All Chicago City sightseeing Trips
18 City sightseeing Trips in Chicago
Most Popular
Essential East Coast, Niagara and Chicago
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.
New York to Hollywood
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
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Mackinac Island
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.
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Chicago, Niagara and New York
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.
Chicago and Niagara ROT
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.
California Coast, Chicago, and NY
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.
California Coast, Chicago, and NY, Ending in Washington
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.
From Washington to Las Vegas
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.
Chicago, Niagara and New York end Washington
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.
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The Great American Crossing
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.
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Toronto, Niagara and Chicago
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.
Usa and Canada Panorama with Chicago
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.
Toronto, Niagara, and Chicago with Western Classics
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.
Toronto, Niagara, and Chicago with Western Classics ending Las Vegas
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.