vacation jobs in Chicago

10,000 vacation job listings in United States. Find daily updated positions from leading job boards.


  • Chicago, IL, United States Network Travel Careers Full-time

    Vacation Specialist | Remote | Training Provided Location: Remote (U.S.) About Us We connect travelers with the world’s best experiences—from Caribbean cruises to luxury resorts and beyond. As part of a host agency with 70+ years in the industry, we empower agents to succeed while delivering white-glove service to our clients. Job Description We’re...


  • Chicago, IL, United States Destination Knot Full-time

    Vacation Specialist | Remote | Training ProvidedWe connect travelers with the world's best experiencesfrom Caribbean cruises to luxury resorts and beyond. As part of a host agency with 70+ years in the industry, we empower agents to succeed while delivering white-glove service to our clients.We're hiring Vacation Specialist who want to work remotely, enjoy...


  • Chicago, IL, United States Network Travel Careers Full-time

    Network Travel Careers is seeking reliable, service-oriented individuals for a fully remote Customer Support - Booking Vacations role. You will assist clients with researching and booking vacation packages, hotels, and cruises, and help ensure a smooth reservation process. This entry-level opportunity includes structured onboarding and ongoing training. No...

  • Remote Cruise

    2 days ago


    Chicago, IL, United States Pacific Journey Consulting Full-time

    Pacific Journey Consulting is seeking a Cruise & Getaway Consultant to help clients research and book cruises, resorts, and vacation packages. You will guide travelers through the reservation process, tailor options to preferences, and ensure smooth bookings. Responsibilities include researching itineraries, discussing dates and budgets, explaining options,...


  • Chicago, Illinois, United States Premier Destination Group Remote Full-time $45,000 - $70,000 Contract

    Job Title: Appointment Setter | Remote About US: We take pride in helping travelers simplify the planning process by connecting them with the perfect accommodations. We specialize in hotel and resort bookings, offering personalized service to clients seeking everything from romantic escapes to group getaways. Our team is passionate about making travel...


  • chicago, illinois, United States Hilton Grand Vacations Full-time

    Hilton Grand Vacations has a tremendous opportunity currently available in Rosemont, IL!! Whether you’re seeking a full-time career position or a fun well-paid job, we invite you to contact us. Hilton Grand Vacations is recognized as a leading, global, vacation-ownership company. Headquartered in Orlando, Florida, Hilton Grand Vacations develops, markets...


  • Chicago, IL, United States Network Travel Careers Full-time

    Network Travel Careers is hiring a Vacation Specialist to work remotely with flexible hours, helping clients plan dream vacations. You’ll access premium tools, exclusive rates, and receive full training to succeed in the role. The position offers remote work with flexible scheduling, including full-time or part-time options, along with travel incentives...


  • Chicago, IL, United States Oscar Health Full-time

    Oscar Health is seeking a Senior Manager of Network Contracting to lead a team driving contracting with large healthcare providers and systems, aligning network strategy with cost management and quality goals. You will oversee negotiations, analyze contracts, mentor staff, and ensure regulatory compliance while expanding a high-value provider network across...


  • Chicago, IL, United States Network Travel Careers Full-time

    Position Overview We are seeking reliable and service-oriented individuals to join our team in a fully remote Customer Support - Booking Vacations role. This position focuses on assisting clients with coordinating vacation arrangements, confirming reservations, and ensuring a smooth booking experience. This is an entry-level opportunity within the travel...


  • Chicago, IL, United States Professional Travel Hub Full-time

    Job Title: Appointment Setter | Remote About US: We take pride in helping travelers simplify the planning process by connecting them with the perfect accommodations. We specialize in hotel and resort bookings, offering personalized service to clients seeking everything from romantic escapes to group getaways. Our team is passionate about making travel...


  • Chicago, IL, United States Wanderwell Collective Full-time

    Vacation Specialist | Remote | Training Provided Location Remote (U.S.) About Us We connect travelers with the world’s best experiences—from Caribbean cruises to luxury resorts and beyond. As part of a host agency with 70+ years in the industry, we empower agents to succeed while delivering white-glove service to our clients. Job Description We’re...


  • Chicago, IL, United States Nexxen Full-time

    Nexxen, based in Chicago, seeks a Senior Manager, Business Development to partner with the Senior Director to build strategic partnerships across a portfolio of solutions, ensuring Nexxen offers innovative partner-powered products.You will broker deals, nurture relationships with partners, work with cross-functional teams, and model ROI to drive...


  • Chicago, IL, United States Pacific Journey Consulting Full-time

    We are looking for a Cruise & Getaway Consultant to help clients research and book cruises, resort stays, and vacation packages. This role involves understanding client preferences, comparing vacation options, and guiding travelers through the reservation process. The consultant helps clients choose experiences suited to their interests, schedules, and...


  • Chicago, IL, United States Oracle Full-time

    The PDC serves as the critical planning and technical-readiness function between program management, engineering, low-voltage vendors (LVVs), and Data Center Build and Deployment Engineers. The role owns the upfront technical and operational review of deployment projects, ensuring requirements are complete, accurate, executable, and ready for field...


  • chicago, illinois, United States T.M. Doyle Teaming Company Full-time

    T.M. Doyle Teaming Co. Inc. — Home Nightly CDL-A Driver | Chicago, IL Serving the nation since 1899 — 100 years of family dedication to transportation Position Details: Dedicated intermodal freight Drop hook / no-touch loads Local regional routes Home most nights with an occasional layover Requirements: Valid Class A CDL 1 year of experience required...


  • Chicago, IL, United States Contract Transport Services, LLC Full-time

    Company OverviewContract Transport Services is a well-established logistics provider with a rich history dating back to 1985. We specialize in dedicated local services, yard management, and truckload transportation across multiple regions. Our focus is on delivering quality service with professionalism and reliability, ensuring our employees find a positive...


  • Chicago, Illinois, United States DOCTORS CHOICE PLACEMENT SERVICES, INC. Full-time

    Job DescriptionPulm/CC & Critical Care Opportunities - 90 minutes from Chicago/Northwest Indiana!! Like the look of this opportunity Make sure to apply fast, as a high volume of applications is expected Scroll down to read the complete job description. PULM/CC: Hospital is seeking BC/BE Pulmonary-Critical Care physician to join an established, successful...


  • Chicago, IL, United States Big G Express Full-time

    CDL-A Drivers NeededUp to $110,000 per year Prioritized Home Time 100% Employee-Owned Call to speak to a recruiter today(844) 500-0551 At Big G Express, we like to say, It s good to be us! That s because of the many outstanding and unique advantages we offer CDL-A truck drivers. As an industry leader, Big G Express has earned our positive reputation...

  • CDL-A Truck Driver

    1 day ago


    Chicago, IL, United States Kenan Advantage Group Full-time

    KAG Specialty Products is hiring OTR CDL‑A Drivers who want to stay out, run hard, and earn BIG.If you’re willing to stay “in system” for at least 14 consecutive days, this is one of the highest‑earning mileage packages in the industry. CDL‑A OTR Drivers — High Mileage = High Money | $110,000+ W‑2 Text APPLY to (330) 778-9566 to get your...


  • Chicago, Illinois, United States Physician Services Full-time

    Job Description Please read the following job description thoroughly to ensure you are the right fit for this role before applying. Ob/Gyn physician Chicago * * * * Leading community health organization is seeking an OB/Gyn physician to add to their growing staff of providers. They provide healthcare to a large Spanish speaking community * Provider...