John Chaffin CTA

Chicago, United States
Why work with an advisor? 
Travel Specialties
  • Food & Wine
  • Culture, History & Arts
  • Safari
  • Independent Tours
  • Ocean Cruising

  • No Destinations
Selling Travel Since
  • English

My Background

One of John’s great loves is Italy; the beautiful landscape, friendly people, and regional food and wines draw him to this wonderful country.  John’s knowledge of Italy is extensive as he travels there as often as possible.  Two of John’s other favorite destinations are the game preserves of Southern Africa and the Galapagos Islands.

John recently visited the countries of Thailand, Laos and Cambodia. He recently climbed the temples in Angor Wat, cruised down the Mekong River in Laos, and enjoyed staying in Bangkok and Hong Kong at the end of the trip.

John avidly participates in travel industry events and trade shows including the annual  Virtuoso Travel Week attended by over 3,000 leaders in the luxury travel market. With John’s experience and passion for travel, you are guaranteed personalized service and expert travel advice on any vacation dream you are seeking.

When John is not traveling, he resides in Wrigleyville and is an avid “foodie” and Chicago sports fan.

Places I Have Traveled

Reviews and Recommendations for John Chaffin


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All reviews are from confirmed guests sharing exclusive insights

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Highly recommend

By: Jan

Reviewed on: 11 Oct 2013

Everything was taken care of. The new trip website helped us get boarding passes.

Highly recommended

By: Donato

Reviewed on: 11 Oct 2013

John is very responsive, a very nice person to work with. understands my needs always and takes good care of me.

There is no one better

By: am2011

Reviewed on: 18 Oct 2013

I have used John for over 20 years. He has arranged trips for us to London, Paris, China, Galapagos Islands, South Africa,Sicily, and numerous US destinations. Every trip has been perfect and more important, if there were some minor issues, John made sure they were corrected.

By: LRHam

Reviewed on: 21 Oct 2013

We were well taken care of and are grateful to John for making last minute changes to our car rental. He followed up on all questions or concerns we had in a timely manner. Thanks John for all your help.

good job, as always

By: bambo

Reviewed on: 26 Nov 2013

John is very polite and responsive. I had to change my ticket 3 times, and John handled it very professionally, punctually and with a kind service. He never get s upset, follows through and does not hesitate to get back to me promptly with any questions or information.

Kudos to John...we're very happy customers!

By: ajw

Reviewed on: 24 Nov 2013

John is just great...I've been working with him for years and he always understands what I'm looking for! He strives to find the best travel experience for our family, and without fail, provides professional, straightforward, engaged service. He finds us good values and is very flexible. Work with John...we're sure you'll be very satisfied.

Excellent trip planner

By: Sue

Reviewed on: 24 Nov 2013

John is extremely helpful in booking flights and recommending hotels. He has a very good sense of what his client will like and then matching that with the appropriate hotel and amenities. I have worked with John for years and will continue to take his advice and suggestions on all future trips

By: Not provided

Reviewed on: 12 Dec 2013

John has been very helpful and professional in arranging and re arranging our trip to Spain. He knows the hotels in Barcelona and had directed me to one I am sure we will all like. I haven't been to Barcelona in 20 years and am going with 3 other people so need all the help I can get from John on restaurants and side excursions out of Barcelona. He has directed me to some good websites for which I am grateful!


By: Abm

Reviewed on: 23 Dec 2013

Every vacation John plans is fabulous. He works very hard to plan every trip to meet or exceed our expectations. He is very creative. Above all, he wants to provide us with value. I have used John for well over twenty years.

Highly recommended

By: Alex

Reviewed on: 02 Jan 2014

John has always been the best planner I had. He always knows what I need or expects and always delivers. I will always use John as my agent whether it's local or overseas. He is simply the best

Highly recommend

By: Mary4341

Reviewed on: 07 Feb 2014

John was beyond patient with us as we planned this trip.  He answered all of our questions and concerns thoroughly and in a timely manner.  He worked diligently to ensure that we would enjoy our cruise experience and kept us informed of upgrades and amenities. Thank you so very much.

Extremely efficient/knowledgeable

By: Susy56

Reviewed on: 05 Mar 2014

Great job as always!

By: ajw298

Reviewed on: 12 Jan 2015

John did a great job for us and found us the flights we were looking for with no worries. I've always appreciated John's professional attitude, competence, dependability, and great customer service!

good job

By: Bambo

Reviewed on: 30 Mar 2015

John, as always, was efficient and prompt in getting me reservations o short notice. He always returns my calls promptly with an answer. Dennis

As always a great trip!

By: ajw298

Reviewed on: 16 Aug 2015

Thanks so much for setting up our travel arrangements so efficiently...excellent as always!


By: Renee

Reviewed on: 23 Oct 2015

We had such an amazing time in Argentina thanks to John! The recommendations John provided were excellent and really made the trip. From accommodations to dinner recommendations, John made the trip fun, exciting, and easy to plan for. He was willing to jump on multiple phone calls to answer our questions and was always responsive. He answered every questions knowledgeably and was such a great resource! We will stick with John for all of our trips!

Very Professional

By: Pam 7

Reviewed on: 06 Nov 2015

John was wonderful to work with. Fast with the return emails and very knowledgable in helping me with my trip to Napa.

