Chicago Fall Tours and Trip packages

Traveling to Chicago in Fall? We offer 25+ tours, trips and vacation packages to Chicago in Fall. Our Chicago in Fall tour packages and trips have 100+ customer reviews. All the Chicago Fall tour packages and trips are carried out by hand-picked, qualified local and international Chicago tour operators.

Duration

7 days23 days

Day Tour
Multiday Tour

Departures

September 2026
October 2026
November 2026

Tour Types

Group tours
Independent tours

Physical Rating

relaxed
easy

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.

Guide Types

Guided Tours
Self Guided Tours

Get a customized trip to Chicago in Fall

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

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Start & End Location

Price

USD 1,366USD 5,260

Budget Tours
Luxury Tours

1 Trip in Chicago

New York to Hollywood - Fall tours

Trip customizable

Best price guaranteed

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.

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

View Tour

Upcoming Departures

Sep 18

10+ seats remaining

Sep 25

10+ seats remaining

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 Fall

Get a customized trip to Chicago in Fall

1 Trip in Chicago

1 Trip in Chicago

New York to Hollywood - Fall tours