10 Best Chicago Multiday Tours in May 2026

Super Sales

Canadian Capitals with Chicago and the entire West Coast - May 2026

No booking fees

Best price guaranteed

Experience the grand sweep of North America’s diverse cities with the 'Canadian Capitals with Chicago and the entire West Coast' tour package, tailored for senior travelers seeking comfort and discovery. Over 20 leisurely days, this guided sightseeing trip begins in Montreal and winds through the vibrant capitals of Canada, the dynamic streets of Chicago and Detroit, and the iconic attractions of the West Coast before concluding in San Francisco. Carefully crafted for those who appreciate a relaxed pace, this journey offers accessible walks and plenty of rest, making it especially appealing for seniors. The itinerary covers noteworthy destinations such as Ottawa, Los Angeles, and multiple cities across both the USA and Canada, with all hotel accommodations, transport, and meals seamlessly included. What sets this tour apart is its harmonious blend of urban exploration and scenic journeys, providing a comprehensive North American experience with all the ease and comfort senior guests deserve.

City sightseeing

Tour Type

Group Tour

Accommodation

Hotel

Age Range

15-99 yrs

Operated in

english

Destinations

San Francisco, Montreal, Chicago

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

Duration20 days

From

USD 4,670

USD 4,530

Saving

USD 140

View Tour

Super Sales

Toronto, Niagara, and Chicago with Western Classics - May 2026

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 4,114

USD 3,991

Saving

USD 123

View Tour

Super Sales

Toronto, Niagara, and Chicago with Western Classics ending Las Vegas - May 2026

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 3,033

USD 2,942

Saving

USD 91

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Super Sales

Essential East Coast and Unmissable West - May 2026

No booking fees

Best price guaranteed

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

Tour Type

Group Tour

Accommodation

Hotel

Age Range

15-99 yrs

Operated in

english

Destinations

New York, San Francisco, Niagara

New York, San Francisco, Niagara Falls, Detroit, Chicago, Los Angeles, Las Vegas, Flagstaff, Bakersfield, Fresno, CA, Boston, Montreal, Quebec City, Ottawa, Toronto

Duration23 days

From

USD 5,423

USD 5,260

Saving

USD 163

View Tour

All Chicago Tours in May 2026

Page 2 of 18 Trips in Chicago during May 2026 with 100 Reviews

Get a customized trip to Chicago in May 2026

Canadian Capitals with Chicago and the entire West Coast - May 2026

Toronto, Niagara, and Chicago with Western Classics - May 2026

Toronto, Niagara, and Chicago with Western Classics ending Las Vegas - May 2026

Essential East Coast and Unmissable West - May 2026

Page 2 of 18 Trips in Chicago during May 2026 with 100 Reviews

Europe

Asia

South America

Africa

North America

Oceania

Polar

Food, wine, events and nightlife

Adventure and sport

Wildlife, landscapes and nature

Boat tours, water sports and marine wildlife

Sightseeing, attractions, culture and history

Air tours, road trips and transfers

Beach, romance, getaways and relaxation

Special interests and hobbies

All Chicago Tours in May 2026

Page 2 of 18 Trips in Chicago during May 2026 with 100 Reviews

Get a customized trip to Chicago in May 2026

Canadian Capitals with Chicago and the entire West Coast - May 2026

Toronto, Niagara, and Chicago with Western Classics - May 2026

Toronto, Niagara, and Chicago with Western Classics ending Las Vegas - May 2026

Essential East Coast and Unmissable West - May 2026

Page 2 of 18 Trips in Chicago during May 2026 with 100 Reviews