10 Best Chicago Multiday Tours in August 2026

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.

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

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Super Sales

From the West with Chicago and NY - August 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

View Tour

Super Sales

Unmissable Canada, Niagara and Chicago - August 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

View Tour

Super Sales

From the West with Chicago and NY, Ending in Washington - August 2026

No booking fees

Best price guaranteed

Cross the United States in comfort on the "From the West with Chicago and NY, Ending in Washington" city sightseeing trip. Spanning 16 days from Los Angeles to Washington D.C., this group tour is tailored for seniors who appreciate easy-paced travel. Visit iconic destinations including New York, Cleveland, and Niagara Falls, with hotels, transport, and meals seamlessly arranged. Its unique feature is the coast-to-coast route, providing a comprehensive look at both major cities and natural wonders across the country.

Sightseeing Tours

Tour Type

Group Tour

Accommodation

Hotel

Age Range

15-99 yrs

Operated in

english

Destinations

Los Angeles, Washington D.C., Ni

Los Angeles, Washington D.C., Niagara Falls, New York, Las Vegas, Flagstaff, Chicago, Cleveland

Duration16 days

From

USD 3,923

View Tour

All Chicago Tours in August 2026

3 Trips in Chicago during August 2026

Get a customized trip to Chicago in August 2026

3 Trips in Chicago during August 2026

From the West with Chicago and NY - August 2026

Unmissable Canada, Niagara and Chicago - August 2026

From the West with Chicago and NY, Ending in Washington - August 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 August 2026

3 Trips in Chicago during August 2026

Get a customized trip to Chicago in August 2026

3 Trips in Chicago during August 2026

From the West with Chicago and NY - August 2026

Unmissable Canada, Niagara and Chicago - August 2026

From the West with Chicago and NY, Ending in Washington - August 2026