WorldStrides Director Orientation: Chicago

We can’t wait to host you at our Director Orientation Trip in Chicago! You’ll meet our team, learn more about organizing a successful trip with your students, and network with like-minded Directors from across the country.

Below you’ll find the weekend’s itinerary. You’ll receive a printed copy of the most updated itinerary when you arrive on-site. All activities are subject to change. If you have any questions, please call Stephanie Harrington at 770-262-8081.

Our host hotel for the weekend is: DoubleTree by Hilton Hotel Chicago Magnificent Mile, 300 East Ohio Street, Chicago, IL 60611. Please do not contact the hotel directly with questions. Your accommodations have been taken care of.


WorldStrides Director Orientation Itinerary:

Saturday, November 11

  • Hotel Check-inĀ at front desk. The hotel does allow for luggage storage if you have an early arrival and your room is not yet ready.
  • 4-4:30pm: Drop by and meet your Director Orientation Weekend staff just off the elevator on the 2nd floor (this is where we’ll meet for our workshop Sunday morning as well). You’ll pickup your welcome bag and name badges for the weekend.
  • 5pm: Depart the lobby, walking to explore Navy Pier followed by Dinner Cruise.
  • 6pm: Dinner Cruise on the Odyssey boards from Navy Pier.
  • Free time on your own or walk back to hotel.

Sunday, November 12

  • Enjoy your included breakfast at your leisure at the hotel restaurant in the lobby.
  • 9-10am: Director Orientation Workshop Session (at the hotel, 2nd floor in the Superior I room).
  • Enjoy free time exploring the Magnificent Mile, followed by lunch as a group.
  • 12:30pm: Lunch is at Ed Debevic’s, a 50’s style Chicago diner famed for their sassy dancing staff.
  • 2pm: After lunch, we’ll head to the John Hancock Building for Tilt, the ultimate 360-degree Chicago view.
  • 4pm: Enjoy an iconic Blue Man Group show.
  • 6:15pm: Tonight, dinner is at Giordano’s, a Chicago classic.
  • Free time on your own or walk back to hotel.

Monday, November 13

  • Enjoy your included breakfast at your leisure at the hotel restaurant in the lobby.
  • We’ll checkout of the hotel and store our luggage with the concierge team while we explore a bit more of Chicago.
  • 8:45am: Depart hotel as a group for Museum of Science and Industry on our private tour bus.
  • 12pm: Head over to the Shedd Aquarium and enjoy lunch while there.
  • Our tour bus will drop us back off at the hotel around 2pm to grab your luggage and head to the airport, or continue exploring on your own.
  • Depart for home.

Important notes:

  • Chicago is a highly walkable city. If you have mobility issues or are concerned about traveling on foot, please let us know ahead of time. We will often walk between activities up to 10 minutes. Please remember to wear comfortable shoes.
  • *Arrival day: If you arrive early and would like to check-in to the hotel early and/or store your luggage at the hotel while you explore, let us know in advance so we can arrange this for you.
  • Transfers to/from airport: You’ll be provided an Uber voucher as required to travel to and from the airport.
  • Attendance at all activities and meals is expected.
  • Departure day: If you need to leave early for a flight and miss any scheduled activities, please let us know in advance. You may store your luggage at the hotel on departure day as well.