Great Customer Service

By: Bubba

Reviewed on: 07 Jan 2016

Had a great time at the Park Hyatt Aviara and in the surrounding area - hikes in arroyos and nature preserves, touring missions, beach towns, sea food, whale watching, theater for New Years Eve, and more. Aviara has that service-based attention to detail that made us feel pampered. When the airline cancelled our flight, John Chaffin helped us get new flights, which actually improved our travel times.

Amazing Bhutan

By: Gastro1

Reviewed on: 11 Sep 2016

Bhutan was incredible in late August. Weather cleared with warm, sunny mornings and light afternoon Monsoon rains (did not deter our adventure). We found the UMA by COMO hotels to be one of the BEST we've stayed at. Sustainable tourism (they provide seeds for vegetables and fruits to local farmers who sell back to the hotel). Staff was outstanding and personal. Highly recommend the villas that were spacious with amazing views and amenities. We trekked averaging 10-12 miles/day up and down mountains to see the main sites (temples that were built on or into mountains such as world famous "tigers nest"). Not many important sites aside from the Dzhongs and temples although fantastic natural beauty. Roads and travel within Bhutan were challenging and slow, but anticipated (took 4 hours to drive 75km from Thimpu to Punakha) but amazing mountain pass and and trek at top made trip worthwhile (although return along same route was tedious). Guide were outstanding Fabulous adventuresome trip.

Quick, experienced advisor

By: nado

Reviewed on: 26 Sep 2016

John is a really friendly advisor who takes care of me quickly and his experience comes through by finding the the best trips for me

Great advice and extras!

By: Lea

Reviewed on: 03 Jan 2017

John went out of his way to prepare our way to the Park Hyatt Aviara Resort Hotel. He attended to even the small details of our trip like getting us better seats on our return flight and alerting the staff so we were welcomed with three days of treats in our rooms. The added benefit of complimentary breakfasts & the spa was a delight to all of us. The hotel's location was another great benefit, allowing us to visit the zoo, the safari and legoland. The food was outstanding at all the restaurants in the hotel. Many thanks to John for a great vacation!

very helpful

By: Gastro17

Reviewed on: 24 Jan 2017

John is easy and accommodating and knows our travel desires.

The Big Island

By: Maureen

Reviewed on: 19 Mar 2017

A true testimony to John Chaffin is this trip. Seven years ago we first met and worked with John when he planned and prepared an amazing trip along the coast of Viet Nam. When we approached John this year, we explained we just wanted a "trip." We discussed several destinations, but he sold us on the Big Island (and we are so glad he did!). John guided us throughout. He could have easily booked the trip and been done. This certainly wasn't a trip to compare to Viet Nam. But John treated it as such. He answered every question, every email and completed every detail! We were, and always are, in very professional hands.


By: Sue

Reviewed on: 22 Jul 2017

We always get the best service when working with John. He is patient and kind and is very knowledgeable.

Great Job, John!

By: ajw298

Reviewed on: 26 Aug 2017

As always, John found us great flights and worked out travel plans for each family member so that our separate trips coordinated well at the points we needed to travel together. A pleasure to work with John :-)


By: Bob

Reviewed on: 23 Oct 2017

Smooth and knowledgeable


By: Maggie

Reviewed on: 11 Apr 2018

Fantastic! John always has amazing advice and recommendations for specific travel needs. We were extremely happy with our last trip and know we are in good hands with John always!

John is THE BEST

By: Misha

Reviewed on: 09 May 2018

See title! John is outstanding

errenea Resort Trip

By: mark

Reviewed on: 16 Jul 2018

Excellent trip. Everything went smoothly. Upgrades and resort credits were a plus. John is a pleasure to work with.

Great time in the City of Brotherly Love

By: Sheamus

Reviewed on: 01 Sep 2018

John is a superb and attentive professional. He has never done us wrong, to paraphrase an old country song.

Top notch agent

By: sbh

Reviewed on: 09 Sep 2018

Always happy to work with John


By: ted

Reviewed on: 11 Jan 2019

always a pleasure

Another Great Trip

By: Maureen

Reviewed on: 20 Mar 2019

Not only is John extremely easy to work with, he is knowledgeable, helpful and professional. His expertise guided us in the right direction AGAIN!


By: Alex

Reviewed on: 16 Aug 2019

John is the fest. I would never use anyone else. His opinion is honest and to the point. Never a disappointment.

Great as always


Reviewed on: 07 Sep 2019

Excellent experience and great communication!

Spain / Portugal trip

By: two drifters

Reviewed on: 04 Oct 2019

It was easy and pleasant to work with John Chaffin. He is very attentive to what my wife and I want to get out of a trip, and in those instances where we don't have much knowledge about a particular location, we have found his suggestions to be very helpful.


By: Sue

Reviewed on: 10 Oct 2019

Great, professional! We Had an amazing room and experience at both our hotels in Spain. John always comes through and plans an amazing trip. He is extremely knowledgeable. I would and have recommended him to all my friends! We can’t wait to plan the next trip with John.

Working with John Chaffin, you will have access to:

  • - Special perks and extra amenities
  • - An experienced travel guide whom you can rely on before, during, and after the trip
  • - Exclusive luxury resorts and properties
  • - Once in a lifetime experiences

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