Travel Advisor
Alaina Gregerson
She/Her
Expertise
- Europe,
- Mexico,
- Continental US,
- Travel at All Budgets,
- City Travel,
- Couples Travel
Based in
The Second City — Chicago, Illinois
Profile details
About
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.
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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!
Alaina 's travel guides & trip reports
7 Days Visiting Paris & Amsterdam
Seasonal Splendor: A Traveler's Guide to the Vibrant Japan Seasons
Discovering Eleuthera: Your Ultimate Bahamas Escape
Favorite hotels
Nomade Tulum
This wellness-focused beach escape is equal parts seaside lounging, cacao ceremonies and sacred fire rituals.
Fora Perks
- ★
10% off food & beverage.
- ★
1 bottle of mezcal per room.
Hôtel Providence Paris
A fast track to Paris’ coolest crowd in the fast-changing 10th, there are just 18 rooms, a lively brasserie and petit bar.
Fora Perks
- ★
Welcome drink.
- ★
Upgrade whenever possible & guaranteed late check-out.
The Hoxton, Chicago
As much about the play as the stay, this Fulton Market favorite has a hotspot restaurant, bar and rooftop pool, plus supremely comfortable bedrooms.
Noelle Nashville Downtown
Noelle is an immersive hotel and creative gathering place in downtown Nashville for adventurous people seeking a true Nashville encounter.
Fora Perks
- ★
$100 food / beverage credit.
- ★
Daily breakfast.
- ★
Upgrade & extended check-in/out whenever possible.
Alaina 's travel photos
Alaina 's reviews
Overall we had a great time! I think leading up to the trip it would have been helpful for us to have a call or run through of the final itinerary before we left. More communication back and forth would have been great so we were left with less “is everything good to go?” leading up to the trip. Holland was easy to navigate and was really small so it was totally okay, but if we were traveling internationally I wouldn’t have felt as confident going into the trip. Overall though we had a great time and all the reservations and recommendations were great!
- Derek S.
Booked travel to Michigan
- July 2024
Working with Alaina was a great decision. She was able to provide great suggestions for planning out our trip like starting off with a hop on/hop off tour to get acclimated to the city and also advised to leave some open time in the itinerary to be able to explore at leisure without structured activities. Everything she ended up scheduling was a great time and she seemed to really know the cities. The trip would not have been the same without her assistance with itinerary planning!
- William James G.
- April 2024
Get in touch with Alaina
Reach out to customize and book your own experience. Or, just to chat about travel in general.
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