Chicago Moderate Tours &amp; Trips

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."

Save this trip to your favorites or other list

-26%$4,228

11 days From$3,132

More

Save this trip to your favorites or other list

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

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."

Save this trip to your favorites or other list

-26%$4,397

14 days From$3,257

More

Save this trip to your favorites or other list

Architectural Masterworks of Frank Lloyd Wright

preferred

4.4/5 Great

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."

Save this trip to your favorites or other list

7 days From$2,649

More

Save this trip to your favorites or other list

Winding Through the Windy City: Art & Architecture in Chicago

preferred

4.4/5 Great

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."

Save this trip to your favorites or other list

6 days From$1,699

More

Save this trip to your favorites or other list

STEM Chicago: Robotics & Game Design With Your Grandchild

preferred

4.4/5 Great

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."

Save this trip to your favorites or other list

6 days From$1,499

More

Save this trip to your favorites or other list

Voyage to All Five Great Lakes: A Small Ship Adventure

preferred

4.4/5 Great

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."

Save this trip to your favorites or other list

11 days From$7,299

More

Save this trip to your favorites or other list

Signature City Chicago

preferred

4.4/5 Great

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."

Save this trip to your favorites or other list

6 days From$1,649

More

Save this trip to your favorites or other list

Cruising the Great Lakes: Toronto to Chicago - Westbound 2025

By Tauck

none

4.2/5 Great

Small Ship Cruise

Lodging level

Premium - 4 star

Physical level

Moderate

Visits

Chicago, Mackinac Island, Toronto

Highlights

The mighty Great Lakes have played a vital role in the history and cultural fabric of North America for centuries... explore their storied waters... and unique cities and towns... that have grown along their shores...Enjoy a 7-night Great Lakes cruise between Chicago and Toronto aboard a beautiful Ponant yacht
plus two-night stays at your choice of premium hotels in these two great anchor cities. You'll sail through Lakes Ontario
Erie
Huron and Michigan
calling on destinations including Detroit

Themes

Small Ship Cruise

What travelers are saying

"Sad to see a once good tour company stumble and fall into mediocrity. That’s Tauck post-Covid. My May 2023 tour of Normandy, Brittany and the Loire Valley was done on the cheap by Tauck, yet cost me thousands of dollars extra as a solo traveler on a special small-group tour.   5-star hotels switched to 3 and 4 (without any compensation or explanation)… many more meals “on your own”… lots of “self-guided” tours of museums and chateaux and castles we knew nothing about… airline quality “rubber chicken” dinners, not in hotel restaurants, but in sad and isolated business convention spaces… poorly-trained newer Tour Directors (like the one on this tour) with limited experience traveling outside her tiny Canadian village or dealing with people from diverse backgrounds. She even confessed that this was a second gig job that took her away from her own business back home! You get what Tauck pays for, but unfortunately, not what YOU pay for.   Speaking to a “Guest Relations” agent was comically pointless. She tried to make everything my fault, which I now understand is par for the course with the “new” post-Covid Tauck. Please reconsider spending huge amounts of your hard-earned money on a tour company that has lost its way and no longer delivers."