Chicago Tours & Trip Packages

Chicago Tours & Trips

10 Chicago trips. Tours from 5 tour companies. 0 reviews.

10 Trips match your criteria (1 - 10 shown)

Highlights of Route 66 Self-Drive
4.8/5 Excellent
100+ reviews
Self-Guided / Independent Tour
Lodging level
Premium - 4 star
Physical level
Easy
Trip pace
Full schedule

Themes

Nature & Wildlife, National Parks

What travelers are saying

"Third holiday with Audley and the best yet. They really know the countries and work with you to put together the perfect itinerary. They think of everything. They are also on hand to deal with any issues that arise while you are away. We’ll be travelling with Audley again."

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Cruising the Great Lakes:  Toronto to Chicago - Westbound 2025
4.4/5 Great
100+ reviews
Small Ship Cruise
Lodging level
Premium - 4 star
Physical level
Moderate

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
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Themes

Small Ship Cruise

What travelers are saying

"My husband and I booked the Yellowstone tour with Tauck expecting so much more with the accommodations, food, and tour director based on the price point. We were sadly disappointed but still tried to enjoy the experience. Rooms were dirty, food were often buffets and other group dinners with some food inedible. We noticed other tours staying in our hotels and paying much less for their tours. One positive was we never touched our luggage which was nice but my small suitcase was damaged during one transfer. Word to the wise… read their emails thoroughly as the email we received a few weeks before our trip reads like a disclaimer for poor service and accommodations."

Trip dates & details
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Cruising the Great Lakes: Chicago to Toronto - Eastbound 2025
4.4/5 Great
100+ reviews
Small Ship Cruise
Lodging level
Premium - 4 star
Physical level
Moderate

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

"My husband and I booked the Yellowstone tour with Tauck expecting so much more with the accommodations, food, and tour director based on the price point. We were sadly disappointed but still tried to enjoy the experience. Rooms were dirty, food were often buffets and other group dinners with some food inedible. We noticed other tours staying in our hotels and paying much less for their tours. One positive was we never touched our luggage which was nice but my small suitcase was damaged during one transfer. Word to the wise… read their emails thoroughly as the email we received a few weeks before our trip reads like a disclaimer for poor service and accommodations."

Trip dates & details
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Rhythms of the Road
4/5 Great
100+ reviews
Group Tour
Lodging level
Standard - 3 star
Physical level
Moderate
Trip pace
Balanced schedule

Themes

Cultural, 50 Plus

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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Trans-American Adventure
4/5 Great
100+ reviews
Group Tour
Lodging level
Standard - 3 star
Physical level
Extreme
Trip pace
Full schedule

Themes

Cultural, 50 Plus

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  "

Trip dates & details
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Highlights of Route 66 with Mother Road Festival & Albuquerque Balloon Fiesta
4/5 Great
100+ reviews
Group Tour
Lodging level
Premium - 4 star
Physical level
Very Easy
Trip pace
Balanced schedule

Themes

Cultural, 50 Plus

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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Highlights of Route 66 and Albuquerque Balloon Fiesta
4/5 Great
100+ reviews
Group Tour
Lodging level
Standard - 3 star
Physical level
Very Easy

Themes

Cultural, 50 Plus

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  "

Trip dates & details
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Highlights of Route 66
4/5 Great
100+ reviews
Group Tour
Lodging level
Standard - 3 star
Physical level
Extreme
Trip pace
Balanced schedule

Themes

Cultural, 50 Plus

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  "

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