(23 Reviews)
100% Recommended

Jacob Robbins-Roth

Coral Springs, FL
Japan and East Asia Travel Agent Specialist

One of the biggest benefits of working with me is, for 2025 I am located in Japan! That means I provide a more hands on travel booking experience since I am at the destination. It also means, I will be in the same time zone as you when you are on ...
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Chicago Travel Agent Specialist

Chicago is a treasure trove of vibrant culture, iconic architecture, and world-renowned cuisine. When a client chooses me as their agent, they are getting a personalized, expert trip planned exactly to their liking. I specialize in crafting unforgettable journeys to Chicago and its picturesque suburbs, including Naperville, Arlington Heights, and Northbrook.   


Chicago’s rich history, from its 1871 Great Fire rebirth to its legacy as a jazz and blues capital, offers a fantastic, historic feel for any visit. Explore the stunning skyline, punctuated by the Willis Tower and the innovative architecture of Millennium Park, or enjoy a scenic stroll along the Lake Michigan shoreline.   


Food lovers can dive into the city’s famous deep-dish pizza, and fans of the arts can revel in the theaters of the Loop or the masterpieces of the Art Institute of Chicago. For the sports lovers, there is plenty of excitement in cheering for the Cubs at Wrigley Field or the Bears at Soldier Field.   Beyond the city, the suburbs add charm and variety to any itinerary. Naperville boasts a quaint riverwalk and a vibrant culinary scene. Arlington Heights offers equestrian events and lush parks, perfect for outdoor adventurers. Northbrook’s upscale shopping and serene nature preserves make it an excellent destination for relaxation and retail therapy (Cha-Ching!). 


Whether you're planning a weekend getaway, a family-friendly adventure, or a luxury retreat, I will design the ideal trip to suit your tastes. From securing top accommodations and recommending hidden gems to organizing seamless transportation, I ensure every detail of your Chicago experience is perfectly customized to your trip preferences Let me bring the magic of Chicago and its suburbs to life in a way that’s uniquely tailored to you.


 


 Here’s a list of fun facts about Chicago and its surrounding areas:


Chicago built the world’s first skyscraper, the Home Insurance Building, in 1885.


The Chicago River is the only river in the world that flows backward, thanks to a 1900 engineering project.


The Ferris wheel was invented for the 1893 World’s Columbian Exposition held in Chicago.


Chicago’s nickname, "The Windy City," originally referred to its politicians, not its weather.


Deep-dish pizza and the Twinkie were both invented in Chicago.


Chicago has more than 200 theaters and 200 art galleries, making it a hub for the arts.The city’s lakefront is home to 26 miles of public beaches.


Naperville’s Riverwalk is considered one of the most picturesque spots in the Midwest.


Arlington Heights boasts the iconic Arlington International Racecourse, famous for thoroughbred horse racing.


Northbrook’s Botanic Gardens feature 385 acres of breathtaking landscapes and unique plant collections.


Chicago’s Willis Tower Skydeck offers views across four states on clear days.


The Art Institute of Chicago holds one of the largest collections of Impressionist paintings outside of Paris

My Reviews

5 of 5 people found this review helpful
Destination Wedding Made Easy!
This is our second time using Jacob's services!
When my coworker invited me and my husband to his multi-day wedding in a suburb of Chicago, Illinois, I was excited yet cautious. We were completely unfamiliar with the area, so we needed help for ease and for sightseeing. We wanted to be on the frugal side, and Jacob was extremely helpful in getting us the best prices without sacrificing comfort. He even got us a better discount than the reserved wedding hotel block at the same hotel! Jacob booked our rental car so we weren't spending exorbent amounts on Uber. For our flights, Jacob asked thoughtful questions like what comforts we wanted to keep or compromise to stay within our budget. He watched a few flights prices rise and drop so we were able to book a nicer airline still within our budget!
Overall, I would recommend Jacob for his personableness, his expertise, and his commitment to following the parameters you communicate (budget, interests, etc.).
By  Valerie Tuccillo  from  Melbourne, Florida
Traveled to  Chicago ~ Illinois ~ USA
I would recommend this agent to my family and friends
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3 of 3 people found this review helpful
Excellent Help
Jacob made our travel plans so easy and enjoyable. He found us great options and was incredibly helpful. Highly recommend!
By  Emma and James Carter  from  Boston, MA
Traveled to  Miami ~ Florida ~ USA
I would recommend this agent to my family and friends
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2 of 2 people found this review helpful
Very Happy, Great Experience
My wife and I had a last minute trip to NY to plan and were worried about securing a hotel. Jacob had us all booked in a matter on minutes and the trip was fantastic. He even hooked us up with a room with a view! Definitely recommend Jacob for your travel needs.
By  Rodger  from  Hilton Head, SC
Traveled to  New York City ~ New York ~ USA
I would recommend this agent to my family and friends
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1 of 1 people found this review helpful
Jacob Was Fantastic!
Planning our trip to New York was a breeze with Jacob's assistance. He took care of every detail, from the flights to the perfect hotel in the heart of the city. His recommendations for local restaurants and must-see attractions were spot on, making our trip even more enjoyable (we didn’t have to come up with stuff to do!). Jacob's knowledge great customer service made our vacation unforgettable. We couldn't have asked for a better travel agent and will definitely be using his services again. Thank you, Jacob, for making our trip so special!
By  Laura and David Mitchell  from  Austin TX
Traveled to  New York City ~ New York ~ USA
I would recommend this agent to my family and friends
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Easy process
Jacob helped us plan a trip to Miami. From helping us pick the best hotel near all the action to guiding us toward the best beaches and nightlife, we had an amazing time. His local knowledge and attention to detail helped make the trip great!
By  Josh  from  Nashville, TN
Traveled to  Miami ~ Florida ~ USA
I would recommend this agent to my family and friends
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Destination Expert:

  • Chicago
  • Naperville
  • Arlington Heights
  • Northbrook
  • Joliet

Travel Specialist:

  • Heritage
  • Arts & Culture
  • Architecture
  • Nightlife
  • Museums

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