Chicago Tours & Trip Packages

Chicago Tours & Trips

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

35 trips exactly matchall of the the filters you selected.
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Mackinac Island  - 2024
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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.
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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"

Trip dates & details
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Chicago to LA
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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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Mackinac Island featuring the Grand Hotel and the Tulip Time Festival - 2024
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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.
Show more

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"

Trip dates & details
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Chicago to Golden Gate
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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

"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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Highlights of Route 66 Self-Drive
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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!"

Trip dates & details
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Monet to Modern at the Art Institute of Chicago
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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

"Our family of four, including two adult children, took the Bicycling: Day Trips to Paradise in Canada. This trip is entirely outsourced to the owners of the inn, there are no Road Scholar employees involved in the trip. Two of us have taken bicycle trips all over the world and the bicycling component of this trip was disorganized, haphazard and almost unsafe. We all filled out forms giving details regarding our bicycle fitting months before the trip. On the first day, the leader Stephen, went around the room and asked the same questions and said everyone would get fitted in the morning before we began the first ride. The morning brought a rack of bikes, all different types in various levels of readiness. There were road bikes, hybrid bikes, mountain bikes and e-bikes. The rides were all on paved surfaces and the mountain bikes were heavy and the additional suspension added weight. The bike I received had rust on the chain and rear sprocket. When I asked about it, was told they were waiting for another van to show up with tools and equipment. Once it arrived, they gave me the lubricant to spray on the rust. My wife’s bike would not shift into the high gear on the front sprocket. Instead of adjusting the derailleur, they suggested spraying it with lubricant. Our one son is over six feet and needed a larger frame bike, even though he detailed it in the bike form months ago, there was no bike to fit him. One of the guides, then went home and brought a larger bike that was a full suspension mountain bike for him. The bike was very heavy, hard to control on the road and he felt unsafe. After two days, one of the guides convinced Stephen that they could adjust a hybrid bike to fit him. Clearly there was no work done to prepare the bikes for the trip. Many of the bikes needed adjusting and all needed lubricant to function easily. For every day, there was a tray of snacks placed out for us to take along the ride. None of the bikes had any baskets or attached bags, so if you didn’t bring a small day pack, there was no way to carry the snacks. For lunch on the rides, they brought exactly one sandwich for each rider. Since most of us get hungry while doing a day of exercise, it would have been helpful to have a few extras. On one day, they ran out of sandwiches and one of the leaders that were riding with us did not get lunch. Do NOT take this trip if you are expecting it to be a bicycling trip. We have used VBT and Discovery Bicycle Tours many times over the past 25 years and they are excellent bike tour companies. Lastly, after sharing these details with Road Scholar after the trip, their response was weak at best. After doing the full reviews and having to call them, their response was to give us $200 credit after spending $8000 on this trip. Not only was that insulting, they assumed that I would take another trip with their organization."

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Architectural Masterworks of Frank Lloyd Wright
Save this trip to your favorites or other list
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

