Chicago Masterclass!

      • Email address verified
      Feb 23 - 25, 2024
      Group size: 1 - 30
      Chicago Masterclass!

      • Email address verified

      Feb 23 - 25, 2024
      Group size: 1 - 30

      About this trip

      Our first Chicago city training is ready to go! Join us with special instructor Kevin Morrissey (the guy who literally "wrote the book") on a special crash course of all things Chicago!

      Chicago is showing up on more student itineraries and has been a staple on adult tours for many years. Understanding this complex city is key to leading successful trips that pass through this amazing place. From the architecture to the history, Chicago has SO many things to point out to your guests and we will train you to feel confident and look like a superstar on your next tour!

      As with all our trainings, this puts you above the rest by taking you behind the scenes, connecting with vendors, experiencing these cities immersively, making you prepared and more hirable when the tour season starts.

      Health & Safety

      In keeping with general industry trends, although we are no longer requiring proof of vaccination, we highly recommend it. 

      We will honor local vendor and city laws requiring:

      • Masks worn in indoor environments

      • Compliance with all current local, state and federal guidelines

      Read our full health & safety policy here.

      Transportation: Trains & Flights

      You are responsible for your flights to/from Chicago as well as all transportation during the training. We will be using local subways to understand the public transportation system as well as logistically how to get from one area to the next.

      Arrival recommendation

      In general, plan for your flight to arrive in the city by 3PM to make it to our orientation classroom at 5PM on Friday, February 23. 

      Departures recommendation

      We will be doing some morning exploring up until about lunchtime. We recommend booking flights after 3PM to ensure you have time to get to the airport. You can, of course, leave early if needed. 

      Daily Schedule

      Day 1 – (Feb. 23) Class begins at 5:00pm CST (We highly recommend booking a flight to arrive no later than 3PM.)

      Day 2 –  (Feb. 24) 9am to roughly 7:00pm.

      Day 3 – (Feb. 25) 8:30am to roughly 1:00PM

      Each day finishes when it finishes; sometimes we run long, sometimes it’s shorter.

      Courtesy Rates on Hotels


      We do not cover the cost of your hotel. You are free to stay wherever you like, however we have secured rates and will be leading our training from the Aloft Mag Mile hotel. A special TripSchool rate and booking link is below. We will also be meeting there in the mornings and hosting a special classroom session there on Friday night. 

      Aloft Mag Mile

      243 E Ontario Street

      Chicago, IL 60611


      Booking link here 

      Need a roommate? Let us know and we'll send you a roommate request link.

      Deposit & Booking Conditions

      $99 non-refundable deposit is required to secure your spot. Full payments due 30 days prior.

      The rest of your program fee is refundable up to 30 days out. 

      Please read our full booking terms and conditions here!

      Preferred Travel Protection Partner

       We offer travel insurance as part of travel protection plans from our partner TripAssure.

      To cover you for the unforeseen, we encourage participants to purchase travel insurance, which may include benefits for trip cancellation, trip interruption, missed connection, travel delay, medical expense/emergency evacuation, baggage and personal effects, baggage delay and more. 

      TripAssure offers the Basic, Deluxe Plan, and Deluxe Plus Plan options. Familiarize yourself with the contents of each plan to ensure to get the one that best suits your needs.

      Get a quote for travel protection as well as view complete plan details & disclaimers.

      What’s included

      • Two Expert instructors
        Kevin Morrissey & Alan Armijo
      • Admission to attractions
        We don't just point to places, we go in, and give you the real experience of touring a city.
      • TripSchool Secrets/Tips
        If you know us, you know we're serious about the hidden, special, and unique places beyond the touristy spots.
      • Cocktail mixers
        First evening enjoy a complimentary cocktail mixer.
      • Food wow moments
        Each day we'll buy you little tastes of the food that makes these places so special.

      What’s not included

      • Roundtrip flights
        Specific flight booking parameters are in the general description above.
      • Lodging
        Book your own lodging. A roommate request sheet and group hotel link will be added closer to trip time.
      • Transportation
        You're responsible for flights, trains and public transportation passes. We'll provide plenty of guidance to get you prepared.
      • Meals
        Only a welcome mixer with appetizers at the beginning

      Available Packages

      Chicago training


      Day 1
      Arrival Chicago

      We meet in the lobby of the Aloft hotel at 3PM. We will then move to a meeting room where we will go over an orientation on the area. Have your questions ready! Through visuals and tech, we will go over the routings, logistics, highlights and tour operator itineraries that are most commonly used for Chicago. 

      After at 6PM, we leave for cocktails and bites!

      Your Organizer

      We provide tour guide and tour operator training, both online and in-person.

      Photo Gallery