10 Best Chicago Multiday Tours in September 2025

Essential East Coast, Niagara and Chicago - September 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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New York to Hollywood - September 2025

Trip customizable

Best price guaranteed

See some of the best locations America has to offer from the Big Apple to the City of Angels! Explore the iconic sights of the United States from east to west from New York to Los Angeles. Visit the birthplace of America in Philadelphia and stroll the National Mall and its famous memorials in the nation's capital. See the famous carving of the 4 American Presidents’ faces at Mount Rushmore and discover the world’s first National Park at Yellowstone. Drive across the historic Route 66, travel across the Mojave Desert, and visit Las Vegas, the entertainment capital of the world

City sightseeing

Tour Type

Group Tour

Accommodation

Hotel, Lodge

Age Range

13-99 yrs

Operated in

english

Destinations

New York, Los Angeles, Californi

New York, Los Angeles, California, Cody, Yellowstone National Park, Salt Lake City, Bryce Canyon, Flagstaff, Las Vegas, Washington D.C., Niagara Falls, Detroit, Chicago, Sioux Falls, Rapid City

Duration17 days

From

USD 3,618

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7% OFF TODAY

Mackinac Island - September 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 - September 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 - September 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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Chicago, Niagara and New York end Washington - September 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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40% OFF TODAY

The Great American Crossing - September 2025

No booking fees

Best price guaranteed

Kick off this extensive 20-day tour in New York and make a stop at every must-see city on the way until you reach the golden coast of the Pacific. The Great American Crossing trip will push the limits of your imagination, taking you on an improbable journey. Visit the cities that reflect the heart and soul of American liberty like Philadelphia and Washington D.C.. Explore the natural beauties of New England from Niagara to the Great Lakes. There is nothing like the urban flair of Chicago, and you will have enough time to explore its architectural nuggets. From there, the landscape will change dramatically as you pass through grand mountain ranges westward. Your time in Bryce Canyon will be as colorful as the rugged terrain, and the Mojave Desert will put you in a unique mood before you end your trip with four days on the shiny coast.

City sightseeingAdventure

Tour Type

Group Tour

Accommodation

Hotel, Lodge, Resort

Age Range

18-75 yrs

Operated in

english

Destinations

New York, San Francisco, Cody, Y

New York, San Francisco, Cody, Yellowstone National Park, Salt Lake City, Bryce Canyon National Park, Flagstaff, Las Vegas, Los Angeles, Central Coast, Washington D.C., Niagara Falls, Detroit, Chicago, Sioux Falls, Rapid City

40% OFF TODAY

Duration20 days

From

USD 7,133

USD 4,280

Saving

USD 2,853

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Toronto, Niagara and Chicago - September 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

View Tour

All Chicago Tours in September 2025

8 Trips in Chicago during September 2025

8 Trips in Chicago during September 2025

Essential East Coast, Niagara and Chicago - September 2025

New York to Hollywood - September 2025

Mackinac Island - September 2025

Chicago, Niagara and New York - September 2025

Chicago and Niagara ROT - September 2025

Chicago, Niagara and New York end Washington - September 2025

The Great American Crossing - September 2025

Toronto, Niagara and Chicago - September 2025

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All Chicago Tours in September 2025

8 Trips in Chicago during September 2025

8 Trips in Chicago during September 2025