All Chicago Tours in October 2026
Page 2 of 21 Trips in Chicago during October 2026 with 100 Reviews
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Essential East Coast and Unmissable West - October 2026
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.
City sightseeing
Super Sales
Essential East Coast and Western Classics, Ending in Las Vegas - October 2026
4.5
We loved to travel with all countries travellers
Now we want to travel South America with Europamundo
City sightseeing
Super Sales
From the West with Chicago and NY, Ending in Washington - October 2026
Cross the United States in comfort on the "From the West with Chicago and NY, Ending in Washington" city sightseeing trip. Spanning 16 days from Los Angeles to Washington D.C., this group tour is tailored for seniors who appreciate easy-paced travel. Visit iconic destinations including New York, Cleveland, and Niagara Falls, with hotels, transport, and meals seamlessly arranged. Its unique feature is the coast-to-coast route, providing a comprehensive look at both major cities and natural wonders across the country.
Sightseeing Tours
Super Sales
Usa and Canada Panorama with Chicago - October 2026
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
Super Sales
Canadian Capitals with Chicago and West Coast - October 2026
Ready to uncover the best of Canada and the USA in comfort? The 'Canadian Capitals with Chicago and West Coast' tour offers a 16-day city sightseeing adventure, starting in Montreal and winding up in the dazzling lights of Las Vegas. Designed specifically with seniors in mind, this group tour balances gentle exploration with enriching experiences, taking you through Toronto’s lively streets, the architectural marvels of Chicago, and the natural beauty of Flagstaff. With accommodations, meals, and all transport arranged, you can immerse yourself in each destination without worry. The unique highlight of this tour is its effortless combination of Canada’s cultural hubs and America’s vibrant cities, making it ideal for seasoned travelers eager for diversity and ease.
City sightseeing
Super Sales
Toronto, Niagara, and Chicago with Western Classics ending Las Vegas - October 2026
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
Super Sales
Toronto, Niagara, and Chicago with Western Classics - October 2026
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
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