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Emily Stewart, Travel Agent in Chicago, IL

Emily Stewart

Chicago, IL Travel Agent
Super Agent

Emily Stewart

Chicago, IL · 6 Years of Experience

Emily Stewart, an independent agent with Travel Leaders Davis, CA
5.0
(21)
100% Recommended
Thanks Emily for a well planned weekend in Chicago. We are all married with kids and wanted to plan a trip away. She recommended the best... Read More >
About
Reviews
My Places

Areas of expertise

Destinations:

Japan, Tokyo, Kyoto, Osaka, Tokyo Disneyland

Interests:

Culinary & Foodie, Couples & Romance, Nightlife, Entertainment, Historical Sites

About Me

If you’re dreaming of Japan, I can help you live it because it was one of my absolute favorite travel destinations! From the moment I checked into the iconic Park Hyatt Tokyo, with its sweeping skyline views and Lost in Translation mystique, I knew I was in for something unforgettable. My trip wasn’t just a tour; it was a full immersion into the core of Tokyo, during the most magical time of year: cherry blossom season.

One night I was seated at Sukiyabashi Jiro, the legendary sushi temple made famous by Jiro Dreams of Sushi, savoring every bite of perfect rice and impossibly fresh fish... and the next, I was deep in a neon-lit game of laser tag in the backstreets of Shinjuku, laughing until I couldn’t breathe. That’s the beauty of Japan: quiet tradition and electric chaos, existing side by side.

I shared this trip with a special friend, and we made the most of every moment — from sipping sake at tiny, tucked-away izakayas to dancing into the early hours at WOMB, one of Tokyo’s most legendary underground nightclubs. The music, the energy, the people — it was the kind of night that doesn’t need translation.

That mix of high-end, hidden-gem, and totally spontaneous? That’s what I bring to every trip I plan. Whether you want to trace cherry blossoms through Kyoto, eat like royalty in Tokyo, or uncover the side of Japan most tourists miss, I know how to build a trip that feels personal, exciting, and unforgettable, because I’ve been there, and I lived it.

REVIEWS

Rating: 5.0
21 reviews
100% Recommended
Your trust is our priority. Every review is submitted by verified travelers after they have booked and completed their trips. Learn more about our review guidelines.
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Showing 21 reviews

Chi-Town
Reviewed By Griffin T - Dallas, Texas | Traveled to Chicago | Illinois | USA
Thanks Emily for a well planned weekend in Chicago. We are all married with kids and wanted to plan a trip away. She recommended the best restaurants (Chicago's food scene is unreal) —we all left a few pounds heavier. Luckily we didn't have any flying delays. 5 stars!
Emily Stewart responded
"My pleasure! So glad you enjoyed yourself."
I would recommend this agent to my family and friends.
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Perfect Trip to Lefkada
Reviewed By Priscilla Trent - New York | Traveled to Lefkada | Greece | Europe
Emily coordinated a trip for my family to go to Lefkada-- and it was incredible. We loved the greenery that the Ionian side of Greece offered. From the amazing food to the breathtaking landscapes, this was exactly what we needed to escape the hustle and bustle of the City. Thanks Emily!
I would recommend this agent to my family and friends.
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Fun Times in Brooklyn
Reviewed By Tiffany R. - Alabama | Traveled to Brooklyn | New York | USA
I went to Brooklyn to visit some friends from college and reached out to Emily to help me find a hotel, flight, and recommend a few things to do. Overall the trip was great and all went smoothly! Thank you!!
I would recommend this agent to my family and friends.
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Arts in Berlin!
Reviewed By Becky Vlaho - New York | Traveled to Berlin | Germany | Europe
I travelled solo to Berlin to get some inspiration for my art. With Emily's recommednations and bookings I wanted to stay weeks longer!! Overall, it was great and appreciate it so much.
I would recommend this agent to my family and friends.
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Trip down to SB
Reviewed By Xavier - Bay Area | Traveled to Santa Barbara | California | USA
We live in the bay area so aren't very far away from Santa Barbara. We wanted to get away from the kids for a romantic anniversary weekend. Emily is quite the romantic herself!! She planned couples massages, an intimate dinner and a wine tour! The best part? On the wine tour I was connected with an old friend from the reserves. Small world! The only thing I would have changed was the checkout said Noon and they wanted us out by 11, but it ended up being ok.
I would recommend this agent to my family and friends.
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My Places

When it comes to travel planning, real-world experience makes a huge difference. Check out the map below to see all the places I have personally visited or booked for my clients. I know these destinations well and can give you reliable guidance.
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