Chicago City sightseeing Trips
City sightseeing trips in Chicago. Looking to explore Chicago on a city sightseeing tour? We offer 10+ city sightseeing tours through-out Chicago, backed by 2 reviews and offering discounts up to 40%. All our trips are offered by expert trip designers and Chicago destination experts, with trip durations ranging from 7 to 23 days.
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10 Best City sightseeing Tours in Chicago
Discover our best City sightseeing tours in Chicago, based on reviews and times booked.
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
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
Curious about the ultimate North American odyssey? The 'Essential East Coast and Unmissable West' tour delivers 23 days of city sightseeing from the bustling avenues of New York to the scenic charms of San Francisco. Crafted for seniors, this journey promises a relaxing pace through a dozen destinations, including Detroit, Chicago, and Los Angeles, as well as key cities in Canada. With comfortable hotels, group transport, and meals included, every detail is managed so you can focus on enjoying each locale. The standout feature is the tour’s extensive itinerary, offering a rare opportunity to experience both coasts and everything in between, all in one seamless trip package.
23 days
fromUSD 5,489
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
From the iconic skyline of New York to the vibrant buzz of Las Vegas, embark on the 'Essential East Coast and Western Classics' tour for 19 unforgettable days. This city sightseeing journey is specially tailored for seniors, offering a gentle pace through historic and cultural highlights in Quebec City, Chicago, Los Angeles, and more. Enjoy the convenience of guided group travel, with hotel stays, transport, and meals all taken care of. The unique selling point of this tour is its carefully balanced itinerary, allowing travelers to experience the best of both coasts without the rush—perfect for those seeking comfort and variety.
19 days
fromUSD 4,798
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
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.
21 days
fromUSD 5,275
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
See all Chicago City sightseeing Tours
Chicago City sightseeing Tours for all Age Groups
Find tours designed for every age group, from young adventurers to senior travelers. Travel with like-minded explorers and enjoy experiences tailored to your needs.
Chicago City sightseeing Tour Types
Discover Chicago City sightseeing tours in your way! Choose from group tours, private experiences, solo adventures, or guided and escorted tours.
