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Matthew Schaffer

Chicago, Illinois Travel Agent
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Matthew Schaffer

Matthew Schaffer

Chicago, Illinois Travel Agent
A Full-Service Travel Leaders Associate Agency
39 Reviews | 100% Recommended
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US and Mexico Travel Agent Specialist

Travel is my passion in life. Every place I have traveled to has not only been a life altering experience, but has also given me amazing moments to cherish and share with family and friends forever. I have found that there is nothing better than a perfectly planned trip, with no worries or inconveniences to distract me from having the best time of my life. That is the reason I am here for you, to help create those perfect moments to last a lifetime. From short trips to Vegas or Chicago, to longer getaways to Mexico, nothing beats a great vacation, and I look forward to helping you plan that adventure out.

My Travel Specialties

Cancun Travel Agent Specialist

Cancun
It’s hard to find another Mexico destination that can rival Cancun, with the stunning beaches, endless outdoor activity choices, cuisine to die for and of course the vibrant nightlife.  Whenever I think of my many trips to Mexico, Cancun always brings ... Read more from my Cancun Travel Agent Specialist bio.

Cabo San Lucas Travel Agent Specialist

Cabo San Lucas
There can be no doubt that Cabo San Lucas is a must visit destination in Mexico.  After all, Cabo is the place famous French explorer, Jacques-Yves Cousteau, called the “Aquarium of the World”.  No matter how many times I visit Cabo, ... Read more from my Cabo San Lucas Travel Agent Specialist bio.

Las Vegas Travel Agent Specialist

As a Las Vegas travel agent advisor, I can tell you that no city buzzes 24 hours like Vegas. About 40 million people stream into the city annually. Many tourists spend time on the Strip, or the legendary 4-mile road that is also known ... Read more from my Las Vegas Travel Agent Specialist bio.

Sedona Travel Agent Specialist

Sedona Sunset
During the 10 years I lived in Arizona I visited some amazingly beautiful sites, but to this day, my favorite destination, hands down, is Sedona.  From the majestic red rocks, to picturesque nature trails or the Tlaquepaque Arts and Crafts Village, Sedona has something for every ... Read more from my Sedona Travel Agent Specialist bio.

Puerto Vallarta Travel Agent Specialist

Puerto Vallarta
While every trip I have taken to Mexico has been special, Puerto Vallarta is definitely in the top 5 of my must visit getaways.  Whether I was taking a family vacation there, or a more private siesta, Puerto Vallarta always proved ... Read more from my Puerto Vallarta Travel Agent Specialist bio.

Grand Canyon Travel Agent Expert

I love representing the Grand Canyon as a travel agent professional. You won't find any natural attraction on earth like this deep ravine. People remember the experience all of their lives. I believe the Grand Canyon truly embodies the West with ... Read more from my Grand Canyon Travel Agent Expert bio.

Destination Wedding Travel Specialist

Riviera Maya
There are few occasions more important in life than your wedding.  This applies not only for the bride and groom, but also for friends and family.  In my mind, there is no better way to celebrate this occasion than with a ... Read more from my Destination Wedding Travel Specialist bio.

Zihuatanejo Travel Agent Specialist

Zihuatenejo
The first time I ever heard of Zihuatanejo was when Stephen King sent his escaped convict Andy Dufresne there in “The Shawshank Redemption.”  At the time I actually thought the place was made-up, but luckily later in life I got a ... Read more from my Zihuatanejo Travel Agent Specialist bio.

Jamaica Travel Agent Specialist

Blue Hole Jamaica
Whenever I hear a Bob Marley tune streaming in my ears, my mind instantly goes that that magical place, Jamaica!!!  The birthplace of reggae and jerk, the Rastafari movement and some of the best beaches in the Caribbean, it’s no wonder to ... Read more from my Jamaica Travel Agent Specialist bio.

Hilton Head Travel Agent Expert

Hilton Head Island
One of the most beautiful destinations in South Carolina, Hilton Head Island, is very special to me. Growing-up my family took a vacation to South Carolina at least once a year.  This is where I learned to golf as a child, ... Read more from my Hilton Head Travel Agent Expert bio.

