Hiring Guide for a Travel Advisor in Chicago
According to BLS, the demand for travel agents is expected to rise as people seek personalized travel experiences.


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How do top companies overcome the demand and shortage of Travel Advisors?
The demand for Travel Advisors is increasing as more people seek personalized travel experiences.
They’re turning to agents for advice on top destinations and resolving travel issues.
To address the challenge of attracting and retaining talented Advisors, companies in Chicago are outsourcing to the global workforce. When outsourcing, choose a cost-effective remote staffing provider that emphasizes ethical practices, offers good perks, and has strong security measures and ISO certification.
A great travel agent should be well-rounded and possess these skills:
- Proficiency in travel planning: Craft personalized and detailed travel plans based on clients’ preferences, budgets, and timelines
- Expertise in itinerary planning: Design comprehensive itineraries and integrate activities, accommodations, transportation, and dining
- In-depth destination knowledge: Extensive knowledge of destinations (cultural, historical, and recreational)
- Understanding of travel regulations: Familiarity with domestic and international regulations, such as visas, customs, and health advisories, is vital for proceeding with smooth, secure travel plans.
- Travel logistics management: Management of logistics, including flights, accommodations, and transportation, minimizes disruptions and ensures seamless travel experiences
- Knowledge of travel insurance: Agents proficient in travel insurance help clients select coverage for cancellations, emergencies, or lost luggage, ensuring peace of mind while completing trips or relaxing at home
- Experience in various tools & programs: Proficiency in tools like Amadeus, Sabre, Travelport, Salesforce, and TripIt
A guide to interviewing Travel Advisors for Chicago: Questions to ask
When interviewing a remote Travel Agent, review their qualifications and verify their suitability. Start with these questions:
- Can you share your experience as a remote travel agent?
- When picking a vacation package for your clients, what do you look for?
- How comfortable are you with cold-calling?
- What would you suggest to a couple looking for a romantic getaway?
- How do you create tour packages for company trips?
- Can you walk me through how you plan a vacation for a family of four?
- How do you manage travel itinerary changes or emergencies when your clients are abroad?
- What action do you take if a client makes a complaint?
- Describe a Travel Advisor Chicago residents could connect with.
- How do you respond to unexpected challenges, learn from client needs, and help the business earn trust?
- What do you do when encountering technical issues (e.g., power or internet connection issues, verification successful waiting delays, ray ID, software outage)?
How much does outsourcing a Travel Advisor for Chicago cost?
Costs when hiring a Travel Advisor vary based on location, experience, and skills. In Chicago, total expenses can rise by about 30% due to health insurance and office space. Additionally, recruitment costs from ads and agencies can reach around 20% of the first-year salary.
To save money, consider outsourcing to countries like the Philippines, Colombia, or India, which can be more budget-friendly. Outsourcing not only reduces overhead but also gives access to a wider talent pool. Try Cloudstaff’s Teambuilder, which can show potential savings.
Steps to hiring remote Travel Advisors with Cloudstaff
Discover how Cloudstaff can simplify the process of hiring remote Travel Advisors.
Match
We use a database of 700,000 candidates and AI technology to find the right match for you.
Interview
We streamline the selection process to ensure you meet only the best candidates.
Offer
We handle all local employment paperwork, from offers to contracts.
Enable
On day one, your new hires have everything they need, including equipment and secure logins.
Induct
Our thorough legal induction ensures all new hires are compliant from the start.
Train
We provide access to training materials and to our learning platform, CS Academy, for ongoing talent development.
Manage
Our team supports productivity, staff relations, and growth, helping your workforce thrive.
Onboarding & training Travel Advisors at Cloudstaff, your Employer of Record
Thinking about outsourcing for your Chicago business but concerned about international staffing laws? Let Cloudstaff handle it.
We manage payroll, taxes, and compliance in countries like the Philippines, Colombia, and India, allowing you to focus on managing your remote Travel Advisors stress-free.
We prioritize cultural fit, seeking candidates fluent in English who align with your business culture. Our hiring process assesses both technical skills and team compatibility. During onboarding, we ensure a smooth integration with clear expectations and thorough training, and our Client Growth Partners maintain regular contact as you continue to expand.
What makes Cloudstaff’s remote staffing solutions different from other outsourcing models?
Cloudstaff is redefining outsourcing with a cutting-edge perspective on remote staffing.
Cloudstaff’s remote staffing solutions
Ethical outsourcing
- Committed to safety, employee growth, and a celebrated work culture
- Transparent pricing, and comprehensive benefits
- Robust Business Continuity Planning (BCP)
#1 Workplace
- Your trusted co-pilot to find the best talent
- Our recruitment experts offer access to over 700,000 skilled remote professionals worldwide, supported by our comprehensive Cloudstaff Academy
Operational brilliance
- Dedicated to your remarkable growth, our Client Growth Partners are always there for you whenever you need them
- We provide exceptional staff, mobilize teams, and manage performance to move your business forward
Enterprise-grade outsourcing
- Significant investment in advanced technology and platforms
- Unrivaled security features tailored for enterprise need
- Leading-edge in tech-enabled solutions with top-tier remote work technology and AI talent augmentation
- We have a Google-alum Chief AI Officer who is advancing our proprietary AI to enhance matching accuracy, ensure a private generative AI environment for secure staff usage, and develop specialized AI toolkits for various industries.
Other outsourcing models
Direct contracting
- Compliance issues due to legal concerns
Freelance hiring
- Tax obligations not met
- Lack of full-time commitment
Traditional outsourcing
- Ethical considerations
- Potential business risks
- Limited post-sales support
Establishing a local entity
- Initial investment requirement of approximately $250k
- Additional considerations for local equipment procurement
- Necessitates investment in local human resources and cultural integration
- Local bureaucratic hurdles

Retaining top Travel Advisors requires more than just recognizing their skills
It’s about making them feel valued. By creating a people-first environment with great perks, a strong rewards system, career growth opportunities, inclusive activities, and support for work-life balance, you can ensure everyone feels essential to the team.

Check out how you can save up to 70% vs traditional hiring costs with our TEAM BUILDER.

Download a custom remote staffing business case tailored to your hiring needs.
Worried about hiring problems or sticking to your budget?
We can help you find the right staff.
