Family Tours from Chicago
4.5 stars on(7,194 reviews)- Choose from 10 Chicago tours
- 150+ verified reviews from TourRadar travelers
- 24/7 customer support
10 best Family tour packages from Chicago
Compiled by
MelissaChicago travel expert at TourRadar
- Mackinac Island featuring the Tulip Time Festival (Chicago, IL to Southfield, MI) (2026)
- Mackinac Island (Chicago, IL to Southfield, MI) (2025)
- Rhythms of the Road (including Hammond)
- Highlights of Route 66
- Chicago, Niagara and New York
- Chicago and Niagara ROT
- Mackinac Island (Chicago, IL to Southfield, MI) (2026)
- Mackinac Island featuring the Tulip Time Festival (Chicago, IL to Southfield, MI) (2025)
- Chicago, Niagara and New York end Washington
- Legendary Route 66
Mackinac Island featuring the Tulip Time Festival (Chicago, IL to Southfield, MI) (2026)
29 Reviews by TourRadar travelers
- Explore Chicago's iconic architecture
- Celebrate at Michigan's Tulip Time Festival
- Relax at Mackinac Island's Grand Hotel
Duration 9 days Destinations Chicago, Holland, Grand Rapids, Mackinac Island, Frankenmuth, Dearborn, Southfield Age Range up to 99 year olds Operated in English Operator Collette From $3,899
10% Off- US$3,509You save $389
- Explore Chicago's iconic architecture
- Tour Mackinac Island by horse-drawn carriage
- Relax at the historic Grand Hotel's porch
Duration 9 days Destinations Chicago, Grand Rapids, Mackinac Island, Frankenmuth, Southfield, Dearborn Age Range 5 to 99 year olds Operated in English Operator Collette From $3,399
10% Off- US$3,059You save $339
Rhythms of the Road (including Hammond)
2 Reviews by TourRadar travelers“The tour took us exactly where we wanted to go. It was someone else doing the organising!”
James, traveled in June 2018
- Explore Chicago's landmarks and try deep-dish pizza
- Ascend the Gateway Arch and visit the westward museum
- Tour Nashville's Music Row and the Country Music Hall of Fame
Duration 10 days Destinations Chicago, St. Louis, Nashville, Memphis, Hammond, Lafayette, New Orleans Age Range up to 99 year olds Operated in English Operator Cosmos From $2,539
8% Off- US$2,339You save $200
Highlights of Route 66
125 Reviews by TourRadar travelers“The best ever, just sooooo good.”
Patrina, traveled in September 2023
- Explore Chicago's iconic Route 66 start
- Ascend the Gateway Arch for city views
- Enjoy live music in Branson's downtown
Duration 16 days Destinations Chicago, Pontiac, Springfield, St. Louis, Branson, Tulsa, Oklahoma City, Elk City, Amarillo, TucumcariSee all destinations Age Range up to 99 year olds Operated in English Operator Cosmos From $3,429
6% Off- US$3,229You save $200
- Explore Millennium Park and The Loop
- Tour Chicago's iconic landmarks and museums
- Enjoy dinner in Cleveland's vibrant Euclid Avenue
Duration 8 days Destinations Chicago, Cleveland, Niagara Falls, Corning, New York City Age Range up to 85 year olds Operated in English Operator Europamundo From $1,704
15% Off- US$1,448You save $255
- Explore Millennium Park and The Loop
- Tour Chicago's iconic landmarks and museums
- Dine in Cleveland's vibrant Little Italy
Duration 8 days Destinations Chicago, Cleveland, Niagara Falls, Detroit Age Range up to 85 year olds Operated in English Operator Europamundo From $1,704
15% Off- US$1,448You save $255
- Explore Chicago's iconic architecture
- Ride a horse-drawn carriage on Mackinac Island
- Tour Alden B. Dow's historic home and studio
Duration 9 days Destinations Chicago, Grand Rapids, Mackinac Island, Frankenmuth, Dearborn, Southfield Age Range up to 99 year olds Operated in English Operator Collette From
15% Off- US$3,699
Mackinac Island featuring the Tulip Time Festival (Chicago, IL to Southfield, MI) (2025)
29 Reviews by TourRadar travelers
- Explore Chicago's iconic architecture
- Celebrate at Holland's Tulip Time Festival
- Stay at Mackinac Island's Grand Hotel
Duration 9 days Destinations Chicago, Mackinac Island, Holland, Grand Rapids, Frankenmuth, Southfield, Dearborn Age Range up to 99 year olds Operated in English Operator Collette From $3,799
10% Off- US$3,419You save $379
- Explore Millennium Park and The Loop
- Tour Chicago's iconic landmarks and museums
- Visit Cleveland's Art Museum and Little Italy
Duration 10 days Destinations Chicago, Cleveland, Niagara Falls, Corning, New York City, Washington DC Age Range up to 85 year olds Operated in English Operator Europamundo From $2,130
15% Off- US$1,811You save $319
Duration 18 days Destinations Chicago, Springfield, St. Louis Age Range up to 99 year olds Operated in Only: German Operator DERTOUR From
15% Off- US$969
More about Chicago
FamilyUSA Travel Guide | All You Need to Know10 Best Backpacking Tours & Trips 2024/2025Best time to visit East Coast USA (Low & High Season)Best Time to Visit the West Coast, USA in 2024/2025 (with California)Best USA Vacation Spots for Couples: Parks, Cities and more5 Best Guided Backpacking Trips & ToursBest 10 Day USA Itineraries 2024/2025 (with Reviews)Best time to visit the USA in 2024/2025Weather in the USA in 2024/202510 Best Family Travel Agencies 2024