10 Best Tours and Trips in Chicago 2025/2026 - Compare Prices

Accommodations

BudgetSimple stays with essential amenities. Typically guesthouses, hostels or hotels rated below 3 stars — clean, no-frills, and great for value-conscious travelers.
Mid-rangeComfortable and reliable 3-star stays. Expect private rooms, en-suite bathrooms, and solid amenities — a great balance between comfort and cost.
PremiumUpscale 4-5 star hotels and lodges. Enjoy high-end service, refined comfort, and premium locations — ideal for travelers seeking extra indulgence.

Chicago, Niagara and New York end Washington

4.5

(2 reviews )

No booking fees

Best price guaranteed

Discover the highlights of America's great cities on the 'Chicago, Niagara and New York end Washington' trip. Spanning 10 days, this easy city sightseeing tour is crafted for seniors who enjoy exploring at a relaxed pace. Starting in Chicago and ending in Washington D.C., the itinerary includes the majestic Niagara Falls and vibrant New York City. With hotels, meals, and transportation fully organized, travelers can enjoy the journey without stress. A key feature of this tour is its thoughtfully selected route, offering a taste of urban diversity while ensuring a comfortable and accessible experience for mature travelers.

City sightseeing

Tour Type

Group Tour

Accommodation

Hotel

Age Range

15-99 yrs

Operated in

english

Destinations

Washington D.C., Chicago, Clevel

Washington D.C., Chicago, Cleveland, Niagara Falls, New York

Duration10 days

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Mackinac Island featuring the Tulip Time Festival

4.7

(98 reviews )

No booking fees

Best price guaranteed

The Grand Hotel was a wonderful experience that everyone should have at least once.

City sightseeing

Tour Type

Group Tour

Accommodation

Hotel, Resort

Age Range

1-99 yrs

Operated in

english

Destinations

Chicago, Southfield, Bay City, M

Chicago, Southfield, Bay City, MI, Mackinac Island, MI, Grand Rapids, MI

Duration9 days

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Canadian Capitals with Chicago and the entire West Coast

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

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Essential East Coast and Western Classics, Ending in Las Vegas

4.3

(4 reviews )

No booking fees

Best price guaranteed

We loved to travel with all countries travellers Now we want to travel South America with Europamundo

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

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Chicago to Golden Gate

No booking fees

Best price guaranteed

From Midwest marvels to California cool, the Chicago to Golden Gate tour is a 14-day odyssey for young adults and families seeking the full American experience. Begin in Chicago and journey west through pastoral Wyoming, the geothermal wonders of Yellowstone, and the majestic Teton Mountains. Savor local mountain culture in Utah and witness the grandeur of the Grand Canyon. A stop on Route 66 leads to Las Vegas’ vibrant nightlife, before the trip winds down with Santa Barbara’s beaches and San Francisco’s iconic cityscapes. What sets this tour apart is its comprehensive route—showcasing the best of America’s landscapes, culture, and legendary road trip spirit.

Adventure

Tour Type

Group Tour

Accommodation

Hotel, Lodge

Age Range

18-75 yrs

Operated in

english

Destinations

Chicago, San Francisco, Las Vega

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

Duration14 days

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The Great American Crossing

No booking fees

Best price guaranteed

Set out on "The Great American Crossing," a 20-day odyssey from New York to San Francisco crafted for young adults craving both iconic cities and sweeping natural landscapes. This guided city sightseeing trip weaves together the spirit of American liberty in Philadelphia and Washington D.C., the urban energy of Chicago, and the natural grandeur of New England, Niagara Falls, and the Great Lakes. As you travel west, the scenery transforms—colorful Bryce Canyon, the vast Mojave Desert, and the glitz of Las Vegas all await before you reach the Pacific’s golden coast. Four days in San Francisco allow time to soak in the city’s laid-back charm. With an easy activity level, this group tour is perfect for young travelers and families seeking adventure without strenuous demands. The standout feature? A meticulously curated route that covers the breadth of the USA, balancing city buzz with outdoor wonders, and offering a true coast-to-coast American experience in one unforgettable trip package.

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

Duration20 days

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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

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Eastern Round ends Chicago

No booking fees

Best price guaranteed

Journey through the heart of America’s eastern region with the 16-day 'Eastern Round ends Chicago' tour. Perfect for seniors who seek a blend of history and culture at an easy pace, this trip weaves together Toronto, Chicago, Detroit, and more. The itinerary is packed with visits to cultural, historic, and religious landmarks, all with group guidance, comfortable accommodation, and all meals included. The unique draw of this package is its comprehensive sweep of the eastern USA, allowing travelers to immerse themselves in a variety of cityscapes and traditions with complete peace of mind.

Cultural, religious and historic sites

Tour Type

Group Tour

Accommodation

Hotel

Age Range

15-99 yrs

Operated in

english

Destinations

Washington D.C., Chicago, Toront

Washington D.C., Chicago, Toronto, Niagara Falls, Detroit, New York, Boston, Montreal, Quebec City, Ottawa

Duration16 days

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

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

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Unmissable Canada, Niagara and Chicago

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, Quebec City

Chicago, Montreal, Quebec City, Ottawa, Toronto, Niagara Falls, Detroit

Duration11 days

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Chicago Tours and Trips 2025/2026

29 Trips in Chicago with 104 Reviews

Chicago, Niagara and New York end Washington

Mackinac Island featuring the Tulip Time Festival

29 Trips in Chicago with 104 Reviews

Canadian Capitals with Chicago and the entire West Coast

Essential East Coast and Western Classics, Ending in Las Vegas

Chicago to Golden Gate

The Great American Crossing

Canadian Capitals with Chicago and West Coast

Eastern Round ends Chicago

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

Unmissable Canada, Niagara and Chicago

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

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Chicago Tours and Trips 2025/2026

29 Trips in Chicago with 104 Reviews

29 Trips in Chicago with 104 Reviews