10 Best Chicago Multiday Tours in September 2026

Super Sales

From the West with Chicago and NY - September 2026

No booking fees

Best price guaranteed

From the glitz of Los Angeles to the buzz of New York, the "From the West with Chicago and NY" tour presents a 14-day sightseeing journey crafted for seniors. This group trip covers Las Vegas, Cleveland, and more, offering a relaxed yet thorough exploration of America’s varied regions. With accommodations, meals, and transport included, you can focus on the rich experiences each stop provides. The true highlight is its coast-to-coast adventure, making it a standout for those seeking a panoramic view of the USA.

Sightseeing Tours

Tour Type

Group Tour

Accommodation

Hotel

Age Range

15-99 yrs

Operated in

english

Destinations

New York, Los Angeles, Niagara F

New York, Los Angeles, Niagara Falls, Las Vegas, Flagstaff, Chicago, Cleveland

Duration14 days

From

USD 3,485

USD 3,380

Saving

USD 105

View Tour

40% OFF TODAY

The Great American Crossing - September 2026

No booking fees

Best price guaranteed

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.

City sightseeingAdventure

Tour Type

Group Tour

Accommodation

Hotel, Lodge, Resort

Age Range

18-75 yrs

Operated in

english

Destinations

New York, San Francisco, Cody, Y

New York, San Francisco, Cody, Yellowstone National Park, Salt Lake City, Bryce Canyon National Park, Flagstaff, Las Vegas, Los Angeles, Central Coast, Washington D.C., Niagara Falls, Detroit, Chicago, Sioux Falls, Rapid City

40% OFF TODAY

Duration20 days

From

USD 7,509

USD 4,505

Saving

USD 3,004

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Super Sales

Unmissable Canada, Niagara and Chicago - September 2026

No booking fees

Best price guaranteed

Journey from French-speaking Montreal to the towering skyline of Chicago on the 11-day 'Unmissable Canada, Niagara and Chicago' sightseeing trip. Tailored for seniors, the itinerary features Montreal, Toronto, Quebec City, Niagara Falls, and more, offering a rich selection of North American highlights. Group guidance, comfortable hotels, and all meals and transport are included for an effortless experience. This tour’s unique benefit is its blend of Canadian culture and American city life, promising a vivid and accessible adventure.

Sightseeing Tours

Tour Type

Group Tour

Accommodation

Hotel

Age Range

15-99 yrs

Operated in

english

Destinations

Chicago, Montreal

Duration11 days

From

USD 2,236

USD 2,169

Saving

USD 67

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Super Sales

Toronto, Niagara and Chicago - September 2026

No booking fees

Best price guaranteed

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.

City sightseeing

Tour Type

Group Tour

Accommodation

Hotel

Age Range

15-99 yrs

Operated in

english

Destinations

Toronto, Chicago

Duration7 days

From

USD 1,275

USD 1,237

Saving

USD 38

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40% OFF TODAY

New York to Hollywood - September 2026

No booking fees

Best price guaranteed

Are you ready to sweep the entire Continental United States from one end to the other in 17 days filled with overwhelming fun, discovery, and unforgettable memories? If the answer is yes, you have come to the right place! This trip will take you on a journey from the hip aura of the East Coast through the unmissable attractions of the Midwest all the way to the gleaming West Coast. The changing country as you ride on the most iconic routes of the US will leave you in awe. Cover both the culture and history-laden urban sights from New York to Chicago. Explore the adventurous outdoors with a local guide in the canyons and national parks of the Southwest, and taste local life in cities like Salt Lake and Sioux. Simply too many to count, the sights covered in this tour present to you the essence of America.

Adventure

Tour Type

Group Tour

Accommodation

Hotel, Lodge

Age Range

18-75 yrs

Operated in

english

Destinations

New York, Los Angeles, Cody, Yel

New York, Los Angeles, Cody, Yellowstone National Park, Salt Lake City, Bryce Canyon National Park, Flagstaff, Las Vegas, Washington D.C., Niagara Falls, Detroit, Chicago, Sioux Falls, Rapid City

40% OFF TODAY

Duration17 days

From

USD 6,811

USD 4,087

Saving

USD 2,724

View Tour

Super Sales

Usa and Canada Panorama with Chicago - September 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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Super Sales

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

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

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Super Sales

Canadian Capitals with Chicago and West Coast - September 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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Super Sales

Canadian Capitals with Chicago and the entire West Coast - September 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

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

View Tour

Super Sales

Toronto, Niagara, and Chicago with Western Classics - September 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

Chicago to L.A - September 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 3,201

View Tour

Super Sales

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

View Tour

Super Sales

Essential East Coast and Unmissable West - September 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 September 2026

Page 2 of 28 Trips in Chicago during September 2026 with 100 Reviews

From the West with Chicago and NY - September 2026

The Great American Crossing - September 2026

Unmissable Canada, Niagara and Chicago - September 2026

Toronto, Niagara and Chicago - September 2026

New York to Hollywood - September 2026

Usa and Canada Panorama with Chicago - September 2026

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

Canadian Capitals with Chicago and West Coast - September 2026

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

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

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

Chicago to L.A - September 2026

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

Essential East Coast and Unmissable West - September 2026

Get a customized trip to Chicago in September 2026

From the West with Chicago and NY - September 2026

The Great American Crossing - September 2026

Unmissable Canada, Niagara and Chicago - September 2026

Toronto, Niagara and Chicago - September 2026

New York to Hollywood - September 2026

Usa and Canada Panorama with Chicago - September 2026

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

Canadian Capitals with Chicago and West Coast - September 2026

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

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

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

Chicago to L.A - September 2026

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

Essential East Coast and Unmissable West - September 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 September 2026

Page 2 of 28 Trips in Chicago during September 2026 with 100 Reviews

Get a customized trip to Chicago in September 2026