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Tours and Trip Packages to Chicago in Fall

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.

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Tours and Trip Packages to Chicago in Fall

Apr 2026 May 2026 Jun 2026 Jul 2026 Aug 2026 Sep 2026 Oct 2026

Showing 1 - 4 of 4 results

Duration

7 days23 days

Day Tour
Multiday Tour

Departures

September 2026
October 2026
November 2026

Price

USD 1,366USD 5,260

Budget Tours
Luxury Tours

Tour Types

Group tours
Independent tours

Age

Young Travelers (Age 18-39)Mature Travelers (Age 40-59)Senior Travelers (Age 60+)

Activities

City sightseeing
Cultural, religious and historic sites
Adventure
Sightseeing Tours
Explorer

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.

Start & End Location

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Guided Tours
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Last Minute Deals

Apr 2026 May 2026 Jun 2026 Jul 2026 Aug 2026 Sep 2026 Oct 2026

Duration

7 days23 days

Day Tour
Multiday Tour

Departures

September 2026
October 2026
November 2026

Tour Types

Group tours
Independent tours

Activities

City sightseeing
Cultural, religious and historic sites
Adventure
Sightseeing Tours
Explorer

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

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Start & End Location

Price

USD 1,366USD 5,260

Budget Tours
Luxury Tours

Tours and Trip Packages to Chicago in Fall

Tours and Trip Packages to Chicago in Fall

Get a customized trip to Chicago in Fall

Page 2 of 4 Trips in Chicago

Page 2 of 4 Trips in Chicago

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Boat tours, water sports and marine wildlife

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Beach, romance, getaways and relaxation

Special interests and hobbies

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Tours and Trip Packages to Chicago in Fall

Tours and Trip Packages to Chicago in Fall

Get a customized trip to Chicago in Fall

Page 2 of 4 Trips in Chicago

Page 2 of 4 Trips in Chicago