Chicago High Adventure Tours & Trip Packages

Chicago High Adventure Tours & Trips

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

2 trips exactly matchall of the the filters you selected. We are displaying some similar trips.
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High Adventure
Voyage to All Five Great Lakes: A Small Ship Adventure
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4.4/5 Great
100+ reviews
Small Group Tour
Lodging level
Standard - 3 star
Physical level
Moderate

Visits

Chicago, Cleveland, Mackinac Island, Niagara Falls, Toronto

Highlights

  • I’m comfortable with some walking throughout the day
  • I expect to get on and off of a coach, and I’m ready to stroll through cities and to stand for a few hours when we’re learning in museums

Themes

Culinary & Wine, High Adventure, Hiking & Walking, Nature & Wildlife, Train & Rail Journeys

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
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Signature City Chicago
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4.4/5 Great
100+ reviews
Small Group Tour
Lodging level
Standard - 3 star
Physical level
Moderate

Visits

Chicago

Highlights

  • I’m comfortable with some walking throughout the day
  • I expect to get on and off of a coach, and I’m ready to stroll through cities and to stand for a few hours when we’re learning in museums

Themes

Culinary & Wine, High Adventure, Hiking & Walking, Nature & Wildlife, Train & Rail Journeys

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
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Other trips you may like [sponsored]
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.
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 LA
Save this trip to your favorites or other list
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
Save this trip to your favorites or other list
More
Mackinac Island featuring the Grand Hotel and the Tulip Time Festival - 2024
Save this trip to your favorites or other list
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
Save this trip to your favorites or other list
More
Chicago to Golden Gate
Save this trip to your favorites or other list
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
Save this trip to your favorites or other list
More
2 trips exactly matchall of the the filters you selected. We are displaying some similar trips.
My selections:
High Adventure

Additional details

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