10 Best Chicago Multiday Tours in October 2025

Essential East Coast, Niagara and Chicago - October 2025

No booking fees

Best price guaranteed

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.

City sightseeing

Tour Type

Group Tour

Accommodation

Hotel

Age Range

15-99 yrs

Operated in

english

Destinations

New York, Chicago, Niagara Falls

New York, Chicago, Niagara Falls, Detroit, Boston, Montreal, Quebec City, Ottawa, Toronto

Duration14 days

From

USD 2,845

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Historic Route 66 - October 2025

Trip customizable

Best price guaranteed

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.

Cultural, religious and historic sites

Tour Type

Independent Tour

Accommodation

Resort, Hotel

Age Range

8-99 yrs

Operated in

English

Destinations

Yosemite National Park, Albuquer

Yosemite National Park, Albuquerque, Chicago, Holbrook, Williams, Las Vegas, Los Angeles, St. Louis, MI, Springfield, Oklahoma City, Amarillo

Duration16 days

From

USD 1,942

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7% OFF TODAY

Mackinac Island - October 2025

No booking fees

Best price guaranteed

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.

City sightseeing

Tour Type

Group Tour

Accommodation

Hotel, Resort

Age Range

1-99 yrs

Operated in

english

Destinations

Chicago, Southfield

7% OFF TODAY

Duration9 days

From

USD 3,749

USD 3,499

Saving

USD 250

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Chicago, Niagara and New York - October 2025

No booking fees

Best price guaranteed

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.

City sightseeing

Tour Type

Group Tour

Accommodation

Hotel

Age Range

15-99 yrs

Operated in

english

Destinations

New York, Chicago, Cleveland, Niagara Falls

Duration8 days

From

USD 1,625

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Chicago and Niagara ROT - October 2025

No booking fees

Best price guaranteed

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.

City sightseeing

Tour Type

Group Tour

Accommodation

Hotel

Age Range

15-99 yrs

Operated in

english

Destinations

Chicago, Cleveland, Niagara Fall

Chicago, Cleveland, Niagara Falls, Detroit

Duration8 days

From

USD 1,625

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California Coast, Chicago, and NY - October 2025

No booking fees

Best price guaranteed

From the Golden Gate to the Big Apple, the "California Coast, Chicago, and NY" city sightseeing tour is tailored for seniors who crave a cross-country adventure at an easy pace. This 14-day group trip starts in San Francisco and ends in New York, visiting Chicago, San Luis Obispo, and more along the way. With all accommodations, transport, and meals taken care of, you’re free to enjoy a seamless coast-to-coast experience. The tour’s USP is its diverse route, offering a comprehensive look at America’s urban and scenic treasures.

City sightseeing

Tour Type

Group Tour

Accommodation

Hotel, Resort

Age Range

15-99 yrs

Operated in

english

Destinations

New York, San Francisco, Los Ang

New York, San Francisco, Los Angeles, Chicago, Cleveland, Niagara Falls, San Luis Obispo

Duration14 days

From

USD 3,442

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California Coast, Chicago, and NY, Ending in Washington - October 2025

No booking fees

Best price guaranteed

The "California Coast, Chicago, and NY, Ending in Washington" trip spans 16 days and is perfect for seniors seeking a thorough city sightseeing experience. Starting in San Francisco and ending in Washington D.C., the tour takes in New York, Cleveland, and other vibrant destinations. With group travel, comfortable hotels, and meals included, you can relax and take in the sights. Its unique selling point is the coast-to-capital route, providing an extensive overview of major American cities in a relaxed format.

City sightseeing

Tour Type

Group Tour

Accommodation

Hotel, Resort

Age Range

15-99 yrs

Operated in

english

Destinations

Washington D.C., San Francisco

Washington D.C., San Francisco, San Luis Obispo, Los Angeles, Chicago, Cleveland, Niagara Falls, New York

Duration16 days

From

USD 4,136

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From Washington to Las Vegas - October 2025

No booking fees

Best price guaranteed

Set off on a grand adventure from the nation’s capital to the entertainment capital of the world with the "From Washington to Las Vegas" city sightseeing tour. Spanning 21 days, this group trip covers Boston, New York, and 10 other destinations throughout the USA and Canada—crafted for seniors who value comfort and cultural immersion. With hotels, transport, and meals seamlessly included, you can relax and enjoy the journey’s diverse highlights. The tour’s unique selling point is its extensive, cross-country route, allowing you to experience a remarkable variety of cities and landscapes in one cohesive package.

City sightseeing

Tour Type

Group Tour

Accommodation

Hotel

Age Range

15-99 yrs

Operated in

english

Destinations

Washington D.C., Las Vegas, Toro

Washington D.C., Las Vegas, Toronto, Niagara Falls, Detroit, Chicago, Los Angeles, Flagstaff, New York, Boston, Montreal, Quebec City, Ottawa

Duration21 days

From

USD 5,275

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Chicago, Niagara and New York end Washington - October 2025

No booking fees

Best price guaranteed

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.