Kiawah Island Travel Agent Specialist

Osprey Point at Kiawah Island Golf Course
There is just something about Kiawah Island that is above and beyond other U.S. coastal islands. I personally believe it is the most stunning island in South Carolina, and quite possibly in the entire U.S.  I might be a bit biased, ... Read more from my Kiawah Island Travel Agent Specialist bio.

Arizona Travel Agent Specialist

When it comes to great U.S. destination states, Arizona will always have a special place in my heart.  This may be because I had an amazing destination wedding in the mountains of Tucson, or maybe because I went to the University of Arizona, ... Read more from my Arizona Travel Agent Specialist bio.

Illinois Travel Agent Specialist

Downtown Chicago Lakefront
Having lived in Chicago for many years of my life I know the ins and outs of the city, whether you are looking for an amazing weekend or a business trip, I promise you your visit will be perfect with my ... Read more from my Illinois Travel Agent Specialist bio.

Maui Travel Agent Specialist

Wailea Maui Beach
Maui is by far my favorite destination in the Hawaiian Islands.  If you are a beach paradise lover like me, you just can’t ask for a better place for a romantic getaway, group travel or a family vacation.  With my help, ... Read more from my Maui Travel Agent Specialist bio.

CERTIFICATES & AWARDS

Certified ASTA Travel Agent

My Travel Stories

Cabo San Lucas
Hawaii

Mexico as Good as Hawaii?

One of the most relaxing vacations I ever took was to Hawaii.  You can't beat waking up every day looking out at the ocean.  My days were filled with enjoying the swim up bar and relaxing on the beach.  Even at night the vibe was just so mellow, everybody seemed so ... Read more from my Mexico as Good as Hawaii? story.

My Reviews

Rating: 5 39 Reviews | 100% Recommended

Good Times

Reviewed By Chelsea - Los Angeles, CA | Traveled to Cabo San Lucas ~ Baja California Sur ~ Mexico
Matt made my trip to Cabo the best! My friends and I had so much fun doing all the activites Matt set up for us. Can't wait for the next one.
I would recommend this agent to my family and friends
5 of 7 people found this review helpful
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Last minute Grand Canyon adventure

Reviewed By Heather - West Chester, PA | Traveled to Grand Canyon ~ Arizona ~ USA
Matthew was fantastic! He planned a last minute trip to the Grand Canyon for me and my boys age 11 and 13. He was so helpful and knowledgeable and made great suggestions with my boys in mind. He was a pleasure to work with and very communicative throughout the process. We are going to plan another trip to the area and will definitely use Matthew again. I would highly recommend his services!
I would recommend this agent to my family and friends
2 of 2 people found this review helpful
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Awesome!!!!!

Reviewed By Debbie - Chicago, IL | Traveled to Jamaica ~ Caribbean
Matt was always available for me no matter when I contacted him. He was able to find the perfect places and activities for all of my requests. I'll be using his services for a long time to come.
I would recommend this agent to my family and friends
3 of 4 people found this review helpful
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Hole in one!!!

Reviewed By Mark - Chicago,Il | Traveled to Kiawah Island ~ South Carolina ~ USA
Matt was so great to work with! I love golfing, but I knew nothing about Kiawah Island. Matt gave me the best golfing trip of my life. I can't wait to take another trip with his help.
I would recommend this agent to my family and friends
5 of 8 people found this review helpful
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Viva Las Vegas!!!

Reviewed By Kyle - Chicago,Il | Traveled to Las Vegas ~ Nevada ~ USA
I have always wanted to go to Vegas but wasn't sure how to make it great. Matt listened to every request I had and made every idea come true. I have never had such a great time in my life! I can't wait to travel with Matt's help again.
I would recommend this agent to my family and friends
5 of 8 people found this review helpful
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Best time ever!!!

Reviewed By David - Chicago, IL | Traveled to Los Cabos ~ Baja California Sur ~ Mexico
We had the best time ever in Cabo. The resort was great and everything we hoped for. I can't wait for Matt to plan another trip for us!!!!
I would recommend this agent to my family and friends
2 of 3 people found this review helpful
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Viva Mexico!!!

