10 Best Chicago Multiday Tours in June 2026

Get a customized trip to Chicago in June 2026

Plan a multi-country or regional adventure across Chicago in June 2026, with help from a local expert.

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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.

Super Sales

Essential East Coast, Niagara and Chicago - June 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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Mackinac Island featuring the Tulip Time Festival - June 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

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Super Sales

Chicago, Niagara and New York - June 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

Duration8 days

From

USD 1,625

USD 1,576

Saving

USD 49

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Super Sales

California Coast, Chicago, and NY - June 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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Super Sales

California Coast, Chicago, and NY, Ending in Washington - June 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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Super Sales

From Washington to Las Vegas - June 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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Super Sales

Chicago, Niagara and New York end Washington - June 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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Super Sales

From the West with Chicago and NY - June 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

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Super Sales

Toronto, Niagara and Chicago - June 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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Super Sales

Usa and Canada Panorama with Chicago - June 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 - June 2026

(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

Chicago and Niagara ROT - June 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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Super Sales

Eastern Round ends Chicago - June 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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Super Sales

Unmissable Canada, Niagara and Chicago - June 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

View Tour

All Chicago Tours in June 2026

20 Trips in Chicago during June 2026 with 100 Reviews

Get a customized trip to Chicago in June 2026

20 Trips in Chicago during June 2026 with 100 Reviews

Essential East Coast, Niagara and Chicago - June 2026

Mackinac Island featuring the Tulip Time Festival - June 2026

Chicago, Niagara and New York - June 2026

California Coast, Chicago, and NY - June 2026

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

From Washington to Las Vegas - June 2026

Chicago, Niagara and New York end Washington - June 2026

From the West with Chicago and NY - June 2026

Toronto, Niagara and Chicago - June 2026

Usa and Canada Panorama with Chicago - June 2026

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

Chicago and Niagara ROT - June 2026

Eastern Round ends Chicago - June 2026

Unmissable Canada, Niagara and Chicago - June 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 June 2026

20 Trips in Chicago during June 2026 with 100 Reviews

Get a customized trip to Chicago in June 2026

20 Trips in Chicago during June 2026 with 100 Reviews