City sightseeing

Tour Type

Group Tour

Accommodation

Hotel

Age Range

15-99 yrs

Operated in

english

Destinations

Washington D.C., Chicago, Clevel

Washington D.C., Chicago, Cleveland, Niagara Falls, New York

Duration10 days

From

USD 2,032

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Eastern Round ends Chicago - October 2025

No booking fees

Best price guaranteed

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.

Cultural, religious and historic sites

Tour Type

Group Tour

Accommodation

Hotel

Age Range

15-99 yrs

Operated in

english

Destinations

Washington D.C., Chicago, Toront

Washington D.C., Chicago, Toronto, Niagara Falls, Detroit, New York, Boston, Montreal, Quebec City, Ottawa

Duration16 days

From

USD 3,251

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Unmissable Canada, Niagara and Chicago - October 2025

No booking fees

Best price guaranteed

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.

Sightseeing Tours

Tour Type

Group Tour

Accommodation

Hotel

Age Range

15-99 yrs

Operated in

english

Destinations

Chicago, Montreal, Quebec City

Chicago, Montreal, Quebec City, Ottawa, Toronto, Niagara Falls, Detroit

Duration11 days

From

USD 2,236

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Toronto, Niagara and Chicago - October 2025

No booking fees

Best price guaranteed

Experience the vibrant energy of North America’s great cities with the 'Toronto, Niagara and Chicago' 7-day city sightseeing tour. Starting in Toronto and ending in Chicago, this trip is designed for seniors looking for a comfortable and comprehensive journey through Detroit, Niagara Falls, and other exciting locales. Hotels, transport, and meals are all included, making it easy to focus on the sights. The tour’s unique feature is its well-paced route, connecting urban and natural highlights in a single, seamless adventure.

City sightseeing

Tour Type

Group Tour

Accommodation

Hotel

Age Range

15-99 yrs

Operated in

english

Destinations

Toronto, Chicago, Niagara Falls

Toronto, Chicago, Niagara Falls, Detroit

Duration7 days

From

USD 1,275

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Usa and Canada Panorama with Chicago - October 2025

No booking fees

Best price guaranteed

Embark on a sweeping journey from Los Angeles to Chicago with the "USA and Canada Panorama with Chicago" guided city sightseeing tour. This 19-day adventure is crafted for seniors who enjoy discovering new places at a comfortable, easy-going pace. The itinerary covers highlights such as Fresno, New York, and nine other destinations, with group travel, hotel accommodations, and meals included. The tour’s USP is its broad scope—offering a rare look at both American and Canadian gems on one seamless itinerary.

City sightseeing

Tour Type

Group Tour

Accommodation

Hotel

Age Range

15-99 yrs

Operated in

english

Destinations

Los Angeles, Chicago, Quebec Cit

Los Angeles, Chicago, Quebec City, Ottawa, Toronto, Niagara Falls, Detroit, Bakersfield, Fresno, CA, New York, Boston, Montreal

Duration19 days

From

USD 4,572

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Toronto, Niagara, and Chicago with Western Classics ending Las Vegas - October 2025

No booking fees

Best price guaranteed

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.

City sightseeing

Tour Type

Group Tour

Accommodation

Hotel

Age Range

15-99 yrs

Operated in

english

Destinations

Toronto, Las Vegas, Los Angeles

Toronto, Las Vegas, Los Angeles, Flagstaff, Niagara Falls, Detroit, Chicago

Duration12 days

From

USD 3,056

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All Chicago Tours in October 2025

19 Trips in Chicago during October 2025

19 Trips in Chicago during October 2025

Essential East Coast, Niagara and Chicago - October 2025

Historic Route 66 - October 2025

Mackinac Island - October 2025

Chicago, Niagara and New York - October 2025

Chicago and Niagara ROT - October 2025

California Coast, Chicago, and NY - October 2025

California Coast, Chicago, and NY, Ending in Washington - October 2025

From Washington to Las Vegas - October 2025

Chicago, Niagara and New York end Washington - October 2025

Eastern Round ends Chicago - October 2025

Unmissable Canada, Niagara and Chicago - October 2025

Toronto, Niagara and Chicago - October 2025

Usa and Canada Panorama with Chicago - October 2025

Toronto, Niagara, and Chicago with Western Classics ending Las Vegas - October 2025

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Food, wine, events and nightlife

Adventure and sport

Wildlife, landscapes and nature

Boat tours, water sports and marine wildlife

Sightseeing, attractions, culture and history

Air tours, road trips and transfers

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Special interests and hobbies

All Chicago Tours in October 2025

19 Trips in Chicago during October 2025

19 Trips in Chicago during October 2025