Reviewed By Julie - Chicago, IL | Traveled to Los Cabos ~ Baja California Sur ~ Mexico
What can I say but everything was great. I will use Matt again in the future and highly recommend his services.
I would recommend this agent to my family and friends
1 of 1 people found this review helpful
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Honeymoon of dreams!!!

Reviewed By Sarah - Chicago, IL | Traveled to Cancun ~ Quintana Roo ~ Mexico
Matt was on top of everything from day 1. He did an amazing job and gave us an unbelievable honeymoon.
I would recommend this agent to my family and friends
2 of 3 people found this review helpful
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Soooo Relaxing!!!

Reviewed By Jason - Chicago, IL | Traveled to Zihuatanejo ~ Guerrero ~ Mexico
From start to finish the whole experience was great! I will definitely use Matt's services again.
I would recommend this agent to my family and friends
2 of 3 people found this review helpful
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Knowledgeable, Expert in his Craft

Reviewed By Kat - South Bend, Indiana | Traveled to Cancun ~ Quintana Roo ~ Mexico
Matthew was so impressive!!! I have used many travel agents in the past, but Matthew is unlike anyone I ever used. With what he knew about Cancun, you would think he grew up there. He helped answer all my questions (and I had a ton hehe), and booked us all we needed to have a fantastic trip. After this experience, Matthew feels like a brother to us!
I would recommend this agent to my family and friends
1 of 1 people found this review helpful
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5 Star Customer Service and Dedication

Reviewed By Kerri - Evanston, IL | Traveled to Jamaica ~ Caribbean
Matthew helped my sister and I plan our first family vacation for the first time in over a decade, so as you can imagine, we had very high standards!

Matthew met us for an initial phone call after business hours, planned our trip exactly the way we wanted, and was there for us when the resort was trying to mess with our trip! I have another trip coming up and will be using Matthew again. I would recommend him to anyone who is new to traveling, or travel agents.
I would recommend this agent to my family and friends
1 of 1 people found this review helpful
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A worthwhile and amazing travel agent

Reviewed By Paul Smith - South Bend, Indiana | Traveled to Cabo San Lucas ~ Baja California Sur ~ Mexico
Matthew was dedicated to making sure my family and I had a wonderful vacation. He worked nonstop to answer all of our questions and provide us with the best possible vacation packages. I recommend him to everyone!
I would recommend this agent to my family and friends
2 of 3 people found this review helpful
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The Best!!!

Reviewed By Mary - Chicago,Il | Traveled to Zihuatanejo ~ Guerrero ~ Mexico
Matt was so great to work with. He listened to everything I wanted and delivered an amazing vacation. Two thumbs up!
I would recommend this agent to my family and friends
3 of 5 people found this review helpful
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Time of my life!!!

Reviewed By Lillian - Washington, D.C. | Traveled to Cancun ~ Quintana Roo ~ Mexico
Matt is simply the best. He made my whole family have the experience of their lives. They all thought I was the reason everything was so great, thx Matt.
I would recommend this agent to my family and friends
4 of 7 people found this review helpful
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Zihua was Paradise!!

Reviewed By Dannielle - Chicago, IL | Traveled to Zihuatanejo ~ Guerrero ~ Mexico
Matt is incredible! Our trip to Zihua was a dream come true. I loved all the tours and activites Matt set up. I think I will try Cabo with him next, I can't wait.
I would recommend this agent to my family and friends
4 of 7 people found this review helpful
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Best Travel Agent!

Reviewed By Tyler - Little Rock, Arkansas | Traveled to Cabo San Lucas ~ Baja California Sur ~ Mexico
Matt went above and beyond for me. He was always available anytime I needed him. My trip to Cabo was everything I wanted and more!
I would recommend this agent to my family and friends
3 of 5 people found this review helpful
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Amazing Trip!!!

