Advisor - Alaina Gallagher

Alaina Gallagher

She/Her
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  • Based in icon

    Based in The Second City — Chicago, Illinois

Ask me about

Europe
Mexico
Continental US
Travel at All Budgets
City Travel
Couples Travel

My Story

Chicago-based advisor with too many tabs open planning trips, getting my heart set on adoptable dogs I don't have room for and keeping up with restaurant openings across the city.

My Travel Style

Moving from budget adventures to more indulgent luxuries, I have loved exploring new cities and cultures. Finding the perfect balance between adventure, leisure, and culture is my driving focus that has been tested from India to Europe to the Caribbean and beyond. We can find the perfect trip for your solo, couples' or group travel at any budget!

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My reviews (12)

J

Jennifer R.

a month ago

Alaina was very prompt and professional in all of her correspondence. She checked in with me multiple times and reminded me of deadlines or next steps. She made the entire process seamless from airport transportation to suggestions on activities. She also provided suggestions and different pricing options for multiple resorts based on our specific requests. I will be using her services again!

a month ago

We are beyond grateful to Alaina for helping plan our mini-moon. From the very beginning, she listened to what we wanted and crafted an itinerary that included the perfect mixture of rest and relaxation. Not only did she handle all the bookings with care and precision, but she also added special surprises throughout our stay that made us feel truly celebrated—like romantic touches in our room, thoughtful notes, and a sunset cruise. Every detail felt personalized and intentional. Thanks to her expertise and kindness, we were able to relax and enjoy every moment without any stress. We can’t recommend her enough for anyone planning a special post wedding trip!

2 months ago

Amazing recommendation! Alaina helped us get into our room with ease and provided excellent service and communication.

2 months ago

Perfect communication and recommendation! Alaina gave us a variety of options to choose from, and this one ended up being perfect for our short stay.

2 months ago

Alaina was excellent and handled everything we needed for such a large group. Even for us into awesome suites we weren't able to book ourselves.

My travel ideas (10)

My travel photos

A tall cactus in a desert with a pink and purple sunrise.
Boats along a river lined with trees
A beach as seen from a trail above with palm trees in the foreground and a rocky hill in the distance.
An upward angle of the Louvre on a sunny day with clouds

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