Chicago Tours in May 2026
Planning for a trip to Chicago during May? We offer 10+ tour packages to Chicago departing in May 2026 that have many customer reviews. Operated by our hand-picked, qualified travel experts, you will experience the best of Chicago on your May holiday.
See all Chicago May 2026 Tours
Best Price Guarantee
Best Price Guarantee
We guarantee the best prices on all our tours. If you find a lower price within 24 hours of booking, we'll match it.
Note: Prices may vary based on availability and demand.
Select from 10+ tours
10 Best May 2026 Tours in Chicago
Join one of these handpicked Chicago May 2026 tour packages, tailored to the season.
From the vibrant streets of New York City to the glitz of Hollywood, the 'New York to Hollywood' tour offers a sweeping 17-day city sightseeing adventure across the USA. Designed for travelers of all ages—families, seniors, and young adults—this easy-paced trip covers iconic highlights including the historic landmarks of Philadelphia, the monumental sights of Washington D.C., the presidential faces of Mount Rushmore, and the natural wonders of Yellowstone National Park. Cruise along legendary Route 66, cross the Mojave Desert, and experience the high-octane energy of Las Vegas before arriving in sunny Los Angeles. The unique selling point of this tour package is its comprehensive, coast-to-coast exploration, offering a seamless blend of urban excitement and natural beauty, all with the comfort of guided group travel.
17 days
fromUSD 3,613
This tour will transport you back in time as you travel down America’s Main Street — Route 66. Begin your journey with a night in the Windy City as you explore the architectural treasures of Chicago. Continue your trip towards Oklahoma City and discover incredible limestone caves and breathtaking memorial bridges enroute. Drive towards the beautiful city of Albuquerque to explore New Mexico's Spanish Colonial past and Native American cultures. Uncover the fascinating art museums of America's oldest capital Sante Fe, revel over the brilliant Redrock Mesas of Petrified Forest National Park and bask in the breathtaking views of the Grand Canyon’s South Rim. Enjoy a full day in Vegas before you head towards the Mojave Desert for Calico Ghost Town, one of the few original mining camps of the Old West. Top your journey off and drive towards the Santa Monica Pier, where you can discover Hollywood landmarks such as the Universal Studios or Anaheim’s Disneyland Park.
16 days
fromUSD 1,942
From the sights of New York to the glamour of Los Angeles, the "New York to Hollywood" tour invites you on a grand 17-day journey across America’s legendary cities and national parks. This guided group tour is ideal for experienced travelers seeking a relaxed yet comprehensive adventure. Begin in New York, then trace the nation’s founding in Philadelphia and Washington D.C. Cross into Canada for a magical Niagara Falls experience before heading west to Detroit, the birthplace of the American auto industry, and Chicago’s iconic skyline. Traverse the wilds of South Dakota’s Badlands and be awed by the monumental faces of Mount Rushmore. The adventure continues through Yellowstone’s geysers, Grand Teton’s peaks, and Utah’s Bryce Canyon before marveling at Lake Powell and the awe-inspiring Grand Canyon. Travel Route 66, soak in Las Vegas’ neon energy, and finish in Los Angeles, where Hollywood’s star-studded streets await. With accommodations, meals, and transportation provided, this trip’s unique selling point is its epic sweep—combining urban landmarks and natural wonders for an unforgettable coast-to-coast American tour package.
17 days
fromUSD 3,727
40% Off Today
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.
20 days
USD 7,133fromUSD 4,280
7% Off Today
This classic Midwestern tour features Illinois and Michigan. Savor two incredible nights amid the luxury of the Grand Hotel on Mackinac Island. Enjoy a horse and buggy tour of Mackinac Island. Explore the wonderful city of Chicago with a local guide. Visit the Bavarian-influenced town of Frankenmuth. In Dearborn, experience the inspirational Henry Ford Museum and view historic homes at Greenfield Village including the famous American workshops of Thomas Edison, Henry Ford and Robert Frost.
9 days
USD 3,749fromUSD 3,499
40% Off Today
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.
14 days
USD 5,876fromUSD 3,526
40% Off Today
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.
11 days
USD 5,652fromUSD 3,391
40% Off Today
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.
17 days
USD 6,570fromUSD 3,942
Hit the open road on a westbound adventure along Route 66, from the skyscrapers of Chicago to the sun-soaked shores of Santa Monica. This 12 day tour isn’t just about the miles - it’s about the stories behind every roadside diner, neon sign, and quirky small town. Walk in Lincoln’s footsteps in Springfield, explore the depths of Meramec Caverns, stand beneath the Gateway Arch, and snap a photo at the Cadillac Ranch. From blue whales in Oklahoma to wild burros in Oatman, this is classic Americana at its most vivid. With iconic sights, local eats, and a deep dive into the soul of the Mother Road, it’s a one-of-a-kind road trip through the heart of the USA.
12 days
fromUSD 6,915
Dreaming of the great American road trip? “Chicago to L.A” is an 11-day tour that captures the spirit of cross-country adventure, guiding you from the urban buzz of Chicago to the sun-drenched coast of Los Angeles. Journey through Yellowstone’s geothermal wonders, marvel at Mount Rushmore, and discover the surreal beauty of Bryce Canyon. Downtown Chicago’s famed architecture, Salt Lake City’s Temple Square, and a host of other iconic stops round out the itinerary. Perfect for families, young adults, and seniors, this easy tour balances city sightseeing with natural marvels, all in the comfort of a guided group. The unique selling point: The chance to experience the breadth of the USA’s landscapes and landmarks, all in one seamless, unforgettable trip package.
11 days
fromUSD 3,252
See all Chicago May 2026 Tours
Top Chicago Tour Activities for May 2026
From adventure tours to city sightseeing and others, here are some popular tour activities in Chicago with departures in May 2026.
Chicago May 2026 Tours for all Age Groups
Chicago tours in May 2026 designed for all ages—families, young adventurers, seniors, and everyone in between.
Chicago May 2026 Tour Types
Discover Chicago May 2026 tours in your way! Choose from group tours, private experiences, solo adventures, or guided and escorted tours.