Reviewed By Patty - Chicago,Il | Traveled to Hilton Head Island ~ South Carolina ~ USA
Wow!!! Thats the only way I can describe what Matt did to make my vacation to Hilton Head so perfect. I had never been to islands of South Carolina and had no idea what I was in for. I loved everything and had never been so relaxed in my life. I will use Matt every time from now on.
I would recommend this agent to my family and friends
2 of 3 people found this review helpful
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Only Way to Travel

Reviewed By Lily - Chicago,Il | Traveled to Sedona ~ Arizona ~ USA
Hands down this was the vacation experience I have ever had. Matt was so helpful any time I had questions and took care of everything so quickly. I can't wait to take another trip with Matt's help again.
I would recommend this agent to my family and friends
5 of 9 people found this review helpful
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Paradise!!!

Reviewed By steve - Chicago, IL | Traveled to Zihuatanejo ~ Guerrero ~ Mexico
Matt made everything a piece of cake. I can't wait for our next trip.
I would recommend this agent to my family and friends
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Honeymoon of dreams!!!

Reviewed By Laura - Chicago, IL | Traveled to Jamaica ~ Caribbean
Matt was so great to work with. I would recommend his services to anybody looking for a great honeymoon.
I would recommend this agent to my family and friends
1 of 2 people found this review helpful
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Great adult only vaca!!!!

Reviewed By Juan - Chicago, IL | Traveled to Cancun ~ Quintana Roo ~ Mexico
Matt gave us everything we asked for and more!!!
I would recommend this agent to my family and friends
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Top notch service!

Reviewed By Mark - Chicago, IL | Traveled to Cabo San Lucas ~ Baja California Sur ~ Mexico
everything was perfect!!! Matt was always available to answer questions and give us exactly what we needed.
I would recommend this agent to my family and friends
1 of 2 people found this review helpful
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Thank you For Being Our Family Travel Agent

Reviewed By Elaine Katz - Wilmette, IL | Traveled to Italy ~ Europe
This is the 3rd time we have used Matthew as our family's travel agent. My husband and I spent years trying to locate a quality agent, and this will be the only agent we will ever use again.

Matthew value's customer service and punctuality, and he is detail-orientated and empathetic. All of his traits are why we continue having wonderful family vacations and why we will always come back to him.

I would recommend this agent to my family and friends
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Made My Vegas Trip Flawless

Reviewed By Nick - Downers Grove, IL | Traveled to Las Vegas ~ Nevada ~ USA
Matthew was very cool. He made sure the guys and I got to and from Vegas for our bachelor party. He helped us lock in the best hotel I ever stayed at. Highly recommend.
I would recommend this agent to my family and friends
1 of 2 people found this review helpful
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Amazing for small or large destination weddings!

Reviewed By Serenity - Skokie, Illinois | Traveled to Hawaii ~ USA
Matthew offered complete and thorough support for my wedding party and guests. He was able to offer immediate support and provide solutions, as needed. Thank you Matthew for making our wedding amazing. We cannot wait to use you again!
I would recommend this agent to my family and friends
1 of 2 people found this review helpful
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LGBTQ+ Friendly and Tailored Travel Services

Reviewed By Dominic - Chicago, Illinois | Traveled to Puerto Vallarta ~ Jalisco ~ Mexico
My partner and I were initially skeptical about using a travel agent, as we were specifically looking for someone who was LGBTQ friendly and able to locate travel destinations that were welcoming of LGBTQ individuals.

Matthew made my partner and I feel comfortable, and tailored his service and customer service to ensure we had a safe/LGBT-centered travel experience.

I will be using Matthew for all future travel plans.
I would recommend this agent to my family and friends
1 of 2 people found this review helpful
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Spring Break 2023

Reviewed By terrie - Laurel, Maryland | Traveled to Arizona ~ USA
From our initial contact explaining what kind of experience we were looking for with our extended family on Spring break, Matt was extremely helping with suggestions and advise on where to stay and what to see and do. He was very quick to respond to any questions we had along the way and offered some great ideas on working with our party of 11. Would highly recommend to anyone wanting to coordinate a successful adventure.
I would recommend this agent to my family and friends
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Soooo Relaxing...

Reviewed By Karyla - Chicago,Il | Traveled to Sedona ~ Arizona ~ USA
Just Amazing!!! I had never been to Sedona and Matt made everything simple for me. He gave me the most relaxing trip of my life.
I would recommend this agent to my family and friends
3 of 6 people found this review helpful
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Perfect Anniversary!!!

