along legendary Route 66, cross the Mojave Desert, and experience the high-octane energy of Las Vegas before arriving in sunny Los Angeles. The unique selling point of this tour package is its comprehensive, coast-to-coast exploration, offering a seamless blend of urban excitement and natural beauty, all with the comfort of guided group travel.
17 days
fromUSD 3,618
From the bright lights of New York to the architectural wonders of Chicago, the 'Essential East Coast, Niagara and Chicago' tour is a 14-day city sightseeing trip designed for seniors. This guided journey covers Detroit, Toronto, and other key destinations, with all logistics managed for your ease. The highlight is its comprehensive route, encompassing both historic and modern marvels in an itinerary that balances excitement with comfort.
14 days
fromUSD 2,845
Set out from the Windy City on the 'Chicago, Niagara and New York' guided tour, a perfect 8-day city sightseeing trip ideal for seniors. This journey includes the awe-inspiring Niagara Falls, the cultural richness of Cleveland, and wraps up in bustling New York. Designed for those seeking gentle exploration, all accommodations, meals, and transport are handled, allowing you to enjoy each destination at your own pace. The special appeal of this tour lies in its seamless blend of urban excitement and natural wonder, making it an excellent choice for those looking for a well-rounded, easy-paced adventure.
8 days
fromUSD 1,625
This tour will transport you back in time as you travel down America’s Main Street — Route 66. Begin your journey with a night in the Windy City as you explore the architectural treasures of Chicago. Continue your trip towards Oklahoma City and discover incredible limestone caves and breathtaking memorial bridges enroute. Drive towards the beautiful city of Albuquerque to explore New Mexico's Spanish Colonial past and Native American cultures. Uncover the fascinating art museums of America's oldest capital Sante Fe, revel over the brilliant Redrock Mesas of Petrified Forest National Park and bask in the breathtaking views of the Grand Canyon’s South Rim. Enjoy a full day in Vegas before you head towards the Mojave Desert for Calico Ghost Town, one of the few original mining camps of the Old West. Top your journey off and drive towards the Santa Monica Pier, where you can discover Hollywood landmarks such as the Universal Studios or Anaheim’s Disneyland Park.
16 days
fromUSD 1,942
From the sights of New York to the glamour of Los Angeles, the "New York to Hollywood" tour invites you on a grand 17-day journey across America’s legendary cities and national parks. This guided group tour is ideal for experienced travelers seeking a relaxed yet comprehensive adventure. Begin in New York, then trace the nation’s founding in Philadelphia and Washington D.C. Cross into Canada for a magical Niagara Falls experience before heading west to Detroit, the birthplace of the American auto industry, and Chicago’s iconic skyline. Traverse the wilds of South Dakota’s Badlands and be awed by the monumental faces of Mount Rushmore. The adventure continues through Yellowstone’s geysers, Grand Teton’s peaks, and Utah’s Bryce Canyon before marveling at Lake Powell and the awe-inspiring Grand Canyon. Travel Route 66, soak in Las Vegas’ neon energy, and finish in Los Angeles, where Hollywood’s star-studded streets await. With accommodations, meals, and transportation provided, this trip’s unique selling point is its epic sweep—combining urban landmarks and natural wonders for an unforgettable coast-to-coast American tour package.
17 days
fromUSD 3,727
40% Off Today
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
USD 7,133fromUSD 4,280
7% Off Today
This classic Midwestern tour features Illinois and Michigan. Savor two incredible nights amid the luxury of the Grand Hotel on Mackinac Island. Enjoy a horse and buggy tour of Mackinac Island. Explore the wonderful city of Chicago with a local guide. Visit the Bavarian-influenced town of Frankenmuth. In Dearborn, experience the inspirational Henry Ford Museum and view historic homes at Greenfield Village including the famous American workshops of Thomas Edison, Henry Ford and Robert Frost.
9 days
USD 3,749fromUSD 3,499
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
fromUSD 2,032
If you’re searching for a leisurely exploration of America’s Great Lakes region, the 'Chicago and Niagara ROT' tour is a fantastic 8-day sightseeing trip. Beginning and ending in Chicago, this journey includes stops in Detroit, the stunning Niagara Falls, and vibrant Cleveland. Geared toward seniors, the itinerary is designed for comfort and ease, with all accommodations, meals, and transport arranged. The standout feature is its circular route, allowing travelers to experience multiple iconic destinations without the hassle of backtracking—making it a particularly convenient tour package for relaxed yet enriching travel.
8 days
fromUSD 1,625
40% Off Today
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
USD 5,876fromUSD 3,526
See all Chicago September 2025 Tours
Top Chicago Tour Activities for September 2025
From city sightseeing tours to cultural, religious and historic sites and others, here are some popular tour activities in Chicago with departures in September 2025.
Chicago September 2025 Tours for all Age Groups
Chicago tours in September 2025 designed for all ages—families, young adventurers, seniors, and everyone in between.
Chicago September 2025 Tour Types
Discover Chicago September 2025 tours in your way! Choose from group tours, private experiences, solo adventures, or guided and escorted tours.