"Our family of four, including two adult children, took the Bicycling: Day Trips to Paradise in Canada. This trip is entirely outsourced to the owners of the inn, there are no Road Scholar employees involved in the trip. Two of us have taken bicycle trips all over the world and the bicycling component of this trip was disorganized, haphazard and almost unsafe. We all filled out forms giving details regarding our bicycle fitting months before the trip. On the first day, the leader Stephen, went around the room and asked the same questions and said everyone would get fitted in the morning before we began the first ride. The morning brought a rack of bikes, all different types in various levels of readiness. There were road bikes, hybrid bikes, mountain bikes and e-bikes. The rides were all on paved surfaces and the mountain bikes were heavy and the additional suspension added weight. The bike I received had rust on the chain and rear sprocket. When I asked about it, was told they were waiting for another van to show up with tools and equipment. Once it arrived, they gave me the lubricant to spray on the rust. My wife’s bike would not shift into the high gear on the front sprocket. Instead of adjusting the derailleur, they suggested spraying it with lubricant. Our one son is over six feet and needed a larger frame bike, even though he detailed it in the bike form months ago, there was no bike to fit him. One of the guides, then went home and brought a larger bike that was a full suspension mountain bike for him. The bike was very heavy, hard to control on the road and he felt unsafe. After two days, one of the guides convinced Stephen that they could adjust a hybrid bike to fit him. Clearly there was no work done to prepare the bikes for the trip. Many of the bikes needed adjusting and all needed lubricant to function easily. For every day, there was a tray of snacks placed out for us to take along the ride. None of the bikes had any baskets or attached bags, so if you didn’t bring a small day pack, there was no way to carry the snacks. For lunch on the rides, they brought exactly one sandwich for each rider. Since most of us get hungry while doing a day of exercise, it would have been helpful to have a few extras. On one day, they ran out of sandwiches and one of the leaders that were riding with us did not get lunch. Do NOT take this trip if you are expecting it to be a bicycling trip. We have used VBT and Discovery Bicycle Tours many times over the past 25 years and they are excellent bike tour companies. Lastly, after sharing these details with Road Scholar after the trip, their response was weak at best. After doing the full reviews and having to call them, their response was to give us $200 credit after spending $8000 on this trip. Not only was that insulting, they assumed that I would take another trip with their organization."

Trip dates & details
Save this trip to your favorites or other list
More
Architectural Masterworks of Frank Lloyd Wright
Save this trip to your favorites or other list
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

"Our family of four, including two adult children, took the Bicycling: Day Trips to Paradise in Canada. This trip is entirely outsourced to the owners of the inn, there are no Road Scholar employees involved in the trip. Two of us have taken bicycle trips all over the world and the bicycling component of this trip was disorganized, haphazard and almost unsafe. We all filled out forms giving details regarding our bicycle fitting months before the trip. On the first day, the leader Stephen, went around the room and asked the same questions and said everyone would get fitted in the morning before we began the first ride. The morning brought a rack of bikes, all different types in various levels of readiness. There were road bikes, hybrid bikes, mountain bikes and e-bikes. The rides were all on paved surfaces and the mountain bikes were heavy and the additional suspension added weight. The bike I received had rust on the chain and rear sprocket. When I asked about it, was told they were waiting for another van to show up with tools and equipment. Once it arrived, they gave me the lubricant to spray on the rust. My wife’s bike would not shift into the high gear on the front sprocket. Instead of adjusting the derailleur, they suggested spraying it with lubricant. Our one son is over six feet and needed a larger frame bike, even though he detailed it in the bike form months ago, there was no bike to fit him. One of the guides, then went home and brought a larger bike that was a full suspension mountain bike for him. The bike was very heavy, hard to control on the road and he felt unsafe. After two days, one of the guides convinced Stephen that they could adjust a hybrid bike to fit him. Clearly there was no work done to prepare the bikes for the trip. Many of the bikes needed adjusting and all needed lubricant to function easily. For every day, there was a tray of snacks placed out for us to take along the ride. None of the bikes had any baskets or attached bags, so if you didn’t bring a small day pack, there was no way to carry the snacks. For lunch on the rides, they brought exactly one sandwich for each rider. Since most of us get hungry while doing a day of exercise, it would have been helpful to have a few extras. On one day, they ran out of sandwiches and one of the leaders that were riding with us did not get lunch. Do NOT take this trip if you are expecting it to be a bicycling trip. We have used VBT and Discovery Bicycle Tours many times over the past 25 years and they are excellent bike tour companies. Lastly, after sharing these details with Road Scholar after the trip, their response was weak at best. After doing the full reviews and having to call them, their response was to give us $200 credit after spending $8000 on this trip. Not only was that insulting, they assumed that I would take another trip with their organization."

Trip dates & details
Save this trip to your favorites or other list
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