Chicago May 2026 Tours and Trip packages

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 to Golden Gate - May 2026

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 - May 2026

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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New York to Hollywood - May 2026

No booking fees

Best price guaranteed

Ready for a cross-country adventure packed with cultural icons and natural wonders? The New York to Hollywood tour is a 17-day trip perfect for young adults and families eager to experience the diverse landscape of the United States. Travel from the energy of New York City through the Midwest’s storied cities and national landmarks, all the way to the glamour of Los Angeles. From city highlights in Chicago to the awe-inspiring canyons of the Southwest, every day introduces a new chapter—history, adventure, and local flavors in cities like Salt Lake and Sioux. Guided activities ensure you see both the must-visit attractions and the hidden sides of America. The trip’s defining feature is its coast-to-coast sweep, offering travelers the chance to capture the spirit of the USA on one unforgettable tour package.

Adventure

Tour Type

Group Tour

Accommodation

Hotel, Lodge

Age Range

18-75 yrs

Operated in

english

Destinations

New York, Los Angeles, Cody, Yel

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

Duration17 days

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Chicago to LA - May 2026

No booking fees

Best price guaranteed

Set out on a landmark adventure from the Windy City to the West Coast on the Chicago to LA trip, an 11-day journey crafted for young adults and families. Start with a lively day in Chicago, exploring its arts, dining, and nightlife, then hit the open road to discover the rugged beauty of Badlands National Park and the Black Hills. Continue through Wyoming’s mountain landscapes, trek the trails of Yellowstone, and marvel at the Grand Canyon’s grandeur. The trip concludes in the glitz of Las Vegas and the laid-back vibes of California. The USP here is the coast-to-coast exploration, offering a dynamic mix of city life, national parks, and classic American road trip appeal.

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

Duration11 days

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Tours and Trip Packages to Chicago in May 2026

Get a customized trip to Chicago in May 2026

4 Trips in Chicago during May 2026

Chicago to Golden Gate - May 2026

The Great American Crossing - May 2026

New York to Hollywood - May 2026

Chicago to LA - May 2026

4 Trips in Chicago during May 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

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Tours and Trip Packages to Chicago in May 2026

Get a customized trip to Chicago in May 2026

4 Trips in Chicago during May 2026

Chicago to Golden Gate - May 2026

The Great American Crossing - May 2026

New York to Hollywood - May 2026

Chicago to LA - May 2026

4 Trips in Chicago during May 2026