Chicago City sightseeing Trips in 2025/2026

Essential East Coast, Niagara and Chicago

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

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

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

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

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

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

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

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

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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Toronto, Niagara and Chicago

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

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

No booking fees

Best price guaranteed

Iconic cities and breathtaking scenery await on the "Toronto, Niagara, and Chicago with Western Classics" guided city sightseeing tour. Perfect for seniors, this 16-day group adventure starts in Toronto and ends in San Francisco, with stops in Fresno, San Francisco, and several other North American gems. Enjoy easy-paced exploration with included hotels, meals, and transport. The unique selling point of this trip is its dual-country itinerary, offering a rare blend of Canadian and American highlights within a single, expertly organized package.

City sightseeing

Tour Type

Group Tour

Accommodation

Hotel

Age Range

15-99 yrs

Operated in

english

Destinations

Toronto, San Francisco, Niagara

Toronto, San Francisco, Niagara Falls, Detroit, Chicago, Los Angeles, Las Vegas, Flagstaff, Bakersfield, Fresno, CA

Duration16 days

From

USD 4,186

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Toronto, Niagara, and Chicago with Western Classics ending Las Vegas

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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Essential East Coast and Western Classics, Ending in Las Vegas

4.5

(2 reviews )

No booking fees

Best price guaranteed

We loved to travel with all countries travellers Now we want to travel South America with Europamundo

City sightseeing

Tour Type

Group Tour

Accommodation

Hotel

Age Range

15-99 yrs

Operated in

english

Destinations

New York, Las Vegas, Niagara Fal

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

Duration19 days

From

USD 4,798

View Tour

All Chicago City sightseeing Trips

17 City sightseeing Trips in Chicago

Essential East Coast, Niagara and Chicago

New York to Hollywood

Mackinac Island

Chicago, Niagara and New York

Chicago and Niagara ROT

California Coast, Chicago, and NY

California Coast, Chicago, and NY, Ending in Washington

From Washington to Las Vegas

Chicago, Niagara and New York end Washington

Toronto, Niagara and Chicago

Usa and Canada Panorama with Chicago

Toronto, Niagara, and Chicago with Western Classics

Toronto, Niagara, and Chicago with Western Classics ending Las Vegas

Essential East Coast and Western Classics, Ending in Las Vegas

17 City sightseeing Trips in Chicago

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All Chicago City sightseeing Trips

17 City sightseeing Trips in Chicago

17 City sightseeing Trips in Chicago