Chicago City sightseeing Trips in 2025/2026

Halloween Super Sales

Essential East Coast and Western Classics, Ending in Las Vegas

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

Halloween Super Sales

Toronto, Niagara, and Chicago with Western Classics

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

Usa and Canada Panorama with Chicago

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

View Tour

Halloween Super Sales

Canadian Capitals with Chicago and West Coast

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

View Tour

All Chicago City sightseeing Trips

Page 2 of 18 City sightseeing Trips in Chicago with 100 Reviews

Design your own personalized City sightseeing trip to Chicago with help from a local expert.

Page 2 of 18 City sightseeing Trips in Chicago with 100 Reviews

Essential East Coast and Western Classics, Ending in Las Vegas

Toronto, Niagara, and Chicago with Western Classics

Usa and Canada Panorama with Chicago

Canadian Capitals with Chicago and West Coast

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 City sightseeing Trips

Page 2 of 18 City sightseeing Trips in Chicago with 100 Reviews

Design your own personalized City sightseeing trip to Chicago with help from a local expert.

Page 2 of 18 City sightseeing Trips in Chicago with 100 Reviews

Essential East Coast and Western Classics, Ending in Las Vegas

Toronto, Niagara, and Chicago with Western Classics

Usa and Canada Panorama with Chicago

Canadian Capitals with Chicago and West Coast