10 Best Chicago Multiday Tours in May 2026

Halloween 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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Halloween Super Sales

From the West with Chicago and NY, Ending in Washington - May 2026

No booking fees

Best price guaranteed

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

Tour Type

Group Tour

Accommodation

Hotel

Age Range

15-99 yrs

Operated in

english

Destinations

Los Angeles, Washington D.C., Ni

Los Angeles, Washington D.C., Niagara Falls, New York, Las Vegas, Flagstaff, Chicago, Cleveland

Duration16 days

From

USD 3,923

USD 3,805

Saving

USD 118

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Halloween 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

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Halloween Super Sales

Canadian Capitals with Chicago and West Coast - May 2026

No booking fees

Best price guaranteed

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

Tour Type

Group Tour

Accommodation

Hotel

Age Range

15-99 yrs

Operated in

english

Destinations

Las Vegas, Montreal, Quebec City

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

Duration16 days

From

USD 4,013

USD 3,893

Saving

USD 120

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Halloween Super Sales

Usa and Canada Panorama with Chicago - May 2026

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

USD 4,435

Saving

USD 137

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Halloween 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

Halloween Super Sales

Chicago to L.A - May 2026

Trip customizable

Best price guaranteed

Experience an adventure from the Windy City on the shores of Lake Michigan all the way to America's second-largest city on the Pacific Coast. Take a day tour of downtown Chicago, featuring Lake Shore Drive, Navy Pier, and the Magnificent Mile. Marvel at the famous carvings of Washington, Jefferson, Lincoln, and Roosevelt at Mount Rushmore. Discover Yellowstone, the world's first National Park. Tour Salt Lake City, including Temple Square, home to the Mormon Tabernacle. Explore the stunning Bryce Canyon National Park and much more on this exciting tour

Explorer

Tour Type

Group Tour

Accommodation

Hotel, Lodge

Age Range

13-99 yrs

Operated in

english

Destinations

Los Angeles, Chicago, Las Vegas

Los Angeles, Chicago, Las Vegas, Sioux Falls, Rapid City, Cody, Yellowstone National Park, Salt Lake City, Bryce Canyon, Flagstaff

Duration11 days

From

USD 3,202

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Halloween Super Sales

Essential East Coast and Western Classics, Ending in Las Vegas - May 2026

4.5

(2 reviews )

No booking fees

Best price guaranteed

We enjoyed very much

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 4,703

USD 4,562

Saving

USD 141

View Tour

All Chicago Tours in May 2026

Page 2 of 22 Trips in Chicago during May 2026 with 100 Reviews

Get a customized trip to Chicago in May 2026

Page 2 of 22 Trips in Chicago during May 2026 with 100 Reviews

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

From the West with Chicago and NY, Ending in Washington - May 2026

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

Canadian Capitals with Chicago and West Coast - May 2026

Usa and Canada Panorama with Chicago - May 2026

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

Chicago to L.A - May 2026

Essential East Coast and Western Classics, Ending in Las Vegas - May 2026

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 22 Trips in Chicago during May 2026 with 100 Reviews

Get a customized trip to Chicago in May 2026

Page 2 of 22 Trips in Chicago during May 2026 with 100 Reviews