10 Best Tours and Trips in Chicago in 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.

Essential East Coast, Niagara And Chicago

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Essential East Coast, Niagara and Chicago

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From the bright lights of New York to the architectural wonders of Chicago, the 'Essential East Coast, Niagara and Chicago' tour is a 14-day city sightseeing trip designed for seniors. This guided journey covers Detroit, Toronto, and other key destinations, with all logistics managed for your ease. The highlight is its comprehensive route, encompassing both historic and modern marvels in an itinerary that balances excitement with comfort.

City sightseeing

Tour Type

Group Tour

Accommodation

Hotel

Age Range

15-99 yrs

Operated in

english

Destinations

New York, Chicago, Niagara Falls

New York, Chicago, Niagara Falls, Detroit, Boston, Montreal, Quebec City, Ottawa, Toronto

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Duration14 days

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Chicago to Golden Gate

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Witness the flair and beauty of America’s gems from the Midwest to the South Coast with a road-trip adventure in 14 jam-packed days. As you travel from Chicago to the west, you will uncover the natural treasures around the Mississippi and the charms of pastoral life in rural Wyoming. Pay a visit to Yellowstone here to have a glimpse of the earth in full motion. You will cover plenty of iconic spots with your local guide. Teton Mountains and the Mormon state of Utah await, where you will experience memorable moments learning about the local mountain culture. Passing through a series of fascinating national parks including the Grand Canyon, make a stop at the Route 66 highlight Seligman. Get into the city vibes in Las Vegas, because a night of boundless gaming and partying will captivate you. Hit Santa Barbara and finally the fashionable San Francisco before you say goodbye.

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

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Duration14 days

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Chicago, Niagara and New York

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Set out from the Windy City on the 'Chicago, Niagara and New York' guided tour, a perfect 8-day city sightseeing trip ideal for seniors. This journey includes the awe-inspiring Niagara Falls, the cultural richness of Cleveland, and wraps up in bustling New York. Designed for those seeking gentle exploration, all accommodations, meals, and transport are handled, allowing you to enjoy each destination at your own pace. The special appeal of this tour lies in its seamless blend of urban excitement and natural wonder, making it an excellent choice for those looking for a well-rounded, easy-paced adventure.

City sightseeing

Tour Type

Group Tour

Accommodation

Hotel

Age Range

15-99 yrs

Operated in

english

Destinations

New York, Chicago, Cleveland, Niagara Falls

8% OFF TODAY

Duration8 days

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From Washington to Las Vegas

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Set off on a grand adventure from the nation’s capital to the entertainment capital of the world with the "From Washington to Las Vegas" city sightseeing tour. Spanning 21 days, this group trip covers Boston, New York, and 10 other destinations throughout the USA and Canada—crafted for seniors who value comfort and cultural immersion. With hotels, transport, and meals seamlessly included, you can relax and enjoy the journey’s diverse highlights. The tour’s unique selling point is its extensive, cross-country route, allowing you to experience a remarkable variety of cities and landscapes in one cohesive package.

City sightseeing

Tour Type

Group Tour

Accommodation

Hotel

Age Range

15-99 yrs

Operated in

english

Destinations

Washington D.C., Las Vegas, Toro

Washington D.C., Las Vegas, Toronto, Niagara Falls, Detroit, Chicago, Los Angeles, Flagstaff, New York, Boston, Montreal, Quebec City, Ottawa

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Duration21 days

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Chicago and Niagara ROT

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If you’re searching for a leisurely exploration of America’s Great Lakes region, the 'Chicago and Niagara ROT' tour is a fantastic 8-day sightseeing trip. Beginning and ending in Chicago, this journey includes stops in Detroit, the stunning Niagara Falls, and vibrant Cleveland. Geared toward seniors, the itinerary is designed for comfort and ease, with all accommodations, meals, and transport arranged. The standout feature is its circular route, allowing travelers to experience multiple iconic destinations without the hassle of backtracking—making it a particularly convenient tour package for relaxed yet enriching travel.

City sightseeing

Tour Type

Group Tour

Accommodation

Hotel

Age Range

15-99 yrs

Operated in

english

Destinations

Chicago, Cleveland, Niagara Fall

Chicago, Cleveland, Niagara Falls, Detroit

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Duration8 days

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California Coast, Chicago, And Ny, Ending In Washington

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California Coast, Chicago, and NY, Ending in Washington

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The "California Coast, Chicago, and NY, Ending in Washington" trip spans 16 days and is perfect for seniors seeking a thorough city sightseeing experience. Starting in San Francisco and ending in Washington D.C., the tour takes in New York, Cleveland, and other vibrant destinations. With group travel, comfortable hotels, and meals included, you can relax and take in the sights. Its unique selling point is the coast-to-capital route, providing an extensive overview of major American cities in a relaxed format.

City sightseeing

Tour Type

Group Tour

Accommodation

Hotel, Resort

Age Range

15-99 yrs

Operated in

english

Destinations

Washington D.C., San Francisco

Washington D.C., San Francisco, San Luis Obispo, Los Angeles, Chicago, Cleveland, Niagara Falls, New York

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Duration16 days

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California Coast, Chicago, and NY

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From the Golden Gate to the Big Apple, the "California Coast, Chicago, and NY" city sightseeing tour is tailored for seniors who crave a cross-country adventure at an easy pace. This 14-day group trip starts in San Francisco and ends in New York, visiting Chicago, San Luis Obispo, and more along the way. With all accommodations, transport, and meals taken care of, you’re free to enjoy a seamless coast-to-coast experience. The tour’s USP is its diverse route, offering a comprehensive look at America’s urban and scenic treasures.

City sightseeing

Tour Type

Group Tour

Accommodation

Hotel, Resort

Age Range

15-99 yrs

Operated in

english

Destinations

New York, San Francisco, Los Ang

New York, San Francisco, Los Angeles, Chicago, Cleveland, Niagara Falls, San Luis Obispo

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Duration14 days

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Chicago to LA

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Prepare for a once-in-a-lifetime adventure traveling across the USA from Chicago to Los Angeles with an 11-day trip. You will draw a parallel to the Northern border of the country passing through iconic locations in search of the American spirit. Enjoy a full day in Chicago with the sights we have in store for you, then take your time discovering the chich restaurants, art centers, and hopping nightlife venues of the Winding City. Head to the stunning backcountry from there, tour the incredible Badlands National Park and get a taste of Native American history in the Black Hills. From then on, it will be all about the mountains of Wyoming. The breezy western air will take over, and soon you will get into the free spirit of the Southwest. Take to the trails of Yellowstone and the Grand Canyon before a majestic finish including Las Vegas and California.

Adventure

Tour Type

Group Tour

Accommodation

Hotel, Lodge

Age Range

18-75 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 National Park, Flagstaff

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Duration11 days

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Eastern Round ends Chicago

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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

8% OFF TODAY

Duration16 days

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Chicago, Niagara And New York End Washington

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Chicago, Niagara and New York end Washington

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No booking fees

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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

8% OFF TODAY

Duration10 days

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Chicago Tours and Trips

30 Trips in Chicago with 101 Reviews

30 Trips in Chicago with 101 Reviews

Essential East Coast, Niagara and Chicago

Chicago to Golden Gate

Chicago, Niagara and New York

From Washington to Las Vegas

Chicago and Niagara ROT

California Coast, Chicago, and NY, Ending in Washington

California Coast, Chicago, and NY

Chicago to LA

Eastern Round ends Chicago

Chicago, Niagara and New York end Washington

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

Chicago Tours and Trips

30 Trips in Chicago with 101 Reviews

30 Trips in Chicago with 101 Reviews