Chicago Tours & Trip Packages

Chicago Tours & Trips

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

35 Trips match your criteria (21 - 35 shown)

Cruising the Great Lakes:  Toronto to Chicago - Westbound 2024
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4.2/5 Great
100+ reviews
Small Ship Cruise
Lodging level
Premium - 4 star
Physical level
Moderate

Visits

Chicago, 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
Show more

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."

Trip dates & details
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Cruising the Great Lakes: Chicago to Toronto - Eastbound 2025
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4.2/5 Great
100+ reviews
Small Ship Cruise
Lodging level
Premium - 4 star
Physical level
Moderate

Visits

Chicago, 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
Show more

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."

Trip dates & details
Save this trip to your favorites or other list
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Cruising the Great Lakes: Chicago to Toronto - Eastbound 2024
Save this trip to your favorites or other list
4.2/5 Great
100+ reviews
Small Ship Cruise
Lodging level
Premium - 4 star
Physical level
Moderate

Visits

Chicago, 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
Show more

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."

Trip dates & details
Save this trip to your favorites or other list
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Cruising the Great Lakes:  Toronto to Chicago - Westbound 2023
Save this trip to your favorites or other list
4.2/5 Great
100+ reviews
Small Ship Cruise
Lodging level
Premium - 4 star
Physical level
Moderate

Visits

Chicago, 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
Show more

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."

Trip dates & details
Save this trip to your favorites or other list
More
Cruising the Great Lakes: Chicago to Toronto - Eastbound 2023
Save this trip to your favorites or other list
4.2/5 Great
100+ reviews
Small Ship Cruise
Lodging level
Premium - 4 star
Physical level
Moderate

Visits

Chicago, 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
Show more

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."

Trip dates & details
Save this trip to your favorites or other list
More
Cruising the Great Lakes:  Toronto to Chicago - Westbound 2021
Save this trip to your favorites or other list
4.2/5 Great
100+ reviews
Small Ship Cruise
Lodging level
Premium - 4 star
Physical level
Moderate

Visits

Chicago, Toronto

Highlights

  • The mighty Great Lakes have played a vital role in the history and cultural fabric of North America for centuries... and our new 12-day small ship cruise invites you to explore their storied waters – and some of the unique cities and towns that have grown along their shoresEnjoy a 7-night Great Lakes cruise between Chicago and Toronto aboard the beautiful yacht Le Champlain
  • 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
Show more

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."

Trip dates & details
Save this trip to your favorites or other list
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Cruising the Great Lakes: Chicago to Toronto - Eastbound 2022
Save this trip to your favorites or other list
4.2/5 Great
100+ reviews
Small Ship Cruise
Lodging level
Premium - 4 star
Physical level
Moderate

Visits

Chicago, 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 the beautiful yachtLe Dumont d'Urville or Le Bellot
  • 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
Show more

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."

Trip dates & details
Save this trip to your favorites or other list
More
Cruising the Great Lakes:  Toronto to Chicago - Westbound 2022
Save this trip to your favorites or other list
4.2/5 Great
100+ reviews
Small Ship Cruise
Lodging level
Premium - 4 star
Physical level
Moderate

Visits

Chicago, 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 the beautiful yacht Le Dumont d'Urville or Le Bellotplus 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
  • Mackinac Island
Show more

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."

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