Reviewed By Phil - Orlando,, FL | Traveled to Maui Island ~ Hawaii ~ USA
Matt planned the perfect wedding anniversary trip for us. My wife and I were so happy the whole time of our trip to Maui. All I can say, is Matt is the best!
I would recommend this agent to my family and friends
2 of 4 people found this review helpful
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So luxurious

Reviewed By Abby - Skokie, IL | Traveled to Zihuatanejo ~ Guerrero ~ Mexico
I loved everything about my trip. Matt crossed every t and dotted every i. All the extras made me never want to come home.
I would recommend this agent to my family and friends
3 of 6 people found this review helpful
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Loved everything about it!

Reviewed By Vic - Highland Park, IL | Traveled to Cabo San Lucas ~ Baja California Sur ~ Mexico
Matt is the best!!! I always wanted to go to Cabo and have a luxurious vacation. Matt fullfilled all of my wishes and more. I will have to take a trip like this more often. I highly recommend using Matt to make your vacation the best!!!
I would recommend this agent to my family and friends
3 of 6 people found this review helpful
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Vegas Baby!!!

Reviewed By Mark - Chicago, IL | Traveled to Las Vegas ~ Nevada ~ USA
We had the best time ever. Matt gave us everything we asked for and made everything a breeze. Can't wait for the next one.
I would recommend this agent to my family and friends
0 of 1 people found this review helpful
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Great Travel Agent

Reviewed By Tyler - St. Louis, Missouri | Traveled to Nashville ~ Tennessee ~ USA
Matt is legit. I could not have traveled to Nashville without him. Matt helped my cousin and I find our flight, hotel, and even gave us some cool things to see while we were there. I appreciated his customer service, sense of humor, kindness and patience.
I would recommend this agent to my family and friends
1 of 3 people found this review helpful
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Heaven on earth!

Reviewed By Jess - Chicago, IL | Traveled to Cabo San Lucas ~ Baja California Sur ~ Mexico
What else can I say but everything was great. My trip to Cabo was the thing of dreams. I can't wait for Matt to plan my next vacation.
I would recommend this agent to my family and friends
1 of 3 people found this review helpful
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Perfectly Perfect in Every Way!!!

Reviewed By Sybil - Northbrook, IL | Traveled to Zihuatanejo ~ Guerrero ~ Mexico
My husband and I love going to Mexico, but this trip to Zihuatenejo was by far better than any trip we tried to plan ourselves. Matt must have spent so much time working on every little detail. We enjoyed every moment together and will definitely use Matt for future vacations.
I would recommend this agent to my family and friends
1 of 3 people found this review helpful
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The Perfect Trip!

Reviewed By Ina - Chicago,Il | Traveled to Puerto Vallarta ~ Jalisco ~ Mexico
My trip to Puerto Vallerta was absolutely perfect! I have gone to Mexico before but I have never had such an amazing experience. I will use Matt for every vacation I take from now on.
I would recommend this agent to my family and friends
2 of 5 people found this review helpful
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Good Times!

Reviewed By Nancy - Chicago,Il | Traveled to Cancun ~ Quintana Roo ~ Mexico
Matt was so amazing. Planning trips used to stress me out, but Matt made everything so easy and got me everything I wanted, and more!
I would recommend this agent to my family and friends
1 of 4 people found this review helpful
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I love Hawaii!!!

Reviewed By Nakia - Chicago,Il | Traveled to Maui Island ~ Hawaii ~ USA
OMG! My vacation was so amazing thanks to Matt. He got me everything I wanted and made my experience in Hawaii with my husband unbelievable. I can't wait to do it again!
I would recommend this agent to my family and friends
2 of 6 people found this review helpful
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Swimming with the Dolphins!!

Reviewed By Jana'e - Los Angeles, CA | Traveled to Puerto Vallarta ~ Jalisco ~ Mexico
I had such a great time in Puerto Vallarta thanks to Matt. He set up an amazing trip for myself and 5 friends. I think the swimming with the dolphins was the highlight for all of us.
I would recommend this agent to my family and friends
1 of 5 people found this review helpful
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My Travel Experience

Places I’ve personally traveled to or destinations I’ve booked for my clients.