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Tours North America United StatesChicago

Chicago Group Tours & Trips

35 Chicago trips. Tours from 23 tour companies. 0 reviews.

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17 trips exactly matchall of the the filters you selected.

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Mackinac Island - 2024

By Collette

premier

4.7/5 Excellent

100+ reviews

Group Tour

Why we love them

With a history that spans back to 1918, they have unparalleled expertise in the guided tour industry and can cater to all types of travelers.

Lodging level

Premium - 4 star

Physical level

Very Easy

Trip pace

Balanced schedule

Visits

Chicago

Highlights

D
Visit the Henry Ford Museum and explore Greenfield Village.
Climb aboard your horse-drawn carriage for an island tour.
Explore the many gardens of the Frederik Meijer Gardens and Sculpture Park.
Spend two nights at the glorious Victorian-era resort, the Grand Hotel.

Themes

Cultural

What travelers are saying

"It was a wonderful trip and experience! We are still sorting all the pictures and memories about it, and some of them I would like to share with you - read my diary about this trip! My Diary about our trip to South Dakota shorturl.at/efoX1"

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-19%$3,996

9 days From$3,249

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Chicago to LA

By Travel Talk

Local Expert

Verified by Travelstride as locally operated and in the top of their field for customer reviews, local knowledge, and safety.

4.9/5 Excellent

100+ reviews

Group Tour

Lodging level

Standard - 3 star

Physical level

Moderate

Visits

Chicago, Los Angeles

Themes

Cultural, Local Immersion & Homestays

What travelers are saying

"Did the Jordan Essential Tour, it was absolutely amazing. This was my first Group Travel Tour and I loved it. I was worried about being the oldest one on the tour (I’m 34), but it was a good mix of ages. It was incredible to travel with people of different nationalities. Our Tour guide Issa was great. At all times he was really helpful. Taught us a lot about Jordanien history and culture. The tour was a great mix of everything...sightseeing, exploring, chillin and partying."

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-26%$3,876

11 days From$2,871

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Mackinac Island featuring the Grand Hotel and the Tulip Time Festival - 2024

By Collette

premier

4.7/5 Excellent

100+ reviews

Group Tour

Why we love them

With a history that spans back to 1918, they have unparalleled expertise in the guided tour industry and can cater to all types of travelers.

Lodging level

Premium - 4 star

Physical level

Very Easy

Trip pace

Balanced schedule

Visits

Chicago

Highlights

D
Visit the Henry Ford Museum and explore Greenfield Village.
Climb aboard your horse-drawn carriage for an island tour.
Visit quaint Frankenmuth, home to the world's largest Christmas store.
Spend two nights at the glorious Victorian-era resort, the Grand Hotel.

Themes

Cultural

What travelers are saying

Trip dates & details

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-19%$4,365

9 days From$3,549

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Chicago to Golden Gate

By Travel Talk

Local Expert

Verified by Travelstride as locally operated and in the top of their field for customer reviews, local knowledge, and safety.

4.9/5 Excellent

100+ reviews

Group Tour

Lodging level

Standard - 3 star

Physical level

Moderate

Visits

Chicago, San Francisco

Themes

Cultural, Local Immersion & Homestays

What travelers are saying

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-26%$4,030

14 days From$2,985

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Architectural Masterworks of Frank Lloyd Wright

By Road Scholar

preferred

4.4/5 Great

100+ reviews

Group Tour

Lodging level

Standard - 3 star

Physical level

Very Easy

Trip pace

Full schedule

Visits

Chicago

Highlights

In historic Oak Park, Illinois, discover Frank Lloyd Wright’s home and studio, designed by Wright and considered by many scholars to be the world’s first example of true modern architecture
Experience the work of Frank Lloyd Wright in Racine through an exploration of the S
C
Johnson Wax Administration Building and Research Tower, considered one of the 25 most important buildings of the 20th Century
Learn about the rich history and culture of architecture in Chicago on an architectural study of the city from the Chicago River

Themes

50 plus, Education / Learning

What travelers are saying

"Because I have Stage 4 cancer, I chose to spend the extra money for trip insurance in case my cancer recurred. When a scan showed that it had, I cancelled my trip. I sent to them the medical documents from the Mayo Clinic confirming my new diagnosis. They sent me an email telling me my oncologist needed to fill in a form. I asked my oncologist to do that and I submitted it by fax on April 6th. When I didn’t hear anything, I sent them more medical documentation and asked them to please push forward my refund as I have travel expenses from a clinical trial coming up. Several days later I received an email that they needed further documentation from my doctor. How much more documentation do you need than the patient has stage 4 metastatic cancer and is starting a clinical trial??? This is heartless to me. Please don’t plan to travel through Road Scholar if you’re medically vulnerable!!"

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7 days From$1,999

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Out and About in Chicago: Art, Architecture, History and More

By Road Scholar

preferred

4.4/5 Great

100+ reviews

Group Tour

Lodging level

Standard - 3 star

Physical level

Very Easy

Trip pace

Full schedule

Visits

Chicago

Highlights

Go inside the Art Institute of Chicago with an expert on the artworks of its world-class, 300,000-piece permanent collection
Study city architecture on a walk with a scholar and from a boat on the Chicago River
Learn about the life and work of the iconic architect Frank Lloyd Wright, through an expert-led exploration of his Prairie-style home and studio in charming and historic Oak Park, Illinois

Themes

50 plus, Education / Learning

What travelers are saying

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6 days From$1,349

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Windy City Adventures With Your Grandchild

By Road Scholar

preferred

4.4/5 Great

100+ reviews

Group Tour

Lodging level

Standard - 3 star

Physical level

Very Easy

Trip pace

Full schedule

Visits

Chicago

Highlights

Learn about Chicago history and architecture from an urban expert on a ship along the Chicago River
Visit iconic Wrigley Field, home of the Chicago Cubs, where an expert takes you to stadium areas most fans never see
With Chicago architecture as your inspiration, take part in a hands-on activity with Internationally known Lego Artist Rocco Buttiere

Themes

50 plus, Education / Learning

What travelers are saying

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6 days From$1,399

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Rhythms of the Road

By Cosmos

none

4/5 Great

100+ reviews

Group Tour

Lodging level

Standard - 3 star

Physical level

Moderate

Trip pace

Balanced schedule

Visits

Chicago, Memphis, Mississippi, Nashville, New Orleans, St. Louis

Themes

50 plus, Cultural

What travelers are saying

"We've taken over 10 group tours using Cosmos and Gate1. This trip last month, 9000 was not very good. -During booking, incorrect information was given about airport-hotel transfers -The whispers (listening devices) didn't work from the get-go, so no whispers were used during the 13 day trip. - Porters are no longer hired to bring your luggage to and from your room. (Very elderly had to handle their own luggage. Our friends had to help many of them.) -A few days into the trip one couple left. At the end of the trip we found out they had covid. Cosmos did not let us know; a few people weren't feeling well and two of our friends then tested positive. -One hotel was awful and not even up to "budget" standards -Many of the stops had castles, churches... but were not included, so be sure to count that in when pricing.  don't plan to use Cosmos ever again. Gate1 is the best in my opinion. When my husband's passport was stolen, they assigned someone to go with him to the embassy, translate, etc...It was above and beyond what we expected  "

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10 days From$2,399

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On Travelstride you can find 35 trips to Chicago and more than 20,000 trips worldwide ranging from budget to luxury and private guided to group tours and everything in between. Only on Stride can you find and compare expert-planned trips from 1,000+ tour operators, cruise lines and local experts. Read traveler and professional reviews so you can confidently find your perfect trip.

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