Chicago Tours & Trip Packages

Chicago Tours & Trips

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

18 Trips match your criteria (1 - 18 shown)

Highlights of Route 66 Self-Drive
4.9/5 Excellent
100+ reviews
Self-Guided / Independent Tour
Lodging level
Premium - 4 star
Physical level
Easy
Trip pace
Full schedule

Visits

Albuquerque, Chicago, Las Vegas, Petrified Forest

Themes

National Parks, Nature & Wildlife

What travelers are saying

"I recently booked a trip to Japan with Audley Travel, and unfortunately, my experience was far from satisfactory. While the initial booking process was smooth and included clear communication via phone calls, the overall experience was disappointing, especially considering the high cost. The initial booking process was straightforward, and I had a couple of phone calls to clearly describe my essential needs for the trip. Communication before the trip was generally fine, but there were notable issues. Audley was unable to confirm all accommodation details, particularly my request for booking connecting rooms for a 4-person family. Instead, we were often crammed into a small room, which was far from ideal. Additionally, I had specifically requested kid-friendly hotels that offered western menu options. This was not the case at our last stop, where the hotel provided exclusively traditional Japanese food, which was not suitable for my family. One significant problem was the overwhelming amount of information provided, both printed and online. Unfortunately, this information was often inconsistent and riddled with mistakes. The tour guides we worked with received different itineraries, causing confusion and frustration. Even worse, the itinerary included activities that were not actually booked, despite being paid for. The same issue occurred with accommodation specifics. Had I known they were not going to be able to book per my request (which they had claimed to be working on), I would have challenged the overall cost and probably used a different provider. During the trip, Audley's support was severely lacking. We repeatedly tried to contact them for solutions to various issues but received no response. Audley works with a local partner in Japan, but they were limited in their ability to resolve our problems and often directed us back to Audley. This resulted in a frustrating loop of no solutions and a waste of time. It also appears that Audley is very short-staffed. We received an out-of-office notice from the person who booked our trip, and no backup or alternative assistance was offered. This lack of support is unacceptable, given the price we paid for their services. Audley Travel also failed to point out important festivals happening on the dates of our travel. This was a significant oversight and something one would definitely expect a competent travel agency to handle. To their credit, Audley Travel did a decent job with very basic needs such as train ticket bookings and airport pickups. However, for everything else, their service was far below expectations. In acknowledgment of their shortcomings, Audley Travel issued a refund, but it was not commensurate with the impact these issues had on our trip. Overall, I do not recommend Audley Travel and will not be booking with them again."

Trip dates & details
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Cruising the Great Lakes:  Toronto to Chicago - Westbound 2025
4.2/5 Great
100+ reviews
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
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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:  Toronto to Chicago - Westbound 2024
4.2/5 Great
100+ reviews
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
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
Save this trip to your favorites or other list
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Cruising the Great Lakes: Chicago to Toronto - Eastbound 2025
4.2/5 Great
100+ reviews
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
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
Save this trip to your favorites or other list
More
Cruising the Great Lakes: Chicago to Toronto - Eastbound 2024
4.2/5 Great
100+ reviews
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
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
Save this trip to your favorites or other list
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Cruising the Great Lakes:  Toronto to Chicago - Westbound 2021
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

"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
Save this trip to your favorites or other list
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Cruising the Great Lakes: Chicago to Toronto - Eastbound 2022
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

"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
Save this trip to your favorites or other list
More
Cruising the Great Lakes:  Toronto to Chicago - Westbound 2022
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

"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
Save this trip to your favorites or other list
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