Small-group city trip · Middle school · USA

New York, Boston & Chicago — 10 Days

Teen city trip: New York City, Boston and Chicago — starts in New York, ends in Chicago

Ages

12–14

Duration

10 days

Dates

Jun 28–Jul 7

Group size

24–36 teens per departure

Overview

Three of America's biggest cities in ten days, for younger teens in grades 7 and 8. The trip starts with three days in New York, staying right by Times Square: Central Park, a Major League Baseball game, the 9/11 Memorial and the Oculus, Greenwich Village, and the view from the open-air sky deck at Hudson Yards.

Then Boston — Harvard Yard, a jet-boat ride, an outdoor escape room, the New England Aquarium, Quincy Market and Newbury Street — before a flight to Chicago for the glass Skydeck of the Willis Tower, the Centennial Wheel at Navy Pier, the Bean in Millennium Park, the Magnificent Mile and a show at the Second City comedy club.

It's a small-group trip of 24 to 36 teens who get around like locals — on foot, by subway and bus in the cities, by train from New York to Boston and by plane to Chicago. The Boston–Chicago flight is an extra US$285.

What's included

City hotels in Manhattan, Boston & ChicagoBreakfast & dinner dailyCentral Park & Times SquareMajor League Baseball game9/11 Memorial & the OculusHudson Yards sky deckHarvard YardJet-boat ride in BostonOutdoor escape roomNew England Aquarium & Quincy MarketWillis Tower SkydeckNavy Pier & the Centennial WheelThe Bean & the Magnificent MileSecond City comedy showAirport transfers in set windows

The itinerary

  • Days 1–3 New York City — Arrival in New York and icebreakers with the new group, then the city: a walk through Central Park, a Major League Baseball game, the 9/11 Memorial and the futuristic Oculus, Greenwich Village, and Hudson Yards with the view from its open-air sky deck.
  • Days 4–6 Boston, Massachusetts — Harvard Yard, a fast jet-boat ride on the water, an outdoor escape room, the New England Aquarium, the food halls and street performers of Quincy Market, and a last stroll down Newbury Street.
  • Days 7–10 Chicago, Illinois — A flight to Chicago: the glass ledge of the Willis Tower Skydeck, 412 metres up; Navy Pier and the Centennial Wheel over Lake Michigan; a photo at the Bean in Millennium Park; the shops of the Magnificent Mile; and a night at the Second City improv club. Flights home from Chicago on day 10.

Where teens stay

Three city hotels: a modern hotel above Times Square in Manhattan; a hotel in Boston's Seaport district; and an all-suite hotel with an indoor pool steps from the Magnificent Mile in Chicago. The exact hotel at each stop is confirmed before departure.

Modern hotel room in ManhattanHotel in Boston's Seaport districtHotel in Chicago at dusk

Meals

Breakfast and dinner are included every day — breakfast at the hotel or a café nearby, dinner out at restaurants. Lunch is not included: teens eat at cafés and restaurants along the way, so plan for it in their spending money. Vegetarian, kosher-style, gluten-free (coeliac) and lactose-free diets and most allergies can be catered for if you tell us in advance.

More photos

Boys standing on the glass ledge of a Chicago skyscraper

Frequently asked questions

Which departure is right for my child?

This trip is only for teens finishing grades 7 and 8 (roughly ages 12–14) — a middle-school program, so your child travels with children their own age. There is one departure: Jun 28–Jul 7. The grade is the one your child is in during the 2026–27 school year — we'll help you match it to your school system. Dates are the operator's official start and end dates.

How do flights and arrival work?

The trip starts in New York City and ends in Chicago, so you book a flight into New York and a flight home from Chicago (ORD). Please check the operator's arrival and departure time windows with us before buying anything non-refundable. Staff meet your child at the airport and take them to the group at no extra cost, and teens flying in from overseas can arrive the night before the official start with the extra hotel night included. From Europe there are plenty of direct flights to New York, where your child goes through US immigration on arrival. The Boston→Chicago flight during the trip is booked by the operator for an extra US$285. On the last day the leaders help with check-in and stay at the airport until flights in the set window have left; flights back to Europe are usually overnight, so your child lands home the next day.

What exactly is included in the price?

Accommodation, breakfast and dinner every day, all the activities in the itinerary, airport transfers for flights within the set time windows, tips and local taxes. Not included: flights to and from the trip, the Boston→Chicago flight (US$285), lunches and snacks, spending money, laundry (a laundromat stop about once a week — the operator supplies the detergent and shows first-timers how it works), the operator's application fee, and travel insurance — optional, but we strongly recommend it.

Is there a discount for enrolling early?

Yes — at the moment the operator takes US$200 off the tuition for early enrolment, so the 10-day trip costs US$4,499 instead of US$4,699 (plus the US$285 flight either way). It's a limited-time offer and the operator can end it at any point, so ask us whether it still applies before you decide. The price shown on this page is the full tuition.

How does the group get around?

Like locals: on foot and by subway and city bus in New York, Boston and Chicago, by train from New York to Boston, and by plane to Chicago. The staff are with the group the whole time — finding your way round a big city's metro is part of the adventure.

Does my child need a visa or an ESTA?

Families arrange travel documents themselves. Teens with a passport from a Visa Waiver country — Czechia and most of the EU included — need an approved ESTA (the online US travel authorisation) before they board, so apply well ahead. Teens from other countries need a B-2 visitor visa, not a student visa. If a teen living outside North America is refused a visa before 1 June, the operator offers a move to another program, a roll-over to the following summer, or a refund minus US$450.

Who else will be in the group?

Mostly American teens — on most programs around 85% of participants come from the US, and the operator tries to limit how many teens from any one other country join each group. For an international teen that means a genuinely English-speaking group, which is a big part of the appeal.

How good does my child's English need to be?

At least a confident beginner level — the operator recommends A2 or above, since everything on the trip happens in English. Your child can ask for an English-speaking roommate, and one-to-one English conversation time with a staff member can be arranged daily or a few times a week.

Can my child come on their own?

Yes, and many do. The first days are built around icebreakers and getting-to-know-you activities, roommates are assigned and rotated, and the staff actively help everyone settle into the group.

Are phones allowed?

Yes. Teens can bring their phone, so you can call or message them directly. The operator also runs a communication centre that's staffed every day of the summer, with someone on call around the clock for emergencies.