About

Welcome to Boundless by Alaina, where your travel dreams get the personal attention they deserve. Our agency emerged from founder Alaina Gallagher’s realization that life's most meaningful adventures shouldn't come from a cookie-cutter template.

After years of mapping out her own journeys and helping friends craft their perfect getaways, Alaina finally turned her passion for personalized travel into something more. Drawing from countless stamps in her passport and an intimate understanding of what makes each traveler unique, she created Boundless to be more than just another travel agency – it's your personal gateway to adventures that feel distinctly yours. Here, we believe that the best trips aren't just about where you go, but how that destination aligns with your individual style, interests, and dreams.

Colorful buildings and a clock tower by Lake Como, surrounded by green hills.

Let's Plan your next trip!

MY FAVORITE SPOTS IN

Chicago

I have been so fortunate to call Chicago home since 2021 and this city hasn’t stopped surprising me! There is something so special about Chicago & I want to share all of my favorite spots for anyone visiting or wanting to try something new in the city!

Rose Mary - No contest. It never lets me down and the service is impeccable. In Joe Flamm we trust ✨

There’s a rotating menu but some of my favorite dishes - Zucchini Fritters, Sweet Potatoes, Radiatore ‘Cacio E Pepe’, Mafaldine, Skradin Risotto & (last but NOT least) Pork Ribs Pampanella
I have to go with Small Cheval! I love the Bucktown location specifically for the location, amount of outdoor seating & recently renovated interior. Make sure to get extra garlic aoli!
Studio West - Pilates

This studio is located in Bucktown (actually pretty close to Small Cheval!) and is a breath of fresh air. Beautifully designed, small class sizes, friendly instructors & accommodating to all levels!
Alice & Wonder - If you want cute Chicago gear, you MUST make a stop at Alice & Wonder! They currently have two locations & are opening more around town. In addition to the Chicago gear, they have the best selection of in style, seasonal clothing!

Don’t forget to stop by their sister store in Southport for the best children’s store!
This category is a tough one because it happens to be my favorite category! I am a sucker for seasonal decor, stationary, unique items for shelf decorating & everything in between.

Foursided! They have two locations and you will not find a better spot to find unique cards, gifts, seasonal decor, prints & more. They also do custom framing if you have a print laying around with a funky shape!