Travel Advisor

Karen Smith
She/Her
Expertise
- Boutique Travel,
- Food & Wine,
- Group Travel,
- Europe,
- City Breaks
Based in
Chicago, but my passport might beg to differ
Profile details
About
Nomad before it was trendy. Born in NYC, lived everywhere (spy? maybe). I craft seamless, stylish trips because travel’s an art — and meant to be fun!
Travel style
Growing up with paper maps, no Wi-Fi and (if lucky) mixtapes on road trips, I bring a Gen X perspective (and attitude) to modern travel planning. With years of experience in event planning and travel, I genuinely enjoy creating seamless, stylish and unforgettable trips. Whether it’s uncovering under-the-radar experiences or crafting itineraries with the ideal mix of adventure and relaxation, I’m here to help you travel thoughtfully.
Karen's travel guides & trip reports
Favorite hotels
Karen's reviews
Amazing service. Karen organised our holiday specific to our requirements and 8 month old baby's needs. Room upgrade, daily gifts left in our room and check ins from hotel management on Karen's behalf has sure made us feel looked after. We are still here and loving every second especially baby Hugo Thank you Karen
- Ian T.
Booked travel to Dubai
- January 2025
I have had the pleasure of using Karen Smith's travel services at Luggage & Labels for several trips, including to New Orleans, Charleston, Savannah, Sonoma Valley, Chicago and Paris. Each experience has been nothing short of exceptional. Karen excels at selecting local hot spots and crafting daily itineraries that immerse you in the local culture. Her curated adventures always include hidden gems that tourists often miss, allowing you to experience destinations like a local. Whether it's the best places for food, drinks, or unique local boutiques, Karen's recommendations are always spot on. One of Karen's standout qualities is her ability to weave local culture into every itinerary. From historical tours to cultural events, she ensures that you get a true taste of the destination. Her attention to detail and personalized approach make every trip memorable and unique. If you're looking for a travel concierge who goes above and beyond to create unforgettable travel experiences, look no further than Karen Smith at Luggage & Labels. She is truly a master at her craft.
- Heather S.
Booked travel to Chicago
- June 2024

Get in touch with Karen
Reach out to customize and book your own experience. Or, just to chat about travel in general.
You can expect a response from Karen within 1–2 business days. You’ll also be subscribed to our traveler newsletter (you can unsubscribe at any time).
