
Alaina Gallagher
She/HerBased in The Second City — Chicago, Illinois
Alaina Gallagher
Ask me about
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!
My reviews (12)
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!
Paris A.
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!
Kameron R.
2 months ago
Amazing recommendation! Alaina helped us get into our room with ease and provided excellent service and communication.
Dallas H.
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.
Derek S.
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.
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!
Paris A.
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!
Kameron R.
2 months ago
Amazing recommendation! Alaina helped us get into our room with ease and provided excellent service and communication.
Dallas H.
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.
My travel ideas (10)

From Manhattan to Brooklyn: The Perfect 3 Days in NYC
New York City is one of the unique cities that can adjust to the traveler and provide a new experience no matter how often you have visited. This can be overwhelming for those embarking on a trip to NYC, which is why I have created a three-day itinerary that can adjust to your travel style as needed to make the trip everything you want and more!

From Manhattan to Brooklyn: The Perfect 3 Days in NYC
New York City is one of the unique cities that can adjust to the traveler and provide a new experience no matter how often you have visited. This can be overwhelming for those embarking on a trip to NYC, which is why I have created a three-day itinerary that can adjust to your travel style as needed to make the trip everything you want and more!

Boutique Design Meets Unbeatable NYC Location at Arlo Midtown
Arlo Midtown represents the evolution of urban hotel design—proof that smart architecture and thoughtful amenities can triumph over square footage limitations. What makes this property special is its ability to layer experiences throughout the building, from a top-rated rooftop bar to The Restaurant at Altair, creating a hotel that extends far beyond your guest room. The combination of genuinely prime Midtown location, exceptional value for what you're receiving, and staff who deliver consistently warm hospitality makes Arlo Midtown a strategic choice for travelers who want to maximize both their time and budget in Manhattan.

Boutique Design Meets Unbeatable NYC Location at Arlo Midtown
Arlo Midtown represents the evolution of urban hotel design—proof that smart architecture and thoughtful amenities can triumph over square footage limitations. What makes this property special is its ability to layer experiences throughout the building, from a top-rated rooftop bar to The Restaurant at Altair, creating a hotel that extends far beyond your guest room. The combination of genuinely prime Midtown location, exceptional value for what you're receiving, and staff who deliver consistently warm hospitality makes Arlo Midtown a strategic choice for travelers who want to maximize both their time and budget in Manhattan.

Cleveland: The Punchline That Punched Back—Your New Favorite City Guide
Before meeting my Clevelander husband, I had all the usual assumptions about this city—industrial grit, burning rivers, heartbreaking sports teams. One visit changed everything. Skepticism turned to surprise, then to wedding vows at those very botanical gardens I'd once have dismissed. Sure, I'm biased now (getting married somewhere will do that), but as someone who had to be completely won over, I'm the perfect guide to show you what makes Cleveland so unexpectedly special. This is your guide from a former doubter who learned the Forest City has much more than meets the eye.

Cleveland: The Punchline That Punched Back—Your New Favorite City Guide
Before meeting my Clevelander husband, I had all the usual assumptions about this city—industrial grit, burning rivers, heartbreaking sports teams. One visit changed everything. Skepticism turned to surprise, then to wedding vows at those very botanical gardens I'd once have dismissed. Sure, I'm biased now (getting married somewhere will do that), but as someone who had to be completely won over, I'm the perfect guide to show you what makes Cleveland so unexpectedly special. This is your guide from a former doubter who learned the Forest City has much more than meets the eye.

Aruba Travel Guide: Sun, Sea & Desert Beauty on One Happy Island
Escape to Aruba, where desert island magic meets Caribbean perfection with consistently warm temperatures and refreshing trade winds year-round. This compact gem offers the perfect balance of relaxation and adventure—snorkel with sea turtles around shipwrecks in the morning, explore dramatic desert landscapes by the afternoon, and savor fresh seafood at sunset. Whether you seek underwater wonders, cultural exploration, or simply perfect beach days, Aruba delivers an accessible paradise where even a short getaway feels like a complete escape.

