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Tours North America United StatesChicago

Chicago Tours & Trips

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

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35 Trips match your criteria (1 - 20 shown)

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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."

Trip dates & details

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-32%$4,228

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

Trip dates & details

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-32%$4,397

14 days From$2,985

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Highlights of Route 66 Self-Drive

By Audley Travel

preferred

4.9/5 Excellent

100+ reviews

Self-Guided / Independent Tour

Lodging level

Premium - 4 star

Physical level

Easy

Trip pace

Full schedule

Visits

Albuquerque, Chicago, Las Vegas, Petrified Forest

Themes

National Parks, Nature & Wildlife

What travelers are saying

"It's hard to describe how lucky we are to have been able to work with Stephanie in planning our honeymoon to Japan. From the very beginning, Stephanie was friendly, flexible, and an absolute wealth of knowledge. We had several meetings with her leading up to our trip to come up with the perfect itinerary. Throughout this, Stephanie was mindful of our budget, without sacrificing anything. During our trip, Audley was available at all hours to help with anything and everything which was such a relief to know we had that resource available to us. I truly cannot imagine having planned this trip without all of Stephanie's guidance and knowledge- and cannot imagine taking another big trip like this without the help of Audley. Thank you again!"

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15 days From$2,967

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Monet to Modern at the Art Institute of Chicago

By Road Scholar

preferred

4.4/5 Great

100+ reviews

Small Group Tour

Lodging level

Standard - 3 star

Physical level

Wheelchair Accessible

Trip pace

Full schedule

Visits

Chicago

Highlights

Enjoy early access to the museum each morning before it opens to the public, expert-led discussions before original works of art without the crowds and admission to all special exhibitions
Explore the Art Institute’s new Modern Wing from the outside, examining its architecture and the spectacular surroundings of Millennium Park on an expert-led architectural walk
Get the back story to the largest gift in the Art Institute's history of 42 masterpieces of contemporary art donated by Chicago based collectors and philanthropists Edlis and Neeson

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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4 days From$949

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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

Trip dates & details

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7 days From$1,999

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Architectural Masterworks of Frank Lloyd Wright

By Road Scholar

preferred

4.4/5 Great

100+ reviews

Small Group Tour

Lodging level

Standard - 3 star

Physical level

Moderate

Visits

Chicago

Highlights

I like to spend much of the day exploring
Whether walking through historic neighborhoods at a moderate pace or out and about on a coach, I prefer to keep my days full
Stairs don’t bother me, and I love to keep up with the group

Themes

Culinary & Wine, National Parks, Nature & Wildlife, Relaxing Retreats, Yoga, Meditation & Wellness, Photography, Holy Land

What travelers are saying

Trip dates & details

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7 days From$2,649

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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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