Travel Advisor

Caitlyn Cronin

She/Her

Expertise

Europe,
Hawai‘i,
City Travel,
Food & Wine

Based in

Chicago, IL

Travel Advisor

Caitlyn Cronin

Profile details

About

Flight attendant. Travel enthusiast. Wine lover. Foodie. Cat mom. Sports fan.

Follow Caitlyn

Travel style

Hi! I’m Caitlyn (or Caity)! I am a seasoned traveler who has been exploring the world since birth. Infused with a passion for travel from a young age, I bring a lifetime of globetrotting experiences to my role as your travel advisor. With a deep understanding of diverse cultures and a keen eye for unique destinations, I am dedicated to curating unforgettable getaways tailored to your needs.

I have a deep love for crafting custom itineraries. With meticulous attention to detail, I weave together the perfect blend of destinations, activities and experiences, ensuring each trip is a seamless and personalized adventure, along with making sure you are eating some seriously good food along the way!

Caitlyn's travel guides & trip reports

Aerial view of a street with shops in Chicago city.

Trip Report

A Foodie's Guide to Chicago's Fulton Market

Being my neighborhood, Fulton Market holds a special place in my heart and I can’t imagine living in any other neighborhood in Chicago. Nestled in the West Loop, Fulton Market is a dynamic and trendy ...

Old San Juan is a vibrant and colorful historic district in the capital of Puerto Rico.

Guide

A Weekend in San Juan

San Juan, the vibrant capital of Puerto Rico, is a captivating blend of rich history, colorful culture and breathtaking coastal beauty. I frequent San Juan as my best friend lives in the city and...

An aerial view of Eiffel Tower with a person holding a glass of wine in front of it.

Guide

A Guide to 48 Hours in Paris

From historical significance to diverse neighborhoods and a vibrant cultural scene, Paris offers a unique and captivating experience for residents and visitors alike. I was originally only scheduled...

VIEW ALL

Favorite hotels

LondonHouse Chicago, Curio Collection by Hilton

Luxury property in a 1920s high-rise building with relaxing rooms offering river views.

Sheraton Grand Tel Aviv

Where modern elegance and beachfront luxury redefine your coastal escape.

Aulani, A Disney Resort & Spa

Disney resort in Hawai'i with excellent accommodations and activities for the entire family.

Outrigger Waikiki Beach Resort on Oahu

Discover the beauty of Waikiki Beach at this iconic resort, offering breathtaking ocean views, luxurious accommodations and a variety of dining and entertainment options.

Caitlyn's travel photos

Advisor posing at restaurant with drink in hand.

Advisor posing on bustling street corner decorated for the holidays.

Advisor posing in an open field on a sunny day.

Advisor posing on a bustling corner of Time's Square on a cloudy day.

12345

Caitlyn Cronin curated by Caitlyn Cronin

Get in touch with Caitlyn

Reach out to customize and book your own experience. Or, just to chat about travel in general.

You can normally expect a response from Caitlyn within a business day or so. You’ll also be subscribed to our travel newsletter (you can unsubscribe at any time).

Sign up for Caitlyn's email list

Stay in-the-know with the latest from Caitlyn, including travel recs, hotel features & exclusive perks.