10 Best Chicago Multiday Tours in May 2026

Halloween Super Sales

Essential East Coast, Niagara and Chicago - May 2026

No booking fees

Best price guaranteed

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

Duration14 days

From

USD 2,845

USD 2,760

Saving

USD 85

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Halloween Super Sales

New York to Hollywood - May 2026

Trip customizable

Best price guaranteed

See some of the best locations America has to offer from the Big Apple to the City of Angels! Explore the iconic sights of the United States from east to west from New York to Los Angeles. Visit the birthplace of America in Philadelphia and stroll the National Mall and its famous memorials in the nation's capital. See the famous carving of the 4 American Presidents’ faces at Mount Rushmore and discover the world’s first National Park at Yellowstone. Drive across the historic Route 66, travel across the Mojave Desert, and visit Las Vegas, the entertainment capital of the world

City sightseeing

Tour Type

Group Tour

Accommodation

Hotel, Lodge

Age Range

13-99 yrs

Operated in

english

Destinations

New York, Los Angeles, Californi

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

Duration17 days

From

USD 3,700

USD 3,589

Saving

USD 111

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42% OFF TODAY

Halloween Super Sales

Chicago to Golden Gate - May 2026

No booking fees

Best price guaranteed

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

42% OFF TODAY

Duration14 days

From

USD 6,037

USD 3,513

Saving

USD 2,524

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Halloween Super Sales

Mackinac Island featuring the Tulip Time Festival - May 2026

4.7

(97 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

Duration9 days

From

USD 3,749

USD 3,637

Saving

USD 112

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Halloween Super Sales

Chicago, Niagara and New York - May 2026

No booking fees

Best price guaranteed

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

Duration8 days

From

USD 1,625

USD 1,576

Saving

USD 49

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Halloween Super Sales

Chicago and Niagara ROT - May 2026

No booking fees

Best price guaranteed

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

Duration8 days

From

USD 1,625

USD 1,576

Saving

USD 49

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Halloween Super Sales

New York to Hollywood - May 2026

Trip customizable

Best price guaranteed

Embark on an unforgettable journey from the East Coast to the West Coast of the United States, exploring iconic cities, national parks, and historic landmarks. Begin in New York City, then travel to Philadelphia and Washington, D.C., where the foundations of American democracy were laid. Head north to Gettysburg and cross into Canada for a night beside the majestic Niagara Falls. Return through the Great Lakes Region to Detroit and on to Chicago, known for its skyline and cultural energy. Continue west through South Dakota, visiting the Badlands and Mount Rushmore, then journey through the Bighorn Mountains to Cody, gateway to the Wild West. Explore the geothermal wonders of Yellowstone and the peaks of Grand Teton before arriving in Salt Lake City. Discover the striking landscapes of Bryce Canyon, Lake Powell, and the Grand Canyon, then follow Historic Route 66 to the neon lights of Las Vegas. Conclude your coast-to-coast adventure in Los Angeles, where you’ll experience the glamour of Hollywood and the spirit of the American dream.

National parks

Tour Type

Group Tour

Accommodation

Hotel

Age Range

8-99 yrs

Operated in

english

Destinations

New York, Los Angeles, Yellowsto

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

Duration17 days

From

USD 3,832

USD 3,717

Saving

USD 115

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Halloween Super Sales

California Coast, Chicago, and NY - May 2026

No booking fees

Best price guaranteed

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

Duration14 days

From

USD 3,400

USD 3,298

Saving

USD 102

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Halloween Super Sales

California Coast, Chicago, and NY, Ending in Washington - May 2026

No booking fees

Best price guaranteed

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

Duration16 days

From

USD 4,043

USD 3,922

Saving

USD 121

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Halloween Super Sales

From Washington to Las Vegas - May 2026

No booking fees

Best price guaranteed

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

Duration21 days

From

USD 5,177

USD 5,022

Saving

USD 155

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Halloween Super Sales

Chicago, Niagara and New York end Washington - May 2026

(1 review )

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

Duration10 days

From

USD 2,032

USD 1,971

Saving

USD 61

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Halloween Super Sales

Eastern Round ends Chicago - May 2026

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

Duration16 days

From

USD 3,251

USD 3,153

Saving

USD 98

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42% OFF TODAY

Halloween Super Sales

Chicago to LA - May 2026

No booking fees

Best price guaranteed

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

42% OFF TODAY

Duration11 days

From

USD 5,584

USD 3,250

Saving

USD 2,335

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42% OFF TODAY

Halloween Super Sales

The Great American Crossing - May 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

42% OFF TODAY

Duration20 days

From

USD 7,509

USD 4,370

Saving

USD 3,139

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All Chicago Tours in May 2026

28 Trips in Chicago during May 2026 with 100 Reviews

Get a customized trip to Chicago in May 2026

Essential East Coast, Niagara and Chicago - May 2026

New York to Hollywood - May 2026

Chicago to Golden Gate - May 2026

Mackinac Island featuring the Tulip Time Festival - May 2026

Chicago, Niagara and New York - May 2026

Chicago and Niagara ROT - May 2026

New York to Hollywood - May 2026

California Coast, Chicago, and NY - May 2026

California Coast, Chicago, and NY, Ending in Washington - May 2026

From Washington to Las Vegas - May 2026

Chicago, Niagara and New York end Washington - May 2026

Eastern Round ends Chicago - May 2026

Chicago to LA - May 2026

The Great American Crossing - May 2026

28 Trips in Chicago during May 2026 with 100 Reviews

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

28 Trips in Chicago during May 2026 with 100 Reviews

Get a customized trip to Chicago in May 2026

28 Trips in Chicago during May 2026 with 100 Reviews