Aruba Travel Guide: Sun, Sea & Desert Beauty on One Happy Island
Escape to Aruba, where desert island magic meets Caribbean perfection with consistently warm temperatures and refreshing trade winds year-round. This compact gem offers the perfect balance of relaxation and adventure—snorkel with sea turtles around shipwrecks in the morning, explore dramatic desert landscapes by the afternoon, and savor fresh seafood at sunset. Whether you seek underwater wonders, cultural exploration, or simply perfect beach days, Aruba delivers an accessible paradise where even a short getaway feels like a complete escape.

Four-Day Aruba Itinerary: Paradise Perfected
A quick flight from the East Coast, minimal rainfall and crystal-clear waters made Aruba the perfect fit for a sisters' trip! The range of activities and ease of communication made coordination and planning seamless. Aruba proved to be the perfect balance of adventure, relaxation, culture and beautiful landscapes.

Four-Day Aruba Itinerary: Paradise Perfected
A quick flight from the East Coast, minimal rainfall and crystal-clear waters made Aruba the perfect fit for a sisters' trip! The range of activities and ease of communication made coordination and planning seamless. Aruba proved to be the perfect balance of adventure, relaxation, culture and beautiful landscapes.

Discover France: The Ultimate Paris to Nice 8-Day Journey
France is one of Europe's crown jewels and deserves a lifetime of exploration, but for us that are not able to do, we have to make the best of our time while there. Paris deserves its own dedicated time, and Nice is a wonderful home base to explore southern France. A great trip for couples, friends or multi-generation getaways to make memories for a lifetime!

Discover France: The Ultimate Paris to Nice 8-Day Journey
France is one of Europe's crown jewels and deserves a lifetime of exploration, but for us that are not able to do, we have to make the best of our time while there. Paris deserves its own dedicated time, and Nice is a wonderful home base to explore southern France. A great trip for couples, friends or multi-generation getaways to make memories for a lifetime!

Drift Nashville: 3 Day Stay & Inspection
Drift Nashville opened in early 2024 after renovating a long-time eye-sore in Nashville along the interstate and close to Nissan Stadium. Those two things - close to the interstate and Nissan Stadium — make this location perfect for many types of travelers. The style is true to the Drift brand. Community is at the forefront, staff is kind and technology makes the stay feel modern.

Drift Nashville: 3 Day Stay & Inspection
Drift Nashville opened in early 2024 after renovating a long-time eye-sore in Nashville along the interstate and close to Nissan Stadium. Those two things - close to the interstate and Nissan Stadium — make this location perfect for many types of travelers. The style is true to the Drift brand. Community is at the forefront, staff is kind and technology makes the stay feel modern.

Discovering Eleuthera: Your Ultimate Bahamas Escape
Eleuthera wasn't initially on my travel radar. However, upon discovering that a hotel I'd had my eye on was nestled on this charming island, we jumped on the chance to explore somewhere new for an annual girls trip — consisting of my sister, mother and myself. Our criteria for the perfect family trip are simple: access to stunning beaches and a range of excursions that offer cultural immersion, natural beauty or adventurous thrills. Little did we know, Eleuthera would exceed all our expectations, delivering an unforgettable experience filled with kind people and unbelievable beauty at every turn!

Discovering Eleuthera: Your Ultimate Bahamas Escape
Eleuthera wasn't initially on my travel radar. However, upon discovering that a hotel I'd had my eye on was nestled on this charming island, we jumped on the chance to explore somewhere new for an annual girls trip — consisting of my sister, mother and myself. Our criteria for the perfect family trip are simple: access to stunning beaches and a range of excursions that offer cultural immersion, natural beauty or adventurous thrills. Little did we know, Eleuthera would exceed all our expectations, delivering an unforgettable experience filled with kind people and unbelievable beauty at every turn!

Seasonal Splendor: A Traveler's Guide to the Vibrant Japan Seasons
Introduced to a love of Japan by my brother many years ago, the unassuming archipelago in the western Pacific Ocean is full of cultural heritage, stunning landscapes and delectable cuisine. The Japan seasons bring unique chapters to each of its regions, providing endless opportunities to marvel at the wonders of this beautiful country. Not only will the landscape inspire you, but the people are warm, welcoming, and add even more to the wonder of Japan's seasons. It doesn't hurt that the transportation makes it easy to navigate — in a timely fashion! — across the country as well.

Seasonal Splendor: A Traveler's Guide to the Vibrant Japan Seasons
Introduced to a love of Japan by my brother many years ago, the unassuming archipelago in the western Pacific Ocean is full of cultural heritage, stunning landscapes and delectable cuisine. The Japan seasons bring unique chapters to each of its regions, providing endless opportunities to marvel at the wonders of this beautiful country. Not only will the landscape inspire you, but the people are warm, welcoming, and add even more to the wonder of Japan's seasons. It doesn't hurt that the transportation makes it easy to navigate — in a timely fashion! — across the country as well.

7 Days Visiting Paris & Amsterdam
Paris and Amsterdam are two of the most visited cities in Europe annually. With an endless list of sites, monuments and neighborhoods to explore, it can be overwhelming to narrow it down for a 7-day trip. This specific itinerary highlights the unique, early Spring highlights of both cities. Whether it is a couple's trip, girl's trip or solo travel, this itinerary will give you the highlights and flexibility to make the most of your trip!

7 Days Visiting Paris & Amsterdam
Paris and Amsterdam are two of the most visited cities in Europe annually. With an endless list of sites, monuments and neighborhoods to explore, it can be overwhelming to narrow it down for a 7-day trip. This specific itinerary highlights the unique, early Spring highlights of both cities. Whether it is a couple's trip, girl's trip or solo travel, this itinerary will give you the highlights and flexibility to make the most of your trip!

From Manhattan to Brooklyn: The Perfect 3 Days in NYC
New York City is one of the unique cities that can adjust to the traveler and provide a new experience no matter how often you have visited. This can be overwhelming for those embarking on a trip to NYC, which is why I have created a three-day itinerary that can adjust to your travel style as needed to make the trip everything you want and more!

From Manhattan to Brooklyn: The Perfect 3 Days in NYC
New York City is one of the unique cities that can adjust to the traveler and provide a new experience no matter how often you have visited. This can be overwhelming for those embarking on a trip to NYC, which is why I have created a three-day itinerary that can adjust to your travel style as needed to make the trip everything you want and more!

Boutique Design Meets Unbeatable NYC Location at Arlo Midtown
Arlo Midtown represents the evolution of urban hotel design—proof that smart architecture and thoughtful amenities can triumph over square footage limitations. What makes this property special is its ability to layer experiences throughout the building, from a top-rated rooftop bar to The Restaurant at Altair, creating a hotel that extends far beyond your guest room. The combination of genuinely prime Midtown location, exceptional value for what you're receiving, and staff who deliver consistently warm hospitality makes Arlo Midtown a strategic choice for travelers who want to maximize both their time and budget in Manhattan.

Boutique Design Meets Unbeatable NYC Location at Arlo Midtown
Arlo Midtown represents the evolution of urban hotel design—proof that smart architecture and thoughtful amenities can triumph over square footage limitations. What makes this property special is its ability to layer experiences throughout the building, from a top-rated rooftop bar to The Restaurant at Altair, creating a hotel that extends far beyond your guest room. The combination of genuinely prime Midtown location, exceptional value for what you're receiving, and staff who deliver consistently warm hospitality makes Arlo Midtown a strategic choice for travelers who want to maximize both their time and budget in Manhattan.

Cleveland: The Punchline That Punched Back—Your New Favorite City Guide
Before meeting my Clevelander husband, I had all the usual assumptions about this city—industrial grit, burning rivers, heartbreaking sports teams. One visit changed everything. Skepticism turned to surprise, then to wedding vows at those very botanical gardens I'd once have dismissed. Sure, I'm biased now (getting married somewhere will do that), but as someone who had to be completely won over, I'm the perfect guide to show you what makes Cleveland so unexpectedly special. This is your guide from a former doubter who learned the Forest City has much more than meets the eye.

Cleveland: The Punchline That Punched Back—Your New Favorite City Guide
Before meeting my Clevelander husband, I had all the usual assumptions about this city—industrial grit, burning rivers, heartbreaking sports teams. One visit changed everything. Skepticism turned to surprise, then to wedding vows at those very botanical gardens I'd once have dismissed. Sure, I'm biased now (getting married somewhere will do that), but as someone who had to be completely won over, I'm the perfect guide to show you what makes Cleveland so unexpectedly special. This is your guide from a former doubter who learned the Forest City has much more than meets the eye.
My travel photos




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