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Chicago United States Tours & Trips
35 Chicago trips. Tours from 23 tour companies. 0 reviews.
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33 trips exactly matchall of the the filters you selected.
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United States
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By Cosmos
none
Group Tour
Lodging level
Standard - 3 star
Physical level
Extreme
Trip pace
Balanced schedule
Visits
Albuquerque, Arizona, Bryce Canyon National Park, California, Chicago, Lake Powell, Las Vegas, Los Angeles, Monument Valley, St. Louis, Texas, Utah, Zion National Park
Themes
50 plus, Cultural
What travelers are saying
"We've taken over 10 group tours using Cosmos and Gate1. This trip last month, 9000 was not very good. -During booking, incorrect information was given about airport-hotel transfers -The whispers (listening devices) didn't work from the get-go, so no whispers were used during the 13 day trip. - Porters are no longer hired to bring your luggage to and from your room. (Very elderly had to handle their own luggage. Our friends had to help many of them.) -A few days into the trip one couple left. At the end of the trip we found out they had covid. Cosmos did not let us know; a few people weren't feeling well and two of our friends then tested positive. -One hotel was awful and not even up to "budget" standards -Many of the stops had castles, churches... but were not included, so be sure to count that in when pricing. don't plan to use Cosmos ever again. Gate1 is the best in my opinion. When my husband's passport was stolen, they assigned someone to go with him to the embassy, translate, etc...It was above and beyond what we expected "
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16 days From$3,069
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By Tauck
none
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."
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12 days From$10,290
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Save this trip to your favorites or other list
By Tauck
none
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
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."
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12 days From$9,490
Price was last confirmed this year
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Plan Your Chicago Trip
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By Tauck
none
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
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."
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12 days From$9,490
Price was last confirmed this year
More
Save this trip to your favorites or other list
By Tauck
none
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
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."
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12 days From$8,690
Price updated 1 year+ ago
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Save this trip to your favorites or other list
By Tauck
none
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
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."
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12 days From$8,990
Price updated 1 year+ ago
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By Tauck
none
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
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."
Save this trip to your favorites or other list
12 days From$8,990
Price updated 1 year+ ago
More
Save this trip to your favorites or other list
By Tauck
none
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 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
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."
Save this trip to your favorites or other list
12 days From$8,690
Price updated 1 year+ ago
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By Collette
premier
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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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.
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."
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-26%$4,228
11 days From$3,132
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Save this trip to your favorites or other list
By Collette
premier
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
"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"
Save this trip to your favorites or other list
-19%$4,365
9 days From$3,549
More
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.
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
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33 trips exactly matchall of the the filters you selected.
My selections:
United States
Best Chicago Tours by Price
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