
Personal Travel Planning for Chicago, Illinois
Thoughtful journeys, planned around you. Personal travel expertise wherever you call home.
Personal travel planning for Chicago
From Chicago, the world is closer than it looks. Travel Wizards is a Virtuoso member agency founded in 1981, planning luxury travel for Chicago residents entirely remotely: one advisor, one relationship, and an itinerary built around you.
Our advisors serve Chicago the same way we serve clients across the country: through personal conversations, careful itinerary design, and support while you are away. Founded in 1981 and still deliberately mid-sized, Travel Wizards is large enough to hold Virtuoso membership and ARC and IATA accreditation, and small enough that your advisor knows your name, your dates, and your preferences. Planning happens remotely by phone, email, or virtual consultation, at your pace.
The journeys we plan for Chicago travelers span the full range of luxury travel: ocean and river cruises on lines we know personally, expedition voyages to Antarctica and the Arctic, private jet journeys, African safaris, honeymoons and anniversary trips, multigenerational family vacations, and fully custom independent itineraries. If you can imagine it, we have likely planned it for someone, and we will tell you honestly what it takes to do it well.
Ready to start? Contact Travel Wizards and tell us where Chicago should take you next. A short conversation is all it takes to begin, and your advisor will take it from there.
Chicago travelers also ask us about closer-to-home escapes, and we are glad to help with those too, from Chicago’s architecture, museums, and lakefront to the Abraham Lincoln sites of Springfield. The point of an advisor is not the size of the trip; it is the quality of the planning behind it.
Because we plan remotely, working with us from Chicago is no different from working with us in person: the same advisor, the same attention, the same advocacy when plans change. Many of our longest client relationships have never involved a single office visit.
If you are comparing options for your next journey, bring us your shortlist. An advisor can tell you which choice suits your travel style, which departure dates offer the best value, and which details are worth arranging before you leave Chicago.
Chicago sits in Illinois, a state celebrated for Chicago’s architecture, museums, and lakefront and the Shawnee National Forest. Many of our Chicago clients are seasoned travelers who want an advisor, not a website, handling the details. We plan remotely, so working with us from Chicago is as easy as a phone call.
Departure planning
The most practical gateway for Chicago is typically Chicago O’Hare International (ORD), though Chicago Midway International (MDW) in Chicago can be the smarter choice for certain destinations. We handle the airfare, the seat selections, and the ground transfers at both ends so the travel days feel as considered as the rest of the itinerary.
Your advisor's perspective
The Chicago clients I work with tend to know what they like; my job is to know what they will like next. For travel, that means honest advice about timing, the right operator for your style, and the details worth paying for, and the ones that are not.
Ryan Bellknapp
Travel experiences
Family Reunions
Plan family reunions around your dates, interests, and preferred travel pace with a Travel Wizards advisor.
Explore experiencesGroup Travel
Plan group travel around your dates, interests, and preferred travel pace with a Travel Wizards advisor.
Explore experiencesHoneymoons
Plan honeymoons around your dates, interests, and preferred travel pace with a Travel Wizards advisor.
Plan from ChicagoCouples Vacations
Plan couples vacations around your dates, interests, and preferred travel pace with a Travel Wizards advisor.
Explore experiencesAnniversary Trips
Plan anniversary trips around your dates, interests, and preferred travel pace with a Travel Wizards advisor.
Explore experiencesBabymoons
Plan babymoons around your dates, interests, and preferred travel pace with a Travel Wizards advisor.
Explore experiencesProposal Trips
Plan proposal trips around your dates, interests, and preferred travel pace with a Travel Wizards advisor.
Explore experiencesDestination Weddings
Plan destination weddings around your dates, interests, and preferred travel pace with a Travel Wizards advisor.
Explore experiencesVow Renewals
Plan vow renewals around your dates, interests, and preferred travel pace with a Travel Wizards advisor.
Explore experiencesFamily Vacations
Plan family vacations around your dates, interests, and preferred travel pace with a Travel Wizards advisor.
Plan from ChicagoMultigenerational Vacations
Plan multigenerational vacations around your dates, interests, and preferred travel pace with a Travel Wizards advisor.
Explore experiencesFriends Trips
Plan friends trips around your dates, interests, and preferred travel pace with a Travel Wizards advisor.
Explore experiencesJourney inspiration

Seville
The Royal Alcázar, the Gothic Seville Cathedral, and Plaza de España, Moorish, Baroque, and Renaissance influences in a single skyline.

Miami
A skyline that glitters at dusk over Biscayne Bay, Art Deco beaches, Latin rhythm, and a gateway to the Caribbean.

Japan
Kyoto's lantern-lit alleys, Tokyo's neon rush, and mountain ryokans where cherry blossoms drift into hot-spring baths.
Planning questions
Does Travel Wizards work with travelers in Chicago?
Yes, and most of our Chicago clients plan entirely remotely. A phone or video conversation is all it takes to begin, and your advisor stays with you through the trip itself.
What does it cost to work with a travel advisor?
The first conversation is always free. For complex custom itineraries a planning fee may apply, which your advisor will explain clearly before you decide anything.
Can you handle complex, multi-stop itineraries?
Yes. Groups, families, and multi-generational trips are some of our favorite planning challenges. Your advisor coordinates every traveler, every room, and every transfer as